Thiamphenicol

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Thiamphenicol
Thiamphenicol stereo.png
Thiamphenicol sf.gif
Systematic (IUPAC) name
2,2-dichloro-N-{(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl}acetamide
Clinical data
AHFS/Drugs.com International Drug Names
Pregnancy cat. ?
Legal status none
Routes IV, IM, oral
Pharmacokinetic data
Bioavailability ?
Metabolism hepatic
Half-life 5.0 hours
Excretion renal
Identifiers
CAS number 15318-45-3 N
ATC code J01BA02 QJ51BA02
PubChem CID 27200
DrugBank DB08621
ChemSpider 25315 YesY
UNII FLQ7571NPM YesY
KEGG D01407 YesY
ChEBI CHEBI:32215 YesY
ChEMBL CHEMBL1236282 N
Chemical data
Formula C12H15Cl2NO5S 
Mol. mass 356.223 g/mol
 N (what is this?)  (verify)

Thiamphenicol (also known as thiophenicol and dextrosulphenidol) is an antibiotic. It is the methyl-sulfonyl analogue of chloramphenicol and has a similar spectrum of activity, but is 2.5 to 5 times as potent. Like chloramphenicol, it is insoluble in water, but highly soluble in lipids. It is used in many countries as a veterinary antibiotic, but is available in China, Morocco and Italy for use in humans. Its main advantage over chloramphenicol is that it has never been associated with aplastic anaemia.

Thiamphenicol is also widely used in Brazil, particularly for the treatment of sexually transmitted infections and pelvic inflammatory disease.[1]

Unlike chloramphenicol, thiamphenicol is not readily metabolized in cattle, poultry, sheep, or humans, but is predominantly excreted unchanged. In pigs and rats the drug is excreted both as parent drug and as thiamphenicol glucuronate (FAO, 1997).

References[edit]

  1. ^ Fuchs FD (2004). "Tetraciclinas e cloranfenicol". In Fuchs FD, Wannmacher L, Ferreira MB (eds.). Farmacologia clínica: fundamentos da terapêutica racional (in Portuguese) (3rd ed.). Rio de Janeiro: Guanabara Koogan. p. 375. ISBN 0-7216-5944-6. 

External links[edit]

  • FAO Food and Nutrition Papers Overview at World Health Organization - Food and Agriculture Organization (1997).
  • Raymond J, Boutros N, Bergeret M (2004). "Role of thiamphenicol in the treatment of community-acquired lung infections". Med Trop (Mars) 64 (1): 33–8. PMID 15224555. 
  • Marchese A, Debbia E, Tonoli E, Gualco L, Schito A (2002). "In vitro activity of thiamphenicol against multiresistant Streptococcus pneumoniae, Haemophilus influenzae and Staphylococcus aureus in Italy.". J Chemother 14 (6): 554–61. PMID 12583545.