Prednylidene

Prednylidene

Systematic (IUPAC) name
(11β)-11,17,21-trihydroxy-16-methylenepregna-1,4-diene-3,20-dione
Identifiers
CAS Number	599-33-7 N
ATC code	H02AB11 (WHO)
PubChem	CID: 20055008
ChemSpider	16735979 Y
UNII	IF8PQP966U Y
Synonyms	(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
Chemical data
Formula	C22H28O5
Molecular mass	372.455
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)

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.