Thiamphenicol

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.^[2]

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 N
PubChem CID	27200
DrugBank	DB08621 Y
ChemSpider	25315 Y
UNII	FLQ7571NPM
KEGG	D01407 Y
ChEBI	CHEBI:32215 Y
ChEMBL	ChEMBL1236282 N
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 Y Key:OTVAEFIXJLOWRX-NXEZZACHSA-N Y
NY (what is this?)  (verify)

Thiamphenicol is also widely used in Brazil, particularly for the treatment of sexually transmitted infections such as pelvic inflammatory disease.^[3]

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.^[2]

Thiamphenicol can be administered as a part of a complex molecule, Thiamphenicol glycinate acetylcysteine.^[4]

References

1. Fisch A, Bryskier A (2005). "Chapter 33 : Phenicols". In Bryskier A (ed.). Antimicrobial Agents. American Society for Microbiology. doi:10.1128/9781555815929.ch33.
2. Francis PG (1997). "Thiamphenicol". Residues of some veterinary drugs in animals and foods. FAO Food and Nutrition Paper (41/9). Rome: Food and Agriculture Organization (FAO), World Health Organization (WHO). ISBN 92-5-103972-0.
3. 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.
4. Serra A, Schito GC, Nicoletti G, Fadda G (2007). "A therapeutic approach in the treatment of infections of the upper airways: thiamphenicol glycinate acetylcysteinate in sequential treatment (systemic-inhalatory route)". International Journal of Immunopathology and Pharmacology. 20 (3): 607–617. doi:10.1177/039463200702000319. PMID 17880774.

Further reading

• Marchese A, Debbia EA, Tonoli E, Gualco L, Schito AM (December 2002). "In vitro activity of thiamphenicol against multiresistant Streptococcus pneumoniae, Haemophilus influenzae and Staphylococcus aureus in Italy". Journal of Chemotherapy. 14 (6): 554–561. doi:10.1179/joc.2002.14.6.554. PMID 12583545. S2CID 22843552.
• Raymond J, Boutros N, Bergeret M (2004). "[Role of thiamphenicol in the treatment of community-acquired lung infections]". Médecine Tropicale. 64 (1): 33–38. PMID 15224555.