Sulfanilamide

Sulfanilamide
Clinical data
AHFS/Drugs.com	salonemide Consumer Drug Information
ATC code	J01EB06 (WHO) D06BA05 (WHO) QJ01EQ06 (WHO);
Identifiers
	IUPAC name 4-aminobenzenesulfonamide;
CAS Number	63-74-1 ;
PubChem CID	5333;
DrugBank	DB00259 ;
ChemSpider	5142 ;
UNII	21240MF57M;
KEGG	D08543 ;
ChEBI	CHEBI:45373 ;
ChEMBL	ChEMBL21 ;
NIAID ChemDB	019103;
CompTox Dashboard (EPA)	DTXSID4023622 ;
ECHA InfoCard	100.000.513
Chemical and physical data
Formula	C6H8N2O2S
Molar mass	172.20 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.08 g/cm3
Melting point	165 °C (329 °F)
	SMILES O=S(=O)(c1ccc(N)cc1)N;
	InChI InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10) ; Key:FDDDEECHVMSUSB-UHFFFAOYSA-N ;
	(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:

^ 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 978-3-527-30673-2.
^ Steinert D (2000). "The Use of Sulfanilamide in World War II". The History of WWII Medicine. Archived from the original on 7 June 2016.
^ "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.
^ "Sulfanilamide". PubChem. National Center for Biotechnology Information (NCBI), U.S. National Library of Medicine.
^ 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.
^ "US FDA Label: AVC (sulfanilamide) Vaginal Cream 15%" (PDF). United States Food & Drug Administration. Archived from the original (PDF) on 16 February 2017. Retrieved 3 October 2021.
^ "Drugs@FDA: FDA-Approved Drugs". www.accessdata.fda.gov. Archived from the original on 30 January 2017. Retrieved 2 October 2021.

[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 978-3-527-30673-2.

[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.

[:0-5] 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. Archived from the original (PDF) on 16 February 2017. Retrieved 3 October 2021.

[7] "Drugs@FDA: FDA-Approved Drugs". www.accessdata.fda.gov. Archived from the original on 30 January 2017. Retrieved 2 October 2021.

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