Calusterone
- Product Name
- Calusterone
- CAS No.
- 17021-26-0
- Chemical Name
- Calusterone
- Synonyms
- U-22550;U-22,550;NSC-88536;Methosarb;4-ANDROSTEN-7β, 17α-DIMETHYL-17β-OL-3-ONE;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
- CBNumber
- CB31178204
- Molecular Formula
- C21H32O2
- Formula Weight
- 316.48
- MOL File
- 17021-26-0.mol
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)
N-Bromosuccinimide Price
- Product number
- SHG0000722
- Product name
- 4-ANDROSTEN-7-BETA, 17-ALPHA-DIMETHYL-17-BETA-OL-3-ONE
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $786.5
- Updated
- 2021/12/16
- Product number
- SHG0000722
- Product name
- 4-ANDROSTEN-7-BETA, 17-ALPHA-DIMETHYL-17-BETA-OL-3-ONE
- Purity
- 95.00%
- Packaging
- 50MG
- Price
- $1963.5
- Updated
- 2021/12/16
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
Calusterone Preparation Products And Raw materials
Raw materials
Preparation Products
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