3D Mol Similar

Itopride hydrochloride

: Iupac Name：N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4-dimethoxybenzamide;hydrochloride; CAS No.: 122892-31-3; Molecular Weight：394.9; Modify Date.: 2022-12-08 12:02

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1. Names and Identifiers

: 1.1 Name; Itopride hydrochloride; 1.2 Synonyms; hsr803 ITOPRIDE HCL n-((4-(2-(dimethylamino)ethoxy)phenyl)methyl)-3,4-dimethoxybenzamidemonohydr n-((4-(2-(dimethylamino)ethoxy)phenyl)methyl)-3,4-dimethoxy-benzamidmonohy n-((4-(2-(dimethylamino)ethoxy)phenyl)methyl)-3,4-dimethoxy-benzamidmonohydrochloride n-(4-(2-(dimethylamino)ethoxy)benzyl)-3,4-dimethoxidebenzamidehydrochloride n-[[4-(2-dimethylaminoethoxy)phenyl]methyl]-3,4-dimethoxy-benzamide hydrochloride; View all

1.3 CAS No.: 122892-31-3

1.4 CID: 129791

1.5 EINECS(EC#): 602-905-1

1.6 Molecular Formula: C20H27ClN2O4 (isomer)

1.7 Inchi: ZTOUXLLIPWWHSR-UHFFFAOYSA-N

1.8 InChIkey: ZTOUXLLIPWWHSR-UHFFFAOYSA-N

1.9 Canonical Smiles: Cl.COC1=CC=C(C=C1OC)C(=O)NCC1=CC=C(OCCN(C)C)C=C1

1.10 Isomers Smiles: Cl.COC1=CC=C(C=C1OC)C(=O)NCC1=CC=C(OCCN(C)C)C=C1

2. Properties

2.1 Melting point: 194-1950C

2.1 StorageTemp: 2-8°C

3. Safety and Handling

3.1 Hazard Codes: N

3.1 Risk Statements: 50

3.1 Safety Statements: 61

3.1 RIDADR: UN 3077 9 / PGIII

3.1 WGK Germany: 3

3.1 RTECS: CV4552000

4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H410 Very toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P273 Avoid release to the environment.
Response	P391 Collect spillage.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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5. Synthesis Route

122892-31-3Total: 1 Synthesis Route

122898-67-3 56 Suppliers

122892-31-3 151 Suppliers

Literatures:
ERREGIERRE S.p.A. Patent: WO2006/51079 A1, 2006 ; Location in patent: Page/Page column 7 ;
Yield: ~95%

6. Precursor and Product

precursor:

122898-67-3

7. Other Information

7.0 in vivo: previoius animal study showed that in conscious dogs with implanted strain gauge force transducers, itopride could stimulate contractile activity in the gastrointestinal tract from stomach to colon. whereas, mosapride was able to stimulate contractile activity only in the gastric antrum and ileum. moreover, in rats s andguinea pig, itopride could accelerate colonic luminal transit, however, both mosapride and cisapride failed to enhance colonic transit. such findings suggested that itopride had a stimulatory action on propelling colonic luminal contents, colonic peristalsis, which was quite different from mosapride and cisapride [2].

7.1 IC 50: 2.04 μm

7.2 references: [1] iwanaga y,kimura t,miyashita n,morikawa k,nagata o,itoh z,kondo y. characterization of acetylcholinesterase-inhibition by itopride. jpn j pharmacol.1994 nov;66(3):317-22.
[2] tsubouchi t,saito t,mizutani f,yamauchi t,iwanaga y. stimulatory action of itopride hydrochloride on colonic motor activity in vitro and in vivo. j pharmacol exp ther.2003 aug;306(2):787-93.

7.3 Merck: 14,5244

7.4 Description: Itopride, a gastroprokinetic benzamide derivative was launched in Japan for the relief of gastrointestinal symptoms in patients with chronic gastritis. ltopride is a dopamine D₂-receptor antagonist that stimulates acetylcholine (Ach) release on the postganglionic cholinergic neurons to cause Ach accumulation at muscarinic receptors and, therefore, enhances Ach-induced gastric contractions. In animal models, itopride was reported to increase GI transit and gastric emptying.

7.5 Chemical Properties: Crystalline Solid

7.6 Originator: Hokuriku (Japan)

7.7 Uses: Dopamine D2-receptor antagonist with anticholinesterase activity. Gastroprokinetic

7.8 Uses: Dopamine D2 receptor blockade,acetylcholinesterase inhibitor

7.9 Uses: Anti-Spasmodics

7.10 Brand name: Ganaton

7.11 General Description: Itopride hydrochloride is a new prokinetic drug.

7.12 Biochem/physiol Actions: Itopride hydrochloride enhances the gastrointestinal motility by blocking the activity of dopamine on the D2 receptors, on the post-synaptic cholinergic nerves and by inducing the liberation of acetylcholine in the myenteric plexus. It also inhibits the hydrolysis of the released acetylcholine with the help of acetylcholinesterase.

7.13 in vitro: itopride was found to inhibit both ache and horse serum butyrylcholinesterase (buche). the itopride ic50 against ache was, however, 100-fold less than that against buche. the recovery of ache activity inhibited by low dose of neostigmine was partial, but that inhibited by itopride was complete. double reciprocal plots showed that both vmax and km were affected by itopride, indicating a "mixed" type inhibition, although primarily being an uncompetitive one. in addition, the inhibitory effect of itopride on cholinesterase (che) activity in guinea pig gastrointestine was much weaker than that on pure ache [1].

8. Computational chemical data

Molecular Weight: 394.9g/mol
Molecular Formula: C₂₀H₂₇ClN₂O₄
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 394.1659350
Monoisotopic Mass: 394.1659350
Complexity: 411
Rotatable Bond Count: 9
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 60
Heavy Atom Count: 27
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADceB7OAAEAAAAAAAAAAAAAAAAAAAAAAAwYAAAAAAAAAABQAAAHgAQAAAADAThmAYyBoPABACIAiFSEACCCAAkIAAIiIEOjMgPJjKEtRuHOSrkxhGaqYe63BLOIAABAAAAQABAAAIAAACAAAAAAAAAAA==

9. Question & Answer

What is the background of Itopride Hydrochloride? Jan 17 2022
Itopride hydrochloride (ItoprideHydrochloride) is a methoxybenzamide class drug, which is the hydrochloride salt of N-[4-[2-(dimethylamino)ethoxy]benzyl]-3,4-dimethoxybenzamide. The raw material of It..
What are the differences between Itopride Hydrochloride and Domperidone? Nov 12 2020
Itopride Hydrochloride and Domperidone are both gastrointestinal prokinetic agents commonly used to treat functional dyspepsia caused by gastric motility disorders. Itopride Hydrochloride is a newer g..

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Itopride hydrochloride CAS 122892-31-3