Details
Stereochemistry | RACEMIC |
Molecular Formula | C22H29NO5.C4H4O4 |
Molecular Weight | 503.5415 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C/C(O)=O.CCC(COC(=O)C1=CC(OC)=C(OC)C(OC)=C1)(N(C)C)C2=CC=CC=C2
InChI
InChIKey=FSRLGULMGJGKGI-BTJKTKAUSA-N
InChI=1S/C22H29NO5.C4H4O4/c1-7-22(23(2)3,17-11-9-8-10-12-17)15-28-21(24)16-13-18(25-4)20(27-6)19(14-16)26-5;5-3(6)1-2-4(7)8/h8-14H,7,15H2,1-6H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
Trimebutine [3,4,5-trimethoxybenzoic acid 2-(dimethylamino)-2-phenylbutylester] is a noncompetitive spasmolytic agent. The actions of trimebutine on the gastrointestinal tract are mediated via (i) an agonist effect on peripheral mu, kappa and delta opiate receptors and (ii) release of gastrointestinal peptides such as motilin and modulation of the release of other peptides, including vasoactive intestinal peptide, gastrin and glucagon. Trimebutine attenuated colonic motility mainly through the inhibition of L-type Ca(2+) channels at higher concentrations, whereas, at lower concentrations, it depolarized membrane potentials by reducing BK(ca) currents, resulting in the enhancement of the muscle contractions.Trimebutine accelerates gastric emptying, induces premature phase III of the migrating motor complex in the intestine and modulates the contractile activity of the colon. It is indicated for the treatment and relief of symptoms associated with the irritable bowel syndrome (spastic colon); and in postoperative paralytic ileus in order to accelerate the resumption of the intestinal transit following abdominal surgery.
CNS Activity
Sources: http://www.aapharma.ca/downloads/en/PIL/Trimebutine_PM.pdf | https://www.ncbi.nlm.nih.gov/pubmed/28714852
Curator's Comment: Trimebutine is CNS active in animals. No human data available.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3735 |
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Target ID: CHEMBL4304 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | TRIMEBUTINE Approved UseTRIMEBUTINE (trimebutine maleate) is indicated:
– for the treatment and relief of symptoms associated with the irritable bowel syndrome (spastic colon); and
– in postoperative paralytic ileus in order to accelerate the resumption of the intestinal transit following abdominal surgery. |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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General pharmacology of the four gastrointestinal motility stimulants bethanechol, metoclopramide, trimebutine, and cisapride. | 1991 Jun |
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Duodenogastric reflux following cholecystectomy in the dog: role of antroduodenal motor function. | 2001 Aug |
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[HPCE determination of trimebutine maleate in rat plasma and its pharmacokinetics]. | 2001 Feb |
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Allergic contact dermatitis due to trimebutine. | 2001 Sep |
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[Prokinetics of gastrointestinal system; its newer aspects with regard to motillity stimulants]. | 2002 Feb |
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Oesophageal motility disorders. | 2002 Jan 12 |
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Effects of tachykinin NK1 receptor antagonists on the viscerosensory response caused by colorectal distention in rabbits. | 2002 Mar |
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Factors affecting gallbladder motility: drugs. | 2003 Jul |
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Spectrophotometric and liquid chromatographic determination of trimebutine maleate in the presence of its degradation products. | 2003 Sep 19 |
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Acute treatment of migraine. Breaking the paradigm of monotherapy. | 2004 Jan 28 |
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H pylori infection and reflux oesophagitis. | 2004 Jun |
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Effect of nor-trimebutine on neuronal activation induced by a noxious stimulus or an acute colonic inflammation in the rat. | 2005 Oct 21 |
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The effect of trimebutine on the psychosocial adjustment to illness in the irritable bowel syndrome. | 2006 |
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Rizatriptan vs. rizatriptan plus trimebutine for the acute treatment of migraine: a double-blind, randomized, cross-over, placebo-controlled study. | 2006 Jul |
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The use of combination therapies in the acute management of migraine. | 2006 Sep |
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Acute migraine: Current treatment and emerging therapies. | 2007 Jun |
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[A randomized and case-control clinical study on trimebutine maleate in treating functional dyspepsia coexisting with diarrhea-dominant irritable bowel syndrome]. | 2007 Nov |
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Inhibitory effects of ramosetron, a potent and selective 5-HT3-receptor antagonist, on conditioned fear stress-induced abnormal defecation and normal defecation in rats: comparative studies with antidiarrheal and spasmolytic agents. | 2008 Feb |
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Activation of peripheral opioid receptors has no effect on heart rate variability. | 2008 Jun |
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Effects of serotonin 5-HT3 receptor antagonists on stress-induced colonic hyperalgesia and diarrhoea in rats: a comparative study with opioid receptor agonists, a muscarinic receptor antagonist and a synthetic polymer. | 2008 May |
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Effect of fibre, antispasmodics, and peppermint oil in the treatment of irritable bowel syndrome: systematic review and meta-analysis. | 2008 Nov 13 |
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Effect of four medications associated with gastrointestinal motility on Oddi sphincter in the rabbit. | 2009 |
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Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
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Effectiveness of trimebutine maleate on modulating intestinal hypercontractility in a mouse model of postinfectious irritable bowel syndrome. | 2010 Jun 25 |
Patents
Sample Use Guides
The adult recommended dose is up to 600 mg daily in divided doses. It may be administered as two 100 mg tablets three times daily before meals or one 200 mg tablet three times daily before meals.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25343691
0.1 mM trimebutine inhibits proliferation of human LOVO colon cancer cells.
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ACTIVE MOIETY
SUBSTANCE RECORD