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
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)
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 |
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Primary | TIGAN Approved UseINDICATIONS & USAGE Tigan is indicated for the treatment of postoperative nausea and vomiting and for nausea associated with gastroenteritis. Launch Date1974 |
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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 |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
PubMed
Title | Date | PubMed |
---|---|---|
Prune belly syndrome and heart defect in one of monozygotic twins, following exposure to Tigan and Bendectin. | 1985 |
|
"Seeing catatonia". | 2005 Fall |
|
A clinical trial of trimethobenzamide/diphenhydramine versus sumatriptan for acute migraines. | 2006 Jun |
|
New structural analogues of curcumin exhibit potent growth suppressive activity in human colorectal carcinoma cells. | 2009 Mar 30 |
|
Acute gastroenteritis: from guidelines to real life. | 2010 |
|
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
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.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C267
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NDF-RT |
N0000009034
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LIVERTOX |
NBK548057
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NDF-RT |
N0000009034
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WHO-ATC |
R06AA10
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NDF-RT |
N0000178372
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DB00662
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W2X096QY97
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138-56-7
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7614
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3198
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DTXSID8023711
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Trimethobenzamide
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5577
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27796
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C100146
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SUB11309MIG
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38685
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W2X096QY97
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205-332-1
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TRIMETHOBENZAMIDE
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100000076925
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CHEMBL1201256
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C61989
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m11147
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957
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)