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-
| Molecular Formula | C22H29NO5 |
| Molecular Weight | 387.4694 |
| Charge | 0 |
| Count |
|
| Stereochemistry | UNKNOWN |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
| 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 |
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 |
|
| [Dysfunction of the Oddi's sphincter]. | 2001 Sep |
|
| Allergic contact dermatitis due to trimebutine. | 2001 Sep |
|
| The role of remote gut inflammation in duodenojejunal dysmotility. | 2002 Apr |
|
| [Prokinetics of gastrointestinal system; its newer aspects with regard to motillity stimulants]. | 2002 Feb |
|
| Oesophageal motility disorders. | 2002 Jan 12 |
|
| 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 |
|
| Establishing a comprehensive questionnaire for detecting drug-induced extrapyramidal symptoms. | 2003 Oct |
|
| H pylori infection and reflux oesophagitis. | 2004 Jun |
|
| [Abdominal migraine as a cause of chronic recurrent abdominal pain in a 9-years-old girl--case report]. | 2005 Aug |
|
| 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 |
|
| The effect of trimebutine on the psychosocial adjustment to illness in the irritable bowel syndrome. | 2006 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
|
| 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
by
admin
on
Edited
Sat Dec 16 18:02:08 GMT 2023
by
admin
on
Sat Dec 16 18:02:08 GMT 2023
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| Record UNII |
DKM38HXX5A
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| Record Status |
Validated (UNII)
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| Record Version |
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58997-91-4
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261-549-1
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5282423
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DKM38HXX5A
Created by
admin on Sat Dec 16 18:02:08 GMT 2023 , Edited by admin on Sat Dec 16 18:02:08 GMT 2023
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PRIMARY |