Thiamphenicol

Thiamphenicol
Clinical data


AHFS/Drugs.com	International Drug Names
Pregnancy category	?
Routes of administration	IV, IM, oral
ATC code	J01BA02 (WHO) QJ51BA02 (WHO)
Legal status
Legal status	none
Pharmacokinetic data
Bioavailability	?
Metabolism	hepatic
Biological 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^Y
KEGG	D01407^Y
ChEBI	CHEBI:32215^Y
ChEMBL	CHEMBL1236282^N
ECHA InfoCard	100.035.762
Chemical and physical data
Formula	C₁₂H₁₅Cl₂NO₅S
Molar mass	356.223 g/mol
3D model (Jmol)	Interactive image
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 (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

↑ Fuchs FD (2004). "Tetraciclinas e cloranfenicol". In Fuchs FD, Wannmacher L, Ferreira MB. Farmacologia clínica: fundamentos da terapêutica racional (in Portuguese) (3rd ed.). Rio de Janeiro: Guanabara Koogan. p. 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. PMID 12583545.

Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin Ribostamycin Kanamycin^# Amikacin Arbekacin Bekanamycin Dibekacin Tobramycin Spectinomycin^# Hygromycin B Paromomycin

-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Plazomicin^† Isepamicin Verdamicin Astromicin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Lymecycline Meclocycline Metacycline Minocycline Oxytetracycline Penimepicycline Rolitetracycline Tetracycline

Glycylcyclines	Tigecycline

Fluorocyclines	Eravacycline^†

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol

Pleuromutilins	Retapamulin Tiamulin Valnemulin

MLS (transpeptidation/translocation)

Macrolides	Azithromycin^# Clarithromycin Dirithromycin Erythromycin^# Flurithromycin Josamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Spiramycin Troleandomycin Tylosin Ketolides Telithromycin Cethromycin Solithromycin^†

Lincosamides	Clindamycin^# Lincomycin Pirlimycin

Streptogramins	Pristinamycin Quinupristin/dalfopristin Virginiamycin

EF-G

Steroid antibacterials	Fusidic acid

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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