The study, in JAMA Pediatrics, covered prescriptions for five classes of antibiotics: penicillin, penicillin with beta-lactamase inhibitor, cephalosporin, sulfonamide and macrolide.
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It found that infants who were given antibiotics -- penicillin, cephalosporin, sulfonamide or macrolide -- had a greater chance of developing allergies such as food allergies, asthma or dermatitis.
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The researchers examined which children had been given prescriptions for penicillin, penicillin with B-lactamase inhibitor, cephalosporin, sulfonamide or macrolide within the first six months of life.
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Metronidazole, in its topical form, is commonly used for adult acne and some vaginal infections, while sulfamethoxazole and trimethoprim, two medications in the sulfonamide family, are used for urinary tract infections.
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Each doubling of another PFA known as N-ethyl-perflourooctane sulfonamide acetic acid (EtFOSAA) was associated with a 17% increased risk of developing diabetes complications like impaired vision and loss of sensation in the extremities.
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Sulfonamide functional group Hydrochlorothiazide is a sulfonamide and a thiazide. Furosemide is a sulfonamide, but not a thiazide. Sulfamethoxazole is an antibacterial sulfonamide Sulfonamide is a functional group (a part of a molecule) that is the basis of several groups of drugs, which are called sulphonamides, sulfa drugs or sulpha drugs. The original antibacterial sulfonamides are synthetic (nonantibiotic) antimicrobial agents that contain the sulfonamide group.
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Indane-5-sulfonamide is the base structure of indanesulfonamides. Indane-5-sulfonamide is a carbonic anhydrase inhibitor.
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Acidification of this salt then precipitates the sulfonamide of the primary amine. A secondary amine in the same reaction will directly form an insoluble sulfonamide. A tertiary amine will not react with the sulfonamide but is insoluble. After adding dilute acid this insoluble amine is converted to a soluble ammonium salt.
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Sulfametrole (INN) is a sulfonamide antibacterial. It can be given with trimethoprim.
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A new combination drug therapy (sulfonamide, ceftriaxone, and amikacin) has also shown promise.
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Pure Sulfacetamide sodium salt is a white or slightly yellow crystalline powder Sulfacetamide is a sulfonamide antibiotic.
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A substantial excess of a sulfonamide needed to put a complete stop to PABA assimilation.Postgate (2013), pp. 90-93 Postgate's research was to study sulfonamide action on a species of bacteria that required PABA from the environment as a vitamin; it gave him valuable experience of competition in enzymology.
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Terephtyl is a long-acting synthetic sulfonamide antibiotic used for the treatment of infection caused by susceptible strains.
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Research was stimulated apace by its success. The discovery and development of this sulfonamide drug opened the era of antibacterials.
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The resulting sulfonamide structure is extremely stable. It can be deprotected to reveal the amine using reductive or strongly acidic conditions.
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Ethacrynic acid is the only medication of this class that is not a sulfonamide. It has a distinct complication of being associated with gastrointestinal toxicity.
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Chinese pig farming uses sulfamethazine, bacitracin, chlortetracycline, tetracycline, florfenicol, sulfonamide, doxycycline, oxytetracycline, fluoroquinolone, macrolide, and trimethoprim. It stopped using colistin as of 26 July 2016.
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Sulfachlorpyridazine (INN, USP) is a sulfonamide antibiotic drug used in poultry farming. It has been marketed as Vetisulid for use in cattle, swine and birds.
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Sulfonylureas were discovered, in 1942, by the chemist Marcel Janbon and co-workers, who were studying sulfonamide antibiotics and discovered that the compound sulfonylurea induced hypoglycemia in animals.
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This functional group appears in a variety of medications, particularly cardiac (antiarrhythmic) drugs, as a sulfonamide moiety. Examples include sotalol, ibutilide, sematilide, dronedarone, dofetilide, E-4031, and bitopertin.
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The enzyme dihydropteroate synthetase is inhibited by sulfonamide antibiotics. Molybdopterin is a cofactor found in virtually all molybdenum and tungsten-containing proteins. Moco biosynthetic pathway in bacteria and humans.
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Storz Ophthalmics Inc, Clearwater, FL, 1995aReynolds JEF (Ed): Martle: The Extra Pharmacopoeia (electronic version). Micromedex, Inc. Englewood, CO. 1995. Dorzolamide is a sulfonamide and topical carbonic anhydrase II inhibitor.
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All triptans have an indole structure identical to the neurotransmitter 5-HT. Classic triptan structure contain side chain on the indole ring, and a basic nitrogen in a similar distance from the indole structure. The main structural difference of the triptans is the position of the sulfonamide and the side chain attached to it (see figure 1 and table 1). Rizatriptan and zolmitriptan have instead of a sulfonamide a triazole and 2-oxazolidone respectively.
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Azabon is a central nervous system stimulant of the sulfonamide class that is also used as a nootropic. As it is a sulpha drug, care must be taken during administration, and certain individuals must avoid azabon altogether to prevent an allergic reaction. Despite being a sulfonamide, azabon has poor antibacterial potency, although this decreased activity is common among other benzenesulfonamides with two substituents on N1. Azabon is synthesized from 3-azabicyclo-[2.2.
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Pyrimethamine is typically given with a sulfonamide and folinic acid. It is used for the treatment of toxoplasmosis, actinomycosis, and isosporiasis, and for the treatment and prevention of Pneumocystis jirovecii pneumonia.
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Xipamide is a sulfonamide diuretic drug marketed by Eli Lilly under the trade names Aquaphor (in Germany) and Aquaphoril (in Austria). It is used for the treatment of oedema and hypertension.
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PEPA is a sulfonamide AMPA receptor positive allosteric modulator, which is up to 100 times more potent than aniracetam in vitro. It produces memory- enhancing effects in rats when administered intravenously.
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A general way to synthesize sulfonamides is to perform a substitution reaction with an amine, a pyridine and a sulfonyl chloride (Figure 1). General structures of the reactants required to synthesize a sulfonamide Figure 1: General structures of the reactants required to synthesize a sulfonamide This method of synthesizing a sulfonamide is often used for the synthesis of glybuzole. Glybuzole can be synthesized using benzenesulfonyl chloride, 2-amino-5-tert- butyl-1,3,4-thiadiazole and pyridine. The reaction that will proceed is a bimolecular nucleophilic substitution reaction (SN2) (Figure 2). The nitrogen atom from the amino-group of 2-amino-5-tert-butyl-1,3,4-thiadiazole will attack the sulfur atom of benzene-sulfonyl chloride, leading to a chloride ion being removed from the benzenesulfonyl chloride.
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Of the three catalysts, Zhan Catalyst-1B and -1C both contain a dimethylsulfonamide moiety attached to the aryl ring, while Zhan Catalyst-II is connected to a resin via a sulfonamide linker.
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The nitrogen-atom of the sulfonamide is bound to a thiadiazole. In this thiadiazole two nitrogen-atoms and one sulfur-atom are present. The thiadiazole is bound to a tert-butyl group.
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Sulfanitran is a sulfonamide antibiotic which is used in the poultry industry. It is a component of Novastat, Polystat, and Unistat, brand names of feed additives for chickens used to control Coccidioides spp.
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136 In order to absolve Gebhardt for his failure to prescribe sulfonamide for Heydrich, Himmler suggested to Gebhardt that he should conduct experiments proving that sulfonamide was useless in the treatment of gangrene and sepsis. In order to vindicate his decision to not administer sulfa drugs in treating Heydrich’s wounds, he carried out a series of experiments on Ravensbrück concentration camp prisoners, breaking their legs and infecting them with various organisms in order to prove the worthlessness of the drugs in treating gas gangrene. He also attempted to transplant the limbs from camp victims to German soldiers wounded on the Russian front. The Ravensbrück experiments were slanted in Gebhardt’s favor; women in the sulfonamide-treated experimental group received little or no nursing care, while those in the untreated control group received better care.
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Sulfisomidine (INN), also known as sulphasomidine (BAN until 2003), . United Kingdom Medicines and Healthcare products Regulatory Agency (December 12, 2003). Retrieved on 2007-08-26 through Archive.org. sulfamethin and sulfaisodimidine, is a sulfonamide antibacterial.
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In addition, the sulfonamide functional group can also mimic the transition state structure. Evidence of boronic acid mimics as transition state analogue inhibitors of human arginase I was elucidated by x-ray crystal structures.
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N-(1-Naphthyl)ethylenediamine is an organic compound. It is commercially available as part of Griess reagents, which find application in quantitative inorganic analysis of nitrates, nitrite and sulfonamide in blood, using the Griess test.
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Sulfonamide drugs were the first broadly effective antibacterials to be used systemically, and paved the way for the antibiotic revolution in medicine. The first sulfonamide, trade-named Prontosil, was a prodrug. Experiments with Prontosil began in 1932 in the laboratories of Bayer AG, at that time a component of the huge German chemical trust IG Farben. The Bayer team believed that coal-tar dyes which are able to bind preferentially to bacteria and parasites might be used to attack harmful organisms in the body.
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Prontosil is an antibacterial drug of the sulfonamide group. It has a relatively broad effect against gram-positive cocci but not against enterobacteria. One of the earliest antimicrobial drugs, it was widely used in the mid-20th century but is little used today because better options now exist. The discovery and development of this first sulfonamide drug opened a new era in medicine, because it greatly widened the success of antimicrobial chemotherapy in an era when many physicians doubted its still largely untapped potential.
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The reaction is used in a chemical test for the detection of aldehydes in combination with ferric chloride. In this test a few drops of aldehyde containing specimen is dissolved in ethanol, the sulfonamide is added together with some sodium hydroxide solution and then the solution is acidified to Congo red. An added drop of ferric chloride will turn the solution an intense red when aldehyde is present. The sulfonamide can be prepared by reaction of hydroxylamine and benzenesulfonyl chloride in ethanol with potassium metal.
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Other minor side effects include a tingle-sensation in hands and feet. Although a sulfonamide; acetazolamide is a non-antibiotic and has not been shown to cause life-threatening allergic cross-reactivity in those with a self-reported sulfonamide allergy. Dosage of 1000 mg/day will produce a 25% decrease in performance, on top of the reduction due to high- altitude exposure. The CDC advises that Dexamethasone be reserved for treatment of severe AMS and HACE during descents, and notes that Nifedipine may prevent HAPE.
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The molecular formula of glybuzole is C12H15N3O2S2. It is also known as desaglybuzole or gludiase. The systematic name is N-(5-tert- butyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide. It consists of a benzene ring connected to sulfonamide.
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Other side effects may include hearing loss and low blood potassium. Torasemide is a sulfonamide and loop diuretic. Use is not recommended in pregnancy or breastfeeding. It works by decreasing the reabsorption of sodium by the kidneys.
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PF-610355 (also known as PF-00610355 or PF-610,355) is an inhalable ultra- long-acting β2 adrenoreceptor agonist (ultra-LABA) that was investigated as a treatment of asthma and COPD by Pfizer. It utilizes a sulfonamide agonist headgroup, that confers high levels of intrinsic crystallinity that could relate to the acidic sulfonamide motif supporting a zwitterionic form in the solid state. Optimization of pharmacokinetic properties minimized systemic exposure following inhalation and reduced systemically-mediated adverse events. Its in vivo duration on action confirmed its potential for once-daily use in humans.
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Selective binding to active Raf is accomplished by the terminal propyl group that binds to a Raf-selective pocket created by a shift of the αC helix. Selectivity for the active conformation of the kinase is further increased by a pH-sensitive deprotonated sulfonamide group that is stabilized by hydrogen bonding with the backbone peptide NH of D594 in the active state. In the inactive state, the inhibitor's sulfonamide group interacts with the backbone carbonyl of that residue instead, creating repulsion. Thus, Vemurafenib binds preferentially to the active state of B-Raf's kinase domain.
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Celecoxib contains a sulfonamide moiety and may cause allergic reactions in those allergic to other sulfonamide-containing drugs. This is in addition to the contraindication in people with severe allergies to other NSAIDs. However, it has a low (reportedly 4%) chance of inducing cutaneous reactions among persons who have a history of such reactions to aspirin or nonselective NSAIDs. NSAIDs may cause serious skin adverse events, including exfoliative dermatitis, Stevens-Johnson syndrome, and toxic epidermal necrolysis; events may occur without warning and in patients without prior known sulfa allergy.
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It is in the sulfonamide class of medications. Sulfadiazine was approved for medical use in the United States in 1941. It is on the World Health Organization's List of Essential Medicines. Sulfadiazine is available as a generic medication.
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Sulfamethoxypyridazine is a sulfonamide antibacterial. It is prescribed for vaginal irritation, and severe acute thrush. It is also used in the treatment of Dermatitis herpetiformis, where it is an alternative therapy to Dapsone. Sulfamethoxypyridazine is supplied as 500mg tablets.
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Glymidine sodium (INN, also known as glycodiazine; trade name Gondafon) is a sulfonamide antidiabetic drug, structurally related to the sulfonylureas. It was first reported in 1964, and introduced to clinical use in Europe in the mid to late 1960s.
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Succinylsulfathiazole (also known as sulfasuxidine) is a sulfonamide. It is also spelled as succinylsulphathiazole. It is a white or yellow-white crystalline powder. It dissolves in aqueous solutions of alkali hydroxides and carbonates but is very slightly soluble in water.
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Folate is necessary for the cell to synthesize nucleic acids (nucleic acids are essential building blocks of DNA and RNA), and in its absence cells will be unable to divide. Hence the sulfonamide antibacterials exhibit a bacteriostatic rather than bactericidal effect.
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Sulfonamide hypersensitivity syndrome is similar to anticonvulsant hypersensitivity syndrome, but the onset is often sooner in the treatment course, generally after 7–14 days of therapy.James, William; Berger, Timothy; Elston, Dirk (2005). Andrews' Diseases of the Skin: Clinical Dermatology. (10th ed.). Saunders. .
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Inhibitors of these organisms are under current investigation. A pyrazole sulfonamide inhibitor has been identified that selectively binds T. brucei, competing for the peptide binding site, thus inhibiting enzymatic activity and eliminating the parasite from the bloodstream of mice with African sleeping sickness.
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It can be synthesized from catechol first by conversion to methylenedioxybenzene, which is brominated and coupled with allyl bromide. Safrole is a versatile precursor to many compounds. Examples are N-acylarylhydrazones, isosters, aryl-sulfonamide derivatives, acidic sulfonylhydrazone derivatives, benzothiazine derivatives. and many more.
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Dichloramine-T or N,N-Dichloro-p-toluenesulfonamide is a chemical used as a disinfectant starting at the beginning of the 20th century. The chemical contains toluene substituted by a sulfonamide grouping, which in turn has two chlorine atoms attached to the nitrogen.
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Sulfadimidine or sulfamethazine is a sulfonamide antibacterial. There are non- standardized abbreviations for it as "sulfadimidine" (abbreviated SDI and more commonly but less reliably SDD) and as "sulfamethazine" (abbreviated SMT and more commonly but less reliably SMZ). Other names include sulfadimerazine, sulfadimezine, and sulphadimethylpyrimidine.
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Ethoxzolamide (alternatively known as ethoxyzolamide) is a sulfonamide medication that functions as a carbonic anhydrase inhibitor. It is used in the treatment of glaucoma and duodenal ulcers, and as a diuretic. It may also be used in the treatment of some forms of epilepsy.
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Examples include the estradiol esters estradiol sulfamate (E2MATE; also a potent steroid sulfatase inhibitor) and EC508 (estradiol 17β-(1-(4-(aminosulfonyl)benzoyl)-L-proline)), the testosterone ester EC586 (testosterone 17β-(1-((5-(aminosulfonyl)-2-pyridinyl)carbonyl)-L-proline)), and sulfonamide esters of levonorgestrel and etonogestrel.
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The molecular formula of glysobuzole is C13H17N3O3S2. It is synonymously found under the name isobuzole. Its systematic name is 4-methoxy-N-[5-(2-methylpropyl)-1,3,4-thiadiazol-2-yl]benzenesulfonamide. Its achiral structure includes a benzene ring connected to a thiadiazole via a sulfonamide.
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Sulfacetamide is a sulfonamide antibiotic. Sulfonamides are synthetic bacteriostatic antibiotics, that are active against gram-positive and gram-negative bacteria. It blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. It is a competitive inhibitor of bacterial para- aminobenzoic acid (PABA).
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The pioneering hydroxamate-based inhibitors were followed by a set of 'new generation' molecules with features including a substituted aryl, a sulfonamide and a hydroxamate zinc-binding group. New generation hydroxamate-based MMP inhibitors In MMI-270 there is also an amino acid sidechain-type substituent on the carbon that is α to the hydroxamate, along with a sidechain on the sulfonamide (which was later shown to be unnecessary). The N-arylsulfonyl-α-aminoacid hydroxamate of MMI-270 mimics the marimastat succinate motif. Cipemastat, which was developed as an MMP-1, -3 and -9 collagenase inhibitor for the treatment of rheumatoid- and osteo- arthritis, also has the marimastat succinate motif.
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Sulfacytine is a short-acting sulfonamide antibiotic, taken orally for treatment against bacterial infections. Sulfonamides, as a group of antibiotics, work by inhibiting the bacterial synthesis of folate. In 2006 the drug was discontinuedFederal Register Section: Food and Drug Administration [Docket No. 2006N–0222] Merck & Co., Inc., et al.
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J Reconstr Microsurg. 1990; 6(2):135-137 Antibiotics such as chloramphenicol, florfenicol, tetracycline, sulfonamide, nitrofuran derivatives, and Pyridinecarboxylic acids are used to eliminate and control the infection of A. hydrophila. Terramycin is placed in fish food during hatchery operations as another chemotherapeutic agent in preventing A. hydrophila.
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Saccharin can be produced in various ways. The original route by Remsen and Fahlberg starts with toluene; another route begins with o-chlorotoluene. Sulfonation of toluene by chlorosulfonic acid gives the ortho and para substituted sulfonyl chlorides. The ortho isomer is separated and converted to the sulfonamide with ammonia.
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Ethoxzolamide, a sulfonamide, inhibits carbonic anhydrase activity in proximal renal tubules to decrease reabsorption of water, sodium, potassium, bicarbonate. It also decreases carbonic anhydrase in the CNS, increasing the seizure threshold. This reduction in carbonic anhydrase also reduces the intraocular pressure in the eye by decreasing aqueous humor.
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Metolazone is a quinazoline, a derivative of the similar diuretic quinethazone, as well as a sulfonamide. It is related to analogs of 1,2,4-benzothiadizine-1,1-dioxide (benzothiadiazine). These drugs are called benzothiadiazides, or thiazides for short. Chemically, metolazone is not a substituted benzothiadiazine, and therefore is not technically a thiazide.
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Common side effects include eye discomfort, eye redness, taste changes, and blurry vision. Serious side effects may include allergic reactions and heart failure. Use is not recommended in those with asthma, a sulfonamide allergy, or a slow heart rate. Dorzolamide is a carbonic anhydrase inhibitor and timolol is a beta blocker.
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A group was substituted for the hydrogen atom as demonstrated in figure 6. The sulfonamide group was chosen to lower lipophilicity and increase solubility as seen in figure 7. Figure 6. PDE5 SAR2 Solubility was further increased by placing a methyl group at R positions as demonstrated in figure 7.
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Mucous membranes, such as the mouth, are also typically involved. Complications include dehydration, sepsis, pneumonia, and multiple organ failure. The most common cause is certain medications such as lamotrigine, carbamazepine, allopurinol, sulfonamide antibiotics, and nevirapine. Other causes can include infections such as Mycoplasma pneumoniae and cytomegalovirus or the cause may remain unknown.
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Sulfafurazole (INN, also known as sulfisoxazole) is a sulfonamide antibacterial with an dimethyl-isoxazole substituent. It has antibiotic activity against a wide range of Gram-negative and Gram-positive organisms. It is sometimes given in combination with erythromycin (see erythromycin/Sulfafurazole) or phenazopyridine. It is used locally in a 4% solution or ointment.
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Circulation of blood was interrupted by tying off blood vessels at both ends of the wound to create a condition similar to that of a battlefield wound. Infection was aggravated by forcing wood shavings and ground glass into the wounds. The infection was treated with sulfonamide and other drugs to determine their effectiveness.
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Candesartan cilexetil (candesartan), Avapro (irbesartan), Cozaar (losartan) and Diovan (valsartan). Chemical Structure of Diovan (valsartan) A vast array of pharmaceuticals and agrochemicals are based on pyrimidines, such as Vitamin B1 (thiamine), the sulfonamide antibiotics, e.g. Madribon (sulfadimethoxime) and –half a century later– the sulfonyl urea herbicides, e.g. Eagle (amidosulfuron) and Londax (bensulfuron-methyl).
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It is primarily active against Plasmodium falciparum, but also against Plasmodium vivax. Due to the emergence of pyrimethamine-resistant strains of P. falciparum, pyrimethamine alone is seldom used now. In combination with a long-acting sulfonamide such as sulfadiazine, it was widely used, such as in Fansidar, though resistance to this combination is increasing.
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These mutants reflect the importance of ABA in seed germination and early embryo development. Pyrabactin (a pyridyl containing ABA activator) is a naphthalene sulfonamide hypocotyl cell expansion inhibitor, which is an agonist of the seed ABA signaling pathway. It is the first agonist of the ABA pathway that is not structurally related to ABA.
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The phenomenon in which organic luminophores show higher photoluminescence efficiency in the aggregated state than in solution is called aggregation-induced emission enhancement (AIEE). Some luminophores, e.g., diketopyrrolopyrrole-based and sulfonamide-based luminophores, only display enhanced emission upon entering the crystalline state. That is, these luminophores are said to exhibit crystallization-induced emission enhancement (CIEE).
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A thiazide-like diuretic is a sulfonamide diuretic that has similar physiological properties to a thiazide diuretic, but does not have the chemical properties of a thiazide, lacking the benzothiadiazine molecular structure. Examples include metolazone and chlorthalidone. Some, such as indapamide are considered thiazide-like diuretics, but do not necessarily have the same mechanism.
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Sulfamethoxazole (SMZ or SMX) is an antibiotic. It is used for bacterial infections such as urinary tract infections, bronchitis, and prostatitis and is effective against both gram negative and positive bacteria such as Listeria monocytogenes and E. coli. Common side effects include nausea, vomiting, loss of appetite, and skin rashes. It is a sulfonamide and bacteriostatic.
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Peryea 1998 Sulfur is one of the oldest of the fungicides and pesticides. Phosphorus, sulfur, zinc, selenium, and iodine are essential nutrients, and aluminium, tin, and lead may be. Sulfur, gallium, selenium, iodine, and bismuth have medicinal applications. Sulfur is a constituent of sulfonamide drugs, still widely used for conditions such as acne and urinary tract infections.
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Sulfacetamide is a sulfonamide antibiotic, that is used as a cream to treat skin infections and as eye drops to treat eye infections. On the skin it is used to treat acne and seborrheic dermatitis. In cream form it is used to treat bacterial infections on the skin. It can also be used orally to treat urinary tract infections.
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It undergoes photocatalytic degradation and the toxicity of the intermediate products is significantly lower than the initial toxicity. The intermediates can be mineralized in contrast to sulfacetamide. Sulfonamide → organic intermediate products (degradation) (in presence of OH−). Oxidation of sulfacetamide by diperiodatocuperate(lll) At higher temperatures sulfacetamide solutions degrade to its hydrolysed product, sulphanilamide with a first-order rate constant.
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Antibiotic therapy with a sulfonamide, most commonly trimethoprim-sulfamethoxazole, is the treatment of choice. Retrieved on January 3, 2009. Freely available with registration. People who take trimethoprim-sulfamethoxazole for other reasons, such as prevention of Pneumocystis jirovecii infection, appear to have fewer Nocardia infections, although this protective effect has been considered unreliable, and some studies have disputed it altogether.
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E7070 is a novel chloroindolyl sulfonamide cell cycle that exhibits potent antitumoractivity in vitro (in a laboratory) and in vivo (in the body). This compound affects cell cycle progression in human tumor cells and is most commonly used to treat cancers such as melanomas and tumor cells but is also used to treat blood-borne cancers such as leukemia.
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Anticonvulsant/sulfonamide hypersensitivity syndrome is a potentially serious hypersensitivity reaction that can be seen with medications with an aromatic amine chemical structure, such as aromatic anticonvulsants (e.g. diphenylhydantoin, phenobarbital, phenytoin, carbamazepine, lamotrigine), sulfonamides, or other medications with an aromatic amine (e.g., procainamide). Cross-reactivity should not occur between medications with an aromatic amine and medications without an aromatic amine (e.g.
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The mechanism of cadmium carbonic anhydrase (CDCA) is essentially the same as that of other carbonic anhydrases in its conversion of carbon dioxide and water into bicarbonate and a proton. Additionally, like the other carbonic anhydrases, CDCA makes the reaction go almost as fast as the diffusion rate of its substrates, and it can be inhibited by sulfonamide and sulfamate derivatives.
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Gebhardt refused Morell's advice, expecting Heydrich to recover without antibiotic therapy. Heydrich died of sepsis on 4 June 1942, eight days after the attack. Gebhardt's refusal to prescribe sulfonamide contributed to Heydrich's death and had many unfortunate implications for concentration camp prisoners, upon whom he later conducted medical experiments. In early 1944, Gebhardt treated Albert Speer for fatigue and a swollen knee.
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The isolated ethyl ester remained the preferred treatment for leprosy until sulfonamide drugs were developed in the 1940s. It was not until years after her death that Hollmann attempted to correct this injustice. He published a paper in 1922 giving credit to Ball, calling the injectable form of the oil the "Ball method." Unfortunately, she still remained forgotten in the scientific record.
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General chemical structure of a sulfanilide A sulfonanilide group is functional group that is a type of sulfonamide group which contains a sulfur atom bonded to two oxygen, one carbon atom, and one nitrogen contained within a derivative of aniline.Wujiang Zhenze Xinmin Chemical Auxiliaries Factory: "Product name — 2-Aminophenol-4-(2-carboxy)sulfonanilide" Intermediates for Dyes and Pesticides — Products. (2006).
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The Hinsberg reaction is a test for the detection of primary, secondary and tertiary amines. In this test, the amine is shaken well with Hinsberg reagent in the presence of aqueous alkali (either KOH or NaOH). A reagent containing an aqueous sodium hydroxide solution and benzenesulfonyl chloride is added to a substrate. A primary amine will form a soluble sulfonamide salt.
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Volatile sulfonamide PFOS precursors include N-methyl perfluorooctane sulfonamidoethanol (N-MeFOSE), a carpet stain repellent, and N-ethyl perfluorooctane sulfonamidoethanol (N-EtFOSE), a paper treatment. Perfluorooctanesulfonamide is a precursor. About 50 precursors were named in the 2004 proposed Canadian ban on PFOS. Later, the OECD came up with a document containing a list of 20 pages with potential precursors to PFOS.
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Prontosil's discovery ushered in the era of antibacterial drugs and had a profound effect on pharmaceutical research, drug laws, and medical history. Sulfonamide-trimethoprim combinations (co-trimoxazole) are still used extensively against opportunistic infections in patients with AIDS, urinary infections and in the treatment of burns. However, in many other situations, sulfa drugs have been replaced by beta-lactam antibacterials.
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A splenectomy was performed, and the chest wound, left lung, and diaphragm were all debrided. Himmler ordered Karl Gebhardt to fly to Prague to assume care. Despite a fever, Heydrich's recovery appeared to progress well. Hitler's personal doctor Theodor Morell suggested the use of the new antibacterial drug sulfonamide, but Gebhardt thought that Heydrich would recover and declined the suggestion.
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Nocardiosis requires at least 6 months of treatment, preferably with trimethoprim/sulfamethoxazole or high doses of sulfonamides. In patients who do not respond to sulfonamide treatment, other drugs, such as ampicillin, erythromycin, or minocycline, may be added. Treatment also includes surgical drainage of abscesses and excision of necrotic tissue. The acute phase requires complete bed rest; as the patient improves, activity can increase.
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The Angeli–Rimini reaction is an organic reaction between an aldehyde and the sulfonamide N-hydroxybenzenesulfonamide in presence of base forming a hydroxamic acid. The Angeli-Rimini reaction The other reaction product is a sulfinic acid. The reaction was discovered by the two Italian chemists Angelo Angeli and Enrico Rimini (1874-1917), and was published in 1896.Angelo Angeli Gazz. Chim. Ital.
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Up until the use of anesthesia became established, surgeries involving healthy tissues involved great pain. Infection from surgery was reduced by the introduction of sterile techniques and disinfectants. The invention and use of antibiotics, beginning with sulfonamide and penicillin, was another step in making elective surgery possible. In 1793, François Chopart performed operative procedure on a lip using a flap from the neck.
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Himmler ordered Dr Karl Gebhardt to fly to Prague to assume care. Despite a fever, Heydrich's recovery appeared to progress well. Dr Theodor Morell, Hitler's personal physician, suggested the use of sulfonamide (an antibacterial drug), but Gebhardt, thinking Heydrich would recover, refused. On 2 June, during a visit by Himmler, Heydrich reconciled himself to his fate by reciting a part of one of his father's operas.
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The overall incidence of adverse drug reactions to sulfa antibiotics is approximately 3%, close to penicillin; hence medications containing sulfonamides are prescribed carefully. It is important to make a distinction between sulfa drugs and other sulfur-containing drugs and additives, such as sulfates and sulfites, which are chemically unrelated to the sulfonamide group and do not cause the same hypersensitivity reactions seen in the sulfonamides.
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Perfluorooctanesulfonamide (PFOSA) is a synthetic organofluorine compound. It is a fluorocarbon derivative and a perfluorinated compound, having an eight- carbon chain and a terminal sulfonamide functional group. PFOSA, a persistent organic pollutant, was an ingredient in 3M's former Scotchgard formulation Supporting Information (PDF). from 1956 until 2003, and the compound was used to repel grease and water in food packaging along with other consumer applications.
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As a sulfonamide antibiotic, sulfanilamide functions by competitively inhibiting (that is, by acting as a substrate analogue) enzymatic reactions involving para-aminobenzoic acid (PABA). PABA is needed in enzymatic reactions that produce folic acid, which acts as a coenzyme in the synthesis of purines and pyrimidines. Mammals do not synthesize their own folic acid so are unaffected by PABA inhibitors, which selectively kill bacteria.
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Zonisamide is a medication used to treat the symptoms of epilepsy and Parkinson's disease. Chemically it is a sulfonamide. It serves as an anticonvulsant used primarily as an adjunctive therapy in adults with Parkinson's disease, partial-onset seizures; infantile spasm, mixed seizure types of Lennox–Gastaut syndrome, myoclonic and generalized tonic clonic seizure. Despite this it is also sometimes used as a monotherapy for partial- onset seizures.
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Sulfonamides are generally effective against most gram-positive and many gram-negative organisms. Specifically enteric bacteria and other eubacteria are affected by the antibiotic as it kills the bacteria by restricting the production of folic acid, which is essential for their growth. However strains of bacteria can be resistant to the antibiotic. If a bacterium is resistant to a sulfonamide, it is resistant to all the forms.
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Trimethoprim/sulfadoxine is contraindicated in cattle or swine that show marked liver parenchymal damage or blood dyscrasias, or those with a history of sulfonamide sensitivity. Milk from an animal treated with trimethoprim/sulfadoxine must not be consumed for at least 96 hours following the most recent treatment; treated animals must not be slaughtered for use in food for at least ten days after the last treatment.
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OSMI-1 was first identified from high- throughput screening using fluorescence polarization. Further optimization led to the development of OSMI-2, OSMI-3, and OSMI-4, which bind OGT with low- nanomolar affinity. X-ray crystallography showed that the quinolinone-6-sulfonamide scaffold of OSMI compounds act as a uridine mimetic. OSMI-2, OSMI-3, and OSMI-4 have negatively charged carboxylate groups; esterification renders these inhibitors cell-permeable.
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Sulfadimethoxine can either be given alone (such as under the commercial name Albon) or in combination with ormetoprim to as a "potentiated sulfonamide" to increase antimicrobial activity. Ormetoprim is a diaminopyridine, inhibiting dihydrofolate reductase, which is further along the pathway for synthesizing folic acid. Though the optimum ratio of sulfadimethoxine to ormetoprim has been found to be 20:1, it is sold pharmaceutically as a 5:1 mixture.
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In the treatment of heart failure, many studies have shown that the long-term use of furosemide can cause varying degrees of thiamine deficiency, so thiamine supplementation is also suggested. Although disputed, it is considered ototoxic: "usually with large intravenous doses and rapid administration and in renal impairment".BNF 45 March 2003 Other precautions include: nephrotoxicity, sulfonamide (sulfa) allergy, and increases free thyroid hormone effects with large doses.
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Malarone: New Malaria Medication With Fewer Side-effects Resistance has been observed. # For babesia, it is often used in conjunction with oral azithromycin. Trimethoprim/sulfamethoxazole (TMP-SMX, Bactrim) is generally considered first-line therapy for PCP (not to be confused with Sulfadiazine+pyrimethamine which is first line for toxoplasmosis). However, atovaquone may be used in patients who cannot tolerate, or are allergic to, sulfonamide medications such as TMP-SMX.
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From about July 1942 to about September 1943, experiments to investigate the effectiveness of sulfonamide, a synthetic antimicrobial agent, were conducted at Ravensbrück.Schaefer, Naomi. The Legacy of Nazi Medicine, The New Atlantis, Number 5, Spring 2004, pp. 54–60. Wounds inflicted on the subjects were infected with bacteria such as Streptococcus, Clostridium perfringens (a major causative agent in gas gangrene) and Clostridium tetani, the causative agent in tetanus.
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Certain sulfur-based steroid esters have a sulfamate or sulfonamide moiety as the ester, typically at the C3 and/or C17β positions. Like many other steroid esters, they are prodrugs. Unlike other steroid esters however, they bypass first-pass metabolism with oral administration and have high oral bioavailability and potency, abolished first-pass hepatic impact, and long elimination half-lives and durations of action. They are under development for potential clinical use.
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In humans, PABA is considered nonessential and, although it has been referred to historically as "vitamin Bx", is no longer recognized as a vitamin, because most people have a microbiome that will generate PABA. Sulfonamide drugs are structurally similar to PABA, and their antibacterial activity is due to their ability to interfere with the conversion of PABA to folate by the enzyme dihydropteroate synthetase. Thus, bacterial growth is limited through folate deficiency.
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Starting in the summer of 1942, medical experiments were conducted without consent on 86 women; 74 of them were Polish inmates. Two types of experiments were conducted on the Polish political prisoners. The first type tested the efficacy of sulfonamide drugs. These experiments involved deliberate cutting into and infecting of leg bones and muscles with virulent bacteria, cutting nerves, introducing substances like pieces of wood or glass into tissues, and fracturing bones.
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As detomidine is an arrhythmogenic agent, extreme care should be exercised in horses with cardiac disease, and in the concurrent administration of other arrhythmogenics. The concurrent use of potentiated sulfonamide antibiotics is considered particularly dangerous. Detomidine is a poor premedication when using ketamine as an anesthetic in horses. Anesthetic recoveries in horses that have received ketamine following a detomidine premedication are often violent with the horse having multiple failures to stand resulting in trauma to itself.
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The authors studied 445 cases of acute pyogenic infections and 74 cases of virus and virus-like infections. Findings included the following: sulfonamide-resistant and penicillin-resistant infections have responded to the treatment. Further finding included: “We have observed that toxemias due to various virus and virus-like infections subside rapidly …” Some of the more impressive results included cases involving septic infection, 57 out of 57 cases recovered. In treating peritonitis, 16 out of 18 patients recovered.
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As an antibacterial, dapsone inhibits bacterial synthesis of dihydrofolic acid, via competition with para- aminobenzoate for the active site of dihydropteroate synthase, thereby inhibiting nucleic acid synthesis. Though structurally distinct from dapsone, the sulfonamide group of antibacterial drugs also work in this way. As an anti-inflammatory, dapsone inhibits the myeloperoxidase-H2O2-halide-mediated cytotoxic system in polymorphonucleocytes. As part of the respiratory burst that neutrophils use to kill bacteria, myeloperoxidase converts hydrogen peroxide () into hypochlorous acid (HOCl).
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Perfluorobutane sulfonamide, also known as FBSA or H-FBSA, is a perfluorinated surfactant. FBSA and its N-alkylated derivatives have been patented by 3M for use in acid etch solutions with low surface tension. According to the inventors, FBSA and its derivatives are expected to have a smaller tendency to accumulate in living organisms than their perfluorooctanyl analogs such as PFOS. Nevertheless, a 2015 study found FBSA in 32 out of 33 samples of Canadian fish.
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The laboratory improved serological tests for syphilis and demonstrated, with the advent of sulfonamide treatment in the United States in the 1930s, its efficacy in gonorrhea. He was also Medical Director of the Marine Hospital in Staten Island. Mahoney was made aware of the possibilities of penicillin treatment by a paper of Wallace Herrell and colleagues from the Mayo Clinic. Particular attention was on the treatment of gonorrhea patients where the pathogen was resistant to sulfonamides.
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Sulfadimethoxine (or sulphadimethoxine, trade names Di-Methox or Albon) is a long-lasting sulfonamide antimicrobial medication used in veterinary medicine. It is used to treat many infections, including respiratory, urinary tract, enteric, and soft tissue infections and can be given as a standalone or combined with ormetoprim to broaden the target range. Like all sulfamides, sulfadimethoxine inhibits bacterial synthesis of folic acid by acting as a competitive inhibitor against PABA. It is the most common drug prescribed to dogs who have coccidiosis.
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Zhan's second generation catalysts are also tethered to a resin or PEG-linked support via the sulfonamide group on the isopropoxystyrene. :Zhan Catalyst-II As with other Grubbs-type catalysts with modified chelating benzylidenes, after one catalytic turnover, the chelate is no longer associated with the propagating catalyst, meaning that the initiate rate, the rate of o-alkoxystyrene rechelation, and the rates of various catalyst decomposition events are the factors that differ between the Zhan catalysts and the parent Hoveyda–Grubbs catalysts.
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Zonisamide is an antiseizure drug chemically classified as a sulfonamide and unrelated to other antiseizure agents. The precise mechanism by which zonisamide exerts its antiseizure effect is unknown, although it is believed that the drug blocks sodium and T-type calcium channels, which leads to the suppression of neuronal hypersynchronization (that is, seizure-form activity). It is also known to be a weak carbonic anhydrase inhibitor (similarly to the anticonvulsant topiramate). It is also known to modulate GABAergic and glutamatergic neurotransmission.
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Glysobuzole (or isobuzole) is an oral antidiabetic drug, it is taken once daily by oral administration and it is water soluble to become pharmaceutically active within the gastrointestinal tract. It is a sulfonamide derivative that is similar to sulfonylureas. Glysobuzole has antihyperglycemic activity, so it is able to lower blood glucose levels by increasing the release of insulin from the pancreatic beta cells. Glysobuzole functions as a modulator in metabolic processes involving insulin and therefore it is used to treat diabetes.
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Eletriptan has higher affinity for the receptor, which is probably a result of the bulky substituents of the structure. The amine is protonated at physiological pH condition, triggering better uptake. The uptake rate of the agonist is different depending on whether the amine in R2 is primary, secondary or tertiary but the latter seem to give the best results. For the R1 substituent an electron rich sulfonamide groups and amide group has shown the best results in receptor binding and activity.
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The structural modifications highlight the importance of binding to residue 523 in the side binding pocket of the cyclooxygenase enzyme, which is an isoleucine in COX-1 and a valine in COX-2. This mutation appears to contribute to COX-2 selectivity by creating steric hindrance between the sulfonamide oxygen and the methyl group of Ile523 that effectively destabilizes the celecoxib-COX-1 complex. Thus, it is reasonable to expect COX-2-selective inhibitors to be more bulky than nonselective NSAIDs.
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Recent work by Zhang and coworkers using chiral sulfonamide phosphine ligands has improved the reaction to feature a broad substrate scope and high enantioselectivity (88–95% ee) without the use of stoichiometric silver additives. In 2007, Buchwald and coworkers reported the synthesis of 3-arylindanones via an asymmetric reductive Heck cyclization using chiral biaryl phosphine ligands to couple aryl triflates or nonaflates. While pseudohalide substrates gave generally good yields and moderate enantioselectivity (50–94% ee), the use of aryl halides resulted in low conversion.
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A Zhan catalyst is a type of ruthenium-based organometallic complex used in olefin metathesis. This class of chemicals is named after the chemist who first synthesized them, Zheng-Yun J. Zhan. These catalysts are ruthenium complexes with functionally substituted alkoxybenzylidene carbene ligands, which can be chemically bonded to the surface of resins, PEG chains, and polymers. Like the structurally similar Hoveyda-Grubbs catalyst, they contain an isopropoxystyrene moiety, but include an extra electron-withdrawing sulfonamide group attached to the carbon para to the phenol oxygen.
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In 1925, Bayer became part of IG Farben, a German conglomerate formed from the merger of six chemical companies: BASF, Bayer, Hoechst (including Cassella and Chemische Fabrik Kalle), Agfa, Chemische Fabrik Griesheim-Elektron, and Chemische Fabrik vorm. Weiler Ter Meer. In the 1930s, Gerhard Domagk, director of Bayer's Institute of Pathology and Bacteriology, working with chemists Fritz Mietzsch and Joseph Klarer, discovered prontosil, the first commercially available antibacterial drug. The discovery and development of this first sulfonamide drug opened a new era in medicine.
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In organic chemistry, the term sulfamide may also refer to the functional group which consists of at least one organic group attached to a nitrogen atom of sulfamide. Symmetric sulfamides can be prepared directly from amines, sulfur dioxide gas and an oxidant: :Sulfonamide synthesis from aniline and sulfur dioxide In this example, the reactants are aniline, triethylamine, and iodine. Sulfur dioxide is believed to be activated through a series of intermediates: Et3N-I+-I−, Et3N-I+-I3− and Et3N+-SO2−. The sulfamide functional group is an increasingly common structural feature used in medicinal chemistry.
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Geiling, obviously unaware of spelling conventions with respect to Francis and Frances, presumed that Frances was a man and offered her the position, which she accepted, starting work in 1936. During Frances' second year, Geiling was retained by the FDA to research unusual deaths related to elixir sulfanilamide, a sulfonamide medicine. Kelsey assisted on this research project, which showed that the 107 deaths were caused by the use of diethylene glycol as a solvent. The next year, the United States Congress passed the Federal Food, Drug, and Cosmetic Act of 1938.
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These additions have been rendered enantioselective through the use of chiral auxiliaries (see above) and chiral catalysts. Although the enantioselectivity of the proline-catalyzed process is good, yields are low and reaction times are long. :File:EAScope2.png Upon treatment with sulfonyl azides, a variety of Grignard reagents or enolates may be converted into azides or amines. A significant side reaction that occurs under these conditions is the diazo transfer reaction: instead of fragmenting into an azide and sulfinic acid, the intermediate triazene salt may break down to a diazo compound and sulfonamide.
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The mechanism of the Eschenmoser fragmentation begins with the condensation of an α,β-epoxyketone (1) with an aryl sulfonylhydrazine (2) to afford the intermediate hydrazone (3). This hydrazone can either be protonated at the epoxide oxygen or deprotonated at the sulfonamide nitrogen to initiate the fragmentation, and thus the fragmentation is catalyzed by acids or bases. Most common reaction conditions, however, are treatment with acetic acid in dichloromethane. The proton transfer leads to intermediate (4), which undergoes the key fragmentation to alkyne (6) and the corresponding carbonyl compound (7).
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The drug combination sulfacetamide/sulfur is a topical acne medication manufactured by Medicis under the trade name Plexion and also available under other trade names such as Clenia, Prascion, and Avar. It combines sodium sulfacetamide, a sulfonamide antibiotic, and sulfur, a keratolytic agent. It is available in four formulations: as a cleansing cloth, cleanser, topical suspension, and as a facial mask. The sulfacetamide inhibits the growth of the bacterium Cutibacterium acnes that is associated with acne, while sulfur facilitates the removal of dead skin cells to prevent clogged pores.
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Among these changes are reducing the quinoline ring, replacing the chlorine with fluorine, inserting an ether linkage in between the two aromatic rings instead of the double bound and adding an amide group for the sulfur. Replacement of the quinoline by benzothiazole, dichlorothienopyridines or alkyl-substituted thiazoles is possible but none of these is superior. 288x288px Zafirlukast is an indole derivative that satisfies the pharmacophore need for an ionizable moiety with a sulfonamide group. Numerous analogues have been organized; nonetheless, everyone of them resulted in diminishing antagonistic activity.
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COX-1 is traditionally defined as a constitutively expressed "housekeeping" enzyme and plays a role in the protection of the gastrointestinal mucosa, kidney hemodynamics, and platelet thrombogenesis. COX-2, on the contrary, is extensively expressed in cells involved in inflammation and is upregulated by bacterial lipopolysaccharides, cytokines, growth factors, and tumor promoters. Celecoxib is approximately 10-20 times more selective for COX-2 inhibition over COX-1. It binds with its polar sulfonamide side chain to a hydrophilic side pocket region close to the active COX-2 binding site.
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University Hospital opened as Hôtel-Dieu (French for House of God) in 1859 and was operated by the Daughters of Charity. In 1913, it was the first hospital in the United States to have air conditioning in its surgical suites, and it was the site of milestone medical research that developed sulfonamide drug treatment for meningitis in the 1940s. The hospital developed a relationship with LSU Health Sciences Center in the 1970s and 1980s. It was purchased by the Louisiana State University System in 1991, renamed and converted into a teaching hospital for the adjacent medical school, which it also oversaw.
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Both YdaH and MtrF are bowl-shaped dimers with a solvent-filled basin extending from the cytoplasm halfway across the membrane bilayer. The protomers of YdaH and MtrF contain nine transmembrane helices and two hairpins which suggested a plausible pathway for substrate transport. A combination of the crystal structure, genetic analyses and substrate accumulation assays indicated that both YdaH and MtrF behave as exporters, capable of removing the folate metabolite p-aminobenzoic acid from bacterial cells. In fact, it was shown that both YdaH and MtrF participate as antibiotic efflux pumps, mediating bacterial resistance to sulfonamide antimetabolite drugs.
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Gebhardt served as Chief Surgeon of the Staff of the Reich during World War II, and under his direction the Hohenlychen Sanatorium became a military hospital for the Waffen-SS. On 27 May 1942, Himmler ordered Gebhardt dispatched to Prague in order to attend to Reinhard Heydrich, who was wounded by an anti-tank grenade during Operation Anthropoid earlier that day. Heydrich was SS-Obergruppenführer and General der Polizei, and the acting Reichsprotektor of the Protectorate of Bohemia and Moravia. When Heydrich developed a fever after surgery for his extensive wounds, Theodor Morell, personal physician to Adolf Hitler, suggested to Gebhardt that he should treat Heydrich with sulfonamide (an early antibiotic).
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M&B; 693 was one of the first generation of sulfonamide antibiotics. It was discovered by Lionel Whitby at the British firm May & Baker Ltd and logged in their Test Book on 2 November, 1937 under Code No M&B; 693\. During the aftermath to the disastrous convoy SC7, in October 1940, Surgeon-Lieutenant John Robertson, RN, of HMS Leith, saved the life of Commodore Lachlan MacKinnon, from the torpedoed Assyrian, who had developed pneumonia, by giving him M&B; 693, despite Robertson never having used it before and not knowing the required dosage. M&B; 693 was successfully used to treat Winston Churchill's bacterial pneumonia.
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The driving force for the reaction is the formation of highly stable molecular nitrogen. The reaction mechanism of the Eschenmoser fragmentation There is a radical variant of this α,β-enone to alkynone fragmentation in which no epoxide is required. 1,3-Dibromo-5,5-dimethylhydantoin (DBDMH) in sec-butanol with the appropriate p-tolylhydrazone has been used to prepare exaltone (cyclopentadecanone) and muscone (the 3-methyl structural analog). The α,β-unsaturated hydrazone is brominated by DBDMH in the allylic position (relative to the sulfonamide nitrogen), leading to a captodatively stabilized radical, and the bromide ion becomes the leaving group in the subsequent nucleophilic attack by an alcoholate ion.
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Sitaxentan is a small molecule that blocks the action of endothelin (ET) on the endothelin-A (ETA) receptor selectively (by a factor of 6000 compared with the ETB). It is a sulfonamide class endothelin receptor antagonist (ERA) and is undergoing Food and Drug Administration (FDA) review for treating pulmonary hypertension. The rationale for benefit compared with bosentan, a nonselective ET blocker, is negligible inhibition of the beneficial effects of ETB stimulation, such as nitric oxide production and clearance of ET from circulation. In clinical trials, the efficacy of sitaxentan has been much the same as bosentan, but the hepatotoxicity of sitaxentan outweighs its benefits.
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Domagk was appointed director of Bayer's Institute of Pathology and Bacteriology, where he continued the studies of Josef Klarer and Fritz Mietzsch, based on works by Paul Ehrlich, to use dyes, at that time a major product of IG Farben, as antibiotics. He found the sulfonamide Prontosil to be effective against streptococcus, and treated his own daughter with it, saving her the amputation of an arm. In 1939, Domagk received the Nobel Prize in Medicine for this discovery, the first drug effective against bacterial infections. He was forced by the Nazi regime to refuse the prize and was arrested by the Gestapo and detained for a week.
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Formation of the active catalyst is achieved by treatment of the bis(sulfonamide) with trimethylaluminum; recovery of the ligand was essentially quantitative. The proposed tetracoordinate aluminum prevent the imide acting as a chelating Lewis base, while enhance the α-vinyl proton of the dienophile and the benzylic proton of the catalyst. 350px The X-ray structure of the catalyst showed a stereodefined environment.Coery, EJ; Sarshar, S; Bordner, J, 1992, J Am Chem Soc, 114, 7938 150px In 1993, Wulff and coworkers found a complex derived from diethylaluminium chloride and a “vaulted” biaryl ligand below catalyzed the enantioselective Diels-Alder reaction between cyclopentadiene and methacrolein.
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Hata was nominated for the Nobel Prize in Chemistry in 1911 and for the Nobel Prize in Physiology or Medicine in 1912 and 1913. The first sulfonamide and the first systemically active antibacterial drug, Prontosil, was developed by a research team led by Gerhard Domagk in 1932 or 1933 at the Bayer Laboratories of the IG Farben conglomerate in Germany, for which Domagk received the 1939 Nobel Prize in Physiology or Medicine. Sulfanilamide, the active drug of Prontosil, was not patentable as it had already been in use in the dye industry for some years. Prontosil had a relatively broad effect against Gram-positive cocci, but not against enterobacteria.
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DuP-697 was a building-block for synthesis of COX-2 inhibitors and served as the basic chemical model for the coxibs that are the only selective COX-2 inhibitors on the market today. DuP-697 is a diaryl heterocycle with cis-stilbene moiety. Structure activity relationship (SAR) studies for diaryl heterocyclic compounds have indicated that a cis- stilbene moiety and changes in the para-position of one of the aryl rings play an important role in COX-2 selectivity. Celecoxib and parecoxib have a sulfonamide substituent (SO2NH2) in para-position on one of the aryl rings while etoricoxib and rofecoxib have a methylsulfone (SO2CH3).
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Among those delayed was the defending champion Cadel Evans, who suffered three punctures on the climb and had lost around two minutes before Wiggins called a truce in the main field, allowing the breakaway to finish the stage over eighteen minutes clear of the pack. Following the raid of the team hotel during the first rest day, the second rest day was marked by a positive drugs test by rider Fränk Schleck, the third-placed rider from the 2011 race. Schleck quit the race after traces of xipamide, a banned sulfonamide diuretic drug, were found in the A-sample of his urine, and was later confirmed by the B-sample.
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Arsphenamine was prepared as part of a campaign to synthesize a series of such compounds and found to exhibit partially selective toxicity. Arsphenamine proved to be the first effective treatment for syphilis, a disease which prior to that time was incurable and led inexorably to severe skin ulceration, neurological damage, and death. Ehrlich's approach of systematically varying the chemical structure of synthetic compounds and measuring the effects of these changes on biological activity was pursued broadly by industrial scientists, including Bayer scientists Josef Klarer, Fritz Mietzsch, and Gerhard Domagk. This work, also based in the testing of compounds available from the German dye industry, led to the development of Prontosil, the first representative of the sulfonamide class of antibiotics.
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Sulfanilamide was cheap to produce and (due to the early date of its original composition of matter patent which made no reference to a medical use) was already off-patent when its antibacterial properties were first made public. Since the sulfanilamide moiety was also easy to link into other molecules, chemists soon gave rise to hundreds of second-generation sulfonamide drugs. As a result, Prontosil failed to make the profits in the marketplace hoped for by Bayer. Although quickly eclipsed by these newer "sulfa drugs" and, in the mid-1940s and through the 1950s by penicillin and other antibacterials that proved more effective against more types of bacteria, Prontosil remained on the market until the 1960s.
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Studies on the binding mechanism of selective COX-2 inhibitors show that they have two reversible steps with both COX-1 and COX-2, but the selectivity for COX-2 is due to another step that is slow and irreversible and is seen only in the inhibition of COX-2, not COX-1. The irreversible step has been attributed to the presence of the sulfonamide (or sulfone) that fits into the side-pocket of COX-2. This has been studied using SC-58125 (an analogue of celecoxib) and mutated COX-2, wherein the valine 523 residue was replaced by isoleucine 523. The irreversible inhibition did not happen, but reversible inhibition was noticed.
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The enzyme GSNO reductase (GSNOR) reduces S-nitrosoglutathione (GSNO) to an unstable intermediate, S-hydroxylaminoglutathione, which then rearranges to form glutathione sulfonamide, or in the presence of GSH, forms oxidized glutathione (GSSG) and hydroxylamine. Through this catabolic process, GSNOR regulates the cellular concentrations of GSNO and plays a central role in regulating the levels of endogenous S-nitrosothiols and controlling protein S-nitrosylation-based signaling. 500px The generation of GSNO can serve as a stable and mobile NO pool which can effectively transduce NO signaling. Unlike other low molecular weight messengers that bind to and activate target cellular receptors, NO signaling is mediated by a coordinating complex between NO and transition metals or target cellular proteins, often via S-nitrosylation of cysteine residues.
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1,5 -Hydrogen abstraction/iodination of the o-methyl group is repeated three times and is most likely followed by cyclization to diiodo intermediate 76, which then undergoes hydrolysis. center A very interesting transformation is observed when sulfonamides of primary amides bearing an aromatic ring at the γ-position are treated with various iodanes and iodine under the irradiation with a tungsten lamp. The reaction leads to 1,2,3,4-tetrahydroquinoline derivatives and is a good preparative method of six-membered cyclic aromatic amines. For instance, sulfonamide 78 undergoes an intramolecular radical cyclization to afford 79 in relatively good yield. center By the same procedure, 3,4-dihydro-2,1-benzothiazine-2,2-dioxides 81 are obtained from the N-alkyl 2-(aryl)ethanesulfonamides via the sulfonamidyl radical.
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Triptan structures were designed from the structure of 5-HT to attain affinity to 5-HT receptors, hence the identical indole structure. The hydroxyl group (-OH) on the hexane of the indole core and the alkyl-amine side chain on position C3 on 5-HT have been replaced with other compounds, such as sulfonamides or azol-ring structured derivatives and different amine-alkyl side chains. An electro-negative group can form a hydrogen bond with Thr in the pocket of the receptor. Sulfonamide derivatives attached to the hexane ring of the indole structure have electro-negative properties, as well as the triazole and 2-oxazolidone on rizatriptan and zolmitriptan respectively. This can increase binding ability of the compound and the efficacy, especially with the 5-HT1D receptor.
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An obvious reaction is their tendency to hydrolyse to the corresponding sulfonic acid: :C6H5SO2Cl + H2O → C6H5SO3H + HCl These compounds react readily with nucleophiles other than water, like alcohols and amines (see Hinsberg reaction). If the nucleophile is an alcohol the product is a sulfonate ester, if it is an amine the product is a sulfonamide. Using sodium sulfite as the nucleophilic reagent, sulfonyl chlorides convert to the sulfinate salts, such as C6H5SO2Na. Chlorosulfonated alkanes are susceptible to crosslinking via reactions with various nucleophiles. Sulfonyl chlorides readily undergo Friedel–Crafts reactions with arenes giving sulfones, for example: :RSO2Cl + C6H6 → RSO2C6H5 \+ HCl The desulfonation of arylsulfonyl chlorides provides a route to aryl chlorides: :ArSO2Cl → ArCl + SO2 1,2,4-Trichlorobenzene is made industrially in this way.
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Prior to enlisting in the Second World War, he gave testimony as an expert medical witness in court martial trials. Ray Fletcher Farquharson during the Second World War On 25 August 1943, Farquharson enlisted in the Royal Canadian Air Force (RCAF) and was assigned to No. 1 Air Command, based in Trenton, Ontario. He was posted to the United Kingdom in 1944 and briefly returned to No. 1 Air Command before being released from service on 22 November 1945 with the rank of wing commander. During the war, he chaired the Penicillin Committee of Canada, which regulated the distribution of penicillin (an antibiotic that largely replaced the sulfonamide used earlier in the war) to the armed forces, and was a consultant to the RCAF's Director of Medical Services.
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During the race's first rest day, the team hotel of the squad, in Bourg-en-Bresse, was searched by French police and gendarmerie. One of the team's riders in the Tour, Rémy Di Gregorio, was arrested in relation to an ongoing anti-doping case, and was immediately suspended by the French team, although the case had been open since 2011, when Di Gregorio was a member of the team. The second rest day was marked by a positive drugs test by Fränk Schleck, the third- placed rider from the 2011 Tour. Schleck was withdrawn from the race by his team after traces of xipamide, a banned sulfonamide diuretic drug, were found in the A-sample of his urine; the presence of xipamide was later confirmed by the B-sample.
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H-89 is a protein kinase inhibitor with greatest effect on protein kinase A (PKA). H-89, derived from H-8 (N-[2-(methylamino)ethyl]-5-isoquinoline- sulfonamide), was initially believed to act specifically as an inhibitor of PKA, being 30 times more potent than H-8 at inhibiting PKA and 10 times less potent at inhibiting protein kinase G. It achieves this through competitive inhibition of the adenosine triphosphate (ATP) site on the PKA catalytic subunit. However, subsequent work has suggested a variety of additional effects such as inhibition of other protein kinases (IC50 values of 80, 120, 135, 270, 2600 and 2800 nM for S6K1, MSK1, PKA, ROCKII, PKBα and MAPKAP-K1b respectively), and direct inhibition of various potassium currents. In addition to its use in studying mechanisms of cell signalling, H-89 has also been used experimentally in vivo.
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He worked on the study, analysis and evaluation of definitive treatment for surgical diseases. In Venezuela he did a series of interventions including pasacro nerve resection in the treatment of pelvic neuralgia, resection of the rectum with contra natura permanent anum, (1932), ovarian homografts (1936), the new technique of lymphatic blockade in infectious processes, carried out with electrosurgery linked with sulfonamide therapy (1938), the radical cure of rectal prolapse with fascia lata (aponeurosis of the thigh) ligation of the femoral artery by gangrene and embolectomy by phlebitis. He also contributed to improving the treatment of Banti syndrome (abnormal growth of the spleen) and portal hypertension (usually caused by liver cirrhosis). Active in the Caracas Polyclinic, the José María Vargas Hospital and the University Hospital, Perez-Carreño was head of descriptive practical anatomy procedures, Head of surgical medicine, Chief of Clinical Surgery and Dean of the Faculty of Medicine, among other duties.
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There McCarty developed a special interest in infectious diseases — in particular, antibacterial sulfonamide drug treatments that were just entering medicine — which he subsequently pursued by moving to New York University to work with William Tillett. A National Research Council Fellowship in the medical sciences and an opening in Oswald T. Avery's laboratory spurred his move to Rockefeller University in 1941. At that time, research in the Avery laboratory was focused on the pneumococcal transformation, the heritable alteration of a pneumococcal strain from a nonvirulent rough form to a virulent smooth encapsulated form. McCarty's arrival at the Rockefeller Institute in September 1941 marked 13 years since this discovery, also known as the Griffith phenomenon. Prior to this discovery, the 1920s had been marked by a medley of disparate observations on Streptococcus pneumoniae that seemed to involve an exchange of receptors among diverse bacteria either grown together in liquid media or exposed to various kinds of extracts and supernatants.
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