Trimethobenzamide

Trimethobenzamide

Systematic (IUPAC) name
N-{[4-(2-dimethylaminoethoxy)phenyl]methyl}- 3,4,5-trimethoxy-benzamide
Clinical data
Trade names	Tigan
AHFS/Drugs.com	monograph
MedlinePlus	a682693
Pregnancy cat.	?
Legal status	℞-only (US)
Routes	Oral, rectal, intramuscular
Pharmacokinetic data
Half-life	7 to 9 hours (mean)
Identifiers
CAS number	138-56-7 Y
ATC code	None
PubChem	CID 5577
DrugBank	APRD01277
ChemSpider	5375 Y
UNII	W2X096QY97 Y
ChEBI	CHEBI:27796 N
ChEMBL	CHEMBL1201256 N
Chemical data
Formula	C21H28N2O5
Mol. mass	388.458 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C21H28N2O5/c1-23(2)10-11-28-17-8-6-15(7-9-17)14-22-21(24)16-12-18(25-3)20(27-5)19(13-16)26-4/h6-9,12-13H,10-11,14H2,1-5H3,(H,22,24) Y Key:FEZBIKUBAYAZIU-UHFFFAOYSA-N Y
N(what is this?)  (verify)

Trimethobenzamide (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]

See also

• Benzamide

References

1. ^ Waknine, Yael (April 6, 2007). "FDA Bans Suppositories With Trimethobenzamide". Medscape. Archived from the original on April 16, 2007. http://web.archive.org/web/20070416054940/http://www.medscape.com/viewarticle/554812. Retrieved 2007-04-06. 

External links

• Tebamide (manufacturer's website)^{[dead link]}
• Tigan (manufacturer's website)^{[dead link]}