Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C22H29NO5 |
| Molecular Weight | 387.4694 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC(COC(=O)C1=CC(OC)=C(OC)C(OC)=C1)(N(C)C)C2=CC=CC=C2
InChI
InChIKey=LORDFXWUHHSAQU-UHFFFAOYSA-N
InChI=1S/C22H29NO5/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/h8-14H,7,15H2,1-6H3
| Molecular Formula | C22H29NO5 |
| Molecular Weight | 387.4694 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
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 |
|---|---|---|
| General pharmacology of the four gastrointestinal motility stimulants bethanechol, metoclopramide, trimebutine, and cisapride. | 1991 Jun |
|
| 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 |
|
| Determination of trimebutine maleate in rat plasma and tissues by using capillary zone electrophoresis. | 2001 Jun |
|
| [Prokinetics of gastrointestinal system; its newer aspects with regard to motillity stimulants]. | 2002 Feb |
|
| Oesophageal motility disorders. | 2002 Jan 12 |
|
| Efficacy of trimebutine therapy in patients with gastroesophageal reflux disease and irritable bowel syndrome. | 2002 Jan-Feb |
|
| Centrally acting agents and visceral sensitivity. | 2002 Jul |
|
| [Physicochemical and pharmacological characteristic and clinical efficacy of an anti-irritable bowel syndrome agent, polycarbophil calcium (Polyful)]. | 2002 Mar |
|
| Effects of tachykinin NK1 receptor antagonists on the viscerosensory response caused by colorectal distention in rabbits. | 2002 Mar |
|
| Quantitative determination of trimebutine maleate and its three metabolites in human plasma by liquid chromatography-tandem mass spectrometry. | 2002 Nov 5 |
|
| Preparation, characterization and taste-masking properties of polyvinylacetal diethylaminoacetate microspheres containing trimebutine. | 2002 Oct |
|
| Factors affecting gallbladder motility: drugs. | 2003 Jul |
|
| Acute treatment of migraine. Breaking the paradigm of monotherapy. | 2004 Jan 28 |
|
| H pylori infection and reflux oesophagitis. | 2004 Jun |
|
| [Pharmacokinetics and bioequivalence of trimebutine dispersive tablet in healthy subjects]. | 2004 Mar |
|
| Determination of trimebutine in pharmaceuticals by differential pulse voltammetry at a glassy carbon electrode. | 2005 Jul 15 |
|
| Rectal instillation of butyrate provides a novel clinically relevant model of noninflammatory colonic hypersensitivity in rats. | 2005 Jun |
|
| Effect of nor-trimebutine on neuronal activation induced by a noxious stimulus or an acute colonic inflammation in the rat. | 2005 Oct 21 |
|
| Prokinetic agents in childen with poor appetite. | 2005 Oct-Dec |
|
| Pharmacokinetic study of trimebutine maleate in rabbit blood using in vivo microdialysis coupled to capillary electrophoresis. | 2005 Sep 15 |
|
| Rizatriptan vs. rizatriptan plus trimebutine for the acute treatment of migraine: a double-blind, randomized, cross-over, placebo-controlled study. | 2006 Jul |
|
| Increasing the effect of triptans in migraine. | 2006 Oct 14 |
|
| The use of combination therapies in the acute management of migraine. | 2006 Sep |
|
| 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 |
|
| Acute migraine: Current treatment and emerging therapies. | 2007 Jun |
|
| [Drug treatment of irritable bowel syndrome: an unmet need]. | 2007 Mar |
|
| Meta-analysis of the effects of prokinetic agents in patients with functional dyspepsia. | 2007 Mar |
|
| [A randomized and case-control clinical study on trimebutine maleate in treating functional dyspepsia coexisting with diarrhea-dominant irritable bowel syndrome]. | 2007 Nov |
|
| Treatment of functional dyspepsia with serotonin agonists: a meta-analysis of randomized controlled trials. | 2007 Oct |
|
| 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 |
|
| 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 |
|
| Effect of fibre, antispasmodics, and peppermint oil in the treatment of irritable bowel syndrome: systematic review and meta-analysis. | 2008 Nov 13 |
|
| Effect of four medications associated with gastrointestinal motility on Oddi sphincter in the rabbit. | 2009 |
|
| Effectiveness of prokinetic agents against diseases external to the gastrointestinal tract. | 2009 Apr |
|
| A nitro-arginine derivative of trimebutine (NO2-Arg-Trim) attenuates pain induced by colorectal distension in conscious rats. | 2009 May |
|
| Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
|
| [Prokinetics in childhood]. | 2010 Jun |
|
| Effectiveness of trimebutine maleate on modulating intestinal hypercontractility in a mouse model of postinfectious irritable bowel syndrome. | 2010 Jun 25 |
|
| Risk factors of drug interaction between warfarin and nonsteroidal anti-inflammatory drugs in practical setting. | 2010 Mar |
|
| 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
| Substance Class |
Chemical
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QA03AA05
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C67413
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A03AA05
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ACTIVE MOIETY |
