U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C21H28N2O5
Molecular Weight 388.4574
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIMETHOBENZAMIDE

SMILES

COC1=CC(=CC(OC)=C1OC)C(=O)NCC2=CC=C(OCCN(C)C)C=C2

InChI

InChIKey=FEZBIKUBAYAZIU-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C21H28N2O5
Molecular Weight 388.4574
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Trimethobenzamide (trade names Tebamide, Tigan) is an antiemetic used to prevent nausea and vomiting. Trimethobenzamide is an antagonist of the D2 receptor, that affects the chemoreceptor trigger zone (CTZ) of the medulla oblongata to suppress nausea and vomiting. The oral bioavailability of trimethobenzamide is 60% to 100%. The time to peak is about 45 minutes after oral administration and; I.M. about 30 minutes after intramuscular administration. The onset action of trimethobenzamide for antiemetic effects is 10-40 minutes after oral administration and; 15-35 minutes after intramuscular administration. The duration of action is 3-4 hours. Trimethobenzamide is generally considered the most potent antiemetic that does not have effects on the serotonergic, dopaminergic, or histaminergic systems, so it has a lower likelihood of causing undesired side effects. Possible side effects include drowsiness, dizziness, headache, diarrhea, muscle cramps, and blurred vision. More serious adverse effects include skin rash, tremors, parkinsonism, and jaundice.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TIGAN
Primary
TIGAN

Cmax

ValueDoseCo-administeredAnalytePopulation
3729 ng/mL
200 mg single, intramuscular
TRIMETHOBENZAMIDE plasma
Homo sapiens
3817 ng/mL
300 mg single, oral
TRIMETHOBENZAMIDE plasma
Homo sapiens
5211 ng/mL
400 mg single, oral
TRIMETHOBENZAMIDE plasma
Homo sapiens
3537 ng/mL
200 mg single, intramuscular
TRIMETHOBENZAMIDE plasma
Homo sapiens
4002 ng/mL
200 mg single, intramuscular
TRIMETHOBENZAMIDE plasma
Homo sapiens
3536 ng/mL
300 mg single, oral
TRIMETHOBENZAMIDE plasma
Homo sapiens
4219 ng/mL
300 mg single, oral
TRIMETHOBENZAMIDE plasma
Homo sapiens
3712 ng/mL
200 mg single, intramuscular
TRIMETHOBENZAMIDE plasma
Homo sapiens
3982 ng/mL
200 mg single, intramuscular
TRIMETHOBENZAMIDE plasma
Homo sapiens
3847 ng/mL
300 mg single, oral
TRIMETHOBENZAMIDE plasma
Homo sapiens
3863 ng/mL
300 mg single, oral
TRIMETHOBENZAMIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
10465 ng × h/mL
200 mg single, intramuscular
TRIMETHOBENZAMIDE plasma
Homo sapiens
10218 ng × h/mL
300 mg single, oral
TRIMETHOBENZAMIDE plasma
Homo sapiens
13647 ng × h/mL
400 mg single, oral
TRIMETHOBENZAMIDE plasma
Homo sapiens
10581 ng × h/mL
200 mg single, intramuscular
TRIMETHOBENZAMIDE plasma
Homo sapiens
10621 ng × h/mL
200 mg single, intramuscular
TRIMETHOBENZAMIDE plasma
Homo sapiens
10041 ng × h/mL
300 mg single, oral
TRIMETHOBENZAMIDE plasma
Homo sapiens
10436 ng × h/mL
300 mg single, oral
TRIMETHOBENZAMIDE plasma
Homo sapiens
10448 ng × h/mL
200 mg single, intramuscular
TRIMETHOBENZAMIDE plasma
Homo sapiens
11544 ng × h/mL
200 mg single, intramuscular
TRIMETHOBENZAMIDE plasma
Homo sapiens
10371 ng × h/mL
300 mg single, oral
TRIMETHOBENZAMIDE plasma
Homo sapiens
9768 ng × h/mL
300 mg single, oral
TRIMETHOBENZAMIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
6.8 h
200 mg single, intramuscular
TRIMETHOBENZAMIDE plasma
Homo sapiens
7.8 h
300 mg single, oral
TRIMETHOBENZAMIDE plasma
Homo sapiens
7.4 h
400 mg single, oral
TRIMETHOBENZAMIDE plasma
Homo sapiens
7 h
200 mg single, intramuscular
TRIMETHOBENZAMIDE plasma
Homo sapiens
6.7 h
200 mg single, intramuscular
TRIMETHOBENZAMIDE plasma
Homo sapiens
7.8 h
300 mg single, oral
TRIMETHOBENZAMIDE plasma
Homo sapiens
7.8 h
300 mg single, oral
TRIMETHOBENZAMIDE plasma
Homo sapiens
6.8 h
200 mg single, intramuscular
TRIMETHOBENZAMIDE plasma
Homo sapiens
6.5 h
200 mg single, intramuscular
TRIMETHOBENZAMIDE plasma
Homo sapiens
8 h
300 mg single, oral
TRIMETHOBENZAMIDE plasma
Homo sapiens
7.6 h
300 mg single, oral
TRIMETHOBENZAMIDE plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Tox targets

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult intramuscular dosage: 2 mL (200 mg) t.i.d. or q.i.d. . Usual Adult oral dosage: 300 mg orally three or four times daily. Usual Adult Rectal dosage: 200 mg 3-4 times a day.
Route of Administration: Other
In Vitro Use Guide
Rat embryos were used for activity evaluation. Embryos were explanted on day 9.5 of gestation and cultured. Whole rat serum was used as a culture medium for the control group while different concentrations of dimenhydrinate (2.5–20 lg/ml), metoclopramide (10–50 lg/ml) and trimethobenzamide HCl (25–100 lg/ml) were added to serum for the experimental groups.
Substance Class Chemical
Record UNII
W2X096QY97
Record Status Validated (UNII)
Record Version