Tinidazole

Identification

Summary

Tinidazole is a nitroimidazole used to treat trichomoniasis, giardiasis, amebiasis, and bacterial vaginosis.

Brand Names
Tindamax
Generic Name
Tinidazole
DrugBank Accession Number
DB00911
Background

A nitroimidazole antitrichomonal agent effective against Trichomonas vaginalis, Entamoeba histolytica, and Giardia lamblia infections.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 247.272
Monoisotopic: 247.062676609
Chemical Formula
C8H13N3O4S
Synonyms
  • 1-(2-(Ethylsulfonyl)ethyl)-2-methyl-5-nitroimidazole
  • Timidazole
  • Tinidazol
  • Tinidazole
  • Tinidazolum
External IDs
  • CP-12,574
  • CP-12574

Pharmacology

Indication

For the treatment of trichomoniasis caused by T. vaginalis in both female and male patients. Also for the treatment of giardiasis caused by G. duodenalis in both adults and pediatric patients older than three years of age and 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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAmebiasis••••••••••••
Treatment ofBacterial vaginosis•••••••••••••••••
Used in combination to treatBacterial vaginosis (bv)Combination Product in combination with: Tioconazole (DB01007)•••••••••••••••••••••••
Used in combination to treatCandidal vulvovaginitisCombination Product in combination with: Tioconazole (DB01007)•••••••••••••••••••••••
Treatment ofGiardiasis••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Tinidazole is a synthetic antiprotozoal agent. Tinidazole demonstrates activity both in vitro and in clinical infections against the following protozoa: Trichomonas vaginalis, Giardia duodenalis (also termed G. lamblia), and Entamoeba histolytica. Tinidazole does not appear to have activity against most strains of vaginal lactobacilli.

Mechanism of action

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, though it is probably similar.

TargetActionsOrganism
ADNA
binder
Humans
Absorption

Rapidly and completely absorbed under fasting conditions. Administration with food results in a delay in Tmax of approximately 2 hours and a decline in Cmax of approximately 10% and an AUC of 901.6 ± 126.5 mcg hr/mL.

Volume of distribution
  • 50 L
Protein binding

Plasma protein binding of tinidazole is 12%.

Metabolism

Hepatic, mainly via CYP3A4. Tinidazole, like metronidazole, is significantly metabolized in humans prior to excretion. Tinidazole is partly metabolized by oxidation, hydroxylation and conjugation. Tinidazole is the major drug-related constituent in plasma after human treatment, along with a small amount of the 2-hydroxymethyl metabolite.

Route of elimination

Tinidazole crosses the placental barrier and is secreted in breast milk. Tinidazole is excreted by the liver and the kidneys. Tinidazole is excreted in the urine mainly as unchanged drug (approximately 20-25% of the administered dose). Approximately 12% of the drug is excreted in the feces.

Half-life

The elimination half-life is 13.2±1.4 hours and the plasma half-life is 12 to 14 hours.

Clearance

Not Available

Adverse Effects
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Toxicity

There are no reported overdoses with tinidazole in humans. In acute studies with mice and rats, the LD 50 for mice was generally > 3,600 mg/kg for oral administration and was > 2,300 mg/kg for intraperitoneal administration. In rats, the LD 50 was > 2,000 mg/kg for both oral and intraperitoneal administration.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirTinidazole may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Tinidazole can be increased when it is combined with Abametapir.
AceclofenacAceclofenac may decrease the excretion rate of Tinidazole which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Tinidazole which could result in a higher serum level.
AcenocoumarolThe risk or severity of bleeding can be increased when Tinidazole is combined with Acenocoumarol.
Food Interactions
  • Avoid alcohol. Avoid concomitant use of alcohol with tinidazole as it may cause flushing, nausea, vomiting, and headaches.
  • Take with food. Administering with food may reduce gastrointestinal upset and epigastric discomfort caused by tinidazole but does not affect bioavailability.

Products

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Product Images
International/Other Brands
Fasigyn
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
TindamaxTablet, film coated250 mg/1OralMission Pharmacal Company2004-05-17Not applicableUS flag
TindamaxTablet, film coated500 mg/1OralDepartment Of State Health Services, Pharmacy Branch2016-11-172017-06-23US flag
TindamaxTablet, film coated500 mg/1OralMission Pharmacal Company2004-05-17Not applicableUS flag
TindamaxTablet, film coated500 mg/1OralPhysicians Total Care, Inc.2010-08-23Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
TindazoleTablet, film coated250 mg/1OralPack Pharmaceuticals LLC2013-10-09Not applicableUS flag
TindazoleTablet, film coated500 mg/1OralRedPharm Drug, Inc.2013-10-09Not applicableUS flag
TindazoleTablet, film coated250 mg/1OralRising Pharma Holdings, Inc.2013-10-09Not applicableUS flag
TindazoleTablet, film coated500 mg/1OralPack Pharmaceuticals LLC2013-10-09Not applicableUS flag
TindazoleTablet, film coated500 mg/1OralRising Pharma Holdings, Inc.2013-10-09Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
GYNOMAX 100 MG/150 MG VAJINAL OVUL, 7 ADETTinidazole (150 mg) + Tioconazole (100 mg)SuppositoryVaginalEXELTIS İLAÇ SAN. VE TİC. A.Ş.2006-07-24Not applicableTurkey flag
GYNOMAX L VAJINAL OVUL, 7 ADETTinidazole (150 mg) + Lidocaine hydrochloride (123.26 mg) + Tioconazole (100 mg)SuppositoryVaginalEXELTIS İLAÇ SAN. VE TİC. A.Ş.2011-09-20Not applicableTurkey flag
GYNOMAX XL 200 MG/ 300 MG/100 MG VAJINAL OVÜL, 3 ADETTinidazole (300 mg) + Lidocaine hydrochloride (123.26 mg) + Tioconazole (200 mg)SuppositoryVaginalEXELTIS İLAÇ SAN. VE TİC. A.Ş.2013-02-04Not applicableTurkey flag
TRİVAG 300 MG / 200 MG/ 100 MG OVÜL, 3 ADETTinidazole (300 mg) + Lidocaine (100 mg) + Tioconazole (200 mg)SuppositoryRectalBİLİM İLAÇ SAN. VE TİC. A.Ş.2017-09-29Not applicableTurkey flag

Categories

ATC Codes
J01RA11 — Ciprofloxacin and tinidazoleJ01RA13 — Norfloxacin and tinidazoleA02BD09 — Lansoprazole, clarithromycin and tinidazoleJ01XD02 — TinidazoleG01AF20 — Combinations of imidazole derivativesG01AF21 — TinidazoleP01AB02 — Tinidazole
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as nitroimidazoles. These are compounds containing an imidazole ring which bears a nitro group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Imidazoles
Direct Parent
Nitroimidazoles
Alternative Parents
Nitroaromatic compounds / 1,2,5-trisubstituted imidazoles / N-substituted imidazoles / Sulfones / Heteroaromatic compounds / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 2 more
Substituents
1,2,5-trisubstituted-imidazole / Allyl-type 1,3-dipolar organic compound / Aromatic heteromonocyclic compound / Azacycle / C-nitro compound / Heteroaromatic compound / Hydrocarbon derivative / N-substituted imidazole / Nitroaromatic compound / Nitroimidazole
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
imidazoles (CHEBI:63627)
Affected organisms
  • Trichomonas vaginalis, Giardia duodenalis, and Entamoeba histolytica

Chemical Identifiers

UNII
033KF7V46H
CAS number
19387-91-8
InChI Key
HJLSLZFTEKNLFI-UHFFFAOYSA-N
InChI
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
IUPAC Name
1-[2-(ethanesulfonyl)ethyl]-2-methyl-5-nitro-1H-imidazole
SMILES
CCS(=O)(=O)CCN1C(C)=NC=C1[N+]([O-])=O

References

General References
  1. Lopez Nigro MM, Carballo MA: Genotoxicity and cell death induced by tinidazole (TNZ). Toxicol Lett. 2008 Jul 30;180(1):46-52. doi: 10.1016/j.toxlet.2008.05.017. Epub 2008 Jun 5. [Article]
  2. Fung HB, Doan TL: Tinidazole: a nitroimidazole antiprotozoal agent. Clin Ther. 2005 Dec;27(12):1859-84. [Article]
  3. FDA Approved Drug Products: Tindamax (tinidazole) tablets for oral use [Link]
Human Metabolome Database
HMDB0015047
KEGG Drug
D01426
PubChem Compound
5479
PubChem Substance
46506396
ChemSpider
5279
BindingDB
50248360
RxNav
10612
ChEBI
63627
ChEMBL
CHEMBL1220
ZINC
ZINC000000113446
PharmGKB
PA10813
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Tinidazole
FDA label
Download (249 KB)
MSDS
Download (73.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentAnti-drug antibody development / Cholangitis, Secondary Biliary / Compliance, Treatment1
4CompletedTreatmentBacterial Vaginosis (BV)1
4CompletedTreatmentHelicobacter Pylori Infection2
4CompletedTreatmentInfections, Helicobacter1
4RecruitingTreatmentHelicobacter Pylori Infection2

Pharmacoeconomics

Manufacturers
  • Mission pharmacal co
Packagers
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • BioComp Pharma
  • Mikart Inc.
  • Mission Pharmacal
  • Novartis AG
  • PD-Rx Pharmaceuticals Inc.
  • Presutti Laboratories Inc.
Dosage Forms
FormRouteStrength
Capsule, coatedOral500 mg
TabletOral37.500 mg
Tablet, coatedOral1000 mg
TabletOral
Tablet, coatedOral
SuppositoryVaginal
TabletOral
Tablet, coatedOral100000 g
TabletOral300 mg
InsertVaginal
TabletOral0.5 g
Tablet, film coatedOral500 mg/1
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral1000 mg
TabletOral1000 mg
SuspensionOral20 g
Tablet, coatedOral500.321 mg
Tablet, coatedOral510 mg
TabletOral1 g
Tablet, coatedOral1 g
Tablet, film coatedOral1 g
TabletOral250 mg/1
TabletOral500 mg/1
InsertVaginal800.00 mg
TabletOral500.000 mg
SuppositoryRectal
Capsule, coatedOral1 g
TabletOral500 mg
Tablet, coatedOral500 mg
Tablet, film coatedOral500 mg
Capsule500 mg
Prices
Unit descriptionCostUnit
Tindamax 500 mg tablet9.02USD tablet
Tinidazole 500 mg tablet4.73USD tablet
Tindamax 250 mg tablet3.25USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)127-128 °CPhysProp
water solubility1.99E+004 mg/LNot Available
logP-0.35HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility3.03 mg/mLALOGPS
logP-0.41ALOGPS
logP-0.58Chemaxon
logS-1.9ALOGPS
pKa (Strongest Basic)3.28Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area95.1 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity56.66 m3·mol-1Chemaxon
Polarizability23.33 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.975
Blood Brain Barrier+0.9308
Caco-2 permeable-0.6003
P-glycoprotein substrateSubstrate0.6257
P-glycoprotein inhibitor INon-inhibitor0.7815
P-glycoprotein inhibitor IINon-inhibitor0.9706
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.7946
CYP450 2D6 substrateNon-substrate0.8931
CYP450 3A4 substrateSubstrate0.5149
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.876
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7518
Ames testAMES toxic0.9106
CarcinogenicityNon-carcinogens0.5986
BiodegradationNot ready biodegradable0.7608
Rat acute toxicity2.1458 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5582
hERG inhibition (predictor II)Non-inhibitor0.5554
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0fb9-9810000000-354c2d3adb67449ebc17
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-004i-4910000000-8c46b903514b344ac47c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0290000000-6e567c97c2cf4ca3fd01
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0390000000-28e470db2eb20392a17a
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-4910000000-8c46b903514b344ac47c
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-157.6669742
predicted
DarkChem Lite v0.1.0
[M-H]-157.8402742
predicted
DarkChem Lite v0.1.0
[M-H]-135.40982
predicted
DeepCCS 1.0 (2019)
[M+H]+158.6214742
predicted
DarkChem Lite v0.1.0
[M+H]+158.4850742
predicted
DarkChem Lite v0.1.0
[M+H]+138.67197
predicted
DeepCCS 1.0 (2019)
[M+Na]+158.0748742
predicted
DarkChem Lite v0.1.0
[M+Na]+158.2360742
predicted
DarkChem Lite v0.1.0
[M+Na]+147.03032
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Nucleotide
Organism
Humans
Pharmacological action
Yes
Actions
Binder
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
References
  1. Fung HB, Doan TL: Tinidazole: a nitroimidazole antiprotozoal agent. Clin Ther. 2005 Dec;27(12):1859-84. [Article]
  2. Lopez Nigro MM, Carballo MA: Genotoxicity and cell death induced by tinidazole (TNZ). Toxicol Lett. 2008 Jul 30;180(1):46-52. doi: 10.1016/j.toxlet.2008.05.017. Epub 2008 Jun 5. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. FDA Approved Drug Products: Tindamax (tinidazole) tablets for oral use [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:46