Itopride

Names

[ Name ]:
Itopride

[Synonym ]:
MFCD00867431
Itopride
Itopride (INN)
UNII-81BMQ80QRL
N-<4-<2-(dimethylamino)ethoxy>benzyl>-3,4-dimethoxybenzamide
Benzamide, N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4-dimethoxy-
Ganaton
[125I]-Itopride
N-{4-[2-(Dimethylamino)ethoxy]benzyl}-3,4-dimethoxybenzamide

Biological Activity

[Description]:

Itopride (HSR803 free base) is a potent and orally active dopamine-2 antagonist and an acetylcholine esterase (AChE) inhibitor. Itopride enhances gastric motility through both antidopaminergic and anti-acetylcholinesterasic actions, can be used as a gastrointestinal prokinetic agent. Itopride can be used for researching gastro-esophageal reflux disease (GERD)[1].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor

Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor

Signaling Pathways >> Neuronal Signaling >> AChE

[Target]

D2 Receptor

Acetylcholinesterase

[In Vitro]

Itopride has prokinetic effects on both the ileum and colon, which are regulated through inhibitory effects on AChE and antagonistic effects on dopamine D2 receptor[3]. Itopride hydrochloride (0.1 nM-1 μM) significantly accelerats the propagation velocity of the peristalsis in ex guinea pig ileum[3].

[In Vivo]

Itopride (30 mg/kg; p.o.) significantly accelerates gastric emptying compared with the vehicle group[4]. Itopride (30 mg/kg; p.o.) displays Cmax of 358 ‰, T1/2 of 24.9 min[4].

[References]

[1]. Iwanaga Y, et al. A novel water-soluble dopamine-2 antagonist with anticholinesterase activity in gastrointestinal motor activity. Comparison with domperidone and neostigmine. Gastroenterology. 1990 Aug;99(2):401-8.

[2]. Kim YS, et al. Effect of itopride, a new prokinetic, in patients with mild GERD: a pilot study. World J Gastroenterol. 2005 Jul 21;11(27):4210-4.

[3]. Hyun Chul Lim, et al. Effect of Itopride Hydrochloride on the Ileal and Colonic Motility in Guinea Pig In Vitro. Effect of Itopride Hydrochloride on the Ileal and Colonic Motility in Guinea Pig In Vitro. Yonsei Med J. 2008 Jun 30;49(3):472-8.

[4]. Kenjiro Matsumoto, et al. Validation of 13 C-Acetic Acid Breath Test by Measuring Effects of Loperamide, Morphine, Mosapride, and Itopride on Gastric Emptying in Mice. Biol Pharm Bull. 2008 Oct;31(10):1917-22.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
510.1±50.0 °C at 760 mmHg

[ Melting Point ]:
185-187 °C(lit.)

[ Molecular Formula ]:
C₂₀H₂₆N₂O₄

[ Molecular Weight ]:
358.431

[ Flash Point ]:
262.3±30.1 °C

[ Exact Mass ]:
358.189270

[ PSA ]:
60.03000

[ LogP ]:
2.43

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.552

[ Water Solubility ]:
18 g/100 mL (20 ºC)

Safety Information

[ Hazard Codes ]:
T,Xi,Xn

[ Risk Phrases ]:
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . R36/37/38:Irritating to eyes, respiratory system and skin .

[ Safety Phrases ]:
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36:Wear suitable protective clothing .

[ HS Code ]:
2924299090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%