Identification
- Summary
Trimethobenzamide is an antiemetic used to treat postoperative nausea and vomiting and nausea associated with gastroenteritis.
- Brand Names
- Tigan
- Generic Name
- Trimethobenzamide
- DrugBank Accession Number
- DB00662
- Background
Trimethobenzamide is a novel antiemetic which prevents nausea and vomiting in humans. Its actions are unclear but most likely involves the chemoreceptor trigger zone (CTZ). In dogs pretreated with trimethobenzamide HCl, the emetic response to apomorphine is inhibited, while little or no protection is afforded against emesis induced by intragastric copper sulfate.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Trimethobenzamide (DB00662)
- Weight
- Average: 388.4574
Monoisotopic: 388.199822016 - Chemical Formula
- C21H28N2O5
- Synonyms
- N-[[4-(2-dimethylaminoethoxy)phenyl]methyl]-3,4,5-trimethoxybenzamide
- Trimethobenzamide
- Trimethobenzamidum
- Trimetobenzamida
Pharmacology
- Indication
For the treatment of postoperative nausea and vomiting and for nausea associated with gastroenteritis.
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- Contraindications & Blackbox Warnings
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Trimethobenzamide is a novel antiemetic which prevents nausea and vomiting in humans. Its actions are unclear but most likely involves the chemoreceptor trigger zone (CTZ). In dogs pretreated with trimethobenzamide HCl, the emetic response to apomorphine is inhibited, while little or no protection is afforded against emesis induced by intragastric copper sulfate.
- Mechanism of action
The mechanism of action of trimethobenzamide as determined in animals is obscure, but may involve the chemoreceptor trigger zone (CTZ), an area in the medulla oblongata through which emetic impulses are conveyed to the vomiting center; direct impulses to the vomiting center apparently are not similarly inhibited.
- Absorption
The relative bioavailability of the capsule formulation compared to the solution is 100%.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic.
- Route of elimination
Between 30 – 50% of a single dose in humans is excreted unchanged in the urine within 48–72 hours.
- Half-life
The mean elimination half-life of trimethobenzamide is 7 to 9 hours.
- Clearance
Not Available
- Adverse Effects
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Oral LD50 in mice is 1600 mg/kg.
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Trimethobenzamide is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Trimethobenzamide is combined with Acetazolamide. Acetophenazine The risk or severity of CNS depression can be increased when Trimethobenzamide is combined with Acetophenazine. Agomelatine The risk or severity of CNS depression can be increased when Trimethobenzamide is combined with Agomelatine. Alfentanil The risk or severity of CNS depression can be increased when Trimethobenzamide is combined with Alfentanil. Alimemazine The risk or severity of CNS depression can be increased when Trimethobenzamide is combined with Alimemazine. Almotriptan The risk or severity of CNS depression can be increased when Trimethobenzamide is combined with Almotriptan. Alosetron The risk or severity of CNS depression can be increased when Trimethobenzamide is combined with Alosetron. Alprazolam The risk or severity of CNS depression can be increased when Alprazolam is combined with Trimethobenzamide. Alverine The risk or severity of CNS depression can be increased when Trimethobenzamide is combined with Alverine. 
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- Avoid alcohol. Ingestion of alcohol may increase the CNS depressant effects of trimethobenzamide causing drowsiness.
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 Ingredients
Ingredient UNII CAS InChI Key Trimethobenzamide hydrochloride WDQ5P1SX7Q 554-92-7 WIIZEEPFHXAUND-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Benzacot / Stemetic / Tebamide (GlaxoSmithKline) / Tribenzagan / Trimazide
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Tigan Injection 100 mg/1mL Intramuscular Par Pharmaceutical, Inc. 2008-08-01 2022-03-31 US 
Tigan Injection 100 mg/1mL Intramuscular General Injectables & Vaccines, Inc 2010-08-01 2024-09-30 US Tigan Suppository 100 mg/1 Rectal Monarch Pharmaceuticals, Inc. 2006-10-10 2006-10-10 US Tigan Injection 100 mg/1mL Intramuscular Henry Schein, Inc 2022-01-11 Not applicable US Tigan Injection 100 mg/1mL Intramuscular Physicians Total Care, Inc. 1974-07-12 2008-05-01 US Tigan Injection 100 mg/2mL Intramuscular Monarch Pharmaceuticals, Inc. 2006-11-15 2006-11-15 US Tigan Capsule 300 mg/1 Oral REMEDYREPACK INC. 2018-05-25 Not applicable US Tigan Capsule 300 mg/1 Oral Pfizer Laboratories Div Pfizer Inc 2001-12-13 2021-09-30 US Tigan Suppository 200 mg/1 Rectal Monarch Pharmaceuticals, Inc. 2006-10-10 2006-10-10 US Tigan Injection 100 mg/1mL Intramuscular Par Pharmaceutical, Inc. 2008-08-01 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Trimethobenzamide Capsule 300 mg/1 Oral Direct_Rx 2019-07-03 Not applicable US Trimethobenzamide Hydrochloride Capsule 300 mg/1 Oral A-S Medication Solutions 2011-01-17 Not applicable US 
Trimethobenzamide Hydrochloride Capsule 300 mg/1 Oral bryant ranch prepack 2003-08-28 Not applicable US Trimethobenzamide Hydrochloride Capsule 300 mg/1 Oral REMEDYREPACK INC. 2017-05-09 2020-04-06 US Trimethobenzamide Hydrochloride Injection 100 mg/1mL Intramuscular Par Pharmaceutical 2012-06-01 2015-02-28 US Trimethobenzamide Hydrochloride Injection, solution 200 mg/1mL Intramuscular AMERICAN REGENT, INC. 2011-04-08 2011-04-08 US Trimethobenzamide hydrochloride Capsule 300 mg/1 Oral Actavis Totowa LLC 2003-09-01 2008-08-20 US Trimethobenzamide Hydrochloride Injection, solution 100 mg/1mL Intramuscular General Injectables & Vaccines 2010-03-01 2017-01-16 US Trimethobenzamide Hydrochloride Capsule 300 mg/1 Oral bryant ranch prepack 2011-01-17 Not applicable US Trimethobenzamide Hydrochloride Capsule 300 mg/1 Oral Remedy Repack 2013-09-27 2014-09-27 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image EMEDUR 100 MG/20 MG SUPOZİTUAR, 5 ADET Trimethobenzamide hydrochloride (100 mg) + Benzocaine (20 mg) Suppository Rectal SANOFİ SAĞLIK ÜRÜNLERİ LTD. ŞTİ. 2020-08-14 Not applicable Turkey 
EMEDUR 200 MG SUPOZITUAR, 100 ADET Trimethobenzamide hydrochloride (200 mg) + Benzocaine (40 mg) Suppository Rectal SANOFİ SAĞLIK ÜRÜNLERİ LTD. ŞTİ. 2020-08-14 2021-06-18 Turkey EMEDUR 200 MG SUPOZITUAR, 5 ADET Trimethobenzamide hydrochloride (200 mg) + Benzocaine (40 mg) Suppository Rectal SANOFİ SAĞLIK ÜRÜNLERİ LTD. ŞTİ. 2020-08-14 2021-06-18 Turkey EMEDUR 200 MG SUPOZITUAR, 50 ADET Trimethobenzamide hydrochloride (200 mg) + Benzocaine (40 mg) Suppository Rectal SANOFİ SAĞLIK ÜRÜNLERİ LTD. ŞTİ. 2020-08-14 2021-06-18 Turkey - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Tigan Trimethobenzamide hydrochloride (100 mg/1) Suppository Rectal Physicians Total Care, Inc. 1994-06-09 2007-05-01 US Trimethobenzamide Hydorchloride Trimethobenzamide hydrochloride (100 mg/1) Suppository Rectal Physicians Total Care, Inc. 2004-05-01 2007-09-07 US Trimethobenzamide Hydorchloride Trimethobenzamide hydrochloride (200 mg/1) Suppository Rectal Physicians Total Care, Inc. 2004-03-01 2007-09-07 US
Categories
- ATC Codes
- R06AA10 — Trimethobenzamide
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as n-benzylbenzamides. These are compounds containing a benzamide moiety that is N-linked to a benzyl group.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzoic acids and derivatives
- Direct Parent
- N-benzylbenzamides
- Alternative Parents
- Phenoxy compounds / Methoxybenzenes / Benzoyl derivatives / Anisoles / Alkyl aryl ethers / Trialkylamines / Secondary carboxylic acid amides / Amino acids and derivatives / Organopnictogen compounds / Organic oxides show 1 more
- Substituents
- Alkyl aryl ether / Amine / Amino acid or derivatives / Anisole / Aromatic homomonocyclic compound / Benzoyl / Carboxamide group / Carboxylic acid derivative / Ether / Hydrocarbon derivative show 13 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- tertiary amino compound, benzamides (CHEBI:27796)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- W2X096QY97
- CAS number
- 138-56-7
- InChI Key
- FEZBIKUBAYAZIU-UHFFFAOYSA-N
- InChI
- InChI=1S/C21H28N2O5/c1-23(2)10-11-28-17-8-6-15(7-9-17)14-22-21(24)16-12-18(25-3)20(27-5)19(13-16)26-4/h6-9,12-13H,10-11,14H2,1-5H3,(H,22,24)
- IUPAC Name
- N-({4-[2-(dimethylamino)ethoxy]phenyl}methyl)-3,4,5-trimethoxybenzamide
- SMILES
- COC1=CC(=CC(OC)=C1OC)C(=O)NCC1=CC=C(OCCN(C)C)C=C1
References
- Synthesis Reference
Vittorio Rossetti, Alessandro Dondoni, Giancarlo Fantin, "N-(4-Hydroxybenzyl)-3,4,5-trimethoxybenzamide and method for producing trimethobenzamide chlorohydrate." U.S. Patent US4507499, issued December, 1969.
US4507499- General References
- Hurley JD, Eshelman FN: Trimethobenzamide HCl in the treatment of nausea and vomiting associated with antineoplastic chemotherapy. J Clin Pharmacol. 1980 May-Jun;20(5-6 Pt 1):352-6. [Article]
- Dundee JW, Halliday F, Nicholl RM, Moore J: Studies of drugs given before anaesthesia. X. Two non-phenothiazine anti-emetics--cyclizine and trimethobenzamide. Br J Anaesth. 1966 Jan;38(1):50-7. [Article]
- FDA Approved Drug Products: TIGAN (trimethobenzamide hydrochloride) capsules [Link]
- FDA Approved Drug Products: TIGAN (trimethobenzamide hydrochloride) injection [Link]
- External Links
- Human Metabolome Database
- HMDB0014800
- KEGG Drug
- D08643
- KEGG Compound
- C07178
- PubChem Compound
- 5577
- PubChem Substance
- 46507787
- ChemSpider
- 5375
- 38685
- ChEBI
- 27796
- ChEMBL
- CHEMBL1201256
- ZINC
- ZINC000000538509
- PharmGKB
- PA164764516
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Trimethobenzamide
- FDA label
- Download (36.7 KB)
- MSDS
- Download (73.5 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Akinesia / Delayed Levodopa Onset / Mobility decreased / Motor Symptoms / Parkinson's Disease (PD) 1 4 Completed Treatment Parkinson's Disease (PD) 1 1 Completed Basic Science Healthy Subjects (HS) 1 1 Completed Basic Science Idiopathic Parkinson's Disease 1
Pharmacoeconomics
- Manufacturers
- King pharmaceuticals inc
- Actavis totowa llc
- Mutual pharmacal co
- Jhp pharmaceuticals llc
- Hospira inc
- Smith and nephew solopak div smith and nephew
- Solopak medical products inc
- Watson laboratories inc
- Packagers
- Actavis Group
- A-S Medication Solutions LLC
- C.O. Truxton Inc.
- Direct Dispensing Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- G & W Labs
- Gipharmex SPA
- H.J. Harkins Co. Inc.
- Hospira Inc.
- International Ethical Labs Inc.
- Iopharm Laboratories Inc.
- JHP Pharmaceuticals LLC
- Kaiser Foundation Hospital
- King Pharmaceuticals Inc.
- Liberty Pharmaceuticals
- Major Pharmaceuticals
- Monarch Pharmacy
- Murfreesboro Pharmaceutical Nursing Supply
- Mutual Pharmaceutical Co.
- Nucare Pharmaceuticals Inc.
- Paddock Labs
- PD-Rx Pharmaceuticals Inc.
- Pecos Pharmaceutical Inc.
- Perrigo Co.
- Pharmedix
- Physician Partners Ltd.
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Qualitest
- Rebel Distributors Corp.
- Redpharm Drug
- Shire Inc.
- Southwood Pharmaceuticals
- Spectrum Pharmaceuticals
- Stat Rx Usa
- Veratex Corp.
- Dosage Forms
Form Route Strength Solution / drops Oral 50 mg/0.5mL Suppository Rectal Tablet, film coated 200 mg Injection, solution Intramuscular Injection, solution Intramuscular 200 mg/2ml Tablet, coated 200 mg Injection Intramuscular 100 mg/20mL Injection Intramuscular 100 mg/1mL Injection Intramuscular 100 mg/2mL Suppository Rectal 100 mg/1 Suppository Rectal 200 mg/1 Capsule Oral 300 mg/1 Injection, solution Intramuscular 100 mg/1mL Injection, solution Intramuscular 200 mg/1mL Suppository Rectal 100 mg Injection Intramuscular 200 mg/2mL Suppository Rectal 200 mg Injection, solution Intramuscular 100 mg Injection, solution Intramuscular 200 mg Capsule Oral 250 mg - Prices
Unit description Cost Unit Trimethobenzamide hcl powder 44.24USD g Tigan 100 mg/ml vial 7.06USD ml Trimethobenzamide HCl 300 mg capsule 1.7USD capsule Tigan 300 mg capsule 1.52USD capsule Trimethobenzamide 100 mg/ml 1.47USD ml Trimethobenzamide 250 mg cap 1.1USD each Trimethobenzamide 300 mg cap 0.99USD each 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) 188.7 °C PhysProp water solubility 40 mg/L Not Available logP 2.29 EL TAYER,N ET AL. (1985) pKa 8.78 EL TAYAR,N ET AL. (1985) - Predicted Properties
Property Value Source Water Solubility 0.0398 mg/mL ALOGPS logP 2.44 ALOGPS logP 2.16 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 14.68 Chemaxon pKa (Strongest Basic) 8.77 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 69.26 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 108.52 m3·mol-1 Chemaxon Polarizability 43.19 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9898 Blood Brain Barrier + 0.8121 Caco-2 permeable + 0.6907 P-glycoprotein substrate Substrate 0.6855 P-glycoprotein inhibitor I Inhibitor 0.6152 P-glycoprotein inhibitor II Non-inhibitor 0.5571 Renal organic cation transporter Non-inhibitor 0.6259 CYP450 2C9 substrate Non-substrate 0.7472 CYP450 2D6 substrate Non-substrate 0.6388 CYP450 3A4 substrate Substrate 0.7204 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8188 Ames test Non AMES toxic 0.7153 Carcinogenicity Non-carcinogens 0.7638 Biodegradation Not ready biodegradable 0.9285 Rat acute toxicity 2.3338 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9673 hERG inhibition (predictor II) Non-inhibitor 0.6758
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:53