9,11-Dehydrocortexolone 17α-butyrate

9,11-Dehydrocortexolone 17α-butyrate (developmental code name CB-03-04) is a synthetic steroidal antiandrogen that was developed for use as a topical medication but was never marketed.[1] It is the C17α butyrate (butanoate) ester of the 9,11-dehydrogenated analogue of 11-deoxycortisol (cortexolone).[1] C17α esters of 11-deoxycortisol were unexpectedly found to possess antiandrogen activity, and 9,11-dehydrocortexolone 17α-butyrate was selected for development based on its optimum drug profile.[1] In rats, the drug has been found to possess strong local antiandrogen activity and to also be active systemically upon subcutaneous injection.[1] In addition, it has been found to possess antigonadotropic activity.[1] In terms of topical antiandrogen potency, 9,11-dehydrocortexolone 17α-butyrate was found to be more potent than flutamide and finasteride and less than or equal to cyproterone acetate in potency.[1] The drug has been suggested for possible development and medical use for the treatment of prostate cancer and benign prostatic hyperplasia.[1]

9,11-Dehydrocortexolone 17α-butyrate
Clinical data
Other namesCB-03-04; 17α-(Butyryloxy)-9,11-didehydrodeoxycorticosterone; 17α-Butanoyloxy-21-hydroxypregna-4,9(11)-diene-3,20-dione
Identifiers
IUPAC name
  • [(8S,10S,13S,14S,17R)-17-(2-hydroxyacetyl)-10,13-dimethyl-3-oxo-2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] butanoate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC25H34O5
Molar mass414.542 g·mol−1
3D model (JSmol)
SMILES
  • CCCC(=O)O[C@@]1(CC[C@@H]2[C@@]1(CC=C3[C@H]2CCC4=CC(=O)CC[C@@]43C)C)C(=O)CO
InChI
  • InChI=1S/C25H34O5/c1-4-5-22(29)30-25(21(28)15-26)13-10-20-18-7-6-16-14-17(27)8-11-23(16,2)19(18)9-12-24(20,25)3/h9,14,18,20,26H,4-8,10-13,15H2,1-3H3/t18-,20+,23+,24+,25+/m1/s1
  • Key:IMSKTQNPYUKZMB-AMMWCUJOSA-N

See also

References
  1. Celasco G, Moroa L, Bozzella R, Ferraboschi P, Bartorelli L, Di Marco R, Quattrocchi C, Nicoletti F (2005). "Pharmacological profile of 9,11-dehydrocortexolone 17alpha-butyrate (CB-03-04), a new androgen antagonist with antigonadotropic activity". Arzneimittelforschung. 55 (10): 581–7. doi:10.1055/s-0031-1296908. PMID 16294504.



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