Dimethisterone
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| Routes of administration |
Oral |
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| Synonyms | Dimethindrone |
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| ECHA InfoCard | 100.001.106 |
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| Formula | C23H32O2 |
| Molar mass | 340.50 g/mol |
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Dimethisterone (INN, USAN, BAN) (brand names Lutagan, Secrosteron), also known as 6α,21-dimethylethisterone, is a steroidal progestin related to ethisterone (17α-ethinyltestosterone). It was developed by the British pharmaceutical company British Drug Houses (which subsequently merged with Merck KGaA) and was first reported in the medical literature in 1959, with introduction for medical use as Secrosteron following in the same year.
Dimethisterone was derived from modification of ethisterone via introduction of methyl groups at the C6α and C21 positions. Relative to ethisterone, it is 12 times as potent orally as a progestogen in animals (Clauberg test), and, unlike ethisterone, is a pure progestogen with no androgenic (or estrogenic) activity in animals even at very high doses (although some weak antimineralocorticoid activity was observed at high doses in animals). However, in spite of its improved potency over ethisterone, it is a weak progestogen relative to most other progestins, in fact one of the weakest known.
Dimethisterone was introduced in the United States as an oral contraceptive in combination with high doses of ethinylestradiol under the brand name Oracon (25 mg dimethisterone, 100 μg ethinylestradiol) in 1965. Due to the fact that it contains a weak progestogen in combination with a large dose of a potent estrogen, this preparation was eventually found to be associated with a substantially increased risk of endometrial cancer in women, and is now no longer marketed.
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