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-
Molecular Formula | C4H4O4 |
Molecular Weight | 116.0722 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
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.
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 |
|||
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 |
---|---|---|
Comparison of the effects of trimebutine and YM114 (KAE-393), a novel 5-HT3 receptor antagonist, on stress-induced defecation. | 1993 Dec 7 |
|
[HPCE determination of trimebutine maleate in rat plasma and its pharmacokinetics]. | 2001 Feb |
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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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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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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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Spectrophotometric and liquid chromatographic determination of trimebutine maleate in the presence of its degradation products. | 2003 Sep 19 |
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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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H pylori infection and reflux oesophagitis. | 2004 Jun |
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[Pharmacokinetics and bioequivalence of trimebutine dispersive tablet in healthy subjects]. | 2004 Mar |
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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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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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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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[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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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 |
|
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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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 |
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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
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.
Substance Class |
Chemical
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Record UNII |
2A051GM4YM
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Record Status |
Validated (UNII)
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