Thiamphenicol

Last updated
Thiamphenicol
Thiamphenicol Structural formula V1.svg
Thiamphenicol sf.gif
Clinical data
Trade names Urfamycin
AHFS/Drugs.com International Drug Names
Routes of
administration
IV, IM, oral
ATC code
Pharmacokinetic data
Metabolism hepatic
Elimination half-life 5.0 hours
Excretion renal
Identifiers
  • 2,2-dichloro-N-{(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl}acetamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.035.762 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C12H15Cl2NO5S
Molar mass 356.21 g·mol−1
3D model (JSmol)
Melting point 164.3 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 Yes check.svgY
  • Key:OTVAEFIXJLOWRX-NXEZZACHSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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 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).

Related Research Articles

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<span class="mw-page-title-main">Cefotaxime</span>

Cefotaxime is an antibiotic used to treat a number of bacterial infections in human, other animals and plant tissue culture. Specifically in humans it is used to treat joint infections, pelvic inflammatory disease, meningitis, pneumonia, urinary tract infections, sepsis, gonorrhea, and cellulitis. It is given either by injection into a vein or muscle.

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Gray baby syndrome is a rare but serious, even fatal, side effect that occurs in newborn infants following the accumulation of antibiotic chloramphenicol. Chloramphenicol is a broad-spectrum antibiotic that has been used to treat a variety of bacteria infections like Streptococcus pneumoniae as well as typhoid fever, meningococcal sepsis, cholera, and eye infections. Chloramphenicol works by binding to ribosomal subunits which blocks transfer ribonucleic acid and prevents the synthesis of bacterial proteins. Chloramphenicol has also been used to treat neonates born before 37 weeks of the gestational period for prophylaxis purposes. In 1958, newborns born prematurely due to rupture of the amniotic sac were given chloramphenicol to prevent possible infections, and it was noticed that these newborns had a higher mortality rate compared with those who were not treated with the antibiotic. Over the years, chloramphenicol has been used less in clinical practices due to the risks of toxicity not only to neonates, but also to adults due to the risk of aplastic anemia. Chloramphenicol is now reserved to treat certain severe bacteria infections that were not successfully treated with other antibiotic medications. Signs and symptoms are summarized in the WHO Model Formulary for Children 2010 under the rare adverse effect section of chloramphenicol.

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References

  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.