Trimethobenzamide

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Trimethobenzamide
Trimethobenzamide2DACS.svg
Systematic (IUPAC) name
N-{[4-(2-dimethylaminoethoxy)phenyl]methyl}-
3,4,5-trimethoxy-benzamide
Clinical data
Trade namesTigan
AHFS/Drugs.commonograph
MedlinePlusa682693
Pregnancy cat.
Legal status
RoutesOral, rectal, intramuscular
Pharmacokinetic data
Bioavailability60-100%
Half-life7 to 9 hours (mean)
Excretionurine (30-50%), faeces
Identifiers
CAS number138-56-7 YesY
ATC codeNone
PubChemCID 5577
DrugBankDB00662
ChemSpider5375 YesY
UNIIW2X096QY97 YesY
ChEBICHEBI:27796 YesY
ChEMBLCHEMBL1201256 N
Chemical data
FormulaC21H28N2O5 
Mol. mass388.458 g/mol
 N (what is this?)  (verify)
 
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Trimethobenzamide
Trimethobenzamide2DACS.svg
Systematic (IUPAC) name
N-{[4-(2-dimethylaminoethoxy)phenyl]methyl}-
3,4,5-trimethoxy-benzamide
Clinical data
Trade namesTigan
AHFS/Drugs.commonograph
MedlinePlusa682693
Pregnancy cat.
Legal status
RoutesOral, rectal, intramuscular
Pharmacokinetic data
Bioavailability60-100%
Half-life7 to 9 hours (mean)
Excretionurine (30-50%), faeces
Identifiers
CAS number138-56-7 YesY
ATC codeNone
PubChemCID 5577
DrugBankDB00662
ChemSpider5375 YesY
UNIIW2X096QY97 YesY
ChEBICHEBI:27796 YesY
ChEMBLCHEMBL1201256 N
Chemical data
FormulaC21H28N2O5 
Mol. mass388.458 g/mol
 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[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]

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]