U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C26H25F2N3O2
Molecular Weight 449.4934
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MK-5932

SMILES

C[C@@]12Cc3cnn(-c4ccc(cc4)F)c3C=C2CC[C@]1(CCc5ccc(cc5C(=N)O)F)O

InChI

InChIKey=USAOJXKZYFGDCJ-UIOOFZCWSA-N
InChI=1S/C26H25F2N3O2/c1-25-14-17-15-30-31(21-6-4-19(27)5-7-21)23(17)12-18(25)9-11-26(25,33)10-8-16-2-3-20(28)13-22(16)24(29)32/h2-7,12-13,15,33H,8-11,14H2,1H3,(H2,29,32)/t25-,26-/m0/s1

HIDE SMILES / InChI

Molecular Formula C26H25F2N3O2
Molecular Weight 449.4934
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Substance Class Chemical
Created
by admin
on Sat Jun 26 02:12:17 UTC 2021
Edited
by admin
on Sat Jun 26 02:12:17 UTC 2021
Record UNII
8WW8T70RDC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MK-5932
Common Name English
BENZAMIDE, 5-FLUORO-2-(2-((4AS,5R)-1-(4-FLUOROPHENYL)-1,4,4A,5,6,7-HEXAHYDRO-5-HYDROXY-4A-METHYLCYCLOPENT(F)INDAZOL-5-YL)ETHYL)-
Systematic Name English
2-(2-((4AS,5R)-1-(4-FLUOROPHENYL)-5-HYDROXY-4A-METHYL-6,7-DIHYDRO-4H-CYCLOPENTA(F)INDAZOL-5-YL)ETHYL)-5-FLUORO-BENZAMIDE
Systematic Name English
5-FLUORO-2-(2-((4AS,5R)-1-(4-FLUOROPHENYL)-1,4,4A,5,6,7-HEXAHYDRO-5-HYDROXY-4A-METHYLCYCLOPENT(F)INDAZOL-5-YL)ETHYL)BENZAMIDE
Systematic Name English
5-FLUORO-2-(2-((4AS,5R)-1-(4-FLUOROPHENYL)-5-HYDROXY-4A-METHYL-1,4,4A,5,6,7-HEXAHYDROCYCLOPENTA(F)INDAZOL-5-YL)ETHYL)BENZAMIDE
Systematic Name English
Code System Code Type Description
CAS
1021539-02-5
Created by admin on Sat Jun 26 02:12:17 UTC 2021 , Edited by admin on Sat Jun 26 02:12:17 UTC 2021
PRIMARY
FDA UNII
8WW8T70RDC
Created by admin on Sat Jun 26 02:12:17 UTC 2021 , Edited by admin on Sat Jun 26 02:12:17 UTC 2021
PRIMARY
PUBCHEM
24945227
Created by admin on Sat Jun 26 02:12:17 UTC 2021 , Edited by admin on Sat Jun 26 02:12:17 UTC 2021
PRIMARY
Related Record Type Details
TARGET->PARTIAL AGONIST
Related Record Type Details
ACTIVE MOIETY
Oxidative N-dealkylation was blocked in a new series of compounds, however oxidation alone was capable of producing full agonist metabolites. Incorporation of an ortho-primary amide and utilization of fluorine to modulate agonism afforded partial agonist MK-5932. Synthesis of the major metabolites of MK-5932 using bioreactor technology revealed that no significant GR-active metabolites were formed. Orally administered MK-5932 displayed anti-inflammatory efficacy in a Rat Oxazolone-induced chronic dermatitis model, while sparing plasma insulin.
ACTIVE MOIETY
MK-5932 is limited by moderate potency in rodents and poor bioavailability in higher species. Inhibition of LPS-induced cytokine release by MK-5932: Human Cytokine IFN.GAMMA. EC50(nM) = 1293+/-668 Emax(%) = 90+/-14; Rat(pooled blood) TNF.ALPHA. EC50(nM) = 2863+/-2393 Emax(%) = 71+/-6, IL-6 EC50(nM) = 471+/-175 Emax(%) = 88+/-1