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
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)
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | TRIMEBUTINE Approved UseTRIMEBUTINE (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 UseUnknown |
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 |
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| Oesophageal motility disorders. | 2002 Jan 12 |
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| Efficacy of trimebutine therapy in patients with gastroesophageal reflux disease and irritable bowel syndrome. | 2002 Jan-Feb |
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| Effects of tachykinin NK1 receptor antagonists on the viscerosensory response caused by colorectal distention in rabbits. | 2002 Mar |
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| Factors affecting gallbladder motility: drugs. | 2003 Jul |
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| Beneficial effect of trimebutine and N-monodesmethyl trimebutine on trinitrobenzene sulfonic acid-induced colitis in rats. | 2004 Dec 3 |
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| Delayed reaction urticaria due to trimebutine. | 2004 Jul |
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| [Pharmacokinetics and bioequivalence of trimebutine dispersive tablet in healthy subjects]. | 2004 Mar |
|
| Determination of trimebutine in pharmaceuticals by differential pulse voltammetry at a glassy carbon electrode. | 2005 Jul 15 |
|
| Rectal instillation of butyrate provides a novel clinically relevant model of noninflammatory colonic hypersensitivity in rats. | 2005 Jun |
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| Pharmacokinetic study of trimebutine maleate in rabbit blood using in vivo microdialysis coupled to capillary electrophoresis. | 2005 Sep 15 |
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| The effect of trimebutine on the psychosocial adjustment to illness in the irritable bowel syndrome. | 2006 |
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| Increasing the effect of triptans in migraine. | 2006 Oct 14 |
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| The use of combination therapies in the acute management of migraine. | 2006 Sep |
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| 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 |
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| Acute migraine: Current treatment and emerging therapies. | 2007 Jun |
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| [Drug treatment of irritable bowel syndrome: an unmet need]. | 2007 Mar |
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| Meta-analysis of the effects of prokinetic agents in patients with functional dyspepsia. | 2007 Mar |
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| Treatment of functional dyspepsia with serotonin agonists: a meta-analysis of randomized controlled trials. | 2007 Oct |
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| 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 Feb |
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| Activation of peripheral opioid receptors has no effect on heart rate variability. | 2008 Jun |
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| 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 |
|
| Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
|
| [Prokinetics in childhood]. | 2010 Jun |
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
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| Code System | Code | Type | Description | ||
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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
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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
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PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD
