SORAPRAZAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H25N3O3
Molecular Weight	367.4415
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COCCO[C@H]1[C@H](O)[C@H](NC2=C1C=CN3C(C)=C(C)N=C23)C4=CC=CC=C4

InChI

InChIKey=PWILYDZRJORZDR-MISYRCLQSA-N

InChI=1S/C21H25N3O3/c1-13-14(2)24-10-9-16-18(21(24)22-13)23-17(15-7-5-4-6-8-15)19(25)20(16)27-12-11-26-3/h4-10,17,19-20,23,25H,11-12H2,1-3H3/t17-,19-,20-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://adisinsight.springer.com/drugs/800015211 | http://katairo.com/development/ | https://www.ema.europa.eu/en/documents/orphan-designation/eu/3/13/1208-public-summary-opinion-orphan-designation-soraprazan-treatment-stargardts-disease_en.pdf | https://www.ncbi.nlm.nih.gov/pubmed/17369284

Soraprazan (remofuscin), a potassium-competitive acid blocker (P-CAB; formerly called an acid pump antagonist [APA]), is being developed by Katairo GmbH for the treatment of Stargardt's disease and dry age-related macular degeneration (AMD). Clinical development is underway for Stargardt's disease and dry age-related macular degeneration in the Netherlands and Germany. On 13 November 2013, orphan designation was granted by the European Commission to Katairo GmbH, Germany, for soraprazan for the treatment of Stargardt’s disease. Soraprazan is a a highly potent reversible, and fast-acting inhibitor of gastric H,K-ATPase. Soraprazan shows immediate inhibition of acid secretion in various in vitro models and in vivo and was found to be more than 2000-fold selective for H,K-ATPase over Na,K- and Ca-ATPases.

Originator

Approval Year

PubMed

Title	Date	PubMed
Soraprazan: setting new standards in inhibition of gastric acid secretion.	2007 Jun	17369284
Medicinal Attributes of Imidazo[1,2-a]pyridine Derivatives: An Update.	2016	27150367

Patents

Sample Use Guides

In Vivo Use Guide

Soraprazan was administrated in oral application of 6, 12 and 24 mg/kg/day for 52 weeks in the Cynomolgus monkey.

Route of Administration: Oral

In Vitro Use Guide

Soraprazan has an IC(50) of 0.1 uM if measured with ion leaky vesicles and of 0.19 uM in isolated gastric glands. With a K(i) of 6.4 nM, a K(d) of 26.4 nM, and a B(max) of 2.89 nmol/mg, this compound is a highly potent and reversible inhibitor of the H,K-ATPase.

Name

Type

Language

SORAPRAZAN

Official Name

English

Soraprazan [WHO-DD]

Common Name

English

soraprazan [INN]

Common Name

English

(7R,8R,9R)-7-(2-METHOXYETHOXY)-2,3-DIMETHYL-9-PHENYL-7,8,9,10-TETRAHYDROIMIDAZO(1,2-H)(1,7)NAPHTYRIDIN-8-OL

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29723