Prednylidene

Prednylidene is a glucocorticoid^[1] for systemic use.

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-octahydrocyclopenta[a]phenanthren-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 N
PubChem CID	20055008
ChemSpider	16735979 Y
UNII	IF8PQP966U
CompTox Dashboard (EPA)	DTXSID50208610
ECHA InfoCard	100.009.060
Chemical and physical data
Formula	C22H28O5
Molar mass	372.461 g·mol−1
3D model (JSmol)	Interactive image
SMILES OCC(=O)[C@@]2(O)C(=C)C[C@H]3[C@@H]4CC\C1=C\C(=O)\C=C/[C@]1(C)[C@H]4[C@@H](O)C[C@]23C
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 Y Key:WSVOMANDJDYYEY-CWNVBEKCSA-N Y
NY (what is this?)  (verify)

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.