| Identification | Back Directory | [Name]
Calusterone | [CAS]
17021-26-0 | [Synonyms]
U-22550
U-22,550
Methosarb
NSC-88536
7β,17α-Dimethyl-17β-hydroxyandrost-4-en-3-one
Androst-4-en-3-one, 17-hydroxy-7,17-dimethyl-, (7β,17β)-
(7S,8R,9S,10R,13S,14S,17S)-17-hydroxy-7,10,13,17-tetramethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one | [Molecular Formula]
C21H32O2 | [MDL Number]
MFCD00866255 | [MOL File]
17021-26-0.mol | [Molecular Weight]
316.48 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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 |
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