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Thiamphenicol

Summary

Thiamphenicol (also known as thiophenicol and dextrosulphenidol) is an antibiotic.[1] 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.[citation needed]

Thiamphenicol
Clinical data
Trade namesUrfamycin
AHFS/Drugs.comInternational Drug Names
Routes of
administration		IV, IM, oral
ATC code
Pharmacokinetic data
Metabolismhepatic
Elimination half-life5.0 hours
Excretionrenal
Identifiers
  • 2,2-dichloro-N-{(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl}acetamide
CAS Number
  • 15318-45-3 ☒N
PubChem CID
  • 27200
DrugBank
  • DB08621 checkY
ChemSpider
  • 25315 checkY
UNII
  • FLQ7571NPM
KEGG
  • D01407 checkY
ChEBI
  • CHEBI:32215 checkY
ChEMBL
  • ChEMBL1236282 ☒N
CompTox Dashboard (EPA)
  • DTXSID5021338 Edit this at Wikidata
ECHA InfoCard100.035.762 Edit this at Wikidata
Chemical and physical data
FormulaC12H15Cl2NO5S
Molar mass356.21 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point164.3 to 166.3 °C (327.7 to 331.3 °F)
  • ClC(Cl)C(=O)N[C@@H]([C@H](O)c1ccc(cc1)S(=O)(=O)C)CO
  • InChI=1S/C12H15Cl2NO5S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-16)15-12(18)11(13)14/h2-5,9-11,16-17H,6H2,1H3,(H,15,18)/t9-,10-/m1/s1 checkY
  • Key:OTVAEFIXJLOWRX-NXEZZACHSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Thiamphenicol is also widely used in Brazil, particularly for the treatment of sexually transmitted infections and pelvic inflammatory disease.[2]

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. ^ A. Fisch, A. Bryskier (2005). "Chapter 33 : Phenicols". Antimicrobial Agents. American Society for Microbiology. doi:10.1128/9781555815929.ch33.
  2. ^ 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. pp. 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. doi:10.1179/joc.2002.14.6.554. PMID 12583545. S2CID 22843552.