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 247 Target ID: CHEMBL2366045 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21618_tindamax_lbl.pdf	Binding Agent 1059

Conditions

Condition	Modality	Highest Phase	Product
Trichomoniasis 18 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21618_tindamax_lbl.pdf	Curative	Approved 8360	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 8360	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 8360	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 1709 inhibitor 1579	inhibitor 1752	inhibitor 1837

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1509 CYP2B6 799 CYP2E1 876	CYP2B6 660

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1673	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-618_Tindamax_BioPharmr.pdf#page=17 Page: 17.0	no
CYP2B6 985	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-618_Tindamax_BioPharmr.pdf#page=17 Page: 17.0	no
CYP2C9 1803	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-618_Tindamax_BioPharmr.pdf#page=17 Page: 17.0	no
CYP2D6 1875	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-618_Tindamax_BioPharmr.pdf#page=17 Page: 17.0	no
CYP2E1 964	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21618_tindamax_lbl.pdf#page=2 Page: 2.0	no
CYP3A4 1909	inhibitor 3240 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 1709	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-618_Tindamax_BioPharmr.pdf#page=16 Page: 16.0	major
CYP2B6 660	substrate 3326 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
[Efficacy of tinidazole-sulfur cream in the treatment of Demodex infection].	2001	12572010
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
Diagnostic advantages and therapeutic options for giardiasis.	2001 Aug	11772266
[Study of bacteriology on local application of Tinidazole stilus in treatment for periodontitis].	2001 Feb	12539636
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Evaluation of diazotized 4-amino-3,5-dinitrobenzoic acid (ADBA) as a new derivatizing reagent.	2001 Sep	14510132
Efficacy of the triple therapy: proton pomp inhibitors, amoxicillin and tynidazole in Helicobacter pylori infection treatment.	2002	12898919
Gastric adenocarcinoma in a patient re-infected with H. pylori after regression of MALT lymphoma with successful anti-H. pylori therapy and gastric resection: a case report.	2002	11914140
Vitamin B12 and folic acid in children with intestinal parasitic infection.	2002 Apr	11999537
Validated HPLC method for the determination of tinidazole in human serum and its application in a clinical pharmacokinetic study.	2002 Aug	12227192
In vitro activity of therapeutic drugs against Histomonas meleagridis (Smith, 1895).	2002 Aug	12211302
[Pharmacotherapeutic aspects of early postoperative period in patients with complicated gastroduodenal ulcer].	2002 Feb	12024723
Gateways to clinical trials.	2002 Jan-Feb	11980386
DNA single strand breaks in peripheral blood lymphocytes induced by three nitroimidazole derivatives.	2002 Jun 14	12044544
The cost-effectiveness of population Helicobacter pylori screening and treatment: a Markov model using economic data from a randomized controlled trial.	2002 Mar	11876711
Spectrophotometric determination of metronidazole and tinidazole in pharmaceutical preparations.	2002 May 15	12008132
Serum mineral levels in children with intestinal parasitic infection.	2003	14571100
Omeprazole plus azithromycin and either amoxicillin or tinidazole for eradication of Helicobacter pylori infection.	2003 Apr	12642739
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	14701947
[The clinical evaluation of tinidazole-iodoform root canal paste on treatment of chronic periapical periodontitis associated with ectopic sinus].	2003 Feb	14661472
[Antiprotozoal drugs].	2003 Feb	12722315
A novel pH- and time-dependent system for colonic drug delivery.	2003 Jul	12889784
Rabeprazole in a one-week eradication therapy of Helicobacter pylori: comparison of different dosages.	2003 Jul	12795749
Helicobacter pylori eradication and peptic ulcer healing: the impact of deleting the proton pump inhibitor and using a once-daily treatment.	2003 Jul 1	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 Jul 1	12818447
Nitroheterocyclic drugs with broad spectrum activity.	2003 Jun	12811546
Late recurrence of resistant Trichomonas vaginalis vaginitis: relapse or re-infection?	2003 Jun	12794219
[Failure of Helicobacter pylori eradication--suggestions for further therapy].	2003 Jun 29	12894674
Effects of metronidazole and tinidazole ointments on models for inflammatory dermatitis in mice.	2003 Mar	12624780
High eradication rates of Helicobacter pylori with a new sequential treatment.	2003 Mar 1	12641522
Two stability-indicating UV spectrophotometric methods for the analysis of hydrolyzed tinidazole.	2003 Mar 10	12615240
Efficacy and tolerability of a combination of ofloxacin and tinidazole in the management of infectious diabetic foot ulcer.	2003 May	14575233
Use of lactoferrin for Helicobacter pylori eradication. Preliminary results.	2003 May-Jun	12702979
Efficacy of antigiardial drugs.	2003 Nov	14585063
Use of bovine lactoferrin for Helicobacter pylori eradication.	2003 Oct	14620619
Lactoferrin: milking ulcers?	2003 Oct	14620616
Giardia intestinalis.	2003 Oct	14501998
Randomized study of different 'second-line' therapies for Helicobacter pylori infection after failure of the standard 'Maastricht triple therapy'.	2003 Oct 15	14535875
[Eradication of Helicobacter pylori].	2003 Oct 5	14626641
Pharmacokinetic evaluation of guar gum-based colon-targeted drug delivery systems of tinidazole in healthy human volunteers.	2003 Oct-Dec	14612342
Comparative study on the effects of ointments of tinidazole, hydrocortisone and clobetasol on animal models for inflammatory dermatitis in mice.	2003 Sep	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 Sep	12920490
Helicobacter pylori eradication: efficacy of conventional therapy in India.	2004 Apr	15117141
Rank order of success favors longer duration of imidazole-based therapy for Helicobacter pylori in duodenal ulcer disease: a randomized pilot study.	2004 Apr	15068413
Sequential treatment for Helicobacter pylori does not share the risk factors of triple therapy failure.	2004 Feb 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 Jan 27	14738914
Treatment of metronidazole-resistant Trichomonas vaginalis with tinidazole: case reports of three patients.	2004 Jun	15167642
Use of imidazole-based eradication regimens for Helicobacter pylori should be abandoned in North India regardless of in vitro antibiotic sensitivity.	2004 Jun	15151614
Effectiveness and pharmaceutical cost of sequential treatment for Helicobacter pylori in patients with non-ulcer dyspepsia.	2004 May 1	15113366
The efficacy of some drugs with known antiprotozoal activity against Histomonas meleagridis in chickens.	2004 May 26	15135862

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 `Thu Jul 06 21:50:33 UTC 2023` Edited by `admin` on `Thu Jul 06 21:50:33 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