Trimethobenzamide

Legal statusLegal status Pharmacokinetic dataBioavailability60-100%Elimination half-life7 to 9 hours (mean)Excretionurine (30-50%), faecesIdentifiersCAS NumberPubChem CIDIUPHAR/BPSDrugBankChemSpiderUNIIChEBIChEMBLCompTox Dashboard (EPA)ECHA InfoCard100.004.848 Chemical and physical dataFormulaC₂₁H₂₈N₂O₅Molar mass388.464 g·mol⁻¹3D model (JSmol) ^NY (what is this?)  (verify)

Trimethobenzamide (trade names Tebamide, Tigan) is an antiemetic used to prevent nausea and vomiting.

Mechanism of action

Trimethobenzamide is an antagonist of the D₂ receptor.^[1] It is believed to affect the chemoreceptor trigger zone (CTZ) of the medulla oblongata to suppress nausea and vomiting.

Side effects

Possible side effects include drowsiness, dizziness, headache, 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.^[2]

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

• Domperidone
• Metoclopramide

References

External links

• Tebamide
• Tigan (manufacturer's website)