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Details

Stereochemistry ACHIRAL
Molecular Formula C8H13N3O4S
Molecular Weight 247.272
Optical Activity UNSPECIFIED
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

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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TINDAMAX
Primary
TINDAMAX
Primary
TINDAMAX
PubMed

PubMed

TitleDatePubMed
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Gateways to clinical trials.
2002 Jan-Feb
Helicobacter pylori eradication: efficacy of conventional therapy in India.
2004 Apr
Rank order of success favors longer duration of imidazole-based therapy for Helicobacter pylori in duodenal ulcer disease: a randomized pilot study.
2004 Apr
Sequential treatment for Helicobacter pylori does not share the risk factors of triple therapy failure.
2004 Feb 15
HPLC and LC-MS studies on stress degradation behaviour of tinidazole and development of a validated specific stability-indicating HPLC assay method.
2004 Jan 27
Treatment of metronidazole-resistant Trichomonas vaginalis with tinidazole: case reports of three patients.
2004 Jun
Use of imidazole-based eradication regimens for Helicobacter pylori should be abandoned in North India regardless of in vitro antibiotic sensitivity.
2004 Jun
[Dientamoeba fragilis: possibly an important cause of persistent abdominal pain in children].
2004 Mar 20
Voltammetric determination of tinidazole using a glassy carbon electrode modified with single-wall carbon nanotubes.
2004 May
Effectiveness and pharmaceutical cost of sequential treatment for Helicobacter pylori in patients with non-ulcer dyspepsia.
2004 May 1
The efficacy of some drugs with known antiprotozoal activity against Histomonas meleagridis in chickens.
2004 May 26
Patents

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%.
Name Type Language
TINIDAZOLE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
1H-IMIDAZOLE, 1-(2-(ETHYLSULFONYL)ETHYL)-2-METHYL-5-NITRO-
Systematic Name English
FASIGIN
Brand Name English
TRICOLAM
Brand Name English
TINIDAZOLE [MI]
Common Name English
TINIDAZOLE [MART.]
Common Name English
CP-12,574
Code English
FASIGYN
Brand Name English
TINIDAZOLE [USP-RS]
Common Name English
TRIMONASE
Brand Name English
TINIDAZOLE [USAN]
Common Name English
TINIDAZOLE [HSDB]
Common Name English
TINIDAZOLE [WHO-DD]
Common Name English
IMIDAZOLE, 1-(2-(ETHYLSULFONYL)ETHYL)-2-METHYL-4-NITRO-
Systematic Name English
1-(2-(ETHYLSULFONYL)ETHYL)-2-METHYL-5-NITROIMIDAZOLE
Systematic Name English
TINIDAZOLE [VANDF]
Common Name English
TINDAMAX
Brand Name English
TINIDAZOLE [USP]
Common Name English
TINIDAZOLE [ORANGE BOOK]
Common Name English
CP-12574
Code English
TINIDAZOLE [INN]
Common Name English
TINIDAZOLE [EP]
Common Name English
SIMPLOTAN
Brand Name English
HAISIGYN
Brand Name English
Classification Tree Code System Code
CFR 21 CFR 530.41
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
WHO-ATC J01RA11
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
WHO-ATC A02BD09
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
WHO-VATC QJ01XD02
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
WHO-ATC J01RA13
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
NDF-RT N0000175435
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
WHO-VATC QP51AA02
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
LIVERTOX 967
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
WHO-ATC J01XD02
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
WHO-ATC P01AB02
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
NDF-RT N0000007663
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
NDF-RT N0000007663
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
Code System Code Type Description
ChEMBL
CHEMBL1220
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
PRIMARY
MERCK INDEX
M10874
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
PRIMARY Merck Index
NCI_THESAURUS
C890
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
PRIMARY
INN
2653
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
PRIMARY
PUBCHEM
5479
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
PRIMARY SWITZERF
DRUG BANK
DB00911
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
PRIMARY
EVMPD
SUB11074MIG
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
PRIMARY
LactMed
19387-91-8
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
PRIMARY
WIKIPEDIA
TINIDAZOLE
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
PRIMARY
MESH
D014011
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
PRIMARY
ECHA (EC/EINECS)
243-014-4
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
PRIMARY
CAS
19387-91-8
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
PRIMARY
EPA CompTox
19387-91-8
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
PRIMARY
RXCUI
10612
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
PRIMARY RxNorm
HSDB
19387-91-8
Created by admin on Tue Mar 06 11:22:09 UTC 2018 , Edited by admin on Tue Mar 06 11:22:09 UTC 2018
PRIMARY