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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Amebiasis •••••••••••• Treatment of Bacterial vaginosis •••••••••••• ••••• Used in combination to treat Bacterial vaginosis (bv) Combination Product in combination with: Tioconazole (DB01007) •••••••••••• ••••••••••• Used in combination to treat Candidal vulvovaginitis Combination Product in combination with: Tioconazole (DB01007) •••••••••••• ••••••••••• Treatment of Giardiasis •••••••••••• - 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.
Target Actions Organism ADNA binderHumans - 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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Tinidazole may decrease the excretion rate of Abacavir which could result in a higher serum level. Abametapir The serum concentration of Tinidazole can be increased when it is combined with Abametapir. Aceclofenac Aceclofenac may decrease the excretion rate of Tinidazole which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Tinidazole which could result in a higher serum level. Acenocoumarol The 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
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Images
- International/Other Brands
- Fasigyn
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Tindamax Tablet, film coated 500 mg/1 Oral Department Of State Health Services, Pharmacy Branch 2016-11-17 2017-06-23 US Tindamax Tablet, film coated 500 mg/1 Oral Mission Pharmacal Company 2004-05-17 Not applicable US Tindamax Tablet, film coated 500 mg/1 Oral Physicians Total Care, Inc. 2010-08-23 Not applicable US Tindamax Tablet, film coated 250 mg/1 Oral Mission Pharmacal Company 2004-05-17 Not applicable US - Generic Prescription Products
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image GYNOMAX 100 MG/150 MG VAJINAL OVUL, 7 ADET Tinidazole (150 mg) + Tioconazole (100 mg) Suppository Vaginal EXELTIS İLAÇ SAN. VE TİC. A.Ş. 2006-07-24 Not applicable Turkey GYNOMAX L VAJINAL OVUL, 7 ADET Tinidazole (150 mg) + Lidocaine hydrochloride (123.26 mg) + Tioconazole (100 mg) Suppository Vaginal EXELTIS İLAÇ SAN. VE TİC. A.Ş. 2011-09-20 Not applicable Turkey GYNOMAX XL 200 MG/ 300 MG/100 MG VAJINAL OVÜL, 3 ADET Tinidazole (300 mg) + Lidocaine hydrochloride (123.26 mg) + Tioconazole (200 mg) Suppository Vaginal EXELTIS İLAÇ SAN. VE TİC. A.Ş. 2013-02-04 Not applicable Turkey TRİVAG 300 MG / 200 MG/ 100 MG OVÜL, 3 ADET Tinidazole (300 mg) + Lidocaine (100 mg) + Tioconazole (200 mg) Suppository Rectal BİLİM İLAÇ SAN. VE TİC. A.Ş. 2017-09-29 Not applicable Turkey
Categories
- ATC Codes
- J01RA11 — Ciprofloxacin and tinidazole
- J01RA — Combinations of antibacterials
- J01R — COMBINATIONS OF ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J01RA — Combinations of antibacterials
- J01R — COMBINATIONS OF ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- J01XD — Imidazole derivatives
- J01X — OTHER ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- G01AF — Imidazole derivatives
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- G01AF — Imidazole derivatives
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- Alimentary Tract and Metabolism
- Alkylating Drugs
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Antiparasitic Agents
- Antiparasitic Products, Insecticides and Repellents
- Antiprotozoals
- Antitrichomonal Agents
- BSEP/ABCB11 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Drugs for Acid Related Disorders
- Drugs for Peptic Ulcer and Gastro-Oesophageal Reflux Disease (Gord)
- Drugs that are Mainly Renally Excreted
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Imidazole Derivatives
- Imidazoles
- Nitro Compounds
- Nitroimidazole Antimicrobial
- Nitroimidazole Derivatives
- Nitroimidazoles
- Noxae
- Toxic Actions
- 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
- 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]
- Fung HB, Doan TL: Tinidazole: a nitroimidazole antiprotozoal agent. Clin Ther. 2005 Dec;27(12):1859-84. [Article]
- FDA Approved Drug Products: Tindamax (tinidazole) tablets for oral use [Link]
- External Links
- Human Metabolome Database
- HMDB0015047
- KEGG Drug
- D01426
- PubChem Compound
- 5479
- PubChem Substance
- 46506396
- ChemSpider
- 5279
- BindingDB
- 50248360
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Anti-drug antibody development / Cholangitis, Secondary Biliary / Compliance, Treatment 1 4 Completed Treatment Bacterial Vaginosis (BV) 1 4 Completed Treatment Helicobacter Infections 1 4 Completed Treatment Helicobacter Pylori Infection 2 4 Recruiting Treatment Helicobacter Pylori Infection 2
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
Form Route Strength Capsule, coated Oral 500 mg Tablet Oral 37.500 mg Tablet, coated Oral 1000 mg Tablet Oral Tablet, coated Oral Suppository Vaginal Tablet Oral Tablet, coated Oral 100000 g Tablet Oral 300 mg Tablet Oral 0.5 g Tablet, film coated Oral 500 mg/1 Tablet, film coated Oral 250 mg/1 Tablet, film coated Oral 1000 mg Tablet Oral 1000 mg Suspension Oral 20 g Tablet, coated Oral 500.321 mg Tablet, coated Oral 510 mg Tablet Oral 1 g Tablet, coated Oral 1 g Tablet, film coated Oral 1 g Tablet Oral 250 mg/1 Tablet Oral 500 mg/1 Insert Vaginal Insert Vaginal 800.00 mg Tablet Oral 500.000 mg Suppository Rectal Capsule, coated Oral 1 g Tablet Oral 500 mg Tablet, coated Oral 500 mg Tablet, film coated Oral 500 mg Capsule 500 mg - Prices
Unit description Cost Unit Tindamax 500 mg tablet 9.02USD tablet Tinidazole 500 mg tablet 4.73USD tablet Tindamax 250 mg tablet 3.25USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 127-128 °C PhysProp water solubility 1.99E+004 mg/L Not Available logP -0.35 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 3.03 mg/mL ALOGPS logP -0.41 ALOGPS logP -0.58 Chemaxon logS -1.9 ALOGPS pKa (Strongest Basic) 3.28 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 95.1 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 56.66 m3·mol-1 Chemaxon Polarizability 23.33 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.975 Blood Brain Barrier + 0.9308 Caco-2 permeable - 0.6003 P-glycoprotein substrate Substrate 0.6257 P-glycoprotein inhibitor I Non-inhibitor 0.7815 P-glycoprotein inhibitor II Non-inhibitor 0.9706 Renal organic cation transporter Non-inhibitor 0.8178 CYP450 2C9 substrate Non-substrate 0.7946 CYP450 2D6 substrate Non-substrate 0.8931 CYP450 3A4 substrate Substrate 0.5149 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.876 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7518 Ames test AMES toxic 0.9106 Carcinogenicity Non-carcinogens 0.5986 Biodegradation Not ready biodegradable 0.7608 Rat acute toxicity 2.1458 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.5582 hERG inhibition (predictor II) Non-inhibitor 0.5554
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 157.6669742 predictedDarkChem Lite v0.1.0 [M-H]- 157.8402742 predictedDarkChem Lite v0.1.0 [M-H]- 135.40982 predictedDeepCCS 1.0 (2019) [M+H]+ 158.6214742 predictedDarkChem Lite v0.1.0 [M+H]+ 158.4850742 predictedDarkChem Lite v0.1.0 [M+H]+ 138.67197 predictedDeepCCS 1.0 (2019) [M+Na]+ 158.0748742 predictedDarkChem Lite v0.1.0 [M+Na]+ 158.2360742 predictedDarkChem Lite v0.1.0 [M+Na]+ 147.03032 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
References
- Fung HB, Doan TL: Tinidazole: a nitroimidazole antiprotozoal agent. Clin Ther. 2005 Dec;27(12):1859-84. [Article]
- 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
- 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
- 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