U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017531s014lbl.pdf | http://www.sciencedirect.com/science/article/pii/B9781416002086500231 | https://www.ncbi.nlm.nih.gov/pubmed/23002952

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.

Originator

Sources: Journal of Pharmacology and Experimental Therapeutics (1959), 126, 264-9.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TIGAN

Approved Use

INDICATIONS & USAGE Tigan is indicated for the treatment of postoperative nausea and vomiting and for nausea associated with gastroenteritis.

Launch Date

1.42819197E11
Primary
TIGAN

Approved Use

INDICATIONS & USAGE Tigan is indicated for the treatment of postoperative nausea and vomiting and for nausea associated with gastroenteritis.

Launch Date

1.42819197E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3536 ng/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
3817 ng/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
3847 ng/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
4219 ng/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
3712 ng/mL
200 mg single, intramuscular
dose: 200 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
3729 ng/mL
200 mg single, intramuscular
dose: 200 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
3537 ng/mL
200 mg single, intramuscular
dose: 200 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4002 ng/mL
200 mg single, intramuscular
dose: 200 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
3982 ng/mL
200 mg single, intramuscular
dose: 200 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
5211 ng/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
3863 ng/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
10041 ng × h/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
10218 ng × h/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
10371 ng × h/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
10436 ng × h/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
10448 ng × h/mL
200 mg single, intramuscular
dose: 200 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
10465 ng × h/mL
200 mg single, intramuscular
dose: 200 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
10581 ng × h/mL
200 mg single, intramuscular
dose: 200 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
10621 ng × h/mL
200 mg single, intramuscular
dose: 200 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
11544 ng × h/mL
200 mg single, intramuscular
dose: 200 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
13647 ng × h/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
9768 ng × h/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.8 h
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
7.8 h
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
8 h
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
7.8 h
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
6.8 h
200 mg single, intramuscular
dose: 200 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
6.8 h
200 mg single, intramuscular
dose: 200 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
7 h
200 mg single, intramuscular
dose: 200 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
6.7 h
200 mg single, intramuscular
dose: 200 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
6.5 h
200 mg single, intramuscular
dose: 200 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
7.4 h
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
7.6 h
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMETHOBENZAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
10 questions about using apomorphine for Parkinson disease.
2005 May
A clinical trial of trimethobenzamide/diphenhydramine versus sumatriptan for acute migraines.
2006 Jun
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015 Jan 5
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017531s014lbl.pdf | http://www.sciencedirect.com/science/article/pii/B9781416002086500231
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
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
Created
by admin
on Fri Dec 15 15:42:37 UTC 2023
Edited
by admin
on Fri Dec 15 15:42:37 UTC 2023
Record UNII
W2X096QY97
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIMETHOBENZAMIDE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
AMETIK DAMLA
Brand Name English
TRIMETHOBENZAMIDE [MI]
Common Name English
Trimethobenzamide [WHO-DD]
Common Name English
TRIMETHOBENZAMIDE [HSDB]
Common Name English
TRIMETHOBENZAMIDE [VANDF]
Common Name English
trimethobenzamide [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C267
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
NDF-RT N0000009034
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
LIVERTOX NBK548057
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
NDF-RT N0000009034
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
WHO-ATC R06AA10
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
NDF-RT N0000178372
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
Code System Code Type Description
DRUG BANK
DB00662
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY
DAILYMED
W2X096QY97
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY
CAS
138-56-7
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PRIMARY
IUPHAR
7614
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY
HSDB
3198
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY
DRUG CENTRAL
2754
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID8023711
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY
LACTMED
Trimethobenzamide
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY
PUBCHEM
5577
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY
CHEBI
27796
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY
MESH
C100146
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY
EVMPD
SUB11309MIG
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY
RXCUI
38685
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY RxNorm
FDA UNII
W2X096QY97
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY
ECHA (EC/EINECS)
205-332-1
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY
WIKIPEDIA
TRIMETHOBENZAMIDE
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY
SMS_ID
100000076925
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201256
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY
NCI_THESAURUS
C61989
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY
MERCK INDEX
m11147
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY Merck Index
INN
957
Created by admin on Fri Dec 15 15:42:37 UTC 2023 , Edited by admin on Fri Dec 15 15:42:37 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY