Tinidazole

CAS No:
19387-91-8 Category:
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Product Details:

  • CAS No: 19387-91-8
  • AHFC code:
  • Synonyms:
  • ATC Code: J01XD02 P01AB02
  • Chemical Formula: C22H36N2O5S
  • Molecular Weight: 247.272
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB00911 (APRD01260)
  • SMILES: CCS(=O)(=O)CCN1C(C)=NC=C1[N+]([O-])=O
  • InChl: HJLSLZFTEKNLFI-UHFFFAOYSA-N
  • PubChem: 5479
  • IUPAC: 1-[2-(ethanesulfonyl)ethyl]-2-methyl-5-nitro-1H-imidazole

Additional Details

Indication:
For the treatment of trichomoniasis caused by T. vaginalis in both female and male patients. Also for the treatment of giardiasis caused by G. duodenalis in both adults and pediatric patients older than three years of age and for the treatment of intestinal amebiasis and amebic liver abscess caused by E. histolytica in both adults and pediatric patients older than three years of age.
Pharmacodynamics:
Tinidazole is a synthetic antiprotozoal agent. Tinidazole demonstrates activity both in vitro and in clinical infections against the following protozoa: Trichomonas vaginalis, Giardia duodenalis (also termed G. lamblia), and Entamoeba histolytica. Tinidazole does not appear to have activity against most strains of vaginal lactobacilli.
Mode of Action:
Tinidazole is a prodrug and antiprotozoal agent. The nitro group of tinidazole is reduced in Trichomonas by a ferredoxin-mediated electron transport system. The free nitro radical generated as a result of this reduction is believed to be responsible for the antiprotozoal activity. It is suggested that the toxic free radicals covalently bind to DNA, causing DNA damage and leading to cell death. The mechanism by which tinidazole exhibits activity against Giardia and Entamoeba species is not known, though it is probably similar.
Metabolism:
Hepatic, mainly via CYP3A4. Tinidazole, like metronidazole, is significantly metabolized in humans prior to excretion. Tinidazole is partly metabolized by oxidation, hydroxylation and conjugation. Tinidazole is the major drug-related constituent in plasma after human treatment, along with a small amount of the 2-hydroxymethyl metabolite.
Toxicity:
There are no reported overdoses with tinidazole in humans. In acute studies with mice and rats, the LD 50 for mice was generally > 3,600 mg/kg for oral administration and was > 2,300 mg/kg for intraperitoneal administration. In rats, the LD 50 was > 2,000 mg/kg for both oral and intraperitoneal administration.
General Reference:
Link Lopez Nigro MM, Carballo MA: Genotoxicity and cell death induced by tinidazole (TNZ). Toxicol Lett. 2008 Jul 30;180(1):46-52. Epub 2008 Jun 5. Pubmed Fung HB, Doan TL: Tinidazole: a nitroimidazole antiprotozoal agent. Clin Ther. 2005 Dec;27(12):1859-84. Pubmed
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