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CAS NO.566-48-3
| Formestane Basic information |
| Product Name: | Formestane |
| Synonyms: | 4-hydroxy-androst-4-ene-17-dione;4-hydroxy-delta(sub4)-androstenedione;4-HYDROXYANDROST-4-ENE-3,17-DIONE;4-HYDROXYANDROSTENEDIONE;4-HYDROXY-4-ANDROSTENE-3,17-DIONE;4-ANDROSTEN-4-OL-3,17-DIONE;4-OHA;CGP-32349 |
| CAS: | 566-48-3 |
| MF: | C19H26O3 |
| MW: | 302.41 |
| EINECS: | |
| Product Categories: | Pharmaceutical Raw Materials;Miscellaneous Biochemicals;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Anti-cancer&immunity |
| Mol File: | 566-48-3.mol |
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| Formestane Chemical Properties |
| mp | 199-202°C |
| storage temp. | 2-8°C |
| form | solid |
| CAS DataBase Reference | 566-48-3(CAS DataBase Reference) |
| Safety Information |
| Hazard Codes | T |
| Risk Statements | 60 |
| Safety Statements | 53-36/37/39-45 |
| WGK Germany | 3 |
| RTECS | BV8152500 |
| MSDS Information |
| Provider | Language |
|---|---|
| Formestane | English |
| SigmaAldrich | English |
| Formestane Usage And Synthesis |
| Anti-cancer drugs |
Formestane also known as lentaron,is an anti-cancer drug, it is primarily used for the treatment of postmenopausal women with advanced breast cancer, it is also effective in prostate cancer. Formestane is a androstenedione derivative, and it belongs to an aromatase inhibitor with aminoglutethimide, it is a hormone antineoplastic agent. In physiological conditions, it may competitively inhibit the synthesis of the enzyme leading to estrogen biosynthesis decrease in tissues, then it plays its role in cancer. When the tumor tissue growth relies on the presence of estrogen, in order to inhibit tumor growth, the elimination of tumor estrogen-mediated growth stimulation is necessary. This product is more selective than aminoglutethimide while its activity is 100 to 1000 times of aminoglutethimide, and it does not inhibit the synthesis of adrenal hormones，without having to recharge cortisone, etc . The in vitro inhibition of aromatase enzyme of this product is 60 times stronger than aminoglutethimide. While it is used alone, the drug can not significantly reduce the pre-menopausal estrogen levels in the blood of women,when it is combined with goserelin (gonadotropin-releasing hormone agonist)， its inhibitory effect of estrogen in premenopausal women is greater than goserelin used alone. Formestane has no cross-resistance with other aromatase inhibitors , it has no side effects of aminoglutethimide. After oral administration，it is rapidly absorbed by gastrointestinal, its peak plasma concentration time is 1 to 1.5 hours, but the peak concentration of individual is of great difference; after intramuscular injection，it can be accumulated at the injection site and be slowly absorbed. It performs Biphasic elimination process, the initial elimination half-life is 2 to 4 days, the terminal elimination half-life is 5 to 10 days. It is mainly metabolized in the liver after oral administration, in the form of glycosides acid metabolites excreted in the urine. The above information is edited by the chemicalbook of Tian Ye. |
| Chemical Properties | Crystallized from aqueous methanol, m.p. 199 ~ 202 ℃; crystallized from ethyl acetate, m.p. 203.5 ~ 206 ℃. UV absorption maximum (99.5% ethanol): 278nm (ε11030). [α] D20 + 181 ° (C = 7.7, chloroform). |
| Application |
aromatase inhibitors ,it is used for progressive breast cancer. male hormones, assimilating protein class. |
| 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). |
| Chemical Properties | Needles |
| Usage | An antitumor drug. An aromatase inhibitor |
| Usage | antineoplastic, aromatase inhibitor |
| Formestane Preparation Products And Raw materials |
| Raw materials | Ethyl acetate-->Dichloromethane-->Sodium carbonate-->Sodium sulfate-->Potassium hydroxide -->tert-Butanol-->Acetylacetone-->Osmium tetraoxide |
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