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sulfanilamide
Sign in to saveAlso known as AVC, 4-Azanylbenzenesulfonamide, SA, Prontosil album, P-Aminobenzenesulfamide, P-Aminobenzenesulfonamide, Sulfamine, Sulphanilamide
Sulfanilamide (also spelled sulphanilamide) is a sulfonamide antibacterial drug. Chemically, it is an organic compound consisting of an aniline derivatized with a sulfonamide group. Powdered sulfanilamide was used by the Allies in World War II to reduce infection rates and contributed to a dramatic reduction in mortality rates compared to previous wars. Sulfanilamide is rarely if ever used systemically due to toxicity and because more effective sulfonamides are available for this purpose. Modern antibiotics have supplanted sulfanilamide on the battlefield; however, sulfanilamide remains in use
Chemical data
- Formula
- C6H8N2O2S
- Molecular weight
- 172.21 g/mol
- IUPAC name
- 4-aminobenzenesulfonimidic acid
- SMILES
- C1=CC(=CC=C1N)S(=N)(=O)O
- InChIKey
- FDDDEECHVMSUSB-UHFFFAOYSA-N
- XLogP
- 0.7
- Polar surface area
- 95.6 Ų
- H-bond donors
- 3
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
47,626 papers- Idiosyncrasy to sulfanilamide.Journal of the American Dental Association (1939) · 1946
- Surfactant effect on the dissolution of sulfanilamide granules.Journal of pharmaceutical sciences · 1985
- [Sulfanilamide therapy of gonorrhea in women].Akusherstvo i ginekologiia · 1947
- Postextraction bacteriemia prevented by sulfanilamide.Dental survey · 1945
- Sulfanilamide in the treatment of leprosy. 1942.Public health reports (Washington, D.C. : 1974) · 2006
via PubMed
~4 min read
Encyclopedic overview
8 sectionsContents
- Mechanism of action
- History
- Chemical and physical properties
- Contraindications
- Adverse effects
- Pharmacokinetics
- External links
- References
Sulfanilamide (also spelled sulphanilamide) is a sulfonamide antibacterial drug. Chemically, it is an organic compound consisting of an aniline derivatized with a sulfonamide group. Powdered sulfanilamide was used by the Allies in World War II to reduce infection rates and contributed to a dramatic reduction in mortality rates compared to previous wars. Sulfanilamide is rarely if ever used systemically due to toxicity and because more effective sulfonamides are available for this purpose. Modern antibiotics have supplanted sulfanilamide on the battlefield; however, sulfanilamide remains in use today in the form of topical preparations, primarily for treatment of vaginal yeast infections such as vulvovaginitis caused by Candida albicans.
The term "sulfanilamides" is also sometimes used to describe a family of molecules containing these functional groups. Examples include: Furosemide, a loop diuretic Sulfadiazine, an antibiotic Sulfamethoxazole, an antibiotic
Excerpted from Wikipedia’s “sulfanilamide” article, available under the CC BY-SA 4.0 licence.