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| | Ethisterone Basic information |
| Product Name: | Ethisterone | | Synonyms: | 4,17ALPHA-PREGNEN-17BETA-OL-20-YN-3-ONE;4,17a-pregnen-17b-ol-20-yn-3-one;4,17A-PREGNEN-17B-OL-20-YNE;4-ANDROSTEN-17-ALPHA-ETHYNYL-17-BETA-OL-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;ANHYDROHYDROXYPROGESTERONE;ANHYDROXYPROGESTERONE;17BETA-HYDROXY-4,17ALPHA-PREGNEN-20-YN-3-ONE | | CAS: | 434-03-7 | | MF: | C21H28O2 | | MW: | 312.45 | | EINECS: | 207-096-5 | | Product Categories: | Steroids;Acetylenes;Biochemistry;Functionalized Acetylenes;Hydroxyketosteroids;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroid and Hormone;progestogen estrogen;Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals;Inhibitors | | Mol File: | 434-03-7.mol |  |
| | Ethisterone Chemical Properties |
| Melting point | 263-269 °C (lit.) | | alpha | D23 +23.8° (dioxane); D25 -32.0° (pyridine) | | Boiling point | 392.36°C (rough estimate) | | density | 1.0697 (rough estimate) | | refractive index | 33 ° (C=1, Pyridine) | | storage temp. | room temp | | solubility | Soluble to 0.05 mg/mL
(0.16 mM) in DMSO | | pka | 13.10±0.60(Predicted) | | form | neat | | 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). | | Merck | 14,3741 | | BRN | 1889895 | | InChIKey | CHNXZKVNWQUJIB-CEGNMAFCSA-N | | CAS DataBase Reference | 434-03-7 | | NIST Chemistry Reference | Ethisterone(434-03-7) |
| Hazard Codes | Xn,T | | Risk Statements | 40-48-61 | | Safety Statements | 22-24/25-45-53 | | RIDADR | UN 2811 | | WGK Germany | 3 | | RTECS | TU5570250 | | HS Code | 29372390 |
| | Ethisterone Usage And Synthesis |
| Description | Ethisterone is an orally bioavailable synthetic progestin and a derivative of testosterone (Item Nos. ISO60154 | 15645) that binds to progesterone and androgen receptors (EC50s = 23 and 23.1 nM, respectively, in yeast). Ethisterone (1 μM) downregulates progesterone receptors in MCF-7 cells. | | Chemical Properties | Off-White Powder | | Originator | Lutocyclin,Ciba | | Uses | Synthetic progestogen; metabolite of Danazol; intermediate in the synthesis of Spironolactone | | Uses | Ethisterone has been used as a component in Dulbecco′s modified eagle medium (DMEM) to culture the transfected COS-7 cell for transient transfection assay and?gene transfection assay. | | Definition | ChEBI: A 17beta-hydroxy steroid that is testosterone in which the 17beta hydrogen is replaced by an ethynyl group. Ethisterone was the first orally active progestin and is a metabolite of danazol. | | Manufacturing Process | 0.5 part of δ5:6-17-ethinyl-androstendiol-(3:17) is dissolved in 10 parts of dry
acetone, the solution is mixed with a solution of 1 part of tertiary aluminum
butylate in 40 parts of absolute toluene and the whole is heated to boiling in a
reflux apparatus for 21 hours. After the reaction mixture has cooled it is
diluted with 100 parts of ether, the solution is washed with dilute mineral acid
and with water, dried and the solvent is evaporated. In this manner there is
obtained δ5:6-17-ethinyl-androstene-3-one-17-ol (ethisterone); MP: 270°-
272°C; it may be recrystallized from ethyl acetate. | | Therapeutic Function | Progestin | | General Description | Ethisterone is a?progestogen. It is a danazol derivative. | | Biochem/physiol Actions | Ethisterone acts as a progestational agent. It is consumed by pregnant mothers to prevent miscarriage. |
| | Ethisterone Preparation Products And Raw materials |
| Raw materials | Dehydroepiandrosterone-->Pregn-4-en-20-yn-3-one, 17-hydroxy--->Pregn-4-ene-3,20-dione, 21-bromo-17-hydroxy--->17A-PREGN-5-EN-20-YNE-3B,17-DIOL-->REICHSTEIN'S SUBSTANCE S 21-ACETATE-->3-Ethoxy-androsta-3,5-dien-17-one-->Androstenedione-->Acetylene | | Preparation Products | 17-ethyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one |
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