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Sulfonamide
chemical compound
WRITTEN BY:
• The Editors of Encyclopaedia Britannica
See Article History
Alternative Title: sulphonamide
Sulfonamide, also spelled Sulphonamide, any member of a class of chemical compounds, the amides of sulfonic acids. The class includes several groups of drugs used in the treatment of bacterial infections, diabetes mellitus, edema, hypertension, and gout.

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history of medicine: Sulfonamide drugs
In 1932 German bacteriologist Gerhard Domagk announced that the red dye Prontosil is active against streptococcal infections in mice and humans. Soon afterward French workers showed that its active antibacterial agent is sulfanilamide. In 1936 English physician

The bacteriostatic sulfonamide drugs, often called sulfa drugs, include sulfanilamide and numerous compounds closely related to it. Other groups of sulfonamide drugs have been developed by exploiting observations made during clinical evaluation of sulfanilamide derivatives. Examples of these drugs are probenecid (q.v.), introduced as an agent for intensifying the action of penicillin but now principally used in treating gout; acetazolamide and furosemide, which are diuretics; and tolbutamide (q.v.), a hypoglycemic. Chlorothiazide and hydrochlorothiazide are effective both as diuretics and in reducing blood pressure.
Sulfonamides are oily liquids or crystalline solids that are almost always prepared by the reaction of a sulfonyl chloride with ammonia or an amine, most commonly in the presence of caustic alkali.
The first sulfonamide drug, introduced in 1932, was a red azo dye called Prontosil (q.v.). As new sulfonamides were synthesized, more effective and less toxic agents were discovered. Some, which are not absorbed, can be administered orally to treat specific localized infections in the gastrointestinal tract. Others are absorbed slowly or excreted slowly and therefore are longer acting.
All the sulfonamides are capable of causing drug intoxication (poisoning), and some patients are hypersensitive to them. The commonest side effects are nausea, vomiting, and mental confusion. The signs of hypersensitivity are fever and skin eruptions. Signs of intoxication include anemia, which results from destruction of red blood cells, and leukopenia, which results from the destruction of white blood cells. Irritation of the kidneys and obstruction of the free flow of urine are undesirable reactions that can be prevented.
Learn More in these related Britannica articles:

history of medicine: Sulfonamide drugs
In 1932 German bacteriologist Gerhard Domagk announced that the red dye Prontosil is active against streptococcal infections in mice and humans. Soon afterward French workers showed that its active antibacterial agent is sulfanilamide. In 1936 English physician…

pharmaceutical industry: Early efforts in the development of anti-infective drugs
…certain azo dyes, which contained sulfonamide groups, were effective in treating streptococcal infections in mice. One of the dyes, known as Prontosil, was later found to be metabolized in the patient to sulfanilamide, which was the active antibacterial molecule. In 1933 Prontosil was given to the first patient, an infant…

carboxylic acid: Related compounds
Sulfonamides are amides of sulfonic acids; for example,…

organosulfur compound: Other sulfinyl and sulfonyl compounds
…with amino compounds, R′NH2, gives sulfonamides and related compounds, RSO2NHR′, whereas reaction of alcohols in the presence of tertiary amines yields sulfonates, RSO2OR′.…

disease: Treatment
…administration of drugs such as sulfonamides or antibiotics. While some of these substances kill the microorganisms, others do not and instead inhibit proliferation of the microorganism and give host defenses an opportunity to function effectively. For other infectious diseases there is no specific therapy. There are, for example, very few…

More About Sulfonamide
6 references found in Britannica articles
Assorted References
• carboxylic acids
o In carboxylic acid: Related compounds
• medical applications
o In history of medicine: Sulfonamide drugs
• organosulfur compounds
o In organosulfur compound: Other sulfinyl and sulfonyl compounds
use in
• pharmaceuticals
o In pharmaceutical industry: Early efforts in the development of anti-infective drugs
• therapeutics
o In disease: Treatment
• treatment of chancroid
o In chancroid
Article History
Article Contributors
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Sulfonamide
CHEMICAL COMPOUND
related topics
• Sulfanilamide
• Sulfa drug
• Organosulfur compound
• Amide
SIMILAR TOPICS
• Acrylamide
• Sulfonic acid
• Urea
• Thiol
• Polysulfide
• Polyamide
• Biotin
• Sulfoxide
• Thiourea
• Xanthate
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Sulfonamide
chemical compound

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