Dimethisterone
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Dimethisterone, formerly sold under the brand names Lutagan and Secrosteron among others, is a
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]
Medical uses
Dimethisterone was used alone in the treatment of
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
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
Synthesis
Chemical syntheses of dimethisterone have been published.[15]
History
Dimethisterone was developed by the
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]
Society and culture
Generic names
Dimethisterone is the
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]
References
- ^ ISBN 978-1-4757-2085-3.
- ^ ISBN 978-94-011-7230-1.
- ^ ISBN 978-1-4613-0867-6.
- ISBN 978-0-327-18698-4.
- ^ ISBN 978-0-8155-1856-3.
- ISBN 978-93-5090-536-4.
- ^ ISBN 978-0-7817-7845-9.
Studies have shown that women who used Oracon, a sequential preparation that employed dimethisterone (weak progestogen) with a large dose of a potent estrogen (ethinyl estradiol), had substantially elevated risks of uterine cancer (6,21). The risk associated with the use of other sequential oral contraceptives remains unclear, mainly because these drugs are no longer marketed.
- ^ S2CID 34304113.
- ^ a b c Vademecum International. J. Morgan Jones Publications. 1959. p. 90.
Secrosteron (dimethisterone) is an orally active purely progestational agent twelve times as potent as ethisterone.
- ^ ISBN 978-3-0348-7053-5.
- ^ IARC Working Group on the Evaluation of the Carcinogenic Risk of Chemicals to Humans (1978). IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans. IARC. p. 379.
- ISBN 978-0-7817-6879-5.
- ^ a b c d e Applezweig N (1962). Steroid Drugs. Blakiston Division, McGraw-Hill. pp. 101–102.
At The British Drug Houses, Ltd., V. Petrow and his group decided that substitution at the 6 position should help to strengthen the progesterone molecule. They prepared a series of 6α and 6β derivatives and, finding enhancement with 6α-methyl, proceeded to modify ethisterone and finally produced 6α,21-dimethylethisterone, which proved to have twelve times the oral activity of ethisterone. This latter product is marketed by British Drug Houses under the name of Secrosteron.
- )
- ISBN 978-3-642-99941-3.
- ^ Medical Proceedings: A South African Journal for the Advancement of Medical Science. Juta and Company. 1959. p. 269.
Secrosteron a new oral progestational substance British Drug Houses (South Africa) (Pty.) Ltd., announce the introduction of Secrosteron, a new fundamental discovery from the Research Laboratories of the British Drug Houses Ltd., London.
- PMID 13475464.
It is the purpose of this paper to introduce and describe a new steroid for oral administration, 17-a-hydroxyprogesterone acetate*, and to compare it with the most widely used oral substance with progestational properties, 20,21-anhydro-17-/3-hydroxyprogesterone. * Prodox, Upjohn Co., Kalamazoo, Michigan [...] It was found that 17-a-hydroxyprogesterone acetate has a progestational activity which is at least twice that of anhydrohydroxyprogesterone.
- ISBN 9789283212065.