Details
Stereochemistry | UNKNOWN |
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 |
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Target ID: CHEMBL3735 |
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Target ID: CHEMBL4304 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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. |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Comparison of the effects of trimebutine and YM114 (KAE-393), a novel 5-HT3 receptor antagonist, on stress-induced defecation. | 1993 Dec 7 |
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Duodenogastric reflux following cholecystectomy in the dog: role of antroduodenal motor function. | 2001 Aug |
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Effects of TAK-637, a novel neurokinin-1 receptor antagonist, on colonic function in vivo. | 2001 Aug |
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[Dysfunction of the Oddi's sphincter]. | 2001 Sep |
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Oesophageal motility disorders. | 2002 Jan 12 |
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Centrally acting agents and visceral sensitivity. | 2002 Jul |
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Laxative and anti-diarrheal activity of polycarbophil in mice and rats. | 2002 Jun |
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[Physicochemical and pharmacological characteristic and clinical efficacy of an anti-irritable bowel syndrome agent, polycarbophil calcium (Polyful)]. | 2002 Mar |
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Quantitative determination of trimebutine maleate and its three metabolites in human plasma by liquid chromatography-tandem mass spectrometry. | 2002 Nov 5 |
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Factors affecting gallbladder motility: drugs. | 2003 Jul |
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Beneficial effect of trimebutine and N-monodesmethyl trimebutine on trinitrobenzene sulfonic acid-induced colitis in rats. | 2004 Dec 3 |
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Delayed reaction urticaria due to trimebutine. | 2004 Jul |
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Rectal instillation of butyrate provides a novel clinically relevant model of noninflammatory colonic hypersensitivity in rats. | 2005 Jun |
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Prokinetic agents in childen with poor appetite. | 2005 Oct-Dec |
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Pharmacokinetic study of trimebutine maleate in rabbit blood using in vivo microdialysis coupled to capillary electrophoresis. | 2005 Sep 15 |
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The effect of trimebutine on the psychosocial adjustment to illness in the irritable bowel syndrome. | 2006 |
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Increasing the effect of triptans in migraine. | 2006 Oct 14 |
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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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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 |
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Risk factors of drug interaction between warfarin and nonsteroidal anti-inflammatory drugs in practical setting. | 2010 Mar |
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Development of a novel combination tablet containing trimebutine maleate and mosapride citrate for the treatment of functional dyspepsia. | 2010 Nov 15 |
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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58997-91-4
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261-549-1
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5282423
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DKM38HXX5A
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SUBSTANCE RECORD