ChemicalBook > Product Catalog > API > Antiparasitic drugs > Antiamoebic and anti-trichomoniasis drugs > Tinidazole
Basic information Pharmacology and mechanism of action Pharmacology and mechanism of action Indications Side effects Contraindications Interactions Preparations References Safety Related Supplier
Tinidazole Chemical Properties
- Melting point:118-120?C
- Boiling point:528.4±30.0 °C(Predicted)
- Density 1.4338 (rough estimate)
- refractive index 1.6320 (estimate)
- storage temp. Refrigerator
- solubility Practically insoluble in water, soluble in acetone and in methylene chloride, sparingly soluble in methanol.
- form neat
- Merck 14,9447
- BRN 618182
- Stability:Stable. Incompatible with strong oxidizing agents.
- CAS DataBase Reference19387-91-8(CAS DataBase Reference)
Tinidazole Usage And Synthesis
- Pharmacology and mechanism of action Similar to metronidazole.
- Pharmacology and mechanism of actionSimilar to metronidazole.
- IndicationsInfections caused by Entamoeba histolytica and Giardia lamblia. Tinidazole is more effective than metronidazole in the treatment of giardiasis.
- Side effects Side effects are similar to but milder than those caused by metronidazole. Gastrointestinal disturbances like nausea, vomiting, anorexia and metallic taste are common. Headache, tiredness, furred tongue and itching may occur. Thrombophlebitis may occur at the site of intravenous infusion .
- ContraindicationsTinidazole should not be taken together with alcohol.
- InteractionsA disulfiram-like reaction might occur if tinidazole is taken together with alcohol.
- Preparations• Fasigyn® (Pfizer). Tablets 150 mg, 200 mg, 300 mg, 500 mg, 1 g. Oral suspension 200 mg per ml. Solution for injection 2 mg per ml.
• Tricolam® (Pfizer). Tablets 500 mg.
• Simplotan® (Pfizer). Tablets 1 g.
- References1. Sawyer PR, Brogden RN, Pinder RM, Speight TM, Avery GS (1976). Tinidazole: a review of its antiprotozoal activity and therapeutic efficacy. Drugs, 11, 424–440.
- Chemical Propertiessolid
- UsesAntiprotozoal (Trichomonas, Giardia); antiamebic; antibacterial.
- UsesFor 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 intestin
- Antimicrobial activityIts antibacterial and antiprotozoal activity is similar to that of metronidazole.The MIC against G. vaginalis is 0.2–2 mg/L; the hydroxy metabolite is significantly more active than that of metronidazole. H. pylori is inhibited by 0.5 mg/L. T. vaginalis and T. fetus at 2.5 mg/L and E. histolytica is inhibited by about 0.3–2.5 mg/L.
- Pharmaceutical ApplicationsA 5-nitroimidazole available for oral administration and, in some countries, for intravenous infusion.
- Mechanism of actionTinidazole has a mechanism of action that parallels that of metronidazole as well as a similar metabolic pathway leading to hydroxylation at the 2-methyl group catalyzed by CYP3A4. Basically, tinidazole appears to mimic the actions of metronidazole, although there are reports that it is effective against some protozoa which are resistant to metronidazole.
- PharmacokineticsOral absorption ：>95%
Cmax 2 g oral：40 mg/L after 2 h
800 mg (30-min infusion)： 12 mg/L 6 min after end infusion
Plasma half-life： 12–14 h
Volume of distribution 0.64 L/kg ：Plasma protein binding 12%
absorption and distribution
After a 2 g oral dose, concentrations remain at c. 10 mg/L at 24 h and 2.5 mg/L at 48 h. Daily doses of 1 g maintain plasma levels in excess of 8 mg/L, irrespective of whether the dose is oral or intravenous. It is well distributed, with concentrations in bile, CSF, breast milk and saliva similar to those reached in plasma.
The drug readily crosses the placenta. In women undergoing first trimester abortion, concentrations of 4.9 mg/kg (placenta) and 7.6 mg/kg (fetus) were found when the plasma concentration was 13.2 mg/L.
Metabolism and excretion
Metabolites include the 2-hydroxymethyl derivative, its glucuronide and two unidentified minor derivatives. In urine about half the drug remains unmetabolized.
The parent drug and its metabolites are excreted primarily in the urine and to a minor extent in the feces. The clearance rate is about 0.73 mL/min per kg and the urinary excretion is about 21% of the dose. Total clearance of the drug is 51 mL/min, renal clearance 10 mL/min. In healthy volunteers given an ： intravenousinfusion of 800 mg [14C]tinidazole over 30 min, a mean of 44% of the dose was excreted in the urine during the first 24 h, increasing to 63% over 5 days： only 12% of the dose appeared in the feces. Unchanged tinidazole comprised 32% of urinary 14C in 0&ndash：12 h urine. The 2-hydroxymethyl metabolite accounted for about 9% of the urinary 14C and was also present in plasma.
In renal failure the pharmacokinetics are not significantly different from those in healthy individuals. It is rapidly removed by hemodialysis and a normal dose should be given after each dialysis： if treatment precedes dialysis a half dose should be infused after the end of the procedure.
- Clinical UseAnaerobic bacterial infections(prophylaxis and treatment)
Giardiasis (single dose) Amebiasis (including amebic liver abscess)
Gastric colonization with H. pylori (in combination with other agents)
- Side effectsTinidazole is generally well tolerated. Infrequent and transient effects include nausea, vomiting, diarrhea and a metallic taste. Disulfiram-like reactions may occur and rare neurological disturbances and transient leukopenia have been described. Rash, which may be severe, urticaria and angioneurotic edema can occur.
- Veterinary Drugs and TreatmentsLittle information is presently available on the use of tinidazole in dogs, cats, or horses. It potentially could be useful for treating anaerobic infections, particularly associated with dental infections in small animals. Because of its antiprotozoal effects, it has been used as an alternative for treating giardiasis in small animals, and it could have efficacy against amebiasis, trichomoniasis or balantidiasis in veterinary species, but documentation of efficacy is not available. Tinidazole has a longer duration of action in dogs and cats than does metronidazole. In humans, oral tinidazole is FDA-approved for treating extraintestinal and intestinal amebiasis, (Entamoeba histolytica), giardiasis (Giardia duodenalis/lamblia), and trichomoniasis (T. vaginalis).
- 1-METHYL-5-NITROIMIDAZOLE 2-METHYL-1H-IMIDAZOL-4-AMINE 1,2-Dimethyl-5-nitroimidazole 2-Methyl-4-nitroimidazole Tinidazole Kresoxim-methyl Methyl Methylparaben Imidazole Nitrobenzene Methyl bromide Methyl acrylate Thiophanate-methyl 2,4,6-TRINITROTOLUENE Parathion-methyl Levamisole Bensulfuron methyl Methyl acetate
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