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Revision as of 08:21, 23 October 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (changes to verified and watched fields - updated 'KEGG_Ref', 'CAS_number_Ref') per Chem/Drugbox validation (report errors or bugs)← Previous edit Revision as of 02:11, 11 January 2012 edit undoCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (changes to verified fields - added verified revid - updated 'KEGG_Ref') per Chem/Drugbox validation (report errors or bugs)Next edit →
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| verifiedrevid = 470615098
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| verifiedrevid = 402698677
| IUPAC_name = ''N''-{methyl}-<br>3,4,5-trimethoxy-benzamide | IUPAC_name = ''N''-{methyl}-<br>3,4,5-trimethoxy-benzamide
| image = Trimethobenzamide.svg | image = Trimethobenzamide.svg
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| ATC_prefix = none | ATC_prefix = none
| PubChem = 5577 | PubChem = 5577
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = APRD01277 | DrugBank = APRD01277
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| UNII = W2X096QY97 | UNII = W2X096QY97
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| ChEBI = 27796 | ChEBI = 27796
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Revision as of 02:11, 11 January 2012

Pharmaceutical compound
Trimethobenzamide
Clinical data
Trade namesTigan
AHFS/Drugs.comMonograph
MedlinePlusa682693
Routes of
administration
Oral, rectal, intramuscular
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
Elimination half-life7 to 9 hours (mean)
Identifiers
IUPAC name
  • N-{methyl}-
    3,4,5-trimethoxy-benzamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.848 Edit this at Wikidata
Chemical and physical data
FormulaC21H28N2O5
Molar mass388.458 g/mol g·mol
3D model (JSmol)
SMILES
  • O=C(c1cc(OC)c(OC)c(OC)c1)NCc2ccc(OCCN(C)C)cc2
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)
  • Key:FEZBIKUBAYAZIU-UHFFFAOYSA-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.

See also

References

  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

  • Tebamide (manufacturer's website)
  • Tigan (manufacturer's website)


Antiemetics (A04)
5-HT3 serotonin ion
channel antagonists
5-HT serotonin G-protein
receptor antagonists
CB1 agonists
(cannabinoids)
D2/D3 antagonists
H1 antagonists
(antihistamines)
mACh antagonists
(anticholinergics)
NK1 antagonists
Others
Categories: