PICOPRAZOLE

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H17N3O3S
Molecular Weight	343.4
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)C1=CC2=C(C=C1C)N=C(N2)[S+]([O-])CC3=NC=CC=C3C

InChI

InChIKey=ASSMECARUIRCML-UHFFFAOYSA-N

InChI=1S/C17H17N3O3S/c1-10-5-4-6-18-15(10)9-24(22)17-19-13-7-11(2)12(16(21)23-3)8-14(13)20-17/h4-8H,9H2,1-3H3,(H,19,20)

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6299338 | https://www.ncbi.nlm.nih.gov/pubmed/6419624 | https://www.ncbi.nlm.nih.gov/pubmed/6259537

Picoprazole is substituted benzimidazole. Picoprazole inhibited the gastric (H+ + K+)-ATPase in a concentration-and time-dependent manner, which may explain its inhibitory action on acid secretion in vitro and in vivo. This compound inhibits acid secretion at the level of the parietal cell by its ability to inhibit the gastric proton pump. Picoprazole affects pepsin secretion probably indirectly via its effect on the parietal cell. Studies on the (Na+ + K+)-ATPase indicated that this enzyme was unaffected by picoprazole.

Approval Year

PubMed

Title	Date	PubMed
[Discovery and development of the proton pump inhibitor].	1992-01	1311779
The potency of substituted benzimidazoles such as E3810, omeprazole, Ro 18-5364 to inhibit gastric H+, K(+)-ATPase is correlatedwith the rate of acid-activation of the inhibitor.	1990-02-15	2154989
[Effects of gastric proton pump inhibitors on gastric secretion and peptic ulcers].	1986-04	2873085
Disulfide cross-linking of H,K-ATPase opens Cl- conductance, triggering proton uptake in gastric vesicles. Studies with specific inhibitors.	1986-02-25	3005257
Ultrastructure of inhibited parietal cells in the rat.	1984-11	6479531
Inhibition of partially purified K+/H+-ATPase from guinea-pig isolated and enriched parietal cells by substituted benzimidazoles.	1984-07	6146367
Microelectrode measurements of K+ and pH in rabbit gastric glands: effect of histamine.	1984-04	6202153
Parietal cell structure during inhibition of acid secretion.	1984	6599538
Effects of KCl and insulin on benzimidazole-inhibited canine gastric secretion.	1983-12	6419624
Inhibition of gastric acid secretion by omeprazole in the dog and rat.	1983-10	6884713
Effect of substituted benzimidazoles on acid secretion in isolated and enriched guinea pig parietal cells.	1983-06	6303916
Inhibition of gastric (H+ + K+)-ATPase by the substituted benzimidazole, picoprazole.	1983-02-09	6299338
Inhibition of acid secretion in isolated gastric glands by substituted benzimidazoles.	1982-12	6293317
Effects of substituted benzimidazole (H 149/94) on gastric acid secretion in humans.	1982-07	6282679
Substituted benzimidazoles inhibit gastric acid secretion by blocking (H+ + K+)ATPase.	1981-03-12	6259537

Patents

Name

Type

Language

picoprazole [INN]

Preferred Name

English

PICOPRAZOLE

Official Name

English

METHYL 6-METHYL-2-(((3-METHYL-2-PYRIDYL)METHYL)SULFINYL)-5-BENZIMIDAZOLECARBOXYLATE

Systematic Name

English

Code System Code Type Description

MESH

C028887