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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-octahydrocyclopenta[a]phenanthren-3-one
ATC code
Identifiers
  • (11β)-11,17,21-trihydroxy-16-methylenepregna-1,4-diene-3,20-dione
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.009.060 Edit this at Wikidata
Chemical and physical data
FormulaC22H28O5
Molar mass372.461 g·mol−1
3D model (JSmol)
  • 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=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[1] 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.


source: https://en.wikipedia.org/wiki/Prednylidene