Sulfanilamide
 | |
|---|---|
| Systematic (IUPAC) name | |
| 4-aminobenzenesulfonamide | |
| Clinical data | |
| AHFS/Drugs.com | Consumer Drug Information |
| Legal status | ? |
| Identifiers | |
| CAS number | 63-74-1  |
| ATC code | J01EB06 D06BA05 QJ01EQ06 |
| PubChem | CID 5333 |
| DrugBank | DB00259 |
| ChemSpider | 5142 |
| UNII | 21240MF57M |
| KEGG | D08543 |
| ChEBI | CHEBI:45373 |
| ChEMBL | CHEMBL21 |
| NIAID ChemDB | 019103 |
| Chemical data | |
| Formula | C6H8N2O2S |
| Mol. mass | 172.20 g/mol |
| SMILES
| |
| |
| Physical data | |
| Density | 1.08 g/cm³ |
| Melt. point | 165 °C (329 °F) |
| (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
Sulfanilamide was first prepared in 1908 by Paul Gelmo as part of his dissertation for a doctoral degree from the Technische Hochsschule of Vienna, Austria.[2] It was patented in 1909.[3]
Gerhard Domagk, who directed the testing of the prodrug Prontosil in 1935,[4] 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,[5] are generally credited with the discovery of sulfanilamide as a chemotherapeutic agent. Domagk was awarded the Nobel Prize for his work.[6]
See also
- Sulfonamide (medicine)
- Nazi human experimentation -- Sulfonamide experiments
- Elixir sulfanilamide
External links
- Sulfanilamides at the US National Library of Medicine Medical Subject Headings (MeSH)
References
- ↑ Michael Kent, Advanced Biology, Oxford University Press, 2000, p. 46 ISBN 978-0-19-914195-1
- ↑ Paul Gelmo (May 14, 1908) "Über Sulfamide der p-Amidobenzolsulfonsäure," Journal für Praktische Chemie, 77 : 369-382.
- ↑ On May 18, 1909, Deutsches Reich Patentschrift number 226,239 for sulfanilamide was awarded to Heinrich Hörlein of the Bayer corporation.
- ↑ G. Domagk, "Ein Beitrag zur Chemotherapie der bakteriellen Infektionen", Deutsche Medizinische Wochenschrift, 61, feb. 15, 1935, p. 250.
- ↑ 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.
- ↑ (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.
| ||||||||||||||||||||||||||
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||