TRIMEBUTINE MALEATE

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

Structure Search

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-

HIDE SMILES / InChI

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	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9364286 | https://www.ncbi.nlm.nih.gov/pubmed/21725804 | http://www.aapharma.ca/downloads/en/PIL/Trimebutine_PM.pdf

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Vascular cell adhesion protein 1 8 Target ID: CHEMBL3735 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28714852 \| https://www.ncbi.nlm.nih.gov/pubmed/26253722	Agonist 2678
Opioid receptors; mu/kappa/delta 33 Target ID: CHEMBL2095181 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9364286 \| https://www.ncbi.nlm.nih.gov/pubmed/1963196 \| https://www.ncbi.nlm.nih.gov/pubmed/2886594	Agonist 2678
Voltage-gated L-type calcium channel 92 Target ID: CHEMBL2095229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21725804 \| https://www.ncbi.nlm.nih.gov/pubmed/21725819 \| https://www.ncbi.nlm.nih.gov/pubmed/2171963	Blocker 537
Calcium-activated potassium channel subunit alpha-1 25 Target ID: CHEMBL4304 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21725804 \| https://www.ncbi.nlm.nih.gov/pubmed/21725819	Blocker 537

Conditions

Condition	Modality	Targets	Highest Phase	Product
Irritable bowel syndrome 60 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26985535	Primary		Approved 8429	TRIMEBUTINE Approved Use TRIMEBUTINE (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.
Spinal cord injury 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28714852	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
General pharmacology of the four gastrointestinal motility stimulants bethanechol, metoclopramide, trimebutine, and cisapride.	1991 Jun	1930352
Comparison of the effects of trimebutine and YM114 (KAE-393), a novel 5-HT3 receptor antagonist, on stress-induced defecation.	1993 Dec 7	8112388
Allergic contact dermatitis due to trimebutine.	2001 Sep	11553143
The role of remote gut inflammation in duodenojejunal dysmotility.	2002 Apr	11975714
[Prokinetics of gastrointestinal system; its newer aspects with regard to motillity stimulants].	2002 Feb	11979811
Oesophageal motility disorders.	2002 Jan 12	11809295
Efficacy of trimebutine therapy in patients with gastroesophageal reflux disease and irritable bowel syndrome.	2002 Jan-Feb	11941952
Centrally acting agents and visceral sensitivity.	2002 Jul	12077076
Laxative and anti-diarrheal activity of polycarbophil in mice and rats.	2002 Jun	12120755
Effects of tachykinin NK1 receptor antagonists on the viscerosensory response caused by colorectal distention in rabbits.	2002 Mar	11861799
Quantitative determination of trimebutine maleate and its three metabolites in human plasma by liquid chromatography-tandem mass spectrometry.	2002 Nov 5	12361732
Factors affecting gallbladder motility: drugs.	2003 Jul	12974504
Beneficial effect of trimebutine and N-monodesmethyl trimebutine on trinitrobenzene sulfonic acid-induced colitis in rats.	2004 Dec 3	15531383
Pharmacokinetic study of trimebutine maleate in rabbit blood using in vivo microdialysis coupled to capillary electrophoresis.	2005 Sep 15	15939564
Rizatriptan vs. rizatriptan plus trimebutine for the acute treatment of migraine: a double-blind, randomized, cross-over, placebo-controlled study.	2006 Jul	16776704
Increasing the effect of triptans in migraine.	2006 Oct 14	17046449
The use of combination therapies in the acute management of migraine.	2006 Sep	19412476
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	17142094
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	16854404
Meta-analysis of the effects of prokinetic agents in patients with functional dyspepsia.	2007 Mar	17295758
Effect of fibre, antispasmodics, and peppermint oil in the treatment of irritable bowel syndrome: systematic review and meta-analysis.	2008 Nov 13	19008265
Effectiveness of prokinetic agents against diseases external to the gastrointestinal tract.	2009 Apr	19220673
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
[Prokinetics in childhood].	2010 Jun	20654867
Effectiveness of trimebutine maleate on modulating intestinal hypercontractility in a mouse model of postinfectious irritable bowel syndrome.	2010 Jun 25	20371236
Development of a novel combination tablet containing trimebutine maleate and mosapride citrate for the treatment of functional dyspepsia.	2010 Nov 15	20826201

Patents

Sample Use Guides

In Vivo Use Guide

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

0.1 mM trimebutine inhibits proliferation of human LOVO colon cancer cells.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:45:10 GMT 2023` Edited by `admin` on `Fri Dec 15 15:45:10 GMT 2023`
Record UNII	2A051GM4YM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRIMEBUTINE MALEATE

Common Name

English

TRIMEBUTINE MALEATE [JAN]

Common Name

English

TRIMEBUTINE MALEATE [MI]

Common Name

English

2-DIMETHYLAMINO-2-PHENYLBUTYL 3,4,5-TRIMETHOXYBENZOATE HYDROGEN MALEATE

Systematic Name

English

TRIMEBUTINE MALEATE SALT

Common Name

English

Trimebutine maleate [WHO-DD]

Common Name

English

NSC-758900

Code

English

TRIMEBUTINE MALEATE [EP MONOGRAPH]

Common Name

English

TRIMEBUTINE MALEATE [MART.]

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID5046017