9,11-Dehydrocortexolone 17α-butyrate

9,11-Dehydrocortexolone 17α-butyrate

Clinical data
Other names	CB-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	872623-99-9
PubChem CID	11704352
ChemSpider	9879075
UNII	88D1Y5GBH5
ChEMBL	ChEMBL3588895
Chemical and physical data
Formula	C25H34O5
Molar mass	414.542 g·mol−1
3D model (JSmol)	Interactive image
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

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. It is the C17α butyrate (butanoate) ester of the 9,11-dehydrogenated analogue of 11-deoxycortisol (cortexolone). 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. In rats, the drug has been found to possess strong local antiandrogen activity and to also be active systemically upon subcutaneous injection. In addition, it has been found to possess antigonadotropic activity. 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. The drug has been suggested for possible development and medical use for the treatment of prostate cancer and benign prostatic hyperplasia.

See also

• Clascoterone (cortexolone 17α-propionate; CB-03-01)
• List of steroidal antiandrogens