Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H29NO5.C7H7NO3S2 |
Molecular Weight | 604.735 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=S)C1=CC(=CC=C1)S(O)(=O)=O.CCC(COC(=O)C2=CC(OC)=C(OC)C(OC)=C2)(N(C)C)C3=CC=CC=C3
InChI
InChIKey=ACKBGPXURGPUEW-UHFFFAOYSA-N
InChI=1S/C22H29NO5.C7H7NO3S2/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;8-7(12)5-2-1-3-6(4-5)13(9,10)11/h8-14H,7,15H2,1-6H3;1-4H,(H2,8,12)(H,9,10,11)
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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Meta-analysis of smooth muscle relaxants in the treatment of irritable bowel syndrome. | 2001 Mar |
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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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Effects of tachykinin NK1 receptor antagonists on the viscerosensory response caused by colorectal distention in rabbits. | 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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Preparation, characterization and taste-masking properties of polyvinylacetal diethylaminoacetate microspheres containing trimebutine. | 2002 Oct |
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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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[Abdominal migraine as a cause of chronic recurrent abdominal pain in a 9-years-old girl--case report]. | 2005 Aug |
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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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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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Increasing the effect of triptans in migraine. | 2006 Oct 14 |
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Spectrophotometric determination of some anti-tussive and anti-spasmodic drugs through ion-pair complex formation with thiocyanate and cobalt(II) or molybdenum(V). | 2007 Apr |
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Pharmacokinetic and bioequivalence evaluation of two formulations of 100 mg trimebutine maleate (Recutin and Polybutin) in healthy male volunteers using the LC-MS/MS method. | 2007 Jan |
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[Drug treatment of irritable bowel syndrome: an unmet need]. | 2007 Mar |
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Meta-analysis of the effects of prokinetic agents in patients with functional dyspepsia. | 2007 Mar |
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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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Risk factors of drug interaction between warfarin and nonsteroidal anti-inflammatory drugs in practical setting. | 2010 Mar |
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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NCI_THESAURUS |
C241
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C111045
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1456509-46-8
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71725148
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5O1CF9IS48
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ACTIVE MOIETY
SUBSTANCE RECORD