Thiamphenicol

Thiamphenicol
Clinical data
Trade names	Urfamycin
AHFS/Drugs.com	International Drug Names
Routes of; administration	IV, IM, oral
ATC code	J01BA02 (WHO) QJ51BA02 (WHO);
Pharmacokinetic data
Metabolism	hepatic
Elimination half-life	5.0 hours
Excretion	renal
Identifiers
	IUPAC name 2,2-dichloro-N-{(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl}acetamide;
CAS Number	15318-45-3 ;
PubChem CID	27200;
DrugBank	DB08621 ;
ChemSpider	25315 ;
UNII	FLQ7571NPM;
KEGG	D01407 ;
ChEBI	CHEBI:32215 ;
ChEMBL	ChEMBL1236282 ;
CompTox Dashboard (EPA)	DTXSID5021338 ;
ECHA InfoCard	100.035.762
Chemical and physical data
Formula	C12H15Cl2NO5S
Molar mass	356.21 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	164.3 to 166.3 °C (327.7 to 331.3 °F)
	SMILES ClC(Cl)C(=O)N[C@@H]([C@H](O)c1ccc(cc1)S(=O)(=O)C)CO;
	InChI 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 ; Key:OTVAEFIXJLOWRX-NXEZZACHSA-N ;
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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.

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

A. Fisch, A. Bryskier (2005). "Chapter 33 : Phenicols". Antimicrobial Agents. American Society for Microbiology. doi:10.1128/9781555815929.ch33.
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

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.

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[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.