Details
| Stereochemistry | UNKNOWN |
| Molecular Formula | C22H29NO5 |
| Molecular Weight | 387.4694 |
| Optical Activity | ( + ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC(COC(=O)C1=CC(OC)=C(OC)C(OC)=C1)(N(C)C)C2=CC=CC=C2
InChI
InChIKey=LORDFXWUHHSAQU-UHFFFAOYSA-N
InChI=1S/C22H29NO5/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/h8-14H,7,15H2,1-6H3
| 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 | ( + / - ) |
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 |
|---|---|---|
| General pharmacology of the four gastrointestinal motility stimulants bethanechol, metoclopramide, trimebutine, and cisapride. | 1991 Jun |
|
| Comparison of the effects of trimebutine and YM114 (KAE-393), a novel 5-HT3 receptor antagonist, on stress-induced defecation. | 1993 Dec 7 |
|
| [HPCE determination of trimebutine maleate in rat plasma and its pharmacokinetics]. | 2001 Feb |
|
| [Dysfunction of the Oddi's sphincter]. | 2001 Sep |
|
| [Prokinetics of gastrointestinal system; its newer aspects with regard to motillity stimulants]. | 2002 Feb |
|
| Centrally acting agents and visceral sensitivity. | 2002 Jul |
|
| Laxative and anti-diarrheal activity of polycarbophil in mice and rats. | 2002 Jun |
|
| [Physicochemical and pharmacological characteristic and clinical efficacy of an anti-irritable bowel syndrome agent, polycarbophil calcium (Polyful)]. | 2002 Mar |
|
| Factors affecting gallbladder motility: drugs. | 2003 Jul |
|
| 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 |
|
| [Abdominal migraine as a cause of chronic recurrent abdominal pain in a 9-years-old girl--case report]. | 2005 Aug |
|
| Novelty stress increases fecal pellet output in mongolian gerbils: effects of several drugs. | 2005 Aug |
|
| Determination of trimebutine in pharmaceuticals by differential pulse voltammetry at a glassy carbon electrode. | 2005 Jul 15 |
|
| Effect of nor-trimebutine on neuronal activation induced by a noxious stimulus or an acute colonic inflammation in the rat. | 2005 Oct 21 |
|
| Prokinetic agents in childen with poor appetite. | 2005 Oct-Dec |
|
| The use of combination therapies in the acute management of migraine. | 2006 Sep |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Effectiveness of prokinetic agents against diseases external to the gastrointestinal tract. | 2009 Apr |
|
| A nitro-arginine derivative of trimebutine (NO2-Arg-Trim) attenuates pain induced by colorectal distension in conscious rats. | 2009 May |
|
| Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
|
| [Prokinetics in childhood]. | 2010 Jun |
|
| 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 11:50:20 GMT 2023
by
admin
on
Sat Dec 16 11:50:20 GMT 2023
|
| Record UNII |
9RKX7S7WFY
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
9RKX7S7WFY
Created by
admin on Sat Dec 16 11:50:20 GMT 2023 , Edited by admin on Sat Dec 16 11:50:20 GMT 2023
|
PRIMARY | |||
|
261-547-0
Created by
admin on Sat Dec 16 11:50:20 GMT 2023 , Edited by admin on Sat Dec 16 11:50:20 GMT 2023
|
PRIMARY | |||
|
5573
Created by
admin on Sat Dec 16 11:50:20 GMT 2023 , Edited by admin on Sat Dec 16 11:50:20 GMT 2023
|
PRIMARY | |||
|
58997-89-0
Created by
admin on Sat Dec 16 11:50:20 GMT 2023 , Edited by admin on Sat Dec 16 11:50:20 GMT 2023
|
PRIMARY |