Sulfanilamide

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Sulfanilamide
Sulfanilamide-skeletal.svg
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Clinical data
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ATC code
Identifiers
CAS Number
PubChem CID
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ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
ECHA InfoCard 100.000.513
Chemical and physical data
Formula C6H8N2O2S
Molar mass 172.20 g/mol
3D model (JSmol)
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 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[edit]

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[edit]

Sulfanilamide was first prepared in 1908 by the Austrian chemist Paul Josef Jakob Gelmo (1879–1961)[6] as part of his dissertation for a doctoral degree from the Technische Hochsschule of Vienna, Austria.[7] It was patented in 1909.[8]

Gerhard Domagk, who directed the testing of the prodrug Prontosil in 1935,[9] 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,[10] are generally credited with the discovery of sulfanilamide as a chemotherapeutic agent. Domagk was awarded the Nobel Prize for his work.[11]

In 1937 Elixir sulfanilamide, a product formulation with diethylene glycol, caused death poisoning of more than 100 people, thus urging new US regulation for drug testing.

See also[edit]

External links[edit]

References[edit]

  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. ^ https://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. ^ Biography of Paul Gelmo: Encyclopedia.com.
  7. ^ Paul Gelmo (May 14, 1908) "Über Sulfamide der p-Amidobenzolsulfonsäure," Journal für Praktische Chemie, 77 : 369-382.
  8. ^ On May 18, 1909, Deutsches Reich Patentschrift number 226,239 for sulfanilamide was awarded to Heinrich Hörlein of the Bayer corporation.
  9. ^ G. Domagk, "Ein Beitrag zur Chemotherapie der bakteriellen Infektionen", Deutsche Medizinische Wochenschrift, 61, feb. 15, 1935, p. 250.
  10. ^ 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.
  11. ^ (in 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.