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
SMILES
C[C@]12CC3=C(C=C1CC[C@@]2(O)CCC4=CC=C(F)C=C4C(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
| 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
Edited
Mon Mar 31 23:20:48 GMT 2025
by
admin
on
Mon Mar 31 23:20:48 GMT 2025
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| Record UNII |
8WW8T70RDC
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| Record Status |
Validated (UNII)
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| Record Version |
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Common Name | English | ||
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Preferred Name | English | ||
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DTXSID401351866
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300000041465
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1021539-02-5
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8WW8T70RDC
Created by
admin on Mon Mar 31 23:20:48 GMT 2025 , Edited by admin on Mon Mar 31 23:20:48 GMT 2025
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24945227
Created by
admin on Mon Mar 31 23:20:48 GMT 2025 , Edited by admin on Mon Mar 31 23:20:48 GMT 2025
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TARGET->PARTIAL AGONIST |
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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.
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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
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