Calusterone Property

Melting point:

127-129°

alpha 

D +57° (CHCl3)

Boiling point:

463.29°C (rough estimate)

Density 

0.9575 (rough estimate)

refractive index 

1.5100 (estimate)

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Solid

pka

15.13±0.70(Predicted)

color 

White to Off-White

Safety

Hazardous Substances Data

17021-26-0(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Calusterone Chemical Properties,Usage,Production

Originator

Methosarb,Upjohn,US,1973

Uses

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