Gestrinone
Gestrinone
CAS: 16320-04-0
Molecular Formula: C21H24O2
Gestrinone - Names and Identifiers
Gestrinone - Physico-chemical Properties
| Molecular Formula | C21H24O2 |
| Molar Mass | 308.41 |
| Density | 1.1040 (rough estimate) |
| Melting Point | 150-152°C |
| Boling Point | 388.8°C (rough estimate) |
| pKa | 12.76±0.40(Predicted) |
| Storage Condition | -20°C Freezer |
| Refractive Index | 1.4900 (estimate) |
| Physical and Chemical Properties | Chemical properties crystallized from ethyl acetate and benzene-cyclohexane (1:1), odorless. Melting point 154 ℃. [α]D20 84.6 (C = 0.41, methanol). |
| Use | Use progesterone. For endometriosis. |
Gestrinone - Risk and Safety
| RTECS | JF7964000 |
Gestrinone - Upstream Downstream Industry
| Raw Materials | Nitrogen Cyclohexane Pyrrolidine Pyruvic acid 2-N-BUTOXYETHYL METHACRYLATE Acetylacetone Magnesium silicate Estradiene dione-3-keta |
Gestrinone - Nature
| specific rotation | D20 84.6° (c = 0.41 in methanol) |
| Merck | 14,4415 |
Last Update：2024-04-10 22:29:15
Gestrinone - Uses and synthesis methods
Introduction
Gestrinone is a synthetic steroid hormone, which has strong anti-estrogen, progesterone and moderate anti-gonadotropin effects. It is currently one of the main drugs for clinical treatment of endometriosis. According to clinical studies, gestrinone can directly act on ectopic lesions to make them shrink and degenerate, the patient's score is significantly reduced, and symptoms such as dysmenorrhea are significantly relieved. At present, there have been studies that gestrinone mainly exerts its effect by inducing apoptosis of ectopic endometrial cells, but the exact mechanism of action still needs to be further explored.
Indications
1. For endometriosis.
2. Used as a family visit contraceptive or after-the-fact contraceptive.
3. For early pregnancy, if combined with prostaglandins, it can improve the success rate of labor induction.
drug interactions
1. combined with rifampicin, barbiturates, phenytoin sodium, etc., can reduce the activity of this product.
2. combined with ampicillin and tetracycline, the contraceptive effect of this drug is reduced.
3. when combined with vitamin c, the contraceptive effect of this drug is enhanced.
application
Gestrinone is a synthetic steroid hormone, which has strong anti-estrogen, progesterone and moderate anti-gonadotropin effects. It is currently one of the main drugs for clinical treatment of endometriosis. According to clinical studies, gestrinone can directly act on ectopic lesions to make them shrink and degenerate, the patient's score is significantly reduced, and symptoms such as dysmenorrhea are significantly relieved. At present, there have been studies that gestrinone mainly exerts its effect by inducing apoptosis of ectopic endometrial cells, but the exact mechanism of action still needs to be further explored.
Pharmacological action
It is a medium-intensity progesterone, with strong anti-progesterone and anti-estrogen activities, and also very weak estrogen and androgen activities. Animal experiments have shown that it can inhibit the secretion of progesterone, and it also has the effect of progesterone on the endometrium, which inactivates and degenerates the endometrium and ectopic lesion cells, which leads to the atrophy of the ectopic lesion. Its anti-fertility effect may be to inhibit ovulation and inhibit endometrial development, change the nature of cervical mucus, affect the speed of egg movement and antagonize endometrial progesterone receptors, thereby interfering with the implantation of pregnant eggs.
Production method
method 1: compound (I) and compound (II) are cycled by Robinson to obtain bicyclic compound (III). After reduction, benzoylation is carried out to obtain (Ⅳ). After partial hydrolysis, treated with acetic anhydride to obtain enolactone (V). After reacting with the Grignard reagent of compound (Ⅵ), it is hydrolyzed to obtain tricyclic compound (VII). Under the action of tetrahydropyrrole, the loop is obtained (Ⅷ). Hydrolysis to obtain (IX), dehydrogenation with dichlorodihydroquinone (DDQ), and introduction of the last double bond to obtain (X). Hydrolysis to remove benzoyl group to form alcohol, and then oxidation to obtain 3, 17-dione (XI). React with ethylene glycol in the presence of acid to obtain 3-ketal (). React with acetylene magnesium bromide, introduce acetylene group, and then remove the protective group to obtain gestrinone.
method 2: add the compound (XIV) to a solution of 2.5ml acetic acid, 2.5ml water and 0.25ml pyruvate, and heat and reflux for lh in nitrogen atmosphere. Cool and pour into the ice water. Add excess sodium bicarbonate and extract with ether. The extract was washed to neutral and distilled in vacuum to obtain 65mg of crude product. The crude product is dissolved in dichloromethane, and the eluent is dichloromethane to obtain 51mg product. Recrystallization with ethyl acetate and benzene-cyclohexane (1:1) mixture to obtain 36mg of gestrinone with a melting point of 154 ℃.
Last Update：2024-04-09 21:54:55
Supplier List
Spot supply
Product Name: Gestrinone Request for quotationCAS: 16320-04-0
Tel: 400-968-2212
Email: 3623107365@qq.com
Mobile: 18916960931
QQ: 3623107365
Wechat: 18916960931
Spot supply
Product Name: Gestrinone Visit Supplier Webpage Request for quotationCAS: 16320-04-0
Tel: +86-400-900-4166
Email: product@acmec-e.com
Mobile: +86-18621343501
QQ: 2881950922
Wechat: 18621343501
WhatsApp: +86-18621343501
Multiple SpecificationsSpot supply
Product Name: R 2323 Visit Supplier Webpage Request for quotationCAS: 16320-04-0
Tel: 609-228-6898
Email: sales@medchemexpress.com
tech@medchemexpress.com
Mobile: 609-228-6898
Spot supply
Product Name: Gestrinone Visit Supplier Webpage Request for quotationCAS: 16320-04-0
Tel: +86 0571-86722205
Email: sales@chinaskyrun.com
Mobile: +8618958170122
QQ: 2531159185
Wechat: chinaskyrun
Spot supply
Product Name: Gestrinone Request for quotationCAS: 16320-04-0
Tel: 400-968-2212
Email: 3623107365@qq.com
Mobile: 18916960931
QQ: 3623107365
Wechat: 18916960931
Spot supply
Product Name: Gestrinone Visit Supplier Webpage Request for quotationCAS: 16320-04-0
Tel: +86-400-900-4166
Email: product@acmec-e.com
Mobile: +86-18621343501
QQ: 2881950922
Wechat: 18621343501
WhatsApp: +86-18621343501
Multiple SpecificationsSpot supply
Product Name: R 2323 Visit Supplier Webpage Request for quotationCAS: 16320-04-0
Tel: 609-228-6898
Email: sales@medchemexpress.com
tech@medchemexpress.com
Mobile: 609-228-6898
Spot supply
Product Name: Gestrinone Visit Supplier Webpage Request for quotationCAS: 16320-04-0
Tel: +86 0571-86722205
Email: sales@chinaskyrun.com
Mobile: +8618958170122
QQ: 2531159185
Wechat: chinaskyrun
View History
Raw Materials for Gestrinone