122892-31-3 Usage
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.
Chemical Properties
Crystalline Solid
Originator
Hokuriku (Japan)
Uses
Different sources of media describe the Uses of 122892-31-3 differently. You can refer to the following data:
1. Dopamine D2-receptor antagonist with anticholinesterase activity. Gastroprokinetic
2. Dopamine D2 receptor blockade,acetylcholinesterase inhibitor
3. Anti-Spasmodics
Brand name
Ganaton
General Description
Itopride hydrochloride is a new prokinetic drug.
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.
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].
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].
IC 50
2.04 μm
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.
Check Digit Verification of cas no
The CAS Registry Mumber 122892-31-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,2,8,9 and 2 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 122892-31:
(8*1)+(7*2)+(6*2)+(5*8)+(4*9)+(3*2)+(2*3)+(1*1)=123
123 % 10 = 3
So 122892-31-3 is a valid CAS Registry Number.
InChI:InChI=1/C20H26N2O4.ClH/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);1H
122892-31-3Relevant articles and documents
Synthesis method of itopride hydrochloride
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Paragraph 0022-0025, (2018/04/21)
The invention discloses a synthesis method of itopride hydrochloride, and relates to the technical field of organic synthesis. Hydroxybenzylamine is taken as starting material, in non-polar solvent, in the presence of an acid-binding agent, the Hydroxybenzylamine and 3,4-dimethoxybenzoyl chloride are subjected to amidation to obtain an intermediate N-(4-hydroxyl) benzyl-3,4-dimenthoxybenzamide, and in polar solvent, in the presence of a catalyst, the intermediate N-(4-hydroxyl) benzyl-3,4-dimenthoxybenzamide and 2-chlorine-N,N-dimethylethylamine are subjected to etherification to obtain the itopride hydrochloride. According to the method, the raw materials are easy to obtain, the route is short, only two steps of synthetic reactions are needed, the high yield of 85-97% can be achieved in each step, by means of amidation and etherification with high product purity, a dangerous process of high-pressure hydrogenation is avoided successfully, and meanwhile, the production and raw materialcosts are greatly reduced.
Itopride preparation method
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, (2017/04/29)
The invention discloses an itopride preparation method, the method comprises the steps of 1, 2-(dimethylamino) chloroethane hydrochloride and hydroxybenzaldehyde synthesizing into 4-(2- dimethylamino ethoxy) benzaldehyde, then synthesizing into 4-(2- dimethylamino ethoxy) benzyl alcohol in alcohol solvent by revivification; 2, in alcohol solvent 3, 4-dimethoxy benzaldehyde and hydroxylamine hydrochloride creating reaction, then in nonpolar solvent synthesizing into 3, 4- dimethoxybenzonitrile by dehydration using the dehydrant; 3, the 4-(2-dimethylamino ethoxy) benzyl alcohol and the 3, 4- dimethoxybenzonitrile synthesizing into itopride in one step; 4, obtaining hydrochloric acid itopride by dissolving itopride in hydrogen chloride alcohol solution and salifying. The adopted raw material in the method is wide in sourcing scope, simple in preparation processing, and is suitable for large scale industrialization production; the preparation process involves no danger process, the production equipment is simple, the synthesized circuit is shorter than the existed circuits, the preparation time is short and the use effect is good.
Novel method for preparing itopride and the intermediate obtained from the method
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, (2016/10/17)
As well as novel intermediates of norcisapride is lengthwisely the present invention refers to and is lengthwisely of formula iii. using the same and manufacturing method relates to manufacturing method. By of the present invention manufacturing method, benzamide derivatives via a stable final is lengthwisely norcisapride high purity and high yield, widely used as an, of the present invention manufacturing method flat plate is transferred to print the can be produced at low cost, is lengthwisely of formula iii. for mass production and available.
