Trimethobenzamide

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Trimethobenzamide
Trimethobenzamide2DACS.svg
Trimethobenzamidefinal.png
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
ATC code
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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
ECHA InfoCard 100.004.848
Chemical and physical data
Formula C21H28N2O5
Molar mass 388.458 g/mol
3D model (Jmol)
 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]

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[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.[2]

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

External links[edit]