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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.[citation needed]

Thiamphenicol
Clinical data
Trade namesUrfamycin
AHFS/Drugs.comInternational Drug Names
Routes of
administration
IV, IM, oral
ATC code
Pharmacokinetic data
Metabolismhepatic
Elimination half-life5.0 hours
Excretionrenal
Identifiers
  • 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 InfoCard100.035.762
Chemical and physical data
FormulaC12H15Cl2NO5S
Molar mass356.21 g·mol−1
3D model (JSmol)
  • Interactive image
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 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 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 edit

  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.

External links edit

  • 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.


thiamphenicol, also, known, thiophenicol, dextrosulphenidol, antibiotic, methyl, sulfonyl, analogue, chloramphenicol, similar, spectrum, activity, times, potent, like, chloramphenicol, insoluble, water, highly, soluble, lipids, used, many, countries, veterinar. 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 citation needed ThiamphenicolClinical dataTrade namesUrfamycinAHFS Drugs comInternational Drug NamesRoutes ofadministrationIV IM oralATC codeJ01BA02 WHO QJ51BA02 WHO Pharmacokinetic dataMetabolismhepaticElimination half life5 0 hoursExcretionrenalIdentifiersIUPAC name 2 2 dichloro N 1R 2R 2 hydroxy 1 hydroxymethyl 2 4 methylsulfonyl phenyl ethyl acetamideCAS Number15318 45 3 NPubChem CID27200DrugBankDB08621 YChemSpider25315 YUNIIFLQ7571NPMKEGGD01407 YChEBICHEBI 32215 YChEMBLChEMBL1236282 NCompTox Dashboard EPA DTXSID5021338ECHA InfoCard100 035 762Chemical and physical dataFormulaC 12H 15Cl 2N O 5SMolar mass356 21 g mol 13D model JSmol Interactive imageMelting point164 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 COInChI 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 YKey OTVAEFIXJLOWRX NXEZZACHSA N Y N Y what is this verify 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 edit 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 clinica fundamentos da terapeutica racional in Portuguese 3rd ed Rio de Janeiro Guanabara Koogan pp 375 ISBN 0 7216 5944 6 External links editFAO 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 nbsp This systemic antibiotic related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Thiamphenicol amp oldid 1152616924, wikipedia, wiki, book, books, library,

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