Sulfanilamide

Sulfanilamide
Clinical data
AHFS/Drugs.comsalonemide Consumer Drug Information
ATC code
Identifiers
  • 4-aminobenzenesulfonamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.000.513 Edit this at Wikidata
Chemical and physical data
FormulaC6H8N2O2S
Molar mass172.20 g·mol−1
3D model (JSmol)
Density1.08 g/cm3
Melting point165 °C (329 °F)
  • O=S(=O)(c1ccc(N)cc1)N
  • InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10) checkY
  • Key:FDDDEECHVMSUSB-UHFFFAOYSA-N checkY
  (verify)

Sulfanilamide (also spelled sulphanilamide) is a sulfonamide antibacterial drug. Chemically, it is an organic compound consisting of an aniline derivatized with a sulfonamide group.[1] 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.[2][3] 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.[4][5][6][7]

The term "sulfanilamides" is also sometimes used to describe a family of molecules containing these functional groups. Examples include:

  1. ^ Actor P, Chow AW, Dutko FJ, McKinlay MA. "Chemotherapeutics". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_173. ISBN 978-3527306732.
  2. ^ Steinert D (2000). "The Use of Sulfanilamide in World War II". The History of WWII Medicine. Archived from the original on 7 June 2016.
  3. ^ "Class 9 Items: Drugs, Chemicals and Biological Stains Sulfa Drugs". Library of Congress Web Archives. Archived from the original on 4 December 2013. Retrieved 13 June 2014.
  4. ^ "Sulfanilamide". PubChem. National Center for Biotechnology Information (NCBI), U.S. National Library of Medicine.
  5. ^ Scholar E (1 January 2007). "Sulfanilamide". In Enna SJ, Bylund DB (eds.). xPharm: The Comprehensive Pharmacology Reference. New York: Elsevier. pp. 1–5. doi:10.1016/b978-008055232-3.62694-7. ISBN 978-0-08-055232-3. Retrieved 2 October 2021.
  6. ^ "US FDA Label: AVC (sulfanilamide) Vaginal Cream 15%" (PDF). United States Food & Drug Administration. Retrieved 3 October 2021.
  7. ^ "Drugs@FDA: FDA-Approved Drugs". www.accessdata.fda.gov. Retrieved 2 October 2021.