ITOPRIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H26N2O4
Molecular Weight	358.4314
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(OC)C=C(C=C1)C(=O)NCC2=CC=C(OCCN(C)C)C=C2

InChI

InChIKey=QQQIECGTIMUVDS-UHFFFAOYSA-N

InChI=1S/C20H26N2O4/c1-22(2)11-12-26-17-8-5-15(6-9-17)14-21-20(23)16-7-10-18(24-3)19(13-16)25-4/h5-10,13H,11-12,14H2,1-4H3,(H,21,23)

HIDE SMILES / InChI

Molecular Formula	C20H26N2O4
Molecular Weight	358.4314
Charge	0
Count

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

Description
Sources: https://www.rlsnet.ru/tn_index_id_36285.htm
Curator's Comment: description was created based on several sources, including http://www.meppo.com/pdf/drugs/2845-GANATON-1415104080.pdf

Itopride is a dopamine D2 receptor antagonist and inhibitor of acetylcholinesterase. It is indicated in the for the treatment of gastrointestinal symptoms caused by reduced gastrointestinal motility, such as functional non-ulcer dyspepsia (chronic gastritis), gastric fullness, rapid satiation, pain or discomfort in the upper abdomen, anorexia, heartburn, nausea, and vomiting. The drug is not approved in the USA or UK but is available in Japan and Western European countries.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acetylcholinesterase 207 Target ID: P22303\|\|\|Q53F46 Gene ID: 43.0 Gene Symbol: ACHE Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7869618	Inhibitor 8297		2.04 µM [IC50]
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1831229	Antagonist 2778		0.16 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Chronic gastritis 4 Sources: http://www.meppo.com/pdf/drugs/2845-GANATON-1415104080.pdf	Palliative	Approved 8429	GANATON Approved Use Gastrointestinal symptoms in chronic gastritis (bloated feeling, upper abdominal pain, anorexia, heartburn, nausea, and vomiting)
Irritable bowel syndrome 60 Sources: https://clinicaltrials.gov/ct2/show/NCT01027260	Primary	Phase II 1132	Unknown Approved Use Unknown
Gastroparesis 9 Sources: https://clinicaltrials.gov/ct2/show/NCT00370084	Primary	Phase I 428	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Randomised, double-blind, comparative study to evaluate the efficacy and safety of ganaton (itopride hydrochloride) and mosapride citrate in the management of functional dyspepsia.	2004 Dec	15871365
Chromatographic determination of itopride hydrochloride in the presence of its degradation products.	2005 Aug	16158999
Evaluation of new gastro-intestinal prokinetic (ENGIP-II) study.	2005 Dec	16821670
Evaluation of new gastro-intestinal prokinetic (ENGIP-I) study.	2005 Oct	16498771
Ergotism with ischemia in all four extremities: a case report.	2006 Dec	20396534
Mirtazapine for severe gastroparesis unresponsive to conventional prokinetic treatment.	2006 Sep-Oct	16959934
Simultaneous determination of rabeprazole sodium and itopride hydrochloride in capsule dosage form by spectrophotometry.	2007 Feb-2008 Nov	19957542
Meta-analysis of the effects of prokinetic agents in patients with functional dyspepsia.	2007 Mar	17295758
Efficacy of prokinetic agents in improving bowel preparation for colonoscopy.	2008	18577886
Pitfalls in designing trials of functional dyspepsia: the ascent and demise of itopride.	2008 Jun	18477673
Spectrophotometric simultaneous determination of rabeprazole sodium and itopride hydrochloride in capsule dosage form.	2008 Mar	17604217
Potentiation by cholinesterase inhibitors of cholinergic activity in rat isolated stomach and colon.	2008 Nov-Dec	18824231
Validation of 13C-acetic acid breath test by measuring effects of loperamide, morphine, mosapride, and itopride on gastric emptying in mice.	2008 Oct	18827355
Quantitative estimation of itopride hydrochloride and rabeprazole sodium from capsule formulation.	2008 Sep	21394269
Acotiamide hydrochloride (Z-338), a novel prokinetic agent, restores delayed gastric emptying and feeding inhibition induced by restraint stress in rats.	2008 Sep	18482254
Preclinical electrogastrography in experimental pigs.	2010 Jun	21217873
Effect of reversible ligands on oxime-induced reactivation of sarin- and cyclosarin-inhibited human acetylcholinesterase.	2015 Feb 3	25522658

Patents

Sample Use Guides

In Vivo Use Guide

The usual adult dosage is 150mg of itopride hydrochloride (3 tablets) per oral administration daily in three divided doses before meals. The dose may be reduced according to the patient’s age and symptoms.

Route of Administration: Oral

In Vitro Use Guide

To study the interaction between itopride and D2 receptors, rat striatum homogenate was used. The striatal homogenate was incubated with [3H]spiperone (at a final concentration of 0.3 nM), 10nM ketanserin and 10M pargyline, and the displacing ligand at a final concentration from 1 pM to 100 uM. Radioactivity was measured using filtration through Whatman GF/B filters and liquid scintillation counting.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:08:12 GMT 2023` Edited by `admin` on `Fri Dec 15 16:08:12 GMT 2023`
Record UNII	81BMQ80QRL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ITOPRIDE

Official Name

English

N-(P-(2-(DIMETHYLAMINO)ETHOXY)BENZYL)VERATRAMIDE

Common Name

English

NSC-759643

Code

English

itopride [INN]

Common Name

English

ITOPRIDE [MI]

Common Name

English

Itopride [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47792