Sulphanilamide

Sulfanilamide

Clinical data
AHFS/Drugs.com	Consumer Drug Information
ATC code	J01EB06 (WHO) D06BA05 (WHO) QJ01EQ06 (WHO)
Identifiers
IUPAC name 4-aminobenzenesulfonamide
CAS Number	63-74-1 Y
PubChem CID	5333
DrugBank	DB00259 Y
ChemSpider	5142 Y
UNII	21240MF57M
KEGG	D08543 Y
ChEBI	CHEBI:45373 Y
ChEMBL	CHEMBL21 Y
NIAID ChemDB	019103
ECHA InfoCard	100.000.513
Chemical and physical data
Formula	C6H8N2O2S
Molar mass	172.20 g/mol
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) Y Key:FDDDEECHVMSUSB-UHFFFAOYSA-N Y

Sulfanilamide (also spelled sulphanilamide) is a sulfonamide antibacterial. 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. Modern antibiotics have supplanted sulfanilamide on the battlefield; however, sulfanilamide remains in use for treatment of vaginal yeast infections.

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

As a sulfonamide antibiotic, sulfanilamide functions by competitively inhibiting (i.e., 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.

Sulfanilamide was first prepared in 1908 by the Austrian chemist Paul Josef Jakob Gelmo (1879–1961) as part of his dissertation for a doctoral degree from the Technische Hochsschule of Vienna, Austria. It was patented in 1909.

Gerhard Domagk, who directed the testing of the prodrug Prontosil in 1935, and Jacques and Thérèse Tréfouël, who along with Federico Nitti and Daniel Bovet in the laboratory of Ernest Fourneau at the Pasteur Institute, determined sulfanilamide as the active form, are generally credited with the discovery of sulfanilamide as a chemotherapeutic agent. Domagk was awarded the Nobel Prize for his work.

In 1937 Elixir sulfanilamide, a product formulation with diethylene glycol, poisoned and killed more than 100 people as a result of acute kidney failure, urging new US regulation for drug testing. In 1938, the Food, Drug and Cosmetic Act was passed.