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
General pharmacology of the four gastrointestinal motility stimulants bethanechol, metoclopramide, trimebutine, and cisapride.	1991 Jun	1930352
Duodenogastric reflux following cholecystectomy in the dog: role of antroduodenal motor function.	2001 Aug	11472328
Effects of TAK-637, a novel neurokinin-1 receptor antagonist, on colonic function in vivo.	2001 Aug	11454917
[HPCE determination of trimebutine maleate in rat plasma and its pharmacokinetics].	2001 Feb	12579881
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
[Dysfunction of the Oddi's sphincter].	2001 Sep	11787376
Allergic contact dermatitis due to trimebutine.	2001 Sep	11553143
The role of remote gut inflammation in duodenojejunal dysmotility.	2002 Apr	11975714
[Prokinetics of gastrointestinal system; its newer aspects with regard to motillity stimulants].	2002 Feb	11979811
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
Laxative and anti-diarrheal activity of polycarbophil in mice and rats.	2002 Jun	12120755
[Physicochemical and pharmacological characteristic and clinical efficacy of an anti-irritable bowel syndrome agent, polycarbophil calcium (Polyful)].	2002 Mar	11915521
Effects of tachykinin NK1 receptor antagonists on the viscerosensory response caused by colorectal distention in rabbits.	2002 Mar	11861799
Quantitative determination of trimebutine maleate and its three metabolites in human plasma by liquid chromatography-tandem mass spectrometry.	2002 Nov 5	12361732
Preparation, characterization and taste-masking properties of polyvinylacetal diethylaminoacetate microspheres containing trimebutine.	2002 Oct	12396292
Factors affecting gallbladder motility: drugs.	2003 Jul	12974504
Establishing a comprehensive questionnaire for detecting drug-induced extrapyramidal symptoms.	2003 Oct	14577334
Spectrophotometric and liquid chromatographic determination of trimebutine maleate in the presence of its degradation products.	2003 Sep 19	12972088
Beneficial effect of trimebutine and N-monodesmethyl trimebutine on trinitrobenzene sulfonic acid-induced colitis in rats.	2004 Dec 3	15531383
Acute treatment of migraine. Breaking the paradigm of monotherapy.	2004 Jan 28	15005810
Delayed reaction urticaria due to trimebutine.	2004 Jul	15180771
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
Determination of trimebutine in pharmaceuticals by differential pulse voltammetry at a glassy carbon electrode.	2005 Jul 15	15967289
Pharmacokinetic study of trimebutine maleate in rabbit blood using in vivo microdialysis coupled to capillary electrophoresis.	2005 Sep 15	15939564
Rizatriptan vs. rizatriptan plus trimebutine for the acute treatment of migraine: a double-blind, randomized, cross-over, placebo-controlled study.	2006 Jul	16776704
Increasing the effect of triptans in migraine.	2006 Oct 14	17046449
The use of combination therapies in the acute management of migraine.	2006 Sep	19412476
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	17142094
Acute migraine: Current treatment and emerging therapies.	2007 Jun	18488069
[Drug treatment of irritable bowel syndrome: an unmet need].	2007 Mar	17374325
Meta-analysis of the effects of prokinetic agents in patients with functional dyspepsia.	2007 Mar	17295758
Treatment of functional dyspepsia with serotonin agonists: a meta-analysis of randomized controlled trials.	2007 Oct	17845684
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	18221252
Effect of fibre, antispasmodics, and peppermint oil in the treatment of irritable bowel syndrome: systematic review and meta-analysis.	2008 Nov 13	19008265
A nitro-arginine derivative of trimebutine (NO2-Arg-Trim) attenuates pain induced by colorectal distension in conscious rats.	2009 May	19416632
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
[Prokinetics in childhood].	2010 Jun	20654867

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 UTC 2023` Edited by `admin` on `Sat Dec 16 11:54:02 UTC 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