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Thiamphenicol

From Wikipedia, the free encyclopedia
Antibiotic

Pharmaceutical compound
Thiamphenicol
Clinical data
Trade namesUrfamycin
AHFS/Drugs.comInternational Drug Names
Routes of
administration
IV,IM,oral
ATC code
Pharmacokinetic data
Metabolismhepatic
Eliminationhalf-life5.0 hours
Excretionrenal
Identifiers
  • 2,2-dichloro-N-{(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl}acetamide
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.035.762Edit this at Wikidata
Chemical and physical data
FormulaC12H15Cl2NO5S
Molar mass356.21 g·mol−1
3D model (JSmol)
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 (also known asthiophenicol anddextrosulphenidol) is anantibiotic.[1] It is themethyl-sulfonyl analogue ofchloramphenicol 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 inlipids. It is used in many countries as aveterinary antibiotic, but is available in China, Taiwan, Brazil, Morocco, and Italy for use in humans. Its main advantage over chloramphenicol is that it has never been associated withaplastic anaemia.[2]

Thiamphenicol is also widely used inBrazil, particularly for the treatment ofsexually transmitted infections such aspelvic 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

[edit]
  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. ^abFrancis 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

[edit]
  • 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.
30S
Aminoglycosides
(initiation inhibitors)
-mycin (Streptomyces)
-micin (Micromonospora)
other
Tetracycline antibiotics
(tRNA binding)
Tetracyclines
Glycylcyclines
50S
Oxazolidinone
(initiation inhibitors)
Peptidyl transferase
Amphenicols
MLS (transpeptidation/translocation)
Macrolides
Azalides
Ketolides
Lincosamides
Oxepanoprolinamides
Streptogramins
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