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Prednylidene

Clinical data
Other names	(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-16-methylidene-6,7,8,9,11,12,14,15-octahydrocyclopentaphenanthren-3-one
ATC code	H02AB11 (WHO)
Identifiers
IUPAC name (11β)-11,17,21-trihydroxy-16-methylenepregna-1,4-diene-3,20-dione
CAS Number	599-33-7
PubChem CID	20055008
ChemSpider	16735979
UNII	IF8PQP966U
CompTox Dashboard (EPA)	DTXSID50208610
ECHA InfoCard	100.009.060
Chemical and physical data
Formula	C22H28O5
Molar mass	372.461 g·mol
3D model (JSmol)	Interactive image
SMILES OCC(=O)2(O)C(=C)C34CC\C1=C\C(=O)\C=C/1(C)4(O)C23C
InChI InChI=1S/C22H28O5/c1-12-8-16-15-5-4-13-9-14(24)6-7-20(13,2)19(15)17(25)10-21(16,3)22(12,27)18(26)11-23/h6-7,9,15-17,19,23,25,27H,1,4-5,8,10-11H2,2-3H3/t15-,16-,17-,19+,20-,21-,22-/m0/s1 Key:WSVOMANDJDYYEY-CWNVBEKCSA-N
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Prednylidene is a glucocorticoid for systemic use.

Substitution at position 16 also leads to more potent corticosteroids. The additional steric bulk introduced by such substituents adjacent to the dihydroxyacetone side chain also protects that moiety against metabolic degradation.

References

1. Buttgereit F, Brand MD, Burmester GR (July 1999). "Equivalent doses and relative drug potencies for non-genomic glucocorticoid effects: a novel glucocorticoid hierarchy". Biochem. Pharmacol. 58 (2): 363–8. doi:10.1016/S0006-2952(99)00090-8. PMID 10423179.

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