Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H28N2O5.ClH |
| Molecular Weight | 424.918 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.COC1=CC(=CC(OC)=C1OC)C(=O)NCC2=CC=C(OCCN(C)C)C=C2
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
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
DescriptionCurator'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
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.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25841474 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | TIGAN Approved UseINDICATIONS & USAGE Tigan is indicated for the treatment of postoperative nausea and vomiting and for nausea associated with gastroenteritis. Launch Date1974 |
|||
| Primary | TIGAN Approved UseINDICATIONS & USAGE Tigan is indicated for the treatment of postoperative nausea and vomiting and for nausea associated with gastroenteritis. Launch Date1974 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
7.8 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 |
|
7.4 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 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 |
|
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 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 |
|
6.5 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 |
|
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 |
|
7.6 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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. | 2015-01-05 |
|
| Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010-12 |
|
| Fabry disease. | 2010-11-22 |
|
| Clinical and economic outcomes associated with potentially inappropriate prescribing in the elderly. | 2010-01-01 |
|
| Standardizing emergency department-based migraine research: an analysis of commonly used clinical trial outcome measures. | 2010-01 |
|
| Acute gastroenteritis: from guidelines to real life. | 2010 |
|
| Vestibulocochlear toxicity in a pair of siblings 15 years apart secondary to aspartame: two case reports. | 2009-09-15 |
|
| Apomorphine in the treatment of Parkinson disease and other movement disorders. | 2009-04 |
|
| New structural analogues of curcumin exhibit potent growth suppressive activity in human colorectal carcinoma cells. | 2009-03-30 |
|
| Use of antiemetic agents in acute gastroenteritis: a systematic review and meta-analysis. | 2008-09 |
|
| [Apomorphine in off state--clinical experience]. | 2007-10-19 |
|
| FDA halts sales of some anti-vomiting suppositories...and are cough medications effective in children? | 2007-05 |
|
| Acute gastroenteritis in children: role of anti-emetic medication for gastroenteritis-related vomiting. | 2007 |
|
| Treatment of polydrug-using opiate dependents during withdrawal: towards a standardisation of treatment. | 2006-11-15 |
|
| Effects of rivastigmine on cognitive function in patients with traumatic brain injury. | 2006-09-12 |
|
| Anesthesiologists' practice patterns for treatment of postoperative nausea and vomiting in the ambulatory Post Anesthesia Care Unit. | 2006-06-01 |
|
| A clinical trial of trimethobenzamide/diphenhydramine versus sumatriptan for acute migraines. | 2006-06 |
|
| 10 questions about using apomorphine for Parkinson disease. | 2005-05 |
|
| "Seeing catatonia". | 2005 |
|
| Trimethobenzamide in elderly patients. | 2004-06 |
|
| Practical considerations in the use of apomorphine injectable. | 2004-03-23 |
|
| Rapid treatment of "wearing off" in Parkinson's disease. | 2004-03-23 |
|
| Prescription medication use during pregnancy and risk of infant leukemia (United States). | 2003-06 |
|
| Intranasal apomorphine rescue therapy for parkinsonian "off" periods. | 1996-06 |
|
| Prune belly syndrome and heart defect in one of monozygotic twins, following exposure to Tigan and Bendectin. | 1985 |
|
| Trimethobenzamide HCl in the treatment of nausea and vomiting associated with antineoplastic chemotherapy. | 1980-05-01 |
|
| Studies of drugs given before anaesthesia. X. Two non-phenothiazine anti-emetics--cyclizine and trimethobenzamide. | 1966-01 |
|
| Use of Trimethobenzamide (Tigan) in Anesthesia. | 1960-12-24 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23002952
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
Edited
Mon Mar 31 18:32:07 GMT 2025
by
admin
on
Mon Mar 31 18:32:07 GMT 2025
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| Record UNII |
WDQ5P1SX7Q
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C267
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57227
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C29522
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SUB04971MIG
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68385
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100000084646
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WDQ5P1SX7Q
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m11147
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CHEMBL1201256
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37882
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
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ACTIVE MOIETY |