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

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
The involvement of flavin-containing monooxygenase but not CYP3A4 in metabolism of itopride hydrochloride, a gastroprokinetic agent: comparison with cisapride and mosapride citrate.	2000 Oct	10997945
Quantitation of itopride in human serum by high-performance liquid chromatography with fluorescence detection and its application to a bioequivalence study.	2005 Apr 25	15734161
How effective is itopride for the treatment of patients with functional dyspepsia?	2006 Sep	16951665
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
Determination of itopride in human plasma by liquid chromatography coupled to tandem mass spectrometric detection: application to a bioequivalence study.	2007 Jan 30	17386535
A double-blind, randomized, placebo-controlled trial of itopride (100 and 200 mg three times daily) on gastric motor and sensory function in healthy volunteers.	2007 Mar	17300287
Meta-analysis of the effects of prokinetic agents in patients with functional dyspepsia.	2007 Mar	17295758
Mosapride in gastrointestinal disorders.	2008	18457463
Itopride and pantoprazole outcomes in diabetic gastroparesis trial (IPOD trial).	2008 Dec	19370958
Prokinetics and fundic relaxants in upper functional GI disorders.	2008 Dec	18940266
Potentiation by cholinesterase inhibitors of cholinergic activity in rat isolated stomach and colon.	2008 Nov-Dec	18824231
Acotiamide hydrochloride (Z-338), a novel prokinetic agent, restores delayed gastric emptying and feeding inhibition induced by restraint stress in rats.	2008 Sep	18482254
Applications of nanomaterials in electrogenerated chemiluminescence biosensors.	2009	22389624
Effectiveness of prokinetic agents against diseases external to the gastrointestinal tract.	2009 Apr	19220673
Determination of itopride hydrochloride in human plasma by RP-HPLC with fluorescence detection and its use in bioequivalence study.	2009 Mar	19101632
Tardive dyskinesia associated with long-term administration of escitalopram and itopride in major depressive disorder.	2009 Mar 17	19121360
Pharmacokinetic and bioequivalence study of itopride HCl in healthy volunteers.	2010	20422945
Idiopathic proximal hemimegacolon in an adult woman.	2010 Apr	20535353
Development and validation of a LC-MS/MS method for the determination of clebopride and its application to a pharmacokinetics study in healthy Chinese volunteers.	2010 Aug 1	20598654
A Simple RP-HPLC Method for Quantitation of Itopride HCl in Tablet Dosage Form.	2010 Oct	21264104
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.

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