TRIMEBUTINE 3-THIOCARBAMOYLBENZENESULFONATE

Possibly Marketed Outside US

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	C7H7NO3S2
Molecular Weight	217.265
Charge	0
Count

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

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	( + / - )

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 2752
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 2752
Voltage-gated L-type calcium channel 95 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 555
Calcium-activated potassium channel subunit alpha-1 26 Target ID: CHEMBL4304 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21725804 \| https://www.ncbi.nlm.nih.gov/pubmed/21725819	Blocker 555

Conditions

Condition	Modality	Targets	Highest Phase	Product
Irritable bowel syndrome 61 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26985535	Primary		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
1271.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16854404/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		NOR-TRIMEBUTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
44.3 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400315_2399006F1331_1_100_1F.pdf#page=19	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		TRIMEBUTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
4533.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16854404/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		NOR-TRIMEBUTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
72.1 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400315_2399006F1331_1_100_1F.pdf#page=19	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		TRIMEBUTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16854404/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		NOR-TRIMEBUTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.83 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400315_2399006F1331_1_100_1F.pdf#page=19	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		TRIMEBUTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
23% OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400315_2399006F1331_1_100_1F.pdf#page=22			TRIMEBUTINE serum	Homo sapiens

Doses

Dose	Population	Adverse events
600 mg 3 times / day multiple, oral Highest studied dose Dose: 600 mg, 3 times / day Route: oral Route: multiple Dose: 600 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/344090/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/344090/	Disc. AE: Vomiting... Other AEs: Tiredness, Sensation of heat... AEs leading to discontinuation/dose reduction: Vomiting (2.4%) Other AEs: Tiredness (grade 1, 15%) Sensation of heat (grade 1, 15%) Sensation of cold (grade 1, 15%) Sources: https://pubmed.ncbi.nlm.nih.gov/344090/

AEs

AE	Significance	Dose	Population
Vomiting	2.4% Disc. AE	600 mg 3 times / day multiple, oral Highest studied dose Dose: 600 mg, 3 times / day Route: oral Route: multiple Dose: 600 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/344090/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/344090/
Sensation of cold	grade 1, 15%	600 mg 3 times / day multiple, oral Highest studied dose Dose: 600 mg, 3 times / day Route: oral Route: multiple Dose: 600 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/344090/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/344090/
Sensation of heat	grade 1, 15%	600 mg 3 times / day multiple, oral Highest studied dose Dose: 600 mg, 3 times / day Route: oral Route: multiple Dose: 600 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/344090/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/344090/
Tiredness	grade 1, 15%	600 mg 3 times / day multiple, oral Highest studied dose Dose: 600 mg, 3 times / day Route: oral Route: multiple Dose: 600 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/344090/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/344090/

PubMed

Title	Date	PubMed
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010-12	21818443
Development of a novel combination tablet containing trimebutine maleate and mosapride citrate for the treatment of functional dyspepsia.	2010-11-15	20826201
Effectiveness of trimebutine maleate on modulating intestinal hypercontractility in a mouse model of postinfectious irritable bowel syndrome.	2010-06-25	20371236
[Prokinetics in childhood].	2010-06	20654867
Risk factors of drug interaction between warfarin and nonsteroidal anti-inflammatory drugs in practical setting.	2010-03	20191029
A nitro-arginine derivative of trimebutine (NO2-Arg-Trim) attenuates pain induced by colorectal distension in conscious rats.	2009-05	19416632
Effectiveness of prokinetic agents against diseases external to the gastrointestinal tract.	2009-04	19220673
Effect of four medications associated with gastrointestinal motility on Oddi sphincter in the rabbit.	2009	19657216
Effect of fibre, antispasmodics, and peppermint oil in the treatment of irritable bowel syndrome: systematic review and meta-analysis.	2008-11-13	19008265
Activation of peripheral opioid receptors has no effect on heart rate variability.	2008-06	18449593
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.	2008-05	18221252
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.	2008-02	18296863
[A randomized and case-control clinical study on trimebutine maleate in treating functional dyspepsia coexisting with diarrhea-dominant irritable bowel syndrome].	2007-11	18261269
Treatment of functional dyspepsia with serotonin agonists: a meta-analysis of randomized controlled trials.	2007-10	17845684
Acute migraine: Current treatment and emerging therapies.	2007-06	18488069
Spectrophotometric determination of some anti-tussive and anti-spasmodic drugs through ion-pair complex formation with thiocyanate and cobalt(II) or molybdenum(V).	2007-04	17142094
[Drug treatment of irritable bowel syndrome: an unmet need].	2007-03	17374325
Meta-analysis of the effects of prokinetic agents in patients with functional dyspepsia.	2007-03	17295758
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.	2007-01	16854404
Increasing the effect of triptans in migraine.	2006-10-14	17046449
The use of combination therapies in the acute management of migraine.	2006-09	19412476
Rizatriptan vs. rizatriptan plus trimebutine for the acute treatment of migraine: a double-blind, randomized, cross-over, placebo-controlled study.	2006-07	16776704
Prokinetic agents in childen with poor appetite.	2006-01-26	16432992
The effect of trimebutine on the psychosocial adjustment to illness in the irritable bowel syndrome.	2006	18386606
Effect of nor-trimebutine on neuronal activation induced by a noxious stimulus or an acute colonic inflammation in the rat.	2005-10-21	15978629
Pharmacokinetic study of trimebutine maleate in rabbit blood using in vivo microdialysis coupled to capillary electrophoresis.	2005-09-15	15939564
[Abdominal migraine as a cause of chronic recurrent abdominal pain in a 9-years-old girl--case report].	2005-08	16245431
Novelty stress increases fecal pellet output in mongolian gerbils: effects of several drugs.	2005-08	16079466
Determination of trimebutine in pharmaceuticals by differential pulse voltammetry at a glassy carbon electrode.	2005-07-15	15967289
Rectal instillation of butyrate provides a novel clinically relevant model of noninflammatory colonic hypersensitivity in rats.	2005-06	15940632
Beneficial effect of trimebutine and N-monodesmethyl trimebutine on trinitrobenzene sulfonic acid-induced colitis in rats.	2004-12-03	15531383
Delayed reaction urticaria due to trimebutine.	2004-07	15180771
H pylori infection and reflux oesophagitis.	2004-06	15138222
[Pharmacokinetics and bioequivalence of trimebutine dispersive tablet in healthy subjects].	2004-03	15171657
Acute treatment of migraine. Breaking the paradigm of monotherapy.	2004-01-28	15005810
Establishing a comprehensive questionnaire for detecting drug-induced extrapyramidal symptoms.	2003-10	14577334
Spectrophotometric and liquid chromatographic determination of trimebutine maleate in the presence of its degradation products.	2003-09-19	12972088
Factors affecting gallbladder motility: drugs.	2003-07	12974504
Quantitative determination of trimebutine maleate and its three metabolites in human plasma by liquid chromatography-tandem mass spectrometry.	2002-11-05	12361732
Preparation, characterization and taste-masking properties of polyvinylacetal diethylaminoacetate microspheres containing trimebutine.	2002-10	12396292
Centrally acting agents and visceral sensitivity.	2002-07	12077076
Laxative and anti-diarrheal activity of polycarbophil in mice and rats.	2002-06	12120755
Efficacy of trimebutine therapy in patients with gastroesophageal reflux disease and irritable bowel syndrome.	2002-04-11	11941952
The role of remote gut inflammation in duodenojejunal dysmotility.	2002-04	11975714
[Physicochemical and pharmacological characteristic and clinical efficacy of an anti-irritable bowel syndrome agent, polycarbophil calcium (Polyful)].	2002-03	11915521
Effects of tachykinin NK1 receptor antagonists on the viscerosensory response caused by colorectal distention in rabbits.	2002-03	11861799
[Prokinetics of gastrointestinal system; its newer aspects with regard to motillity stimulants].	2002-02	11979811
[HPCE determination of trimebutine maleate in rat plasma and its pharmacokinetics].	2001-02	12579881
Comparison of the effects of trimebutine and YM114 (KAE-393), a novel 5-HT3 receptor antagonist, on stress-induced defecation.	1993-12-07	8112388
General pharmacology of the four gastrointestinal motility stimulants bethanechol, metoclopramide, trimebutine, and cisapride.	1991-06	1930352

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 `Tue Apr 01 17:22:11 GMT 2025` Edited by `admin` on `Tue Apr 01 17:22:11 GMT 2025`
Record UNII	5O1CF9IS48
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRIMEBUTINE 3-THIOCARBAMOYLBENZENESULFONATE

Common Name

English

GIC 1001

Preferred 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

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C241