Trimethobenzamide

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.

Trimethobenzamide
Clinical data
Trade namesTigan, Tebamide
AHFS/Drugs.comMonograph
MedlinePlusa682693
Pregnancy
category
  • US: C (Risk not ruled out)
    Routes of
    administration    		Oral, rectal, intramuscular
    ATC code
    Legal status
    Legal status
    Pharmacokinetic data
    Bioavailability60-100%
    Elimination half-life7 to 9 hours (mean)
    Excretionurine (30-50%), faeces
    Identifiers
    CAS Number
    PubChem CID
    IUPHAR/BPS
    DrugBank
    ChemSpider
    UNII
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    ECHA InfoCard100.004.848
    Chemical and physical data
    FormulaC21H28N2O5
    Molar mass388.458 g/mol g·mol−1
    3D model (JSmol)
     NY (what is this?)  (verify)

    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
    Trimethobenzamide synthesis: Hoffmann La Roche, U.S. Patent 2,879,293 (1959).

    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
    1. Smith HS, Cox LR, Smith BR (2012). "Dopamine receptor antagonists". Ann Palliat Med. 1 (2): 137–42. doi:10.3978/j.issn.2224-5820.2012.07.09. PMID 25841474.
    2. Waknine, Yael (April 6, 2007). "FDA Bans Suppositories With Trimethobenzamide". Medscape. Retrieved 2007-04-06.


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