Structure via PubChem · Public domain (PubChem)
trimethobenzamide
Sign in to saveAlso known as Tigan®, trimethobenzamide hydrochloride, N-[[4-(2-dimethylaminoethoxy)phenyl]methyl]-3,4,5-trimethoxybenzamide, Trimetobenzamida, N-[[4-(2-Dimethylaminoethoxy)phenyl]methyl]-3,4,5-trimethoxybenzamide, Trimethobenzamidum
Trimethobenzamide (trade names Tebamide, Tigan) is an antiemetic used to prevent nausea and vomiting.
Chemical data
- Formula
- C21H28N2O5
- Molecular weight
- 388.5 g/mol
- IUPAC name
- N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4,5-trimethoxybenzamide
- SMILES
- CN(C)CCOC1=CC=C(C=C1)CNC(=O)C2=CC(=C(C(=C2)OC)OC)OC
- InChIKey
- FEZBIKUBAYAZIU-UHFFFAOYSA-N
- XLogP
- 2.3
- Polar surface area
- 69.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1974
- Admin. routes
- oral, parenteral
- Indications
- allergic disease
via ChEMBL · EBI
Research
113 papers- Trimethobenzamide.2012
- Trimethobenzamide.2006
- Trimethobenzamide in elderly patients.Mayo Clinic proceedings · 2004
- Trimethobenzamide antiemetic in immediate postoperative period. Double-blind study in 2,000 cases.JAMA · 1962
- Trimethobenzamide HCl in the treatment of nausea and vomiting associated with antineoplastic chemotherapy.Journal of clinical pharmacology · 1980
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 388.199822
- Has use
- medication
Show 6 more facts
- chemical formula
- C₂₁H₂₈N₂O₅
- medical condition treated
- vomiting
- canonical SMILES
- CN(C)CCOC1=CC=C(C=C1)CNC(=O)C2=CC(=C(C(=C2)OC)OC)OC
- World Health Organisation international non-proprietary name
- trimethobenzamide
- subject has role
- antiemetic
- Commons category
- Trimethobenzamide
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
7 sectionsContents
- Mechanism of action
- Side effects
- Formulations
- Synthesis
- See also
- References
- External links
{{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470615098 | IUPAC_name = N-{[4-(2-dimethylaminoethoxy)phenyl]methyl}-3,4,5-trimethoxy-benzamide | image = Trimethobenzamide2DACS.svg | image_class = skin-invert-image | image2 = Trimethobenzamidefinal.png | image_class2 = bg-transparent | width = 250px
| tradename = Tigan, Tebamide | Drugs.com = | MedlinePlus = a682693 | pregnancy_AU = | pregnancy_US = C | legal_AU = | legal_UK = | legal_US = Rx-only | routes_of_administration = Oral, rectal, intramuscular
Excerpted from Wikipedia’s “trimethobenzamide” article, available under the CC BY-SA 4.0 licence.
Available in 8 languages
via Wikidata sitelinks · CC0