Thiamphenicol

Thiamphenicol

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 category	?
Legal status	none
Routes of administration	IV, IM, oral
Pharmacokinetic data
Bioavailability	?
Metabolism	hepatic
Half-life	5.0 hours
Excretion	renal
Identifiers
CAS Registry Number	15318-45-3 N
ATC code	J01BA02 QJ51BA02
PubChem	CID 27200
DrugBank	DB08621 Y
ChemSpider	25315 Y
UNII	FLQ7571NPM Y
KEGG	D01407 Y
ChEBI	CHEBI:32215 Y
ChEMBL	CHEMBL1236282 N
Chemical data
Formula	C12H15Cl2NO5S
Molecular mass	356.223 g/mol
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  Y Key:OTVAEFIXJLOWRX-NXEZZACHSA-N  Y
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

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. PMID 12583545.