Sulfanilamide

Sulfanilamide
Systematic (IUPAC) name
4-aminobenzenesulfonamide
Clinical data
AHFS/Drugs.com Consumer Drug Information
Identifiers
CAS Number 63-74-1 YesY
ATC code J01EB06 (WHO) D06BA05 QJ01EQ06
PubChem CID 5333
DrugBank DB00259 YesY
ChemSpider 5142 YesY
UNII 21240MF57M YesY
KEGG D08543 YesY
ChEBI CHEBI:45373 YesY
ChEMBL CHEMBL21 YesY
NIAID ChemDB 019103
Chemical data
Formula C6H8N2O2S
Molar mass 172.20 g/mol
Physical data
Density 1.08 g/cm3
Melting point 165 °C (329 °F)
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Sulfanilamide (also spelled sulphanilamide) is a sulfonamide antibacterial. Chemically, it is an organic compound consisting of an aniline derivatized with a sulfonamide group.[1] Powdered sulfanilamide was used by the Allies in WWII to reduce infection rates and contributed to a dramatic reduction in mortality rates compared to previous wars.[2][3] Modern antibiotics have supplanted sulfanilamide on the battlefield; however, sulfanilamide remains in use for treatment of vaginal yeast infections.[4]

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

Mechanism of action

As a sulfonamide antibiotic, sulfanilamide functions by competitively inhibiting (i.e., by acting as a substrate analogue) enzymatic reactions involving para-aminobenzoic acid (PABA).[5] 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.

History

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.[6] It was patented in 1909.[7]

Gerhard Domagk, who directed the testing of the prodrug Prontosil in 1935,[8] 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,[9] are generally credited with the discovery of sulfanilamide as a chemotherapeutic agent. Domagk was awarded the Nobel Prize for his work.[10]

See also

External links

References

  1. ↑ Actor, P.; Chow, A. W.; Dutko, F. J.; McKinlay, M. A. (2005), "Chemotherapeutics", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a06_173
  2. ↑ http://www.mtaofnj.org/content/WWII%20Combat%20Medic%20-%20Dave%20Steinert/wwii.htm#The%20Use%20of%20Sulfanilamide%20in%20World%20War%20II
  3. ↑ http://www.med-dept.com/sulfa.php
  4. ↑ http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5333
  5. ↑ Michael Kent, Advanced Biology, Oxford University Press, 2000, p. 46 ISBN 978-0-19-914195-1
  6. ↑ Paul Gelmo (May 14, 1908) "Über Sulfamide der p-Amidobenzolsulfonsäure," Journal für Praktische Chemie, 77 : 369-382.
  7. ↑ On May 18, 1909, Deutsches Reich Patentschrift number 226,239 for sulfanilamide was awarded to Heinrich Hörlein of the Bayer corporation.
  8. ↑ G. Domagk, "Ein Beitrag zur Chemotherapie der bakteriellen Infektionen", Deutsche Medizinische Wochenschrift, 61, feb. 15, 1935, p. 250.
  9. ↑ 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.
  10. ↑ (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.
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