LINAPRAZAN

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

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 31 Target ID: CHEMBL2095173 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17081503	Inhibitor 8297		0.13 µM [IC50]

PubMed

Title	Date	PubMed
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 Sep	21417620
An in vitro methodology for forecasting luminal concentrations and precipitation of highly permeable lipophilic weak bases in the fasted upper small intestine.	2012 Dec	22890986
Regurgitation is less responsive to acid suppression than heartburn in patients with gastroesophageal reflux disease.	2012 Jun	22343515
Concomitant symptoms itemized in the Reflux Disease Questionnaire are associated with attenuated heartburn response to acid suppression.	2012 Sep	22777339

Patents

Sample Use Guides

In Vivo Use Guide

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

Route of Administration: Oral

Name

Type

Language

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

AZD-0865

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C29723