MAPRACORAT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H26F4N2O2
Molecular Weight	462.4798
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=NC2=C(C=C1)C(NC[C@](O)(CC(C)(C)C3=CC(F)=CC4=C3OCC4)C(F)(F)F)=CC=C2

InChI

InChIKey=VJGFOYBQOIPQFY-XMMPIXPASA-N

InChI=1S/C25H26F4N2O2/c1-15-7-8-18-20(5-4-6-21(18)31-15)30-14-24(32,25(27,28)29)13-23(2,3)19-12-17(26)11-16-9-10-33-22(16)19/h4-8,11-12,30,32H,9-10,13-14H2,1-3H3/t24-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19422381 | https://www.ncbi.nlm.nih.gov/pubmed/25245083 | https://adisinsight.springer.com/drugs/800025062

Mapracorat (BAY-865319, BOL-303242-X or ZK-245186) is a selective non-steroid glucocorticoid receptor agonist exerting anti-inflammatory activity. Mapracorat showed partial attenuation of the classical NF-κB pathway, consistent with traditional steroids. However, mapracorat uniquely potentiated a novel anti-inflammatory mechanism through rapid upregulation of RelB, an anti-inflammatory member of the NF-κB alternative pathway. Mapracorat was being studied in the treatment of ocular and skin inflammatory diseases.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glucocorticoid receptor 172 Target ID: P04150 Gene ID: 2908.0 Gene Symbol: NR3C1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19422381	Agonist 2678

PubMed

Title	Date	PubMed
BOL-303242-X, a novel selective glucocorticoid receptor agonist, with full anti-inflammatory properties in human ocular cells.	2009 Dec 8	20011631
Characterization of ZK 245186, a novel, selective glucocorticoid receptor agonist for the topical treatment of inflammatory skin diseases.	2009 Oct	19422381
Reduced myocilin expression in cultured monkey trabecular meshwork cells induced by a selective glucocorticoid receptor agonist: comparison with steroids.	2010 Jan	19696178
Mapracorat, a novel selective glucocorticoid receptor agonist, inhibits hyperosmolar-induced cytokine release and MAPK pathways in human corneal epithelial cells.	2010 Sep 2	20824100

Patents

Sample Use Guides

In Vivo Use Guide

The study investigated antipsoriatic efficacy of mapracorat 0.1% ointment

Route of Administration: Topical

In Vitro Use Guide

Mapracorat potently inhibited the production of GM-CSF and TNF-α in LPS-stimulated Raw 264.7 macrophages. Mapracorat also substantially attenuated the expression of COX-2 and the production of PGE(2). The inhibition of mapracorat on the inflammatory response was dose-dependent, and substantially inhibitory effects were observed at concentrations in the 10-100 nM range.

Name

Type

Language

MAPRACORAT

Official Name

English

MAPRACORAT [USAN]

Common Name

English

BOL-303242X

Code

English

(2R)-1,1,1-TRIFLUORO-4-(5-FLUORO-2,3-DIHYDRO-1-BENZOFURAN-7-YL)-4-METHYL-2-(((2- METHYLQUINOLIN-5-YL)AMINO)METHYL)PENTAN-2-OL

Systematic Name

English

ZK-245186

Code

English

BOL-303242-X

Code

English

ZK245186

Code

English

7-BENZOFURANPROPANOL, 5-FLUORO-2,3-DIHYDRO-GAMMA,GAMMA-DIMETHYL-ALPHA-(((2-METHYL-5- QUINOLINYL)AMINO)METHYL)-ALPHA-(TRIFLUOROMETHYL)-,(ALPHAR)-

Common Name

English

mapracorat [INN]

Common Name

English

Code System Code Type Description

USAN

YY-91