Chemical Property of 4-Androsten-4-ol-3,17-dione
Chemical Property:
- Appearance/Colour:Needles
- Vapor Pressure:9.02E-08mmHg at 25°C
- Melting Point:199-202 °C
- Refractive Index:1.545
- Boiling Point:475.4 °C at 760 mmHg
- PKA:9.31±0.60(Predicted)
- Flash Point:255.4 °C
- PSA：54.37000
- Density:1.19 g/cm3
- LogP:3.97310
- Storage Temp.:2-8°C
- Solubility.:Chloroform (Slightly), Methanol (Slightly)
- XLogP3:2.6
- Hydrogen Bond Donor Count:1
- Hydrogen Bond Acceptor Count:3
- Rotatable Bond Count:0
- Exact Mass:302.18819469
- Heavy Atom Count:22
- Complexity:590
- Purity/Quality:
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99% *data from raw suppliers
Formestane *data from reagent suppliers
Safty Information:
- Pictogram(s):
T
- Hazard Codes:T
- Statements:
60
- Safety Statements:
53-36/37/39-45
- MSDS Files:
-
SDS file from LookChem
Total 1 MSDS from other Authors
Useful:
- Canonical SMILES:CC12CCC(=O)C(=C1CCC3C2CCC4(C3CCC4=O)C)O
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Uses
aromatase inhibitors ,it is used for progressive breast cancer.
male hormones, assimilating protein class. An antitumor drug. An aromatase inhibitor. An antitumor drug. An aromatase inhibitor antineoplastic, aromatase inhibitor
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production method
Androst-4-ene-3,17-dione (Ⅰ) (1.432g, 5mmo1) is dissolved in 50ml tert-butanol ,add 38mg (0.15mmo1) osmium tetroxide in 2ml t-butanol solution at room temperature, and then 5ml 35% hydrogen peroxide is added, followed by stirring at room temperature for 3 days. After dilution of 100ml brine, and extract with dichloromethane (2 × 100m1). The extract is washed with 100ml brine, , 50ml 10% sodium bisulfite solution, 50ml 10% sodium carbonate solution and 100ml brine, dry over anhydrous sodium sulfate, and concentrate. The residue (1.824g) of the compound (Ⅱ), is dissolved in methanol (10ml),add potassium hydroxide (393mg, 7mmo1) in 3ml methanol . Plus Albert, stirring 10min at 55 ℃. Add 0.3ml of acetic acid and 100ml of brine, and extract with dichloromethane (2 × 100ml). Complex solution, combine, wash with 100ml brine, dry with anhydrous sodium sulfate, and concentrate. The residue (1.727g) by column chromatography on silica gel, wash with hexane-ethyl acetate (7: 3) to give 715mg formestane, yield 47%, mp 200~202 ℃ (acetone).
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Description
4-hydroxy Androstenedione (4-HAD) is a steroidal inhibitor of aromatase (also known as cytochrome P450 19A1; Ki = 27 nM). As aromatase catalyzes the conversion of androgens to estrogens, aromatase inhibitors, including 4-HAD, are used against hormone-sensitive breast cancer in menopausal women. They are also abused in combination with anabolic steroids in racehorses and athletes. This product is intended for forensic and research applications. Formestane is a potent aromatase inhibitor launched in the UK as a second-line
endocrine treatment for breast cancer. As a synthetic derivative of androstanedione, the
natural substrate for the biosynthesis of estrogen by the enzyme aromatase, formastane
selectively inhibits aromatase and binds to its steroid receptor site to cause a rapid and
sustained fall in circulating estrogen level and, therefore, inhibits tumor growth. In patients
with existing bulky primary tumors, formestane effectively reduces the size of the tumors.
Formastane has apparent tolerability advantages and less side effects than other agents such
as aminoglutethimide.
