Trimethobenzamide

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Trimethobenzamide
Trimethobenzamide2DACS.svg
Trimethobenzamidefinal.png
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
  • US: C (Risk not ruled out)
Routes of
administration
Oral, rectal, intramuscular
Legal status
Legal status
Pharmacokinetic data
Bioavailability 60-100%
Biological half-life 7 to 9 hours (mean)
Excretion urine (30-50%), faeces
Identifiers
CAS Number 138-56-7 YesY
ATC code R06AA10 (WHO)
PubChem CID 5577
IUPHAR/BPS 7614
DrugBank DB00662 YesY
ChemSpider 5375 YesY
UNII W2X096QY97 YesY
ChEBI CHEBI:27796 YesY
ChEMBL CHEMBL1201256 N
Chemical data
Formula C21H28N2O5
Molar mass 388.458 g/mol
 NYesY (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[edit]

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[edit]

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[edit]

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[edit]

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[edit]

References[edit]

  1. ^ Waknine, Yael (April 6, 2007). "FDA Bans Suppositories With Trimethobenzamide". Medscape. Archived from the original on April 16, 2007. Retrieved 2007-04-06. 

External links[edit]