Gestoral
ethisterone
CAS: 434-03-7
Molecular Formula: C21H28O2
Gestoral - Names and Identifiers
| Name | ethisterone |
| Synonyms | Gestoral ethisterone Ethisterone pregneninolone ethynyl testosterone ANHYDROXYPROGESTERONE 17a-ethynyl testosterone anhydrohydroxyprogesterone ANHYDROHYDROXYPROGESTERONE 4,17A-PREGNEN-17B-OL-20-YNE 17-alpha-ethynyltestosterone 17-hydroxypregn-4-en-20-yn-3-one 4,17a-pregnen-17b-ol-20-yn-3-one 4,17ALPHA-PREGNEN-17BETA-OL-20-YN-3-ONE 17a-ethynyl-17b-hydroxy-4-androsten-3-one (17alpha)-17-hydroxypregn-4-en-20-yn-3-one 17BETA-HYDROXY-4,17ALPHA-PREGNEN-20-YN-3-ONE 4-ANDROSTEN-17-ALPHA-ETHYNYL-17-BETA-OL-3-ONE (8xi,9xi,14xi,17alpha)-17-hydroxypregn-4-en-20-yn-3-one (8xi,9xi,10xi,13xi,14xi,17alpha)-17-hydroxypregn-4-en-20-yn-3-one (8R,9S,10R,13S,14S,17R)-17-ETHYNYL-17-HYDROXY-10,13-DIMETHYL-1,2,6,7,8,9,10,11,12,13,14,15,16,17-TETRADECAHYDRO-CYCLOPENTA[A]PHENANTHREN-3-ONE |
| CAS | 434-03-7 |
| EINECS | 207-096-5 |
| InChI | InChI=1/C21H28O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,13,16-18,23H,5-12H2,2-3H3/t16-,17+,18+,19+,20+,21+/m1/s1 |
| InChIKey | CHNXZKVNWQUJIB-CEGNMAFCSA-N |
Gestoral - Physico-chemical Properties
| Molecular Formula | C21H28O2 |
| Molar Mass | 312.45 |
| Density | 1.0697 (rough estimate) |
| Melting Point | 263-269 °C (lit.) |
| Boling Point | 392.36°C (rough estimate) |
| Specific Rotation(α) | D23 +23.8° (dioxane); D25 -32.0° (pyridine) |
| Flash Point | 190.2°C |
| Water Solubility | soluble in chloroform, DMSO (0.05 mg/ml), acetone (slightly ), ethanol (<1 mg/ml at 25°C), and water (<1 mg/ml at 25°C). |
| Solubility | Soluble in chloroform, DMSO (0.05 mg/ml), acetone (slightly ), ethanol (<1 mg/ml at 25 |
| Vapor Presure | 7.59E-10mmHg at 25°C |
| Appearance | White crystalline powder |
| Merck | 14,3741 |
| BRN | 1889895 |
| pKa | 13.10±0.60(Predicted) |
| Storage Condition | room temp |
| Refractive Index | 33 ° (C=1, Pyridine) |
| MDL | MFCD00003656 |
| Physical and Chemical Properties | Melting Point: 266 - 273
|
| Use | For the treatment of uterine bleeding or menorrhagia |
| In vivo study | In mice, Ethisterone (dose range: 40 μg-5 mg/day × 6) stimulated body weight gain but had a weak effect on the rate of sulfate incorporation. Ethisterone caused a rapid increase in the labeling rate, and bone needle cells of mature female frogs and Herring began to appear spontaneously in the center of the marginal zone of the joint plate, and the number was more than 10 times that of the control group on the fifth day. |
Gestoral - Risk and Safety
| Risk Codes | R40 - Limited evidence of a carcinogenic effect R48 - Danger of serious damage to health by prolonged exposure R61 - May cause harm to the unborn child |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S53 - Avoid exposure - obtain special instructions before use. |
| UN IDs | UN 2811 |
| WGK Germany | 3 |
| RTECS | TU5570250 |
| HS Code | 29372390 |
Gestoral - Standard
Authoritative Data Verified Data
This product is 17b-hydroxy ~ 17a-ethynyl ~ androstin-4-en-3-one. The content of C21H2802 shall be between 97.0% and 103.0% based on the dry product.
Last Update：2024-01-02 23:10:35
Gestoral - Trait
Authoritative Data Verified Data
- This product is white or off-white crystalline powder; Odorless or almost odorless.
- This product is slightly soluble in pyridine, slightly soluble in chloroform, and almost insoluble in water.
specific rotation
take this product, precision weighing, and pyridine dissolved and quantitative dilution of solution containing about 10 mg per 1 ml, according to the law (General 0621), the specific rotation should be 28 ° to 33 °.
Last Update：2022-01-01 13:37:19
Gestoral - Introduction
Ethisterone is a progestin that can treat prostate cancer.
Last Update：2022-10-16 17:25:13
Gestoral - Differential diagnosis
Authoritative Data Verified Data
- take about 2mg of this product, add 4ml of anhydrous ethanol-sulfuric acid (1:1), heat and dissolve in water bath, the solution is red, set the UV lamp (365nm) to view. Bright red fluorescence.
- take about 2mg of this product, add ethanol 2ml, l%2, 6-di-tert-butyl p-formic acid ethanol solution 1ml and sodium hydroxide test solution 2ml, heat in water bath for 30 minutes, let cool, it was dark blue.
- take about 2mg of this product, put it in a clean test tube, add 2ml of ethanol and 1ml of ammonia-made silver nitrate solution, heat it in a water bath, and the silver is free and attached to the wall of the test tube to generate a silver mirror.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 617).
Last Update：2022-01-01 13:37:20
Gestoral - Exam
Authoritative Data Verified Data
Related substances
take an appropriate amount of this product, add solvent [chloroform-methanol (3:1)] to dissolve and dilute to make a solution containing about 10 mg per 1ml, as a test solution; take 1ml of precision, 200ml flask, diluted with the above solvent to the scale, shake, as a control solution. According to the book layer chromatography (General rule 0502) test, draw 10ul of each of the above two solutions, respectively point on the same silica gel G thin layer plate, with chloroform-methanol (95:5) as the developing solvent, it was developed, dried, sprayed with sulfuric acid-ethanol (2:8), heated at 120 ° C. For 5 minutes, and examined under a UV lamp (365nm). If the test solution shows impurity spots, the fluorescence intensity should not be deeper (0.5%) compared with the main spots of the control solution.
loss on drying
take this product and dry it at 105°C for 4 hours, and the weight loss shall not exceed 0.5% (General rule 0831).
Last Update：2022-01-01 13:37:21
Gestoral - Content determination
Authoritative Data Verified Data
take this product, precision weighing, plus absolute ethanol dissolution and quantitative dilution of about 10ug per lml solution, according to UV-visible spectrophotometry (General 0401), the absorbance was measured at a wavelength of 240nm and calculated as the absorption coefficient of C21H2802 was 520.
Last Update：2022-01-01 13:37:21
Gestoral - Category
Authoritative Data Verified Data
progesterone drugs.
Last Update：2022-01-01 13:37:22
Gestoral - Storage
Authoritative Data Verified Data
light shielding, sealed storage.
Last Update：2022-01-01 13:37:22
Gestoral - Norgestrel tablets
Authoritative Data Verified Data
This product contains norgestrel (C21H2802) should be labeled amount of 90.0% ~ 110.0%.
trait
This product is white tablet.
identification
- about 10mg of the extract obtained under the measurement of the content was taken and dissolved by adding 1 ml of ethanol, and then 5 to 6 drops of a silver nitrate test solution were added, thereby generating a white precipitate.
- take an appropriate amount of the extract obtained under the content determination item, add anhydrous ethanol to make a solution containing about 10ug per 1 ml, and measure it by UV-Vis spectrophotometry (General 0401), there is a maximum absorption at a wavelength of 240nm, and the absorbance is 0.50 to 0.54.
examination
should be in accordance with the relevant provisions under The tablet item (General rule 0101).
Content determination
Take 20 tablets of this product, precise weighing, fine grinding, precise weighing appropriate amount (about 50mg equivalent to two 50mg), set the separation funnel, extracted with petroleum ether for 4 times, discard the petroleum ether extract, remove the petroleum ether in the separatory funnel, and then extract 4 times with chloroform, 15ml each time. Combine the chloroform extract, put it in a constant weight container, and remove the chloroform by evaporation until it is nearly dry, the residue was dried at 105 ° C. For 2 hours, and accurately weighed to obtain the weight of C21H2802 contained in the Test quantity.
category
The same as the one of the two.
specification
(l)5mg (2)10mg (3)25mg
storage
light shielding, sealed storage.
Last Update：2022-01-01 13:37:22
Gestoral - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| introduction | acetyl progesterone is a white or white-like crystalline powder; odorless or almost odorless. This product is slightly soluble in pyridine, slightly soluble in chloroform, and almost insoluble in water. Clinically used for functional uterine bleeding, abnormal menstruation, amenorrhea, dysmenorrhea, etc. |
| preparation | add 4AD10g, 40 ml of ethanol, 20 ml of dichloromethane and 0.02g of PTS to the reaction bottle, stir, cool to 10 ℃, add 9 ml of triethyl orthoformate, control the temperature to 18~20 ℃ for heat preservation and reaction for 120 minutes, and point the plate (developing agent: petroleum ether: acetone = 5:2) the raw material point basically disappears, add 50 ml of ice water, stop the reaction, stir for 30-40 minutes, add triethylamine dropwise, adjust PH = 8, concentrate under reduced pressure below 50 ℃ until the remaining amount of ethanol is 1W, add 50 ml of water to cool to about 20 ℃, stir for 2 hours , filter and drain. Drying at 40 ℃. Control moisture 0.2%. Yield: 110%. 130 grams of toluene isobutanol, 55 grams of isobutanol and 10 grams of potassium hydroxide are put into the reaction bottle, stirred and heated until reflux, the distillation speed is controlled for 6 hours, and half of isobutanol is evaporated. After atmospheric dehydration, vacuum is opened, decompression concentration is carried out (vacuum degree is above 0.09Mpa), and toluene is recovered to the white or white-like solid powder of the system. Put 50 ml of tetrahydrofuran, when the internal temperature drops to 20 ℃, add acetylene gas, control the internal temperature of 10 ℃ and ventilate for 2 hours until the introduced acetylene gas is no longer absorbed. Cooling, when the internal temperature drops to -15 ℃, slowly add 10 grams of ether solution of tetrahydrofuran, and ventilate at -5 ℃ for 8 hours. After the reaction, exhaust the acetylene gas in the tank, pump in hydrochloric acid water, adjust the pH value to 7.5, control the temperature to 10~20 ℃, and continue stirring 15~20 minutes. Concentrate, control the internal temperature ≤ 40 ℃, vacuum ≥ 0.07Mpa, concentrate under reduced pressure until there is basically no tetrahydrofuran effluent, add water entrainment, continue to concentrate under reduced pressure until the internal temperature reaches 60 ℃ ~ 70 ℃, stop concentrating, add water, cool down to 30 ℃, continue stirring for 60 minutes minutes, filter, and wash with water until neutral. Dry. 9.6 grams of crude acetyl progesterone was obtained. 96% yield, HPLC 97.7%. Add 5g of crude product, 7.5 ml of DMF, 10 ml of ethanol and 8 ml of chloroform into the reaction bottle, and heat and reflux for 1 hour. Cooling, filtering, rinsing and drying. Get 4.3 grams of high-quality acetyl progesterone. 86% yield, HPLC 99.2%. |
| biological activity | Ethisterone is a progestin that can treat prostate cancer. |
| Target | Value |
| use | similar to yellow progesterone, suitable for the treatment of bleeding or menorrhagia, can also be used to prevent threatened abortion and habitual abortion. Progesterone is luteinizing hormone, secreted by the corpus luteum and placenta, and is now mostly synthesized artificially. for the treatment of uterine bleeding or menorrhagia |
| Production method | After the addition and hydrolysis of dehydroepiandrosterone acetate and acetylene, 17-acetylene testosterone is obtained by oxidation. |
Last Update：2024-04-10 22:29:15
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