TRIMEBUTINE

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

Structure Search

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

HIDE SMILES / InChI

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
Comparison of the effects of trimebutine and YM114 (KAE-393), a novel 5-HT3 receptor antagonist, on stress-induced defecation.	1993 Dec 7	8112388
Duodenogastric reflux following cholecystectomy in the dog: role of antroduodenal motor function.	2001 Aug	11472328
Effects of TAK-637, a novel neurokinin-1 receptor antagonist, on colonic function in vivo.	2001 Aug	11454917
Determination of trimebutine maleate in rat plasma and tissues by using capillary zone electrophoresis.	2001 Jun	11438965
Meta-analysis of smooth muscle relaxants in the treatment of irritable bowel syndrome.	2001 Mar	11207510
The role of remote gut inflammation in duodenojejunal dysmotility.	2002 Apr	11975714
Centrally acting agents and visceral sensitivity.	2002 Jul	12077076
Laxative and anti-diarrheal activity of polycarbophil in mice and rats.	2002 Jun	12120755
Preparation, characterization and taste-masking properties of polyvinylacetal diethylaminoacetate microspheres containing trimebutine.	2002 Oct	12396292
Establishing a comprehensive questionnaire for detecting drug-induced extrapyramidal symptoms.	2003 Oct	14577334
Delayed reaction urticaria due to trimebutine.	2004 Jul	15180771
[Abdominal migraine as a cause of chronic recurrent abdominal pain in a 9-years-old girl--case report].	2005 Aug	16245431
Rectal instillation of butyrate provides a novel clinically relevant model of noninflammatory colonic hypersensitivity in rats.	2005 Jun	15940632
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
[Drug treatment of irritable bowel syndrome: an unmet need].	2007 Mar	17374325
Meta-analysis of the effects of prokinetic agents in patients with functional dyspepsia.	2007 Mar	17295758
[A randomized and case-control clinical study on trimebutine maleate in treating functional dyspepsia coexisting with diarrhea-dominant irritable bowel syndrome].	2007 Nov	18261269
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	18221252
Effect of fibre, antispasmodics, and peppermint oil in the treatment of irritable bowel syndrome: systematic review and meta-analysis.	2008 Nov 13	19008265
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
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 17:15:31 GMT 2023` Edited by `admin` on `Fri Dec 15 17:15:31 GMT 2023`
Record UNII	QZ1OJ92E5R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRIMEBUTINE

Official Name

English

trimebutine [INN]

Common Name

English

.BETA.-(DIMETHYLAMINO)-.BETA.-ETHYLPHENETHYL ALCOHOL 3,4,5-TRIMETHOXYBENZOATE (ESTER)

Common Name

English

TRIMEBUTINE [MI]

Common Name

English

Trimebutine [WHO-DD]

Common Name

English

TRIMEBUTINA

Brand Name

English

Classification Tree Code System Code

WHO-VATC

QA03AA05