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 278 Target ID: CHEMBL2366045 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21618_tindamax_lbl.pdf	Binding Agent 1064

Conditions

Condition	Modality	Highest Phase	Product
Trichomoniasis 18 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21618_tindamax_lbl.pdf	Curative	Approved 8429	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 1.11542403E12
Giardiasis 12 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21618_tindamax_lbl.pdf	Curative	Approved 8429	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 1.11542403E12
Amebiasis 11 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21618_tindamax_lbl.pdf	Curative	Approved 8429	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 1.11542403E12

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 Co-administed with:: Doxycycline(100mg, PO, Q2D7) Sources: https://clinicaltrials.gov/ct2/show/NCT00322465	unhealthy, 27.8 n = 73 Health Status: unhealthy Condition: Urethritis Age Group: 27.8 Sex: M Population Size: 73 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 n = 196 Health Status: unhealthy Condition: Bacterial Vaginosis Age Group: 28.5 Sex: F Population Size: 196 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 n = 60 Health Status: unhealthy Condition: Chronic Endometritis Age Group: 31.93 Sex: F Population Size: 60 Sources: https://clinicaltrials.gov/ct2/show/results/NCT02648698	Sources: https://clinicaltrials.gov/ct2/show/results/NCT02648698

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2B6 810 CYP2E1 882	CYP2B6 664

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-618_Tindamax_BioPharmr.pdf#page=17 Page: 17.0	no
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-618_Tindamax_BioPharmr.pdf#page=17 Page: 17.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-618_Tindamax_BioPharmr.pdf#page=17 Page: 17.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-618_Tindamax_BioPharmr.pdf#page=17 Page: 17.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21618_tindamax_lbl.pdf#page=2 Page: 2.0	no
CYP3A4 1925	inhibitor 3277 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 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-618_Tindamax_BioPharmr.pdf#page=16 Page: 16.0	major
CYP2B6 664	substrate 3367 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
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
eMolecules	594781	https://www.emolecules.com/cgi-bin/more?vid=594781

PubMed

Title	Date	PubMed
Adenosine deaminase activity in the gastric mucosa of duodenal ulcer patients in relation to the severity of chronic gastritis and gastric acid secretion.	2001	11780574
Efficacy of Helicobacter pylori eradication therapies: a single centre observational study.	2001	11545677
Factors affecting Helicobacter pylori eradication using a seven-day triple therapy with a proton pump inhibitor, tinidazole and clarithromycin, in Brazilian patients with peptic ulcer.	2001 Jan-Feb	11378678
[In vitro measurement of nitazoxanide sensitivity of 4 Giardia duodenalis isolates obtained from different hosts].	2001 Jan-Feb	11332050
[Role of Helicobacter pylori infection in insulin-dependent diabetes mellitus].	2001 Jun	11404721
Evaluation of genetic damage induced by a nitroimidazole derivative in human lymphocytes: Tinidazole (TNZ).	2001 Jun	11377093
Efficacy and tolerability of antibiotics in patients undergoing H. pylori eradication.	2001 Mar-Apr	11379334
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Two new treatment regimens for Helicobacter pylori eradication: a randomised study.	2001 Nov	11785713
Levofloxacin based regimens for the eradication of Helicobacter pylori.	2002 Dec	12468950
DNA single strand breaks in peripheral blood lymphocytes induced by three nitroimidazole derivatives.	2002 Jun 14	12044544
Spectrophotometric determination of metronidazole and tinidazole in pharmaceutical preparations.	2002 May 15	12008132
Sequential eradicating therapy: a treatment that does not discriminate Helicobacter pylori strains in patients with nonulcer dyspepsia?	2002 Oct	12385470
A simple and rapid liquid chromatographic method for the determination of metronidazole and its hydroxymetabolite in plasma and cutaneous microdialysates.	2002 Sep-Oct	12602792
Oral tinidazole treatment during pregnancy and teratogenesis.	2003 Dec	14643044
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	12725603
A novel pH- and time-dependent system for colonic drug delivery.	2003 Jul	12889784
Use of bovine lactoferrin for Helicobacter pylori eradication.	2003 Oct	14620619
[Eradication of Helicobacter pylori].	2003 Oct 5	14626641
Comparative study on the effects of ointments of tinidazole, hydrocortisone and clobetasol on animal models for inflammatory dermatitis in mice.	2003 Sep	14639966
One-week low-dose triple therapy without anti-acid treatment has sufficient efficacy on Helicobacter pylori eradication and ulcer healing.	2003 Sep-Oct	14571829
Use of imidazole-based eradication regimens for Helicobacter pylori should be abandoned in North India regardless of in vitro antibiotic sensitivity.	2004 Jun	15151614

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 `Sat Dec 16 16:20:29 UTC 2023` Edited by `admin` on `Sat Dec 16 16:20:29 UTC 2023`
Record UNII	033KF7V46H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TINIDAZOLE

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

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

HAISIGYN

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