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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 of MAPRACORAT

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

Molecular Formula C25H26F4N2O2
Molecular Weight 462.4798
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P04150
Gene ID: 2908.0
Gene Symbol: NR3C1
Target Organism: Homo sapiens (Human)
PubMed

PubMed

TitleDatePubMed
BOL-303242-X, a novel selective glucocorticoid receptor agonist, with full anti-inflammatory properties in human ocular cells.
2009 Dec 8
Mapracorat, a novel selective glucocorticoid receptor agonist, inhibits hyperosmolar-induced cytokine release and MAPK pathways in human corneal epithelial cells.
2010 Sep 2
Patents

Sample Use Guides

The study investigated antipsoriatic efficacy of mapracorat 0.1% ointment
Route of Administration: Topical
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.
Substance Class Chemical
Created
by admin
on Thu Jul 06 23:04:42 UTC 2023
Edited
by admin
on Thu Jul 06 23:04:42 UTC 2023
Record UNII
145V79YBVP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MAPRACORAT
INN   USAN  
USAN   INN  
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
Created by admin on Thu Jul 06 23:04:43 UTC 2023 , Edited by admin on Thu Jul 06 23:04:43 UTC 2023
PRIMARY
NCI_THESAURUS
C166458
Created by admin on Thu Jul 06 23:04:43 UTC 2023 , Edited by admin on Thu Jul 06 23:04:43 UTC 2023
PRIMARY
DRUG BANK
DB12041
Created by admin on Thu Jul 06 23:04:43 UTC 2023 , Edited by admin on Thu Jul 06 23:04:43 UTC 2023
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CAS
887375-26-0
Created by admin on Thu Jul 06 23:04:43 UTC 2023 , Edited by admin on Thu Jul 06 23:04:43 UTC 2023
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EVMPD
SUB91929
Created by admin on Thu Jul 06 23:04:43 UTC 2023 , Edited by admin on Thu Jul 06 23:04:43 UTC 2023
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EPA CompTox
DTXSID401029572
Created by admin on Thu Jul 06 23:04:43 UTC 2023 , Edited by admin on Thu Jul 06 23:04:43 UTC 2023
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FDA UNII
145V79YBVP
Created by admin on Thu Jul 06 23:04:43 UTC 2023 , Edited by admin on Thu Jul 06 23:04:43 UTC 2023
PRIMARY
PUBCHEM
24795088
Created by admin on Thu Jul 06 23:04:43 UTC 2023 , Edited by admin on Thu Jul 06 23:04:43 UTC 2023
PRIMARY
INN
9214
Created by admin on Thu Jul 06 23:04:43 UTC 2023 , Edited by admin on Thu Jul 06 23:04:43 UTC 2023
PRIMARY
SMS_ID
100000141482
Created by admin on Thu Jul 06 23:04:43 UTC 2023 , Edited by admin on Thu Jul 06 23:04:43 UTC 2023
PRIMARY
ChEMBL
CHEMBL2103876
Created by admin on Thu Jul 06 23:04:43 UTC 2023 , Edited by admin on Thu Jul 06 23:04:43 UTC 2023
PRIMARY
WIKIPEDIA
MAPRACORAT
Created by admin on Thu Jul 06 23:04:43 UTC 2023 , Edited by admin on Thu Jul 06 23:04:43 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY