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Details

Stereochemistry RACEMIC
Molecular Formula C22H29NO5.C7H8O3S
Molecular Weight 559.671
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIMEBUTINE TOSYLATE

SMILES

CC1=CC=C(C=C1)S(O)(=O)=O.CCC(COC(=O)C2=CC(OC)=C(OC)C(OC)=C2)(N(C)C)C3=CC=CC=C3

InChI

InChIKey=GFFDXKKSLGNXFJ-UHFFFAOYSA-N
InChI=1S/C22H29NO5.C7H8O3S/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;1-6-2-4-7(5-3-6)11(8,9)10/h8-14H,7,15H2,1-6H3;2-5H,1H3,(H,8,9,10)

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 ( + / - )

Molecular Formula C7H8O3S
Molecular Weight 172.202
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Comparison of the effects of trimebutine and YM114 (KAE-393), a novel 5-HT3 receptor antagonist, on stress-induced defecation.
1993 Dec 7
Allergic contact dermatitis due to trimebutine.
2001 Sep
The role of remote gut inflammation in duodenojejunal dysmotility.
2002 Apr
[Prokinetics of gastrointestinal system; its newer aspects with regard to motillity stimulants].
2002 Feb
Oesophageal motility disorders.
2002 Jan 12
Efficacy of trimebutine therapy in patients with gastroesophageal reflux disease and irritable bowel syndrome.
2002 Jan-Feb
Centrally acting agents and visceral sensitivity.
2002 Jul
Laxative and anti-diarrheal activity of polycarbophil in mice and rats.
2002 Jun
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
Beneficial effect of trimebutine and N-monodesmethyl trimebutine on trinitrobenzene sulfonic acid-induced colitis in rats.
2004 Dec 3
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
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
Meta-analysis of the effects of prokinetic agents in patients with functional dyspepsia.
2007 Mar
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 14:53:34 GMT 2023
Edited
by admin
on Sat Dec 16 14:53:34 GMT 2023
Record UNII
M62HUT52HM
Record Status Validated (UNII)
Record Version
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Name Type Language
TRIMEBUTINE TOSYLATE
Common Name English
TRIMEBUTINE 4-TOLUENESULFONATE
Common Name English
BENZOIC ACID, 3,4,5-TRIMETHOXY-, 2-(DIMETHYLAMINO)-2-PHENYLBUTYL ESTER, 4-METHYLBENZENESULFONATE (1:1)
Systematic Name English
Code System Code Type Description
PUBCHEM
71737038
Created by admin on Sat Dec 16 14:53:34 GMT 2023 , Edited by admin on Sat Dec 16 14:53:34 GMT 2023
PRIMARY
FDA UNII
M62HUT52HM
Created by admin on Sat Dec 16 14:53:34 GMT 2023 , Edited by admin on Sat Dec 16 14:53:34 GMT 2023
PRIMARY
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