Details
| Stereochemistry | UNKNOWN |
| Molecular Formula | C22H29NO5.C4H4O4 |
| Molecular Weight | 503.5415 |
| Optical Activity | ( - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C/C(O)=O.CCC(COC(=O)C1=CC(OC)=C(OC)C(OC)=C1)(N(C)C)C2=CC=CC=C2
InChI
InChIKey=FSRLGULMGJGKGI-BTJKTKAUSA-N
InChI=1S/C22H29NO5.C4H4O4/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;5-3(6)1-2-4(7)8/h8-14H,7,15H2,1-6H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
| Molecular Formula | C22H29NO5 |
| Molecular Weight | 387.4694 |
| Charge | 0 |
| Count |
|
| Stereochemistry | UNKNOWN |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
| Molecular Formula | C4H4O4 |
| Molecular Weight | 116.0722 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
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 |
|
| Duodenogastric reflux following cholecystectomy in the dog: role of antroduodenal motor function. | 2001 Aug |
|
| Effects of TAK-637, a novel neurokinin-1 receptor antagonist, on colonic function in vivo. | 2001 Aug |
|
| Meta-analysis of smooth muscle relaxants in the treatment of irritable bowel syndrome. | 2001 Mar |
|
| [Dysfunction of the Oddi's sphincter]. | 2001 Sep |
|
| The role of remote gut inflammation in duodenojejunal dysmotility. | 2002 Apr |
|
| Oesophageal motility disorders. | 2002 Jan 12 |
|
| Efficacy of trimebutine therapy in patients with gastroesophageal reflux disease and irritable bowel syndrome. | 2002 Jan-Feb |
|
| Centrally acting agents and visceral sensitivity. | 2002 Jul |
|
| Laxative and anti-diarrheal activity of polycarbophil in mice and rats. | 2002 Jun |
|
| Establishing a comprehensive questionnaire for detecting drug-induced extrapyramidal symptoms. | 2003 Oct |
|
| Beneficial effect of trimebutine and N-monodesmethyl trimebutine on trinitrobenzene sulfonic acid-induced colitis in rats. | 2004 Dec 3 |
|
| Acute treatment of migraine. Breaking the paradigm of monotherapy. | 2004 Jan 28 |
|
| H pylori infection and reflux oesophagitis. | 2004 Jun |
|
| [Pharmacokinetics and bioequivalence of trimebutine dispersive tablet in healthy subjects]. | 2004 Mar |
|
| The effect of trimebutine on the psychosocial adjustment to illness in the irritable bowel syndrome. | 2006 |
|
| 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 |
|
| Acute migraine: Current treatment and emerging therapies. | 2007 Jun |
|
| Meta-analysis of the effects of prokinetic agents in patients with functional dyspepsia. | 2007 Mar |
|
| [A randomized and case-control clinical study on trimebutine maleate in treating functional dyspepsia coexisting with diarrhea-dominant irritable bowel syndrome]. | 2007 Nov |
|
| Treatment of functional dyspepsia with serotonin agonists: a meta-analysis of randomized controlled trials. | 2007 Oct |
|
| 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 |
|
| Activation of peripheral opioid receptors has no effect on heart rate variability. | 2008 Jun |
|
| 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 |
|
| Effect of fibre, antispasmodics, and peppermint oil in the treatment of irritable bowel syndrome: systematic review and meta-analysis. | 2008 Nov 13 |
|
| Effect of four medications associated with gastrointestinal motility on Oddi sphincter in the rabbit. | 2009 |
|
| Effectiveness of prokinetic agents against diseases external to the gastrointestinal tract. | 2009 Apr |
|
| Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
|
| Effectiveness of trimebutine maleate on modulating intestinal hypercontractility in a mouse model of postinfectious irritable bowel syndrome. | 2010 Jun 25 |
|
| Development of a novel combination tablet containing trimebutine maleate and mosapride citrate for the treatment of functional dyspepsia. | 2010 Nov 15 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 11:50:24 GMT 2023
by
admin
on
Sat Dec 16 11:50:24 GMT 2023
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| Record UNII |
H4XZJ9GX7T
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| Record Status |
Validated (UNII)
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| Record Version |
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58997-92-5
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H4XZJ9GX7T
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261-550-7
Created by
admin on Sat Dec 16 11:50:24 GMT 2023 , Edited by admin on Sat Dec 16 11:50:24 GMT 2023
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