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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
Molecular Weight:
316.48
MDL Number:
MFCD00866255
MOL File:
17021-26-0.mol
Last updated:2023-07-12 16:37:11

Calusterone Properties

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
FDA UNII 0678G6Q58A
NCI Drug Dictionary Methosarb

Calusterone price

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
American Custom Chemicals Corporation SHG0000722 4-ANDROSTEN-7-BETA, 17-ALPHA-DIMETHYL-17-BETA-OL-3-ONE 95.00% 17021-26-0 5MG $786.5 2021-12-16 Buy
American Custom Chemicals Corporation SHG0000722 4-ANDROSTEN-7-BETA, 17-ALPHA-DIMETHYL-17-BETA-OL-3-ONE 95.00% 17021-26-0 50MG $1963.5 2021-12-16 Buy
Product number Packaging Price Buy
SHG0000722 5MG $786.5 Buy
SHG0000722 50MG $1963.5 Buy

Calusterone Chemical Properties,Uses,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

Calusterone Suppliers

Global( 6)Suppliers
Supplier Tel Email Country ProdList Advantage
Chemsky (shanghai) International Co.,Ltd 021-50135380 shchemsky@sina.com China 15421 60
Shanghai Saikerui Biotechnology Co. , Ltd. 021-58000709 15900491054 info@scrbio.com China 9262 58
(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 7β,17α-Dimethyl-17β-hydroxyandrost-4-en-3-one Methosarb NSC-88536 U-22,550 U-22550 Androst-4-en-3-one, 17-hydroxy-7,17-dimethyl-, (7β,17β)- 4-ANDROSTEN-7β, 17α-DIMETHYL-17β-OL-3-ONE 17021-26-0 Intermediates & Fine Chemicals Pharmaceuticals Steroids