U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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.

CNS Activity

Originator

Approval Year

Target Info

Target Info

Primary TargetPharmacologyConditionPotency
Condition Info

Condition Info

ConditionModalityTargetsHighest PhaseProduct
Primary
TINDAMAX
Primary
TINDAMAX
Primary
TINDAMAX
PMID

PMID

TitleDatePMID
Evaluation of diazotized 4-amino-3,5-dinitrobenzoic acid (ADBA) as a new derivatizing reagent.
2001 Sep
Efficacy of the triple therapy: proton pomp inhibitors, amoxicillin and tynidazole in Helicobacter pylori infection treatment.
2002
Single-dose therapy for giardiasis in school-age children.
2002 Dec
Design and in vitro evaluation of oral colon targeted drug delivery systems for tinidazole.
2002 Dec
Serum mineral levels in children with intestinal parasitic infection.
2003
[Incidence of anaerobic bacteria in respiratory tract infections].
2003
On the hydrolytic behavior of tinidazole, metronidazole, and ornidazole.
2003 Apr
Primary and secondary antibiotic resistance of Helicobacter pylori strains isolated in central Italy during the years 1998-2002.
2003 Aug
Ciprofloxacin-tinidazole combination, fluconazole- azithromicin-secnidazole-kit and doxycycline- metronidazole combination therapy in syndromic management of pelvic inflammatory disease: a prospective randomized controlled trial.
2003 Dec
Oral tinidazole treatment during pregnancy and teratogenesis.
2003 Dec
[The clinical evaluation of tinidazole-iodoform root canal paste on treatment of chronic periapical periodontitis associated with ectopic sinus].
2003 Feb
[Antiprotozoal drugs].
2003 Feb
Triple therapy for 7 days vs. triple therapy for 7 days plus omeprazole for 21 days in treatment of active duodenal ulcer with Helicobacter pylori infection. A double blind placebo controlled trial.
2003 Jan
A novel pH- and time-dependent system for colonic drug delivery.
2003 Jul
Rabeprazole in a one-week eradication therapy of Helicobacter pylori: comparison of different dosages.
2003 Jul
Helicobacter pylori eradication and peptic ulcer healing: the impact of deleting the proton pump inhibitor and using a once-daily treatment.
2003 Jul 1
Efficacy of the combination of 2 g oral tinidazole and acidic buffering vaginal gel in comparison with vaginal clindamycin alone in bacterial vaginosis: a randomized, investigator-blinded, controlled trial.
2003 Jul 1
Comparison of chloroquine, albendazole and tinidazole in the treatment of children with giardiasis.
2003 Jun
Nitroheterocyclic drugs with broad spectrum activity.
2003 Jun
Late recurrence of resistant Trichomonas vaginalis vaginitis: relapse or re-infection?
2003 Jun
[Failure of Helicobacter pylori eradication--suggestions for further therapy].
2003 Jun 29
Diagnosis and eradication of Helicobacter pylori in patients with duodenal ulceration in the community.
2003 Mar
Triple eradication therapy counteracts functional impairment associated with Helicobacter pylori infection in Mongolian gerbils.
2003 Mar
Efficacy and tolerability of a combination of ofloxacin and tinidazole in the management of infectious diabetic foot ulcer.
2003 May
[Oleyl pyroglutamate for use as transdermal enhancer and its enhancing mechanism].
2003 May
Use of lactoferrin for Helicobacter pylori eradication. Preliminary results.
2003 May-Jun
Efficacy of antigiardial drugs.
2003 Nov
Use of bovine lactoferrin for Helicobacter pylori eradication.
2003 Oct
Lactoferrin: milking ulcers?
2003 Oct
Giardia intestinalis.
2003 Oct
Role of antibiotic sensitivity testing before first-line Helicobacter pylori eradication treatments.
2003 Oct 15
Randomized study of different 'second-line' therapies for Helicobacter pylori infection after failure of the standard 'Maastricht triple therapy'.
2003 Oct 15
[Eradication of Helicobacter pylori].
2003 Oct 5
Pharmacokinetic evaluation of guar gum-based colon-targeted drug delivery systems of tinidazole in healthy human volunteers.
2003 Oct-Dec
Comparative study on the effects of ointments of tinidazole, hydrocortisone and clobetasol on animal models for inflammatory dermatitis in mice.
2003 Sep
Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data.
2003 Sep
Sequential treatment for Helicobacter pylori eradication in duodenal ulcer patients: improving the cost of pharmacotherapy.
2003 Sep 15
Levofloxacin-based triple therapy vs. quadruple therapy in second-line Helicobacter pylori treatment: a randomized trial.
2003 Sep 15
Effects of metronidazole and tinidazole on NTPDase1 and ecto-5'-nucleotidase from intact cells of Trichomonas vaginalis.
2003 Sep 26
One-week low-dose triple therapy without anti-acid treatment has sufficient efficacy on Helicobacter pylori eradication and ulcer healing.
2003 Sep-Oct
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
Patent

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