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Identification
NameTrimethobenzamide
Accession NumberDB00662  (APRD01277)
TypeSmall Molecule
GroupsApproved
DescriptionTrimethobenzamide 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.
Structure
Thumb
Synonyms
N-[[4-(2-Dimethylaminoethoxy)phenyl]methyl]-3,4,5-trimethoxybenzamide
Trimethobenzamidum
Trimetobenzamida
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Tigancapsule300 mg/1oralPfizer Laboratories Div Pfizer Inc2001-12-13Not applicableUs
Tiganinjection100 mg/mLintramuscularRebel Distributors Corp2007-11-01Not applicableUs
Tigancapsule300 mg/1oralREMEDYREPACK INC.2013-03-11Not applicableUs
Tiganinjection100 mg/mLintramuscularPar Pharmaceutical, Inc.2007-11-01Not applicableUs
Tiganinjection100 mg/mLintramuscularPar Pharmaceutical, Inc.2007-11-01Not applicableUs
Tiganinjection, solution100 mg/mLintramuscularGeneral Injectables & Vaccines, Inc2010-08-01Not applicableUs
Trimethobenzamide Hydrochlorideinjection100 mg/mLintramuscularREMEDYREPACK INC.2014-01-09Not applicableUs
Trimethobenzamide Hydrochlorideinjection100 mg/mLintramuscularPar Pharmaceutical, Inc.2012-06-01Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Trimethobenzamide Hydrochloridecapsule300 mg/1oralbryant ranch prepack2003-08-28Not applicableUs
Trimethobenzamide Hydrochloridecapsule300 mg/1oralRebel Distributors Corp.2003-08-28Not applicableUs
Trimethobenzamide Hydrochlorideinjection, solution100 mg/mLintramuscularGeneral Injectables & Vaccines, Inc2010-03-01Not applicableUs
Trimethobenzamide Hydrochloridecapsule300 mg/1oralAvera Mc Kennan Hospital2015-07-16Not applicableUs
Trimethobenzamide Hydrochloridecapsule300 mg/1oralLake Erie Medical DBA Quality Care Products LLC2010-07-13Not applicableUs
Trimethobenzamide Hydrochloridecapsule300 mg/1oralMutual Pharmaceutical Company, Inc.2003-08-28Not applicableUs
Trimethobenzamide Hydrochloridecapsule300 mg/1oralGAVIS Pharmaceuticals, LLC2011-01-17Not applicableUs
Trimethobenzamide Hydrochloridecapsule300 mg/1oralPhysicians Total Care, Inc.2007-01-05Not applicableUs
Trimethobenzamide Hydrochloridecapsule300 mg/1oralREMEDYREPACK INC.2011-08-18Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BenzacotNot Available
StemeticNot Available
TebamideGlaxoSmithKline
TribenzaganNot Available
TrimazideNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Trimethobenzamide Hydrochloride
Thumb
  • InChI Key: WIIZEEPFHXAUND-UHFFFAOYSA-N
  • Monoisotopic Mass: 424.176499755
  • Average Mass: 424.918
DBSALT000501
Categories
UNIIW2X096QY97
CAS number138-56-7
WeightAverage: 388.4574
Monoisotopic: 388.199822016
Chemical FormulaC21H28N2O5
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzamides
Direct ParentN-benzylbenzamides
Alternative Parents
Substituents
  • N-benzylbenzamide
  • Benzoic acid or derivatives
  • Methoxybenzene
  • Phenylmethylamine
  • Phenol ether
  • Benzylamine
  • Benzoyl
  • Anisole
  • Alkyl aryl ether
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of postoperative nausea and vomiting and for nausea associated with gastroenteritis.
PharmacodynamicsTrimethobenzamide 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 actionThe 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.
Related Articles
AbsorptionThe relative bioavailability of the capsule formulation compared to the solution is 100%.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationBetween 30 – 50% of a single dose in humans is excreted unchanged in the urine within 48–72 hours.
Half lifeThe mean elimination half-life of trimethobenzamide is 7 to 9 hours.
ClearanceNot Available
ToxicityOral LD50 in mice is 1600 mg/kg.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9898
Blood Brain Barrier+0.8121
Caco-2 permeable+0.6907
P-glycoprotein substrateSubstrate0.6855
P-glycoprotein inhibitor IInhibitor0.6152
P-glycoprotein inhibitor IINon-inhibitor0.5571
Renal organic cation transporterNon-inhibitor0.6259
CYP450 2C9 substrateNon-substrate0.7472
CYP450 2D6 substrateNon-substrate0.6388
CYP450 3A4 substrateSubstrate0.7204
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8188
Ames testNon AMES toxic0.7153
CarcinogenicityNon-carcinogens0.7638
BiodegradationNot ready biodegradable0.9285
Rat acute toxicity2.3338 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9673
hERG inhibition (predictor II)Non-inhibitor0.6758
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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
Dosage forms
FormRouteStrength
Injectionintramuscular100 mg/mL
Injection, solutionintramuscular100 mg/mL
Capsuleoral300 mg/1
Prices
Unit descriptionCostUnit
Trimethobenzamide hcl powder44.24USD g
Tigan 100 mg/ml vial7.06USD ml
Trimethobenzamide HCl 300 mg capsule1.7USD capsule
Tigan 300 mg capsule1.52USD capsule
Trimethobenzamide 100 mg/ml1.47USD ml
Trimethobenzamide 250 mg cap1.1USD each
Trimethobenzamide 300 mg cap0.99USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point188.7 °CPhysProp
water solubility40 mg/LNot Available
logP2.29EL TAYER,N ET AL. (1985)
pKa8.78EL TAYAR,N ET AL. (1985)
Predicted Properties
PropertyValueSource
Water Solubility0.0398 mg/mLALOGPS
logP2.44ALOGPS
logP2.16ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)14.36ChemAxon
pKa (Strongest Basic)8.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.26 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity108.52 m3·mol-1ChemAxon
Polarizability43.19 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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
  1. 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. [PubMed:7400373 ]
  2. 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. [PubMed:5908416 ]
External Links
ATC CodesR06AA10
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (36.7 KB)
MSDSDownload (73.5 KB)
Interactions
Drug Interactions
Drug
EthanolEthanol may increase the central nervous system depressant (CNS depressant) activities of Trimethobenzamide.
Food InteractionsNot Available
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23