Prednylidene

Prednylidene

File:Prednylidene.png
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 checkY
UNII	IF8PQP966U
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
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 checkY Key:WSVOMANDJDYYEY-CWNVBEKCSA-N checkY
☒NcheckY (what is this?)  (verify)

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.