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Dimethisterone
Chemical compound From Wikipedia, the free encyclopedia
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Dimethisterone, formerly sold under the brand names Lutagan and Secrosteron among others, is a progestin medication which was used in birth control pills and in the treatment of gynecological disorders but is now no longer available.[1][2][3][4] It was used both alone and in combination with an estrogen.[1][5] It is taken by mouth.[6]
Side effects of dimethisterone are similar to those of other progestins. When used in combination with high doses of an estrogen, an increased risk of endometrial cancer can occur.[7] Dimethisterone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[8][9][10] It has some antimineralocorticoid activity and no other important hormonal activity.[8][9][10]
Dimethisterone was first described and was introduced for medical use in 1959.[1][8] It started being used in birth control pills in 1965.[5] However, due to its low potency and consequent inability to prevent the increased risk of endometrial cancer with estrogens, dimethisterone was soon discontinued for such purposes.[7]
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Medical uses
Dimethisterone was used alone in the treatment of gynecological disorders and in combination with ethinylestradiol in birth control pills.[7][11]
Side effects
Side effects of dimethisterone are similar to those of other progestins.[citation needed]
Pharmacology
Pharmacodynamics
Dimethisterone was derived from modification of ethisterone via introduction of methyl groups at the C6α and C21 positions.[12][13] Relative to ethisterone, it is 12 times as potent orally as a progestogen in animals (Clauberg test),[8][13] and, unlike ethisterone,[14] 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).[8][9][10] However, in spite of its improved potency over ethisterone, it is a weak progestogen relative to most other progestins,[3] in fact one of the weakest known.[2]
Chemistry
Dimethisterone, also known as 6α,21-dimethylethisterone or as 6α,21-dimethyl-17α-ethynyltestosterone, as well as 17α-ethynyl-6α,21-dimethylandrost-4-en-17β-ol-3-one or as 6α,21-dimethyl-17β-hydroxy-17α-pregn-4-en-20-yn-3-one, is a synthetic androstane steroid and a derivative of testosterone.[1]
Synthesis
Chemical syntheses of dimethisterone have been published.[15]
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History
Dimethisterone 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,[1][8] with introduction for medical use under the brand name Secrosteron following in the same year.[13][16] It 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.[5] 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.[7]
The improved potency of dimethisterone due to 6α-methylation reportedly served as the basis for the synthesis of medroxyprogesterone acetate.[13] Whereas hydroxyprogesterone acetate (the 6α-demethylated analogue of medroxyprogesterone acetate) is around twice as potent as ethisterone orally,[17] medroxyprogesterone acetate shows 10 to 25 times the potency of ethisterone.[13]
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Society and culture
Generic names
Dimethisterone is the generic name of the drug and its INN, USAN, and BAN.[1]
Brand names
Dimethisterone was marketed alone under the brand names Lutagan and Secrosteron and in combination with ethinylestradiol under the brand names Oracon, Ovin, Secrodyl, Secrovin, and Tova.[1][5][18]
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References
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