Lynestrenol
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| Synonyms | Lynenol; 19-Nor-17α-pregn-4-en-20-yn-17-ol |
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| ECHA InfoCard | 100.000.139 |
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| Formula | C20H28O |
| Molar mass | 284.436 g/mol |
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Lynestrenol (INN, USAN, BAN, JAN), also known as 17α-ethynyl-3-desoxy-19-nortestosterone or 17α-ethynylestr-4-en-17β-ol, is a steroidal progestin of the 19-nortestosterone group. It is a synthetic, orally active progestogen and has a strong progestogenic effect on the uterine endometrium (transforming proliferative endometrium into secretory one), inhibits secretion of gonadotropins, suppresses maturation of follicles in the ovaries and ovulation, and reduces menstrual bleeding. It is used as an oral contraceptive and in the treatment of gynecological disorders.
Lynestrenol itself does not bind to the progesterone receptor and is inactive as a progestogen. It is a prodrug, and upon oral administration, is rapidly and almost completely converted into norethisterone, a potent progestogen, in the liver during first-pass metabolism. No other metabolites besides norethisterone are formed from lynestrenol. As such, its pharmacological activity is essentially identical to that of norethisterone. The conversion of lynestrenol into norethisterone is catalyzed by CYP2C9 (28.0%), CYP2C19 (49.8%), and CYP3A4 (20.4%), while other enzymes are each responsible for no more than 1.0% of the total conversion. It appears that lynestrenol first undergoes hydroxylation of the C3 position, forming etynodiol as an intermediate, followed by oxygenation of the hydroxyl group to form norethisterone.
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