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)
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Sulfanilamide (also spelled sulphanilamide) is a sulfonamide antibacterial. Chemically, it is a molecule containing the sulfonamide functional group attached to an aniline. As a sulfonamide antibiotic, it functions by competitively inhibiting (i.e., by acting as a substrate analogue) enzymatic reactions involving para-aminobenzoic acid (PABA).[1] PABA is needed in enzymatic reactions that produce folic acid which acts as a coenzyme in the synthesis of purine, pyrimidine and other amino acids.

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

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.[2] It was patented in 1909.[3]

Gerhard Domagk, who directed the testing of the prodrug Prontosil in 1935,[4] 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,[5] are generally credited with the discovery of sulfanilamide as a chemotherapeutic agent. Domagk was awarded the Nobel Prize for his work.[6]

See also[edit]

External links[edit]

References[edit]

  1. ^ Michael Kent, Advanced Biology, Oxford University Press, 2000, p. 46 ISBN 978-0-19-914195-1
  2. ^ Paul Gelmo (May 14, 1908) "Über Sulfamide der p-Amidobenzolsulfonsäure," Journal für Praktische Chemie, 77 : 369-382.
  3. ^ On May 18, 1909, Deutsches Reich Patentschrift number 226,239 for sulfanilamide was awarded to Heinrich Hörlein of the Bayer corporation.
  4. ^ G. Domagk, "Ein Beitrag zur Chemotherapie der bakteriellen Infektionen", Deutsche Medizinische Wochenschrift, 61, feb. 15, 1935, p. 250.
  5. ^ 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.
  6. ^ (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.