Details
| Stereochemistry | UNKNOWN |
| 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 |
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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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| [Dysfunction of the Oddi's sphincter]. | 2001 Sep |
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| Allergic contact dermatitis due to trimebutine. | 2001 Sep |
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| The role of remote gut inflammation in duodenojejunal dysmotility. | 2002 Apr |
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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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| [Physicochemical and pharmacological characteristic and clinical efficacy of an anti-irritable bowel syndrome agent, polycarbophil calcium (Polyful)]. | 2002 Mar |
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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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| Establishing a comprehensive questionnaire for detecting drug-induced extrapyramidal symptoms. | 2003 Oct |
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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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| [Abdominal migraine as a cause of chronic recurrent abdominal pain in a 9-years-old girl--case report]. | 2005 Aug |
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| Prokinetic agents in childen with poor appetite. | 2005 Oct-Dec |
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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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| Increasing the effect of triptans in migraine. | 2006 Oct 14 |
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| The use of combination therapies in the acute management of migraine. | 2006 Sep |
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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 |
|
| Acute migraine: Current treatment and emerging therapies. | 2007 Jun |
|
| [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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| [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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| Treatment of functional dyspepsia with serotonin agonists: a meta-analysis of randomized controlled trials. | 2007 Oct |
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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 |
|
| 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 |
|
| 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
Created
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admin
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Edited
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by
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Sat Dec 16 11:50:20 GMT 2023
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| Record UNII |
U4UUZ24TRB
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| Record Status |
Validated (UNII)
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| Record Version |
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58997-90-3
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U4UUZ24TRB
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261-548-6
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admin on Sat Dec 16 11:50:20 GMT 2023 , Edited by admin on Sat Dec 16 11:50:20 GMT 2023
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