MK-5932

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H25F2N3O2
Molecular Weight	449.4924
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]12CC3=C(C=C1CC[C@@]2(O)CCC4=C(C=C(F)C=C4)C(N)=O)N(N=C3)C5=CC=C(F)C=C5

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	449.4924
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 Dec 16 10:36:23 UTC 2023` Edited by `admin` on `Sat Dec 16 10:36:23 UTC 2023`
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

SMS_ID

300000041465

Created by admin on Sat Dec 16 10:36:23 UTC 2023 , Edited by admin on Sat Dec 16 10:36:23 UTC 2023

PRIMARY

CAS

1021539-02-5

Created by admin on Sat Dec 16 10:36:23 UTC 2023 , Edited by admin on Sat Dec 16 10:36:23 UTC 2023

PRIMARY

FDA UNII

8WW8T70RDC

Created by admin on Sat Dec 16 10:36:23 UTC 2023 , Edited by admin on Sat Dec 16 10:36:23 UTC 2023

PRIMARY

PUBCHEM

24945227

Created by admin on Sat Dec 16 10:36:23 UTC 2023 , Edited by admin on Sat Dec 16 10:36:23 UTC 2023

PRIMARY

Related Record Type Details


					FZW85LW99M

GLUCOCORTICOID RECEPTOR

TARGET->PARTIAL AGONIST

Related Record Type Details


					8WW8T70RDC

MK-5932

ACTIVE MOIETY

Comments:

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.


					8WW8T70RDC

MK-5932

ACTIVE MOIETY

Comments:

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