Topterone

Topterone
Names

IUPAC name (8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-17-propyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
Identifiers
CAS Registry Number	60607-35-4
InChI InChI=1S/C22H34O2/c1-4-10-22(24)13-9-19-17-6-5-15-14-16(23)7-11-20(15,2)18(17)8-12-21(19,22)3/h14,17-19,24H,4-13H2,1-3H3/t17-,18+,19+,20+,21+,22+/m1/s1 Key: LZSOOHLAZHOTHJ-GUCLMQHLSA-N
Jmol-3D images	Image
PubChem	9797605
SMILES CCC[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)O
Properties
Molecular formula	C₂₂H₃₄O₂
Molar mass	330.50 g·mol⁻¹
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Topterone, WIN 17,665 (17 alpha-propyltestosterone) is an antiandrogen.^[1]

Synthesis

Reaction of the tetrahydropyranyl ether of dehydroepiandrosterone with propyl magnesium bromide gives after removal of the protecting group the corresponding 17α-propyl derivative. Oppenauer oxidation leads to the corresponding conjugated ketone. There is thus obtained topterone.^[2]

References

↑ Ferrari, RA; Chakrabarty, K; Creange, JE; Beyler, AL; Potts, OG; Schane, HP (1980). "Endocrine profile of topterone, a topical antiandrogen, in three species of laboratory animals". Methods and findings in experimental and clinical pharmacology 2 (2): 65–9. PMID 7339330.
↑ A. L. Beyler and R. A. Ferrari, DE 2633925 (1977).