LINAPRAZAN

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H26N4O2
Molecular Weight	366.4567
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(C)N2C=C(C=C(NCC3=C(C)C=CC=C3C)C2=N1)C(=O)NCCO

InChI

InChIKey=GHVIMBCFLRTFHI-UHFFFAOYSA-N

InChI=1S/C21H26N4O2/c1-13-6-5-7-14(2)18(13)11-23-19-10-17(21(27)22-8-9-26)12-25-16(4)15(3)24-20(19)25/h5-7,10,12,23,26H,8-9,11H2,1-4H3,(H,22,27)

HIDE SMILES / InChI

Molecular Formula	C21H26N4O2
Molecular Weight	366.4567
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17081503 | https://www.ncbi.nlm.nih.gov/pubmed/17950677 | https://www.ncbi.nlm.nih.gov/pubmed/18184117 | https://www.ncbi.nlm.nih.gov/pubmed/23205582

Linaprazan is a member of a new group of acid-suppressing agents, which unlike proton pump inhibitors, act through potassium-competitive inhibition of the H+,K+-ATPase located in the apical membrane of parietal cells. It displayed rapid inhibition of acid production and had a prolonged, dose-dependent duration of effect. Linaprazan reduced porcine renal Na(+),K(+)-ATPase activity by 9+/-2%, demonstrating a high selectivity for H(+),K(+)-ATPase. It provided similar efficacy to esomeprazole in terms of esophagitis healing and heartburn control.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Potassium-transporting ATPase 38 Target ID: CHEMBL2095173 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17081503	Inhibitor 8504		0.13 µM [IC50]

PubMed

Title	Date	PubMed
Predictors of either rapid healing or refractory reflux oesophagitis during treatment with potent acid suppression.	2014-09	25039978
Impact of regurgitation on health-related quality of life in gastro-oesophageal reflux disease before and after short-term potent acid suppression therapy.	2014-05	23831734
Evaluation of the use of Classical Nucleation Theory for predicting intestinal crystalline precipitation of two weakly basic BSC class II drugs.	2014-03-12	24345794
H+/K+-ATPase inhibitors: a patent review.	2013-01	23205582
An in vitro methodology for forecasting luminal concentrations and precipitation of highly permeable lipophilic weak bases in the fasted upper small intestine.	2012-12	22890986
Concomitant symptoms itemized in the Reflux Disease Questionnaire are associated with attenuated heartburn response to acid suppression.	2012-09	22777339
Regurgitation is less responsive to acid suppression than heartburn in patients with gastroesophageal reflux disease.	2012-06	22343515
Co-administration of a nanosuspension of a poorly soluble basic compound and a solution of a proton pump inhibitor--the importance of gastrointestinal pH and solubility for the in vivo exposure.	2011-09	21417620
Predicting intestinal precipitation--a case example for a basic BCS class II drug.	2010-10	20717839
A randomized, comparative trial of a potassium-competitive acid blocker (AZD0865) and esomeprazole for the treatment of patients with nonerosive reflux disease.	2008-01	18184117
A randomized, comparative study of three doses of AZD0865 and esomeprazole for healing of reflux esophagitis.	2007-12	17950677

Patents

Sample Use Guides

In Vivo Use Guide

25, 50, 75 mg given once daily for 4 weeks

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:21:01 GMT 2025` Edited by `admin` on `Mon Mar 31 18:21:01 GMT 2025`
Record UNII	E0OU4SC8DP
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

AZD-0865

Preferred Name

English

LINAPRAZAN

Official Name

English

linaprazan [INN]

Common Name

English

8-(((2,6-DIMETHYLPHENYL)METHYL)AMINO)-N-(2-HYDROXYETHYL)-2,3-DIMETHYLIMIDAZO(1,2-A)PYRIDINE-6-CARBOXAMIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29723