4-hydroxyandrost-4-ene-3,17-dione
4-androsten-4-ol-3,17-dione
CAS: 566-48-3
Molecular Formula: C20H28O2
4-hydroxyandrost-4-ene-3,17-dione - Names and Identifiers
| Name | 4-androsten-4-ol-3,17-dione |
| Synonyms | Formestane B, Aromatase inhibitor 4-androsten-4-ol-3,17-dione 4-hydroxyandrost-4-ene-3,17-dione (8xi,9xi,14xi)-4-methylandrost-4-ene-3,17-dione |
| CAS | 566-48-3 |
| EINECS | 625-331-3 |
| InChI | InChI=1/C20H28O2/c1-12-14-5-4-13-15-6-7-18(22)20(15,3)10-8-16(13)19(14,2)11-9-17(12)21/h13,15-16H,4-11H2,1-3H3/t13?,15?,16?,19-,20-/m0/s1 |
| InChIKey | OSVMTWJCGUFAOD-KZQROQTASA-N |
4-hydroxyandrost-4-ene-3,17-dione - Physico-chemical Properties
| Molecular Formula | C20H28O2 |
| Molar Mass | 300.435 |
| Density | 1.1g/cm3 |
| Melting Point | 199-202°C |
| Boling Point | 435.1°C at 760 mmHg |
| Flash Point | 162.4°C |
| Vapor Presure | 9.02E-08mmHg at 25°C |
| Appearance | morphological solid |
| pKa | 9.31±0.60(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.545 |
| Physical and Chemical Properties | The chemical properties are crystallized from aqueous methanol with a melting point of 199~202 ℃; Crystallized from ethyl acetate with a melting point of 203.5~206 ℃. UV maximum absorption (99.5% ethanol):278nm(ε11030). [α]D20 +181 (C = 7.7, chloroform). |
| Use | Used as an aromatase inhibitor |
4-hydroxyandrost-4-ene-3,17-dione - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | R60 - May impair fertility |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| WGK Germany | 3 |
| RTECS | BV8152500 |
4-hydroxyandrost-4-ene-3,17-dione - Upstream Downstream Industry
4-hydroxyandrost-4-ene-3,17-dione - Nature
| specific rotation | D20 181° (c = 7.7 in chloroform) |
Last Update：2024-04-10 22:29:15
4-hydroxyandrost-4-ene-3,17-dione - Uses and synthesis methods
overview
Formestane (Formestane) is a second-generation aromatase inhibitor (Aromatase Inhibitors) developed by Ciba-Geigy Pharmaceutical Company and also called Formestane. It was launched in 1993. Its chemical name is 4-hydroxyandrostene-4-ene-3, 17-dione. Its molecular formula is C19H26O3 and its relative molecular mass is 302.41. It is a derivative of the physiological steroid hormone androstenedione (Androstenedione) with high specificity, it can effectively combine with aromatase, block the binding of endogenous androgens and enzymes, and cause androgens to be unable to be converted into estrogen, thereby reducing the level of estrogen in plasma and achieving the effect of inhibiting breast cancer cells.
clinical application
This drug can selectively inhibit aromatase, block the biological process of conversion from androgen to estrogen in peripheral tissues and cancer tissues, greatly reduce estrogen in the body, thereby inhibiting the growth of breast cancer. Due to its high specificity of inhibiting aromatase, it does not affect the synthesis of adrenal cortex hormones, so it does not need to supplement glucocorticoids and does not cause the accumulation of androgen precursors. Because this drug can significantly reduce the level of estrogen and androgen, in the phase III clinical findings of this drug, patients using this drug 28% achieve objective remission and 26% achieve stable disease. The phase II clinical study of this drug found that in women who received this drug as a second-line treatment, the average duration of remission was 13-33 months, which was significantly better than that of amulomide and medroxyprogesterone.
Pharmacokinetics
Formestane and other aromatase inhibitors have no cross-resistance and no side effects of amulomide. After oral administration, the gastrointestinal tract absorbs rapidly, and the peak time of blood drug concentration is 1~1.5 hours, but the peak concentration varies greatly among individuals. After intramuscular injection, it can be accumulated at the injection site and absorbed slowly. It is manifested as a biphasic elimination process, with an initial elimination half-life of 2 to 4 days and a final elimination half-life of 5 to 10 days. After oral administration, it is mainly metabolized in the liver and excreted from the urine in the form of glycoside acid metabolites.
precautions
It is forbidden for premenopausal, pregnant and lactating women. Patients with liver and kidney dysfunction do not require dose adjustment. You should be careful when driving or operating the machine, as occasional reports of dizziness, lethargy or lethargy. This drug is not suitable for children.
use
1. Aromatase inhibitor. For progressive breast cancer.
2, male hormones, anabolic proteins.
production method
androst-4-ene-3, 17-dione (I)(1.432g,5 mmo1) is dissolved in 50ml of tert-butanol, 38mg(0.15 mmo1) osmium tetroxide is added in a solution of 2ml of tert-butanol at room temperature, then 5ml of 35% hydrogen peroxide is added and stirred at room temperature for 3 days. After diluting with 100ml of saline, extract with dichloromethane (2 × 100 m1). The extract was washed with 100ml of salt water, 50ml of 10% sodium bisulfite solution, 50ml of 10% sodium carbonate solution and 100ml of salt water in turn, and anhydrous sodium sulfate was dried and concentrated. The residue (1.824g) is compound (II), dissolved in 10ml of methanol, and potassium hydroxide (393mg,7 mmo1) is added in 3ml of methanol solution. After adding, stir at 55 ℃ for 10min. 0.3ml acetic acid and 100ml saline were added and extracted with dichloromethane (2 × 100ml). Phase recovery solution, combined, washed with 100ml salt water, anhydrous sodium sulfate dried and concentrated. The residue (1.727g) was eluted by silica gel column chromatography and hexane-ethyl acetate (7:3) to obtain 715mg of formetan with 47% yield and melting point of 200~202 ℃ (acetone).
Last Update：2024-04-10 22:29:15
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Product Name: Formestane Request for quotation
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
View History
Raw Materials for 4-hydroxyandrost-4-ene-3,17-dione
Sodium carbonate
Androst-4-ene-3,17-dione, 2-hydroxy-, (2α)-
Androstane-3,17-dione, 4,5-dihydroxy- (6CI,9CI)
Androst-4-ene-3,17-dione, 2-hydroxy-, (2α)-
Androstane-3,17-dione, 4,5-dihydroxy- (6CI,9CI)