Trimethobenzamide
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| Systematic (IUPAC) name | |
|---|---|
|
N-{[4-(2-dimethylaminoethoxy)phenyl]methyl}- 3,4,5-trimethoxy-benzamide | |
| Clinical data | |
| Trade names | Tigan, Tebamide |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a682693 |
| Pregnancy category |
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| Routes of administration | Oral, rectal, intramuscular |
| Legal status | |
| Legal status |
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| Pharmacokinetic data | |
| Bioavailability | 60-100% |
| Biological half-life | 7 to 9 hours (mean) |
| Excretion | urine (30-50%), faeces |
| Identifiers | |
| CAS Number |
138-56-7  |
| ATC code | R06AA10 (WHO) |
| PubChem | CID 5577 |
| IUPHAR/BPS | 7614 |
| DrugBank |
DB00662 |
| ChemSpider |
5375 |
| UNII |
W2X096QY97 |
| ChEBI |
CHEBI:27796 |
| ChEMBL |
CHEMBL1201256  |
| Chemical data | |
| Formula | C21H28N2O5 |
| Molar mass | 388.458 g/mol |
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| (what is this?) (verify) | |
Trimethobenzamide (trade names Tebamide, Tigan) is an antiemetic used to prevent nausea and vomiting. It is often prescribed for patients with gastroenteritis, medication-induced nausea, and other illnesses. 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. In the United States, it requires a prescription.
Mechanism of action
Although the specific mechanism through which trimethobenzamide functions is unknown, it is believed to affect the chemoreceptor trigger zone (CTZ) of the medulla oblongata.
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.
Formulations
Trimethobenzamide is marketed under the brand names Tebamide and Tigan, manufactured by GlaxoSmithKline and King Pharmaceuticals, respectively. It is available as oral capsules and injectable formulations.
Trimethobenzamide was also available as a rectal suppository, but such formulations were banned by the U.S. Food and Drug Administration on April 6, 2007 due to unproven efficacy.[1]
Synthesis
Alkylation of the sodium salt of p-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).
See also
References
- ↑ Waknine, Yael (April 6, 2007). "FDA Bans Suppositories With Trimethobenzamide". Medscape. Archived from the original on April 16, 2007. Retrieved 2007-04-06.