Sulfanilamide

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Sulfanilamide
Sulfanilamide-skeletal.svg
Systematic (IUPAC) name
4-aminobenzenesulfonamide
Clinical data
AHFS/Drugs.com Consumer Drug Information
Legal status ?
Identifiers
CAS number 63-74-1 YesY
ATC code J01EB06 D06BA05 QJ01EQ06
PubChem CID 5333
DrugBank DB00259
ChemSpider 5142 YesY
UNII 21240MF57M YesY
KEGG D08543 YesY
ChEBI CHEBI:45373 YesY
ChEMBL CHEMBL21 YesY
NIAID ChemDB 019103
Chemical data
Formula C6H8N2O2S 
Mol. mass 172.20 g/mol
Physical data
Density 1.08 g/cm³
Melt. point 165 °C (329 °F)
 YesY (what is this?)  (verify)

Sulfanilamide (also spelled sulphanilamide) is a sulfonamide antibacterial. Chemically, it is an organic compound consisting of an aniline derivitized 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[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 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[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. ^ 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.