Sulfanilamide

Sulfanilamide
Sulfanilamide
Systematic (IUPAC) name
4-aminobenzenesulfonamide
Clinical data
AHFS/Drugs.com Consumer Drug Information
Pregnancy cat.  ?
Legal status  ?
Identifiers
CAS number 63-74-1 YesY
ATC code J01EB06 D06BA05 QJ01EQ06
PubChem CID 5333
DrugBank APRD00438
ChemSpider 5142 YesY
UNII 21240MF57M YesY
KEGG D08543 YesY
ChEBI CHEBI:45373 N
ChEMBL CHEMBL21 YesY
Chemical data
Formula C6H8N2O2S 
Mol. mass 172.20 g/mol
SMILES eMolecules & PubChem
Physical data
Density 1.08 g/cm³
Melt. point 165 °C (329 °F)
 N(what is this?)  (verify)

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:

Gerhard Domagk, who directed the testing of the prodrug Prontosil in 1935,[2] and Jacques and Thérèse Tréfouël, who along with Federico Nitti and Daniel Bovet in the laboratory of Ernest Fourneau at the Pasteur Institute, discovered the active component, 4-aminobenzenesulfonamide,[3] are generally credited with the discovery of sulfanilamide as a chemotherapeutic agent. Domagk was awarded the Nobel Prize for his work.[4]

See also

External links

References

  1. ^ Michael Kent, Advanced Biology, Oxford University Press, 2000, p. 46 ISBN 9780199141951
  2. ^ G. Domagk, "Ein Beitrag zur Chemotherapie der bakteriellen Infektionen", Deutsche Medizinische Wochenschrift, 61, feb. 15, 1935, p. 250.
  3. ^ 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.
  4. ^ (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.



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  • Sulfanilamide — Général Nom IUPAC 4 aminobenzenesulfonamide Synonymes …   Wikipédia en Français

  • sulfanilamide — ● sulfanilamide nom masculin Dénomination courante du para aminobenzène sulfonamide, qui est l amide de l acide sulfanilique et qui a été le premier sulfamide antibactérien. sulfanilamide [sulfanilamid] n. m. ou f. ÉTYM. Après 1937; angl.… …   Encyclopédie Universelle

  • sulfanilamide — sulfanilamide. См. сульфаниламид. (Источник: «Англо русский толковый словарь генетических терминов». Арефьев В.А., Лисовенко Л.А., Москва: Изд во ВНИРО, 1995 г.) …   Молекулярная биология и генетика. Толковый словарь.

  • sulfanilamide — [sul΄fənil′ə mīd΄, sul΄fə nil′əmid] n. [< SULFANILIC ACID + AMIDE] a white, crystalline compound, C6H8N2O2S, formerly used in treating gonorrhea, streptococcal infections, etc.: a synthetic coal tar product …   English World dictionary

  • sulfanilamide — sulfanilamidas statusas T sritis chemija apibrėžtis Antibiotikas. formulė H₂NC₆H₄SO₂NH₂ atitikmenys: angl. sulfanilamide rus. стрептоцид; сульфаниламид ryšiai: sinonimas – streptocidas sinonimas – 4 aminobenzensulfamidas …   Chemijos terminų aiškinamasis žodynas

  • sulfanilamide — noun Etymology: sulfanilic acid (C6H7NO3S, from International Scientific Vocabulary sulf + aniline + ic) + amide Date: 1937 a crystalline sulfonamide C6H8N2O2S that is the parent compound of most of the sulfa drugs …   New Collegiate Dictionary

  • sulfanilamide — /sul feuh nil euh muyd , mid/, n. Pharm. a white, crystalline amide of sulfanilic acid, C6H8N2O2S, formerly used in the treatment of bacterial infections: replaced by its derivatives and by antibiotics. [1935 40; SULFANIL(IC ACID) + AMIDE] * * * …   Universalium

  • sulfanilamide — noun Any of a class of amino substituted aromatic sulfonamides that are used as antifungal antibiotics; but especially the parent compound 4 aminobenzenesulfonamide …   Wiktionary

  • sulfanilamide — The first sulfonamide used for its chemotherapeutic effect in infections caused by some β hemolytic streptococci, meningococci, gonococci, Clostridium welchii, and in certain infections of the urinary tract, especially those due to Escherichia… …   Medical dictionary

  • sulfanilamide — n. white crystalline amide of sulfanilic acid that was formerly used to treat bacterial infections …   English contemporary dictionary

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