Sulfanilamide

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Sulfanilamide
Clinical data
AHFS/Drugs.comsalonemide Consumer Drug Information
ATC code
Identifiers
  • 4-aminobenzenesulfonamide
JSmol)
Density1.08 g/cm3
Melting point165 °C (329 °F)
  • O=S(=O)(c1ccc(N)cc1)N
  • InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10) checkY
  • Key:FDDDEECHVMSUSB-UHFFFAOYSA-N checkY
  (verify)

Sulfanilamide (also spelled sulphanilamide) is a

antibiotics have supplanted sulfanilamide on the battlefield; however, sulfanilamide remains in use today in the form of topical preparations, primarily for treatment of vaginal yeast infections such as vulvovaginitis caused by Candida albicans.[4][5][6][7]

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

Mechanism of action

As a sulfonamide antibiotic, sulfanilamide functions by

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.[11]

However, this effect can be reversed by adding the end products of one-carbon transfer reactions, such as thymidine, purines, methionine, and serine. PABA can also reverse the effects of sulfonamides.[5][12][11]

History

Sulfanilamide was first prepared in 1908 by the Austrian chemist Paul Josef Jakob Gelmo (1879–1961)[13][14] as part of his dissertation for a doctoral degree from the Technische Hochschule of Vienna.[15] It was patented in 1909.[16]

Gerhard Domagk, who directed the testing of the prodrug Prontosil in 1935,[17] and Jacques Tréfouël 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,[18] are generally credited with the discovery of sulfanilamide as a chemotherapeutic agent. Domagk was awarded the Nobel Prize for his work.[19]

In 1937,

Food, Drug and Cosmetic Act was passed. It was only the solvent and not the sulfanilamide that was the problem, as sulfanilamide was widely and safely used at the time in both tablet and powder form.[20]

Chemical and physical properties

Laboratory synthesized sulfanilamide

Sulfanilamide is a yellowish-white or white crystal or fine powder. It has a density of 1.08 g/cm3 and a melting point of 164.5-166.5 °C. The pH of a 0.5% aqueous solution of Sulfanilamide is 5.8 to 6.1. It has a λmax of 255 and 312 nm.[5]

Solubility: One gram of sulphanilamide dissolves in approximately 37 ml alcohol or in 5 ml acetone. It is practically insoluble in chloroform, ether, or benzene.[5]

Contraindications

Sulfanilamide is contraindicated in those known to be hypersensitive to sulfonamides, in nursing mothers, during pregnancy near term, and in infants less than two months of age.[5]

Adverse effects

Since sulfanilamide is used almost exclusively in topical vaginal preparations these days, adverse effects are typically limited to hypersensitivity or local skin reactions. If absorbed, systemic side effects commonly seen with sulfanilamides may occur.[5]

Pharmacokinetics

A small amount of sulfanilamide is absorbed following topical application or when administered as a vaginal cream or suppository (through the vaginal mucosa). It is metabolized by acetylation like other sulfonamides and excreted through the urine.[5]

See also

External links

References

  1. ISBN 978-3527306732
    .
  2. ^ Steinert D (2000). "The Use of Sulfanilamide in World War II". The History of WWII Medicine. Archived from the original on 2016-06-07.
  3. ^ "Class 9 Items: Drugs, Chemicals and Biological Stains Sulfa Drugs". Library of Congress Web Archives. Archived from the original on 2013-12-04. Retrieved 2014-06-13.
  4. ^ "Sulfanilamide". PubChem. National Center for Biotechnology Information (NCBI), U.S. National Library of Medicine.
  5. ^
    ISBN 978-0-08-055232-3
    . Retrieved 2021-10-02.
  6. ^ "US FDA Label: AVC (sulfanilamide) Vaginal Cream 15%" (PDF). United States Food & Drug Administration. Retrieved 3 October 2021.
  7. ^ "Drugs@FDA: FDA-Approved Drugs". www.accessdata.fda.gov. Retrieved 2021-10-02.
  8. PMID 11377864
    .
  9. ISBN 978-0-19-914195-1
    .
  10. ISBN 9780444894762
    .
  11. ^
    OCLC 993810322
    .
  12. ISSN 1058-4838
    .
  13. ISSN 1521-3897
    .
  14. ^ "Paul Gelmo". Encyclopedia.com.
  15. doi:10.1002/prac.19080770129
    .
  16. ^ On May 18, 1909, Deutsches Reich Patentschrift number 226,239 for sulfanilamide was awarded to Heinrich Hörlein of the Bayer corporation.
  17. S2CID 70515565
    .
  18. ^ 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.
  19. ^ Bovet D (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.
  20. ^ Ballentine C. "Sulfanilamide Disaster" (PDF). fda.gov. FDA. Retrieved 5 May 2022.
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