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Details

Stereochemistry ACHIRAL
Molecular Formula C8H13N3O4S
Molecular Weight 247.272
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TINIDAZOLE

SMILES

CCS(=O)(=O)CCN1C(C)=NC=C1[N+]([O-])=O

InChI

InChIKey=HJLSLZFTEKNLFI-UHFFFAOYSA-N
InChI=1S/C8H13N3O4S/c1-3-16(14,15)5-4-10-7(2)9-6-8(10)11(12)13/h6H,3-5H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C8H13N3O4S
Molecular Weight 247.272
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Tinidazole is a synthetic antiprotozoal agent, formally known as 1-[2-(ethylsulfonyl)ethyl]-2-methyl-5-nitroimidazole and a second-generation 2-methyl-5-nitroimidazole. 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. Tindamax oral tablets are indicated for the treatment of trichomoniasis caused by T. vaginalis in both female and male patients assuming the organism has been identified by appropriate diagnostic procedures. Because trichomoniasis is a sexually transmitted disease with potentially serious sequelae, partners of infected patients should be treated simultaneously in order to prevent re-infection. Tindamax oral tablets are also indicated for the treatment of giardiasis caused by G. duodenalis (also termed G. lamblia) in both adults and pediatric patients older than three years of age. Another indication for Tindamax oral tablets is 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. It is not indicated in the treatment of asymptomatic cyst passage. The most common side effects reported with tinidazole are upset stomach, bitter taste and itchiness. Other side effects include headache, physical fatigue, and dizziness. Anecdotally, people who have taken both metronidazole and tinidazole report toxicity is much the same except the side effects don't last as long with the latter. Drinking alcohol while taking tinidazole causes an unpleasant disulfiram-like reaction which includes nausea, vomiting, headache, increased blood pressure, flushing, and shortness of breath.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
TINDAMAX
Curative
TINDAMAX
Curative
TINDAMAX

Cmax

ValueDoseCo-administeredAnalytePopulation
47.7 μg/mL
2 g single, oral
TINIDAZOLE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
901.6 μg × h/mL
2 g single, oral
TINIDAZOLE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
13.2 h
2 g single, oral
TINIDAZOLE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
88%
2 g single, oral
TINIDAZOLE plasma
Homo sapiens

Doses

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
a single 2 g oral dose taken with food
Route of Administration: Oral
In Vitro Use Guide
The survival of Trichomonas vaginalis at each concentration of tinidazole was presented as a cumulative frequency. At the concentration of 1 um/ml, none of the organisms were killed; but at the concentration of 6 um/ml, the mortality rate was 100%.
Substance Class Chemical
Record UNII
033KF7V46H
Record Status Validated (UNII)
Record Version