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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

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
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
Comparison of the effects of trimebutine and YM114 (KAE-393), a novel 5-HT3 receptor antagonist, on stress-induced defecation.
1993 Dec 7
Duodenogastric reflux following cholecystectomy in the dog: role of antroduodenal motor function.
2001 Aug
Meta-analysis of smooth muscle relaxants in the treatment of irritable bowel syndrome.
2001 Mar
Oesophageal motility disorders.
2002 Jan 12
Centrally acting agents and visceral sensitivity.
2002 Jul
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
Preparation, characterization and taste-masking properties of polyvinylacetal diethylaminoacetate microspheres containing trimebutine.
2002 Oct
Spectrophotometric and liquid chromatographic determination of trimebutine maleate in the presence of its degradation products.
2003 Sep 19
[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
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
[Drug treatment of irritable bowel syndrome: an unmet need].
2007 Mar
Meta-analysis of the effects of prokinetic agents in patients with functional dyspepsia.
2007 Mar
Effect of four medications associated with gastrointestinal motility on Oddi sphincter in the rabbit.
2009
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 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
Created by admin on Sat Dec 16 11:54:02 GMT 2023 , Edited by admin on Sat Dec 16 11:54:02 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C111045
Created by admin on Sat Dec 16 11:54:02 GMT 2023 , Edited by admin on Sat Dec 16 11:54:02 GMT 2023
PRIMARY
CAS
1456509-46-8
Created by admin on Sat Dec 16 11:54:02 GMT 2023 , Edited by admin on Sat Dec 16 11:54:02 GMT 2023
PRIMARY
PUBCHEM
71725148
Created by admin on Sat Dec 16 11:54:02 GMT 2023 , Edited by admin on Sat Dec 16 11:54:02 GMT 2023
PRIMARY
FDA UNII
5O1CF9IS48
Created by admin on Sat Dec 16 11:54:02 GMT 2023 , Edited by admin on Sat Dec 16 11:54:02 GMT 2023
PRIMARY