trimethobenzamide

Trade name: tigan

Small moleculeapproved

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

Phase 1
2
Phase 2
0
Phase 3
0
Phase 4
2

Earliest trial started May 1, 2007 (NCT00489255)

Timeline

1970s

  1. Jul 12, 1974

    Par Pharmaceuticals — Earliest FDA Approval

  2. Jul 12, 1974

    King Pharmaceuticals — NDA Secondary Org

  3. Jul 12, 1974

    Par Pharmaceuticals — NDA Secondary Org

  4. Jul 12, 1974

    Par Pharmaceuticals — NDA Organization

  5. Jul 12, 1974

    Endo Pharmaceuticals — Marketing Organization

  6. Jul 12, 1974

    PH HEALTH — Marketing Organization

1980s

  1. Oct 19, 1982

    Watson Pharmaceuticals — Marketing Organization

  2. Apr 3, 1987

    Hospira — Marketing Organization

2000s

  1. Aug 20, 2003

    Lupin — Marketing Organization

  2. Aug 28, 2003

    Sun Pharmaceuticals — Marketing Organization

2010s

  1. Mar 8, 2011

    Lutipold — Marketing Organization

  2. Mar 8, 2011

    Sankyo — Marketing Organization

  3. Mar 8, 2011

    Daiichi Sankyo — Marketing Organization

  4. Jan 1, 2014

    Earliest Phase 1 Sponsor(trial)

2020s

  1. Nov 21, 2023

    Heritage Pharma — Marketing Organization

  2. Nov 21, 2023

    Avet Lifesciences — Marketing Organization

  3. Oct 16, 2025

    BPI — Marketing Organization

Indications

Mechanism of action

Approval history

  • approvedJul 12, 1974

Chemistry & pharmacology

Loading structure…

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

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 IDPhaseStart dateSponsor(s)
NCT02373072Phase 1Mar 1, 2015Pfizer
NCT02262767Phase 1Nov 1, 2014Pfizer
NCT01770145Phase 4Dec 1, 2012Parkinson's Disease and Movement Disorder Center of Boca Raton, US WorldMeds
NCT00489255Phase 4May 1, 2007INC Research, Ipsen
Showing 4 of 4 trials
Page 1 / 1

Organizations

Research & Development (5)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
PfizerFor profit2212014
INC ResearchFor profit1012007
IpsenFor profit1112007
Parkinson's Disease and Movement Disorder Center of Boca RatonAcademic/Hospital1012012
US WorldMedsFor profit1112012
5 organizations
Page 1 / 1

Marketing (17)

OrganizationOrg typeRelationshipDate
Avet LifesciencesFor profitMKTGNov 21, 2023
BPIFor profitMKTGOct 16, 2025
Daiichi SankyoFor profitMKTGMar 8, 2011
Endo PharmaceuticalsFor profitMKTGJul 12, 1974
Heritage PharmaFor profitMKTGNov 21, 2023
HospiraFor profitMKTGApr 3, 1987
King PharmaceuticalsFor profitNDA2Jul 12, 1974
LupinFor profitMKTGAug 20, 2003
LutipoldFor profitMKTGMar 8, 2011
PH HEALTHFor profitMKTGJul 12, 1974
Par PharmaceuticalsFor profitNDA2Jul 12, 1974
Par PharmaceuticalsFor profitNDAJul 12, 1974
SOLOPAKFor profitMKTG
SankyoFor profitMKTGMar 8, 2011
Smith & NephewFor profitMKTG
Sun PharmaceuticalsFor profitMKTGAug 28, 2003
Watson PharmaceuticalsFor profitMKTGOct 19, 1982