trimethobenzamide
Trade name: tigan
Approved
Jul 12, 1974
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. — NCATS
Clinical trial activity
4 trials · 5 clinical orgs · 16 marketing orgs
Earliest trial started May 1, 2007 (NCT00489255)
Timeline
1970s
- Jul 12, 1974
Par Pharmaceuticals — Earliest FDA Approval
- Jul 12, 1974
King Pharmaceuticals — NDA Secondary Org
- Jul 12, 1974
Par Pharmaceuticals — NDA Secondary Org
- Jul 12, 1974
Par Pharmaceuticals — NDA Organization
- Jul 12, 1974
Endo Pharmaceuticals — Marketing Organization
- Jul 12, 1974
PH HEALTH — Marketing Organization
1980s
- Oct 19, 1982
Watson Pharmaceuticals — Marketing Organization
- Apr 3, 1987
Hospira — Marketing Organization
2000s
- Aug 20, 2003
Lupin — Marketing Organization
- Aug 28, 2003
Sun Pharmaceuticals — Marketing Organization
2010s
- Mar 8, 2011
Lutipold — Marketing Organization
- Mar 8, 2011
Sankyo — Marketing Organization
- Mar 8, 2011
Daiichi Sankyo — Marketing Organization
- Jan 1, 2014
Earliest Phase 1 Sponsor(trial)
2020s
- Nov 21, 2023
Heritage Pharma — Marketing Organization
- Nov 21, 2023
Avet Lifesciences — Marketing Organization
- Oct 16, 2025
BPI — Marketing Organization
Indications
Mechanism of action
- Unspecified targetOTHER
Unknown
- Dopamine D2 receptorOTHER
DRD2 other
- Unspecified targetUnknown
Unknown
Approval history
- approvedJul 12, 1974
Chemistry & pharmacology
SMILES
COc1cc(C(=O)NCc2ccc(OCCN(C)C)cc2)cc(OC)c1OC- Mol. weight
- 388.46 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral, Parenteral
- Availability
- Prescription Only
Oral
Yes
Parenteral
Yes
Topical
No
Sources
- ChEMBLCHEMBL1201256 ↗
- WikipediaTrimethobenzamide ↗
- NCATSWDQ5P1SX7Q ↗
- ChEMBLCHEMBL1200887 ↗
Also known as
- emedur
- n-[[4-(2-dimethylaminoethoxy)phenyl]methyl]-3,4,5-trimethoxybenzamide
- n-[[4-(2-dimethylaminoethoxy)phenyl]methyl]-3,4,5-trimethoxybenzamide
- tebamide
- t-gen
- ticon
- tigan
- tigan
- tigan
- tigan
- tigan
- tigan
- tigan
- trimethobenzamide
- trimethobenzamide
- trimethobenzamide
- trimethobenzamide
- trimethobenzamide
- trimethobenzamide
- trimethobenzamide
- trimethobenzamide
- trimethobenzamide
- trimethobenzamide hcl
- trimethobenzamide hcl
- trimethobenzamide hcl
- trimethobenzamide hydrochloride
- trimethobenzamide hydrochloride
- trimethobenzamide hydrochloride
- trimethobenzamide hydrochloride
- trimethobenzamide monohydrochloride
- trimethobenzamidum
- trimethobenzamidum
- trimetobenzamida
- trimetobenzamida
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT02373072 | Phase 1 | Mar 1, 2015 | Pfizer |
| NCT02262767 | Phase 1 | Nov 1, 2014 | Pfizer |
| NCT01770145 | Phase 4 | Dec 1, 2012 | Parkinson's Disease and Movement Disorder Center of Boca Raton, US WorldMeds |
| NCT00489255 | Phase 4 | May 1, 2007 | INC Research, Ipsen |
Organizations
Research & Development (5)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Pfizer | For profit | 2 | 2 | 1 | 2014 |
| INC Research | For profit | 1 | 0 | 1 | 2007 |
| Ipsen | For profit | 1 | 1 | 1 | 2007 |
| Parkinson's Disease and Movement Disorder Center of Boca Raton | Academic/Hospital | 1 | 0 | 1 | 2012 |
| US WorldMeds | For profit | 1 | 1 | 1 | 2012 |
Marketing (17)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Avet Lifesciences | For profit | MKTG | Nov 21, 2023 |
| BPI | For profit | MKTG | Oct 16, 2025 |
| Daiichi Sankyo | For profit | MKTG | Mar 8, 2011 |
| Endo Pharmaceuticals | For profit | MKTG | Jul 12, 1974 |
| Heritage Pharma | For profit | MKTG | Nov 21, 2023 |
| Hospira | For profit | MKTG | Apr 3, 1987 |
| King Pharmaceuticals | For profit | NDA2 | Jul 12, 1974 |
| Lupin | For profit | MKTG | Aug 20, 2003 |
| Lutipold | For profit | MKTG | Mar 8, 2011 |
| PH HEALTH | For profit | MKTG | Jul 12, 1974 |
| Par Pharmaceuticals | For profit | NDA2 | Jul 12, 1974 |
| Par Pharmaceuticals | For profit | NDA | Jul 12, 1974 |
| SOLOPAK | For profit | MKTG | — |
| Sankyo | For profit | MKTG | Mar 8, 2011 |
| Smith & Nephew | For profit | MKTG | — |
| Sun Pharmaceuticals | For profit | MKTG | Aug 28, 2003 |
| Watson Pharmaceuticals | For profit | MKTG | Oct 19, 1982 |