TRIMEBUTINE 3-THIOCARBAMOYLBENZENESULFONATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H29NO5.C7H7NO3S2
Molecular Weight	604.735
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of TRIMEBUTINE 3-THIOCARBAMOYLBENZENESULFONATE

Structure Search

SMILES

NC(=S)C1=CC(=CC=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=ACKBGPXURGPUEW-UHFFFAOYSA-N

InChI=1S/C22H29NO5.C7H7NO3S2/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;8-7(12)5-2-1-3-6(4-5)13(9,10)11/h8-14H,7,15H2,1-6H3;1-4H,(H2,8,12)(H,9,10,11)

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	C7H7NO3S2
Molecular Weight	217.265
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
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
Allergic contact dermatitis due to trimebutine.	2001 Sep	11553143
Oesophageal motility disorders.	2002 Jan 12	11809295
Efficacy of trimebutine therapy in patients with gastroesophageal reflux disease and irritable bowel syndrome.	2002 Jan-Feb	11941952
Centrally acting agents and visceral sensitivity.	2002 Jul	12077076
Effects of tachykinin NK1 receptor antagonists on the viscerosensory response caused by colorectal distention in rabbits.	2002 Mar	11861799
Establishing a comprehensive questionnaire for detecting drug-induced extrapyramidal symptoms.	2003 Oct	14577334
Beneficial effect of trimebutine and N-monodesmethyl trimebutine on trinitrobenzene sulfonic acid-induced colitis in rats.	2004 Dec 3	15531383
H pylori infection and reflux oesophagitis.	2004 Jun	15138222
[Pharmacokinetics and bioequivalence of trimebutine dispersive tablet in healthy subjects].	2004 Mar	15171657
Novelty stress increases fecal pellet output in mongolian gerbils: effects of several drugs.	2005 Aug	16079466
Effect of nor-trimebutine on neuronal activation induced by a noxious stimulus or an acute colonic inflammation in the rat.	2005 Oct 21	15978629
Pharmacokinetic study of trimebutine maleate in rabbit blood using in vivo microdialysis coupled to capillary electrophoresis.	2005 Sep 15	15939564
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
Acute migraine: Current treatment and emerging therapies.	2007 Jun	18488069
Effect of four medications associated with gastrointestinal motility on Oddi sphincter in the rabbit.	2009	19657216
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
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 `Sat Dec 16 11:54:02 GMT 2023` Edited by `admin` on `Sat Dec 16 11:54:02 GMT 2023`
Record UNII	5O1CF9IS48
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRIMEBUTINE 3-THIOCARBAMOYLBENZENESULFONATE

Common Name

English

3-CARBAMOTHIOYLBENZENESULFONIC ACID, (2-(DIMETHYLAMINO)-2-PHENYL-BUTYL) 3,4,5-TRIMETHOXYBENZOATE

Systematic Name

English

BENZOIC ACID, 3,4,5-TRIMETHOXY-, 2-(DIMETHYLAMINO)-2-PHENYLBUTYL ESTER, 3-(AMINOTHIOXOMETHYL)BENZENESULFONATE (1:1)

Systematic Name

English

GIC 1001

Code

English

GIC-1001

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C241