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Details

Stereochemistry UNKNOWN
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
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
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
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
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
Factors affecting gallbladder motility: drugs.
2003 Jul
Establishing a comprehensive questionnaire for detecting drug-induced extrapyramidal symptoms.
2003 Oct
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
[Abdominal migraine as a cause of chronic recurrent abdominal pain in a 9-years-old girl--case report].
2005 Aug
Rectal instillation of butyrate provides a novel clinically relevant model of noninflammatory colonic hypersensitivity in rats.
2005 Jun
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
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
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
[Drug treatment of irritable bowel syndrome: an unmet need].
2007 Mar
Activation of peripheral opioid receptors has no effect on heart rate variability.
2008 Jun
Effectiveness of prokinetic agents against diseases external to the gastrointestinal tract.
2009 Apr
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Risk factors of drug interaction between warfarin and nonsteroidal anti-inflammatory drugs in practical setting.
2010 Mar
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, (+)-
Common Name English
(+)-TRIMEBUTINE
Common Name English
BENZOIC ACID, 3,4,5-TRIMETHOXY-, 2-(DIMETHYLAMINO)-2-PHENYLBUTYL ESTER, (+)-
Systematic Name English
Code System Code Type Description
FDA UNII
9RKX7S7WFY
Created by admin on Sat Dec 16 11:50:20 GMT 2023 , Edited by admin on Sat Dec 16 11:50:20 GMT 2023
PRIMARY
ECHA (EC/EINECS)
261-547-0
Created by admin on Sat Dec 16 11:50:20 GMT 2023 , Edited by admin on Sat Dec 16 11:50:20 GMT 2023
PRIMARY
PUBCHEM
5573
Created by admin on Sat Dec 16 11:50:20 GMT 2023 , Edited by admin on Sat Dec 16 11:50:20 GMT 2023
PRIMARY
CAS
58997-89-0
Created by admin on Sat Dec 16 11:50:20 GMT 2023 , Edited by admin on Sat Dec 16 11:50:20 GMT 2023
PRIMARY