As a representitive of the compounds of the class of progestins, this drug is used for various forms of cancer, in particular cancer of the breast, kidneys, and others. Synonyms of this drug are megestat, niagestin, megeis, and others.
Norethindrone: Norethindrone, 17a-ethynyl-17^-hydroxyestra-4-en-4-one (28.3.12), is made from 19-nor-4-androsten-3,17-dione (28.3.10), which is in turn synthesized by partial reduction of the aromatic region of the 3-O-methyl ether of estrone with lithium in liquid ammonia, and simultaneously of the keto-group at C17 to and hydroxyl group, which is then oxidized back to a keto-group by chromium (VI) oxide in acetic acid. The conjugated with the double bond carbonyl group at C3 is then transformed to dienol ethyl ether (28.3.11) using ethyl orthoformate. The obtained product is ethynylated by acetylene in the presence of potassium ieri-butoxide. After hydrochloric acid hydrolysis, of the formed O-potassium derivative, during which the enol ether is also hydrolyzed, and the remaining double bond is shifted, the desired norethindrone (28.3.12) is obtained [80-85].
h3c o ch3o'
2.CrO3 / CH3COOH
2.CrO3 / CH3COOH
h3c o h3c o
HC(OC2H5)3/PyHCl h3c o c2h5o'
h3c oh h3c oh
This drug can be used as a carboxylic acid ester, in particular, as an acetate. It causes the mucous membranes of the uterus to move into the secretory phase, which facilitates development of impregnated oocytes. It reduces the excitability and contractility of uterine musculature. It is used for amenorrhea, uterine bleeding, infertility, miscarriage, myoma, mastopathy, endometrial cancer, and other pathologies. Synonyms of this drug are conce-plan, norfor, brevinor, and many others.
Norgestrel: Norgestrel, (±)-13-ethyl-17a-17/i-hydroxyestr-4-en-3-one (28.3.13), differs from norethindrone in the presence of an ethyl group at C13 of the steroid system. It is synthesized by ethynylating 18-Methylestr-4-ene-3,17-dione [86-92].
The presence of an ethyl group at C13 of the steroid system makes it less active than progesterone; however, it retains activity when taken orally, which provides effective contraception. Synonyms of this drug are anovlar, norlest, milligynon, loestrin, and others.
Ethisterone: Ethisterone, 17-ethynyl-17-hydroxyandrosten-4-en-3-one (28.4.14), is made by ethynylation of the androstenolon with acetylene and successive oxidation of the hydroxyl group at C3 of the steroid system [93,94].
Ethisterone differs from norethindrone in the presence of two methyl groups at C10 and C13 of the steroid system. It makes it less active than progesterone; however, this drug retains its activity when taken orally, which provides highly effective contraception. Synonyms of this drug are pranone, oraluton, pregnoral, and others.
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