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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 of TRIMEBUTINE MALEATE

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
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

Curator's Comment: Trimebutine is CNS active in animals. No human data available.

Originator

Sources: FR1344455
Curator's Comment: reference retrieved from https://www.google.com/patents/US20040209960 | http://www.funakoshi.co.jp/data/datasheet/SPB/MI7957.pdf

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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.
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
General pharmacology of the four gastrointestinal motility stimulants bethanechol, metoclopramide, trimebutine, and cisapride.
1991 Jun
Duodenogastric reflux following cholecystectomy in the dog: role of antroduodenal motor function.
2001 Aug
[HPCE determination of trimebutine maleate in rat plasma and its pharmacokinetics].
2001 Feb
Allergic contact dermatitis due to trimebutine.
2001 Sep
[Prokinetics of gastrointestinal system; its newer aspects with regard to motillity stimulants].
2002 Feb
Oesophageal motility disorders.
2002 Jan 12
Effects of tachykinin NK1 receptor antagonists on the viscerosensory response caused by colorectal distention in rabbits.
2002 Mar
Factors affecting gallbladder motility: drugs.
2003 Jul
Spectrophotometric and liquid chromatographic determination of trimebutine maleate in the presence of its degradation products.
2003 Sep 19
Acute treatment of migraine. Breaking the paradigm of monotherapy.
2004 Jan 28
H pylori infection and reflux oesophagitis.
2004 Jun
Effect of nor-trimebutine on neuronal activation induced by a noxious stimulus or an acute colonic inflammation in the rat.
2005 Oct 21
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
The use of combination therapies in the acute management of migraine.
2006 Sep
Acute migraine: Current treatment and emerging therapies.
2007 Jun
[A randomized and case-control clinical study on trimebutine maleate in treating functional dyspepsia coexisting with diarrhea-dominant irritable bowel syndrome].
2007 Nov
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
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
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
Effectiveness of trimebutine maleate on modulating intestinal hypercontractility in a mouse model of postinfectious irritable bowel syndrome.
2010 Jun 25
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
0.1 mM trimebutine inhibits proliferation of human LOVO colon cancer cells.
Name Type Language
TRIMEBUTINE MALEATE
EP   MART.   MI   WHO-DD  
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
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
ECHA (EC/EINECS)
251-845-9
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
PUBCHEM
5282423
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
MERCK INDEX
m11138
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY Merck Index
DRUG BANK
DBSALT001129
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
ChEMBL
CHEMBL190044
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
RXCUI
262296
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY RxNorm
CAS
39133-32-9
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
SUPERSEDED
FDA UNII
2A051GM4YM
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
NSC
758900
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
EVMPD
SUB04966MIG
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
SMS_ID
100000091111
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY
CAS
34140-59-5
Created by admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
PRIMARY