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
Stimulatory action of itopride hydrochloride on colonic motor activity in vitro and in vivo.	2003 Aug	12724347
Efficacy and tolerability of itopride hydrochloride in patients with non-ulcer dyspepsia.	2003 Jun	14579989
Establishing a comprehensive questionnaire for detecting drug-induced extrapyramidal symptoms.	2003 Oct	14577334
Comparative evaluation of the efficacy and tolerability of itopride hydrochloride and domperidone in patients with non-ulcer dyspepsia.	2004 Aug	15847356
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
[The onset of physiological activity in the stomach in the postoperative period. A comparative study with a prokinetic preparation, Ganaton].	2004 Oct	15663103
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
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
Effect of itopride, a new prokinetic, in patients with mild GERD: a pilot study.	2005 Jul 21	16015691
Management of diabetic gastroparesis.	2005 Mar	16173296
Evaluation of new gastro-intestinal prokinetic (ENGIP-I) study.	2005 Oct	16498771
Effects of itopride hydrochloride on plasma gut-regulatory peptide and stress-related hormone levels in healthy human subjects.	2006	16717477
Ergotism with ischemia in all four extremities: a case report.	2006 Dec	20396534
A placebo-controlled trial of itopride in functional dyspepsia.	2006 Feb 23	16495395
Itopride for functional dyspepsia.	2006 Jun 1	16738281
[Functional dyspepsia. Itopride improves symptoms].	2006 Oct	17058905
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
Efficacy of prokinetic agents in improving bowel preparation for colonoscopy.	2008	18577886
Prokinetics and fundic relaxants in upper functional GI disorders.	2008 Dec	18940266
Itopride in functional dyspepsia: results of two phase III multicentre, randomised, double-blind, placebo-controlled trials.	2008 Jun	17965059
Effect of itopride on gastric emptying in longstanding diabetes mellitus.	2008 May	18179609
Potentiation by cholinesterase inhibitors of cholinergic activity in rat isolated stomach and colon.	2008 Nov-Dec	18824231
Quantitative estimation of itopride hydrochloride and rabeprazole sodium from capsule formulation.	2008 Sep	21394269
Applications of nanomaterials in electrogenerated chemiluminescence biosensors.	2009	22389624
[The use of prokinetics for the correction of motor and tonic digestive disorders].	2009	19469257
Effectiveness of prokinetic agents against diseases external to the gastrointestinal tract.	2009 Apr	19220673
Acupuncture as a treatment for functional dyspepsia: design and methods of a randomized controlled trial.	2009 Aug 23	19698147
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
Functional dyspepsia: a pragmatic approach.	2010	21180236
Idiopathic proximal hemimegacolon in an adult woman.	2010 Apr	20535353
Evaluation of anti-GERD activity of gastro retentive drug delivery system of itopride hydrochloride.	2010 Aug	20515421
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
Effect of probiotic Lactobacillus (Lacidofil® cap) for the prevention of antibiotic-associated diarrhea: a prospective, randomized, double-blind, multicenter study.	2010 Dec	21165295
Banha-sasim-tang as an herbal formula for the treatment of functional dyspepsia: a randomized, double-blind, placebo-controlled, two-center trial.	2010 Jul 30	20670451
Preclinical electrogastrography in experimental pigs.	2010 Jun	21217873
A Simple RP-HPLC Method for Quantitation of Itopride HCl in Tablet Dosage Form.	2010 Oct	21264104
Pharmacotherapy for gastroparesis: an attempt to evaluate a safer alternative.	2010 Oct	21103416
A case of spontaneous regression of advanced gastric cancer.	2010 Oct	20890436
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