Calusterone

Originator

Methosarb,Upjohn,US,1973

The Uses of Calusterone

Synthetic androgen epimeric with Bolasterone (B674970). Has been used in treatment of breast cancer. Controlled substance (anabolic steroid).

Definition

ChEBI: Calusterone is a 3-hydroxy steroid. It has a role as an androgen.

Manufacturing Process

As described in US Patent 3,029,263, one possibility is a multistep synthesis starting from 3β,17β-dihydroxy-17α-methyl-5-androstene.
Alternatively, as described in US Patent 3,341,557, 6-dehydro-17- methyltestosterone may be used as the starting material. A mixture of 0.4 g of cuprous chloride, 20 ml of 4M methylmagnesium bromide in ether and 60 ml of redistilled tetrahydrofuran was stirred and cooled in an ice bath during the addition of a mixture of 2.0 g of 6-dehydro-17-methyltestosterone, 60 ml of redistilled tetrahydrofuran and 0.2 g of cuprous chloride. The ice bath was removed and stirring was continued for four hours. Ice and water were then carefully added, the solution acidified with 3 N hydrochloric acid and extracted several times with ether. The combined ether extracts were washed with a brine-sodium carbonate solution, brine and then dried over anhydrous magnesium sulfate, filtered and then poured over a 75-g column of magnesium silicate (Florisil) packed wet with hexanes (Skellysolve B). The column was eluted with 250 ml of hexanes, 0.5 liter of 2% acetone, two liters of 4% acetone and 3.5 liters of 6% acetone in hexanes.
Four 250-ml fractions were collected followed by 150 ml fractions. The residues from fractions 8 to 16 were combined and rechromatographed over a 125-g column of magnesium silicate. The solumn was eluted with 6% acetone in hexanes which was collected in 150 ml portions. Fractions 18 to 29 were combined and dissolved in acetone, decolorized with charcoal, and recrystallized from acetone. One gram of a crystalline mixture of the 7epimers of 7,17-dimethyltestosterone was obtained melting at 120° to 140°C.

Therapeutic Function

Antineoplastic