TINIDAZOLE

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 Search

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

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21618_tindamax_lbl.pdf
Curator's Comment: description was created based on several sources, including: http://www.drugbank.ca/drugs/DB00911 https://en.wikipedia.org/wiki/Tinidazole

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 Target	Pharmacology	Condition	Potency
DNA 282 Target ID: CHEMBL2366045 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21618_tindamax_lbl.pdf	Binding Agent 1076

Conditions

Condition	Modality	Highest Phase	Product
Trichomoniasis 18 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21618_tindamax_lbl.pdf	Curative	Approved 8583	TINDAMAX Approved Use Trichomoniasis: Tindamax oral tablets are indicated for the treatment of trichomoniasis caused by T.vaginalis in both female and male patients. The organism should be 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. Launch Date 2005
Giardiasis 13 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21618_tindamax_lbl.pdf	Curative	Approved 8583	TINDAMAX Approved Use Tindamax oral tablets are 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. Launch Date 2005
Amebiasis 11 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21618_tindamax_lbl.pdf	Curative	Approved 8583	TINDAMAX Approved Use Tindamax oral tablets are indicated 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. It is not indicated in the treatment of asymptomatic cyst passage. Launch Date 2005

C_max

Value	Dose	Co-administered	Analyte	Population
47.7 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021618s003lbl.pdf	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:		TINIDAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
901.6 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021618s003lbl.pdf	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:		TINIDAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
13.2 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021618s003lbl.pdf	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:		TINIDAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
88% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021618s003lbl.pdf	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:		TINIDAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

Doses

Dose	Population	Adverse events
2 g 1 times / day single, oral Recommended Dose: 2 g, 1 times / day Route: oral Route: single Dose: 2 g, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00322465	unhealthy, 27.8 Health Status: unhealthy Age Group: 27.8 Sex: M Sources: https://clinicaltrials.gov/ct2/show/NCT00322465	Sources: https://clinicaltrials.gov/ct2/show/NCT00322465
500 mg/kg 2 times / day multiple, oral Recommended Dose: 500 mg/kg, 2 times / day Route: oral Route: multiple Dose: 500 mg/kg, 2 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00334633	unhealthy, 28.5 Health Status: unhealthy Age Group: 28.5 Sex: F Sources: https://clinicaltrials.gov/ct2/show/NCT00334633	Sources: https://clinicaltrials.gov/ct2/show/NCT00334633
1 g 1 times / day multiple, oral Recommended Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/results/NCT02648698	unhealthy, 31.93 Health Status: unhealthy Age Group: 31.93 Sex: F Sources: https://clinicaltrials.gov/ct2/show/results/NCT02648698	Sources: https://clinicaltrials.gov/ct2/show/results/NCT02648698

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2B6 926 CYP2E1 1060	CYP2B6 776

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-618_Tindamax_BioPharmr.pdf#page=17 Page: 17.0	no
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-618_Tindamax_BioPharmr.pdf#page=17 Page: 17.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-618_Tindamax_BioPharmr.pdf#page=17 Page: 17.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-618_Tindamax_BioPharmr.pdf#page=17 Page: 17.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21618_tindamax_lbl.pdf#page=2 Page: 2.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-618_Tindamax_BioPharmr.pdf#page=17 Page: 17.0	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-618_Tindamax_BioPharmr.pdf#page=16 Page: 16.0	major
CYP2B6 776	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-618_Tindamax_BioPharmr.pdf#page=16 Page: 16.0	minor

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:63627	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63627
ChemicalBook	CB2674744	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2674744
eMolecules	594781	https://www.emolecules.com/cgi-bin/more?vid=594781
MolPort	MolPort-000-810-622	https://www.molport.com/shop/molecule-link/MolPort-000-810-622
MolPort	MolPort-006-819-596	https://www.molport.com/shop/molecule-link/MolPort-006-819-596
Selleck Chemicals	tinidazole	http://www.selleckchem.com/products/tinidazole.html
ZINC	ZINC000000113446	http://zinc15.docking.org/substances/ZINC000000113446

PubMed

Title	Date	PubMed
Treatment of metronidazole-resistant Trichomonas vaginalis with tinidazole: case reports of three patients.	2004-06	15167642
Use of imidazole-based eradication regimens for Helicobacter pylori should be abandoned in North India regardless of in vitro antibiotic sensitivity.	2004-06	15151614
The efficacy of some drugs with known antiprotozoal activity against Histomonas meleagridis in chickens.	2004-05-26	15135862
Effectiveness and pharmaceutical cost of sequential treatment for Helicobacter pylori in patients with non-ulcer dyspepsia.	2004-05-01	15113366
Voltammetric determination of tinidazole using a glassy carbon electrode modified with single-wall carbon nanotubes.	2004-05	15171287
Helicobacter pylori eradication: efficacy of conventional therapy in India.	2004-04	15117141
Rank order of success favors longer duration of imidazole-based therapy for Helicobacter pylori in duodenal ulcer disease: a randomized pilot study.	2004-04	15068413
[Dientamoeba fragilis: possibly an important cause of persistent abdominal pain in children].	2004-03-20	15074181
Sequential treatment for Helicobacter pylori does not share the risk factors of triple therapy failure.	2004-02-15	14871280
HPLC and LC-MS studies on stress degradation behaviour of tinidazole and development of a validated specific stability-indicating HPLC assay method.	2004-01-27	14738914
Ciprofloxacin-tinidazole combination, fluconazole- azithromicin-secnidazole-kit and doxycycline- metronidazole combination therapy in syndromic management of pelvic inflammatory disease: a prospective randomized controlled trial.	2003-12	14701947
Oral tinidazole treatment during pregnancy and teratogenesis.	2003-12	14643044
Pharmacokinetic evaluation of guar gum-based colon-targeted drug delivery systems of tinidazole in healthy human volunteers.	2003-11-13	14612342
Efficacy of antigiardial drugs.	2003-11	14585063
One-week low-dose triple therapy without anti-acid treatment has sufficient efficacy on Helicobacter pylori eradication and ulcer healing.	2003-10-24	14571829
Role of antibiotic sensitivity testing before first-line Helicobacter pylori eradication treatments.	2003-10-15	14535876
Randomized study of different 'second-line' therapies for Helicobacter pylori infection after failure of the standard 'Maastricht triple therapy'.	2003-10-15	14535875
[Eradication of Helicobacter pylori].	2003-10-05	14626641
Use of bovine lactoferrin for Helicobacter pylori eradication.	2003-10	14620619
Lactoferrin: milking ulcers?	2003-10	14620616
Giardia intestinalis.	2003-10	14501998
Effects of metronidazole and tinidazole on NTPDase1 and ecto-5'-nucleotidase from intact cells of Trichomonas vaginalis.	2003-09-26	14553936
Sequential treatment for Helicobacter pylori eradication in duodenal ulcer patients: improving the cost of pharmacotherapy.	2003-09-15	12969091
Levofloxacin-based triple therapy vs. quadruple therapy in second-line Helicobacter pylori treatment: a randomized trial.	2003-09-15	12969089
Comparative study on the effects of ointments of tinidazole, hydrocortisone and clobetasol on animal models for inflammatory dermatitis in mice.	2003-09	14639966
Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data.	2003-09	12920490
Primary and secondary antibiotic resistance of Helicobacter pylori strains isolated in central Italy during the years 1998-2002.	2003-08	14567457
Helicobacter pylori eradication and peptic ulcer healing: the impact of deleting the proton pump inhibitor and using a once-daily treatment.	2003-07-01	12848630
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.	2003-07-01	12818447
A novel pH- and time-dependent system for colonic drug delivery.	2003-07	12889784
Rabeprazole in a one-week eradication therapy of Helicobacter pylori: comparison of different dosages.	2003-07	12795749
[Failure of Helicobacter pylori eradication--suggestions for further therapy].	2003-06-29	12894674
Comparison of chloroquine, albendazole and tinidazole in the treatment of children with giardiasis.	2003-06	12831522
Nitroheterocyclic drugs with broad spectrum activity.	2003-06	12811546
Late recurrence of resistant Trichomonas vaginalis vaginitis: relapse or re-infection?	2003-06	12794219
Efficacy and tolerability of a combination of ofloxacin and tinidazole in the management of infectious diabetic foot ulcer.	2003-05	14575233
[Oleyl pyroglutamate for use as transdermal enhancer and its enhancing mechanism].	2003-05	12958846
Use of lactoferrin for Helicobacter pylori eradication. Preliminary results.	2003-04-19	12702979
On the hydrolytic behavior of tinidazole, metronidazole, and ornidazole.	2003-04	12661060
Diagnosis and eradication of Helicobacter pylori in patients with duodenal ulceration in the community.	2003-03	12779020
Triple eradication therapy counteracts functional impairment associated with Helicobacter pylori infection in Mongolian gerbils.	2003-03	12674217
[The clinical evaluation of tinidazole-iodoform root canal paste on treatment of chronic periapical periodontitis associated with ectopic sinus].	2003-02	14661472
[Antiprotozoal drugs].	2003-02	12722315
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.	2003-01	12725603
Serum mineral levels in children with intestinal parasitic infection.	2003	14571100
[Incidence of anaerobic bacteria in respiratory tract infections].	2003	12959026
Single-dose therapy for giardiasis in school-age children.	2002-12	12757214
Design and in vitro evaluation of oral colon targeted drug delivery systems for tinidazole.	2002-12	12683661
Efficacy of the triple therapy: proton pomp inhibitors, amoxicillin and tynidazole in Helicobacter pylori infection treatment.	2002	12898919
Evaluation of diazotized 4-amino-3,5-dinitrobenzoic acid (ADBA) as a new derivatizing reagent.	2001-09	14510132

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%.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 07:43:29 GMT 2025` Edited by `admin` on `Wed Apr 02 07:43:29 GMT 2025`
Record UNII	033KF7V46H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TINIDAZOLE

Official Name

English

HAISIGYN

Preferred 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

TINIDAZOLE [JAN]

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

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

NSC-758189

Code

English

TINIDAZOLE [ORANGE BOOK]

Common Name

English

Tinidazole [WHO-DD]

Common Name

English

CP-12574

Code

English

tinidazole [INN]

Common Name

English

SIMPLOTAN

Brand Name

English

TINIDAZOLE [USP MONOGRAPH]

Common Name

English

TINIDAZOLE [EP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 530.41