Sulfanilamide

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Sulfanilamide
Sulfanilamide-skeletal.svg
Sulfanilamida-3D.png
Clinical data
AHFS/Drugs.com Consumer Drug Information
ATC code
Identifiers
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)
  (verify)

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 World War II 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 (that is, by acting as a substrate analogue) enzymatic reactions involving para-aminobenzoic acid (PABA).[5][6] 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 the Austrian chemist Paul Josef Jakob Gelmo (1879–1961)[7] as part of his dissertation for a doctoral degree from the Technische Hochschule of Vienna.[8] It was patented in 1909.[9]

Gerhard Domagk, who directed the testing of the prodrug Prontosil in 1935,[10] 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,[11] are generally credited with the discovery of sulfanilamide as a chemotherapeutic agent. Domagk was awarded the Nobel Prize for his work.[12]

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.

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 Archived 2016-06-07 at the Wayback Machine.
  3. ^ "Archived copy". Archived from the original on 2013-12-04. Retrieved 2014-06-13. 
  4. ^ Pubchem. "Sulfanilamide". pubchem.ncbi.nlm.nih.gov. 
  5. ^ Castelli, Laura A.; Nguyen, Nga P.; Macreadie, Ian G. (2001-05-01). "Sulfa drug screening in yeast: fifteen sulfa drugs compete with p-aminobenzoate in Saccharomyces cerevisiae". FEMS Microbiology Letters. 199 (2): 181–184. doi:10.1111/j.1574-6968.2001.tb10671.x. ISSN 0378-1097. 
  6. ^ Kent, Michael (2000). Advanced Biology. Oxford University Press. p. 46. ISBN 978-0-19-914195-1. 
  7. ^ "Paul Gelmo". Encyclopedia.com. 
  8. ^ Gelmo, Paul (May 14, 1908). "Über Sulfamide der p-Amidobenzolsulfonsäure". Journal für Praktische Chemie. 77: 369–382. 
  9. ^ On May 18, 1909, Deutsches Reich Patentschrift number 226,239 for sulfanilamide was awarded to Heinrich Hörlein of the Bayer corporation.
  10. ^ Domagk, G. (February 15, 1935). "Ein Beitrag zur Chemotherapie der bakteriellen Infektionen". Deutsche Medizinische Wochenschrift. 61: 250. 
  11. ^ Tréfouël, J.; Tréfouël, T.; Nitti, F.; Bovet, D. (November 23, 1935). "Activité du p-aminophénylsulfamide sur l'infection streptococcique expérimentale de la souris et du lapin". C. R. Soc. Biol. 120: 756. 
  12. ^ Bovet, Daniel (1988). "Les étapes de la découverte de la sulfamidochrysoïdine dans les laboratoires de recherche de la firme Bayer à Wuppertal-Elberfeld (1927–1932)". Une chimie qui guérit : Histoire de la découverte des sulfamides. Médecine et Société (in French). Paris: Payot. p. 307. 
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