Sulfanilamide

Sulfanilamide

Systematic (IUPAC) name
4-aminobenzenesulfonamide
Clinical data
AHFS/Drugs.com	Consumer Drug Information
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	63-74-1 Y
ATC code	J01EB06 D06BA05 QJ01EQ06
PubChem	CID 5333
DrugBank	APRD00438
ChemSpider	5142 Y
UNII	21240MF57M Y
KEGG	D08543 Y
ChEBI	CHEBI:45373 N
ChEMBL	CHEMBL21 Y
Chemical data
Formula	C6H8N2O2S
Mol. mass	172.20 g/mol
SMILES	eMolecules & PubChem
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
Physical data
Density	1.08 g/cm³
Melt. point	165 °C (329 °F)
N(what is this?)  (verify)

Sulfanilamide (also spelled sulphanilamide) is a sulfonamide antibacterial. Chemically, it is a molecule containing the sulfonamide functional group attached to an aniline. As a sulfonamide antibiotic, it functions by competitively inhibiting (i.e., by acting as a substrate analogue) enzymatic reactions involving para-aminobenzoic acid (PABA).^[1] PABA is needed in enzymatic reactions that produce folic acid which acts as a coenzyme in the synthesis of purine, pyrimidine and other amino acids.

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

• Furosemide, a loop diuretic
• Sulfadiazine, an antibiotic
• Sulfamethoxazole, an antibiotic

Gerhard Domagk, who directed the testing of the prodrug Prontosil in 1935,^[2] and Jacques and Thérèse Tréfouël, who along with Federico Nitti and Daniel Bovet in the laboratory of Ernest Fourneau at the Pasteur Institute, discovered the active component, 4-aminobenzenesulfonamide,^[3] are generally credited with the discovery of sulfanilamide as a chemotherapeutic agent. Domagk was awarded the Nobel Prize for his work.^[4]

See also

• Sulfonamide (medicine)
• Nazi human experimentation -- Sulfonamide experiments
• Elixir sulfanilamide

External links

• MeSH Sulfanilamides

References

1. ^ Michael Kent, Advanced Biology, Oxford University Press, 2000, p. 46 ISBN 9780199141951
2. ^ G. Domagk, "Ein Beitrag zur Chemotherapie der bakteriellen Infektionen", Deutsche Medizinische Wochenschrift, 61, feb. 15, 1935, p. 250.
3. ^ J. et T. Tréfouël, F. Nitti and D. Bovet, "Activité du p-aminophénylsulfamide sur l’infection streptococcique expérimentale de la souris et du lapin", C. R. Soc. Biol., 120, nov. 23, 1935, p. 756.
4. ^ (French) Daniel Bovet, "Les étapes de la découverte de la sulfamidochrysoïdine dans les laboratoires de recherche de la firme Bayer à Wuppertal-Elberfeld (1927-1932)", in Une chimie qui guérit : Histoire de la découverte des sulfamides, Coll. "Médecine et Société", Payot, Paris, 1988, p. 307.