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

Details

Stereochemistry ACHIRAL
Molecular Formula C21H28N2O5.ClH
Molecular Weight 424.9191
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIMETHOBENZAMIDE HYDROCHLORIDE

SMILES

CN(C)CCOc1ccc(cc1)CN=C(c2cc(c(c(c2)OC)OC)OC)O.Cl

InChI

InChIKey=WIIZEEPFHXAUND-UHFFFAOYSA-N
InChI=1S/C21H28N2O5.ClH/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);1H

HIDE SMILES / InChI

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
Studies of drugs given before anaesthesia. X. Two non-phenothiazine anti-emetics--cyclizine and trimethobenzamide.
1966 Jan
Prune belly syndrome and heart defect in one of monozygotic twins, following exposure to Tigan and Bendectin.
1985
Intranasal apomorphine rescue therapy for parkinsonian "off" periods.
1996 Jun
Trimethobenzamide in elderly patients.
2004 Jun
Practical considerations in the use of apomorphine injectable.
2004 Mar 23
Rapid treatment of "wearing off" in Parkinson's disease.
2004 Mar 23
Anesthesiologists' practice patterns for treatment of postoperative nausea and vomiting in the ambulatory Post Anesthesia Care Unit.
2006 Jun 1
Treatment of polydrug-using opiate dependents during withdrawal: towards a standardisation of treatment.
2006 Nov 15
Effects of rivastigmine on cognitive function in patients with traumatic brain injury.
2006 Sep 12
Acute gastroenteritis in children: role of anti-emetic medication for gastroenteritis-related vomiting.
2007
[Apomorphine in off state--clinical experience].
2007 Mar-Apr
FDA halts sales of some anti-vomiting suppositories...and are cough medications effective in children?
2007 May
Use of antiemetic agents in acute gastroenteritis: a systematic review and meta-analysis.
2008 Sep
Apomorphine in the treatment of Parkinson disease and other movement disorders.
2009 Apr
New structural analogues of curcumin exhibit potent growth suppressive activity in human colorectal carcinoma cells.
2009 Mar 30
Standardizing emergency department-based migraine research: an analysis of commonly used clinical trial outcome measures.
2010 Jan
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.
Name Type Language
TRIMETHOBENZAMIDE HYDROCHLORIDE
MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
TRIMETHOBENZAMIDE HYDROCHLORIDE [MART.]
Common Name English
TRIMETHOBENZAMIDE HYDROCHLORIDE [USP]
Common Name English
BENZAMIDE, N-((4-(2-(DIMETHYLAMINO)ETHOXY)PHENYL)METHYL)-3,4,5-TRIMETHOXY-, MONOHYDROCHLORIDE
Common Name English
TRIMETHOBENZAMIDE HYDROCHLORIDE [USP-RS]
Common Name English
NSC-37882
Code English
TRIMETHOBENZAMIDE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
TRIMETHOBENZAMIDE HYDROCHLORIDE [WHO-DD]
Common Name English
TRIMETHOBENZAMIDE HYDROCHLORIDE [MI]
Common Name English
N-(P-(2-(DIMETHYLAMINO)ETHOXY)BENZYL)-3,4,5-TRIMETHOXYBENZAMIDE MONOHYDROCHLORIDE
Common Name English
TRIMETHOBENZAMIDE HCL
Common Name English
TRIMETHOBENZAMIDE HYDROCHLORIDE [VANDF]
Common Name English
TIGAN
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C267
Created by admin on Sat Jun 26 00:53:41 UTC 2021 , Edited by admin on Sat Jun 26 00:53:41 UTC 2021
Code System Code Type Description
USP_CATALOG
1692006
Created by admin on Sat Jun 26 00:53:41 UTC 2021 , Edited by admin on Sat Jun 26 00:53:41 UTC 2021
PRIMARY USP-RS
RXCUI
57227
Created by admin on Sat Jun 26 00:53:41 UTC 2021 , Edited by admin on Sat Jun 26 00:53:41 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C29522
Created by admin on Sat Jun 26 00:53:41 UTC 2021 , Edited by admin on Sat Jun 26 00:53:41 UTC 2021
PRIMARY
EVMPD
SUB04971MIG
Created by admin on Sat Jun 26 00:53:41 UTC 2021 , Edited by admin on Sat Jun 26 00:53:41 UTC 2021
PRIMARY
PUBCHEM
68385
Created by admin on Sat Jun 26 00:53:41 UTC 2021 , Edited by admin on Sat Jun 26 00:53:41 UTC 2021
PRIMARY
MERCK INDEX
M11147
Created by admin on Sat Jun 26 00:53:41 UTC 2021 , Edited by admin on Sat Jun 26 00:53:41 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
209-075-6
Created by admin on Sat Jun 26 00:53:41 UTC 2021 , Edited by admin on Sat Jun 26 00:53:41 UTC 2021
PRIMARY
EPA CompTox
554-92-7
Created by admin on Sat Jun 26 00:53:41 UTC 2021 , Edited by admin on Sat Jun 26 00:53:41 UTC 2021
PRIMARY
DRUG BANK
DBSALT000501
Created by admin on Sat Jun 26 00:53:41 UTC 2021 , Edited by admin on Sat Jun 26 00:53:41 UTC 2021
PRIMARY
CAS
554-92-7
Created by admin on Sat Jun 26 00:53:41 UTC 2021 , Edited by admin on Sat Jun 26 00:53:41 UTC 2021
PRIMARY
FDA UNII
WDQ5P1SX7Q
Created by admin on Sat Jun 26 00:53:41 UTC 2021 , Edited by admin on Sat Jun 26 00:53:41 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201256
Created by admin on Sat Jun 26 00:53:41 UTC 2021 , Edited by admin on Sat Jun 26 00:53:41 UTC 2021
PRIMARY