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| Clinical data | |
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| Trade names | Tigan, Tebamide |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a682693 |
| Routes of administration | Oral, rectal,intramuscular |
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| Pharmacokinetic data | |
| Bioavailability | 60-100% |
| Eliminationhalf-life | 7 to 9 hours (mean) |
| Excretion | urine (30-50%), faeces |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.004.848 |
| Chemical and physical data | |
| Formula | C21H28N2O5 |
| Molar mass | 388.464 g·mol−1 |
| 3D model (JSmol) | |
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Trimethobenzamide (trade namesTebamide,Tigan) is anantiemetic used to preventnausea andvomiting.
Trimethobenzamide is anantagonist of theD2 receptor.[1] It is believed to affect thechemoreceptor trigger zone (CTZ) of themedulla oblongata to suppressnausea andvomiting.
Possible side effects include drowsiness, dizziness, headache, muscle cramps, and blurred vision. More serious adverse effects include skin rash, tremors,parkinsonism, andjaundice.
Trimethobenzamide is marketed under the brand namesTebamide andTigan, manufactured byGlaxoSmithKline andKing Pharmaceuticals, respectively. It is available as oral capsules and injectable formulations.
Trimethobenzamide was also available as a rectalsuppository, but such formulations were banned by the U.S.Food and Drug Administration on April 6, 2007, due to unproven efficacy.[2]
Alkylation of the sodium salt ofp-hydroxybenzaldehyde (1) with 2-dimethylaminoethyl chloride affords the ether (2). Reductive amination of the aldehyde in the presence of ammonia gives diamine (3). Acylation of that product with 3,4,5-trimethoxybenzoyl chloride affords trimethobenzamide (4).