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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 of TRIMEBUTINE

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

Description

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

Approval Year

PubMed

PubMed

TitleDatePubMed
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
Duodenogastric reflux following cholecystectomy in the dog: role of antroduodenal motor function.
2001 Aug
Effects of TAK-637, a novel neurokinin-1 receptor antagonist, on colonic function in vivo.
2001 Aug
[HPCE determination of trimebutine maleate in rat plasma and its pharmacokinetics].
2001 Feb
Determination of trimebutine maleate in rat plasma and tissues by using capillary zone electrophoresis.
2001 Jun
Meta-analysis of smooth muscle relaxants in the treatment of irritable bowel syndrome.
2001 Mar
[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
Oesophageal motility disorders.
2002 Jan 12
Centrally acting agents and visceral sensitivity.
2002 Jul
Laxative and anti-diarrheal activity of polycarbophil in mice and rats.
2002 Jun
[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
Preparation, characterization and taste-masking properties of polyvinylacetal diethylaminoacetate microspheres containing trimebutine.
2002 Oct
Factors affecting gallbladder motility: drugs.
2003 Jul
Establishing a comprehensive questionnaire for detecting drug-induced extrapyramidal symptoms.
2003 Oct
Spectrophotometric and liquid chromatographic determination of trimebutine maleate in the presence of its degradation products.
2003 Sep 19
Beneficial effect of trimebutine and N-monodesmethyl trimebutine on trinitrobenzene sulfonic acid-induced colitis in rats.
2004 Dec 3
Acute treatment of migraine. Breaking the paradigm of monotherapy.
2004 Jan 28
Delayed reaction urticaria due to trimebutine.
2004 Jul
H pylori infection and reflux oesophagitis.
2004 Jun
[Pharmacokinetics and bioequivalence of trimebutine dispersive tablet in healthy subjects].
2004 Mar
[Abdominal migraine as a cause of chronic recurrent abdominal pain in a 9-years-old girl--case report].
2005 Aug
Novelty stress increases fecal pellet output in mongolian gerbils: effects of several drugs.
2005 Aug
Determination of trimebutine in pharmaceuticals by differential pulse voltammetry at a glassy carbon electrode.
2005 Jul 15
Rectal instillation of butyrate provides a novel clinically relevant model of noninflammatory colonic hypersensitivity in rats.
2005 Jun
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
Pharmacokinetic study of trimebutine maleate in rabbit blood using in vivo microdialysis coupled to capillary electrophoresis.
2005 Sep 15
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
[Drug treatment of irritable bowel syndrome: an unmet need].
2007 Mar
Meta-analysis of the effects of prokinetic agents in patients with functional dyspepsia.
2007 Mar
Treatment of functional dyspepsia with serotonin agonists: a meta-analysis of randomized controlled trials.
2007 Oct
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
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
[Prokinetics in childhood].
2010 Jun
Effectiveness of trimebutine maleate on modulating intestinal hypercontractility in a mouse model of postinfectious irritable bowel syndrome.
2010 Jun 25
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

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.
Name Type Language
TRIMEBUTINE
INN   MI   WHO-DD  
INN  
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
TRIMEBUTINA
Brand Name English
TRIMEBUTINE [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QA03AA05
Created by admin on Tue Oct 22 06:00:48 UTC 2019 , Edited by admin on Tue Oct 22 06:00:48 UTC 2019
NCI_THESAURUS C67413
Created by admin on Tue Oct 22 06:00:48 UTC 2019 , Edited by admin on Tue Oct 22 06:00:48 UTC 2019
WHO-ATC A03AA05
Created by admin on Tue Oct 22 06:00:48 UTC 2019 , Edited by admin on Tue Oct 22 06:00:48 UTC 2019
Code System Code Type Description
EVMPD
SUB11299MIG
Created by admin on Tue Oct 22 06:00:48 UTC 2019 , Edited by admin on Tue Oct 22 06:00:48 UTC 2019
PRIMARY
WIKIPEDIA
TRIMEBUTINE
Created by admin on Tue Oct 22 06:00:48 UTC 2019 , Edited by admin on Tue Oct 22 06:00:48 UTC 2019
PRIMARY
CAS
39133-31-8
Created by admin on Tue Oct 22 06:00:48 UTC 2019 , Edited by admin on Tue Oct 22 06:00:48 UTC 2019
PRIMARY
ChEMBL
CHEMBL190044
Created by admin on Tue Oct 22 06:00:48 UTC 2019 , Edited by admin on Tue Oct 22 06:00:48 UTC 2019
PRIMARY
MESH
D014287
Created by admin on Tue Oct 22 06:00:48 UTC 2019 , Edited by admin on Tue Oct 22 06:00:48 UTC 2019
PRIMARY
INN
2773
Created by admin on Tue Oct 22 06:00:48 UTC 2019 , Edited by admin on Tue Oct 22 06:00:48 UTC 2019
PRIMARY
EPA CompTox
39133-31-8
Created by admin on Tue Oct 22 06:00:48 UTC 2019 , Edited by admin on Tue Oct 22 06:00:48 UTC 2019
PRIMARY
NCI_THESAURUS
C80588
Created by admin on Tue Oct 22 06:00:48 UTC 2019 , Edited by admin on Tue Oct 22 06:00:48 UTC 2019
PRIMARY
ECHA (EC/EINECS)
254-309-2
Created by admin on Tue Oct 22 06:00:48 UTC 2019 , Edited by admin on Tue Oct 22 06:00:48 UTC 2019
PRIMARY
DRUG BANK
DB09089
Created by admin on Tue Oct 22 06:00:48 UTC 2019 , Edited by admin on Tue Oct 22 06:00:48 UTC 2019
PRIMARY
PUBCHEM
5573
Created by admin on Tue Oct 22 06:00:48 UTC 2019 , Edited by admin on Tue Oct 22 06:00:48 UTC 2019
PRIMARY
MERCK INDEX
M11138
Created by admin on Tue Oct 22 06:00:48 UTC 2019 , Edited by admin on Tue Oct 22 06:00:48 UTC 2019
PRIMARY Merck Index
RXCUI
10819
Created by admin on Tue Oct 22 06:00:48 UTC 2019 , Edited by admin on Tue Oct 22 06:00:48 UTC 2019
PRIMARY RxNorm