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Dimethisterone

Dimethisterone
Skeletal formula of dimethisterone
Ball-and-stick model of the dimethisterone molecule
Clinical data
Trade namesLutagan, Secrosteron, others
Other namesDimethindrone; 6α,21-Dimethylethisterone; 6α,21-Dimethyl-17α-ethynyltestosterone; 17α-Ethynyl-6α,21-dimethylandrost-4-en-17β-ol-3-one; 6α,21-Dimethyl-17β-hydroxy-17α-pregn-4-en-20-yn-3-one
Routes of
administration		By mouth
Drug classProgestogen; Progestin
Identifiers
  • (6S,8R,9S,10R,13S,14S,17S)-17-hydroxy-6,10,13-trimethyl-17-prop-1-ynyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.001.106 Edit this at Wikidata
Chemical and physical data
FormulaC23H32O2
Molar mass340.507 g·mol−1
3D model (JSmol)
  • CC#C[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C[C@@H](C4=CC(=O)CC[C@]34C)C)C)O
  • InChI=1S/C23H32O2/c1-5-9-23(25)12-8-19-17-13-15(2)20-14-16(24)6-10-21(20,3)18(17)7-11-22(19,23)4/h14-15,17-19,25H,6-8,10-13H2,1-4H3/t15-,17+,18-,19-,21+,22-,23-/m0/s1
  • Key:LVHOURKCKUYIGK-RGUJTQARSA-N

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]

  1. ^ a b c Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 430–. ISBN 978-1-4757-2085-3.
  2. ^ Paoletti R, Pasetto N, Ambrus JL (6 December 2012). The Menopause and Postmenopause: The Proceedings of an International Symposium held in Rome, June 1979. Springer Science & Business Media. pp. 374–. ISBN 978-94-011-7230-1.
  3. ^ Voigt LF, Weiss NS (6 December 2012). "Epidemiology of endometrial cancer". In Surwit EA, Alberts D (eds.). Endometrial Cancer. Springer Science & Business Media. pp. 11–. ISBN 978-1-4613-0867-6.
  4. ^ Patterson R (21 December 2012). Drugs in Litigation: Damage Awards Involving Prescription and Nonprescription Drugs. LexisNexis. pp. 483–484. ISBN 978-0-327-18698-4.
  5. ^ a b Cite error: The named reference Publishing2013 was invoked but never defined (see the help page).
  6. ^ Gadappa S, Yelikar K, Deshpande S (7 May 2015). "Drugs in Obstetrics and Gynecology". In Yelikar K (ed.). Practical Cases in Obstetrics & Gynecology. JP Medical Ltd. pp. 98–. ISBN 978-93-5090-536-4.
  7. ^ a b Cite error: The named reference BarakatMarkman2009 was invoked but never defined (see the help page).
  8. ^ a b c Cite error: The named reference pmid13814263 was invoked but never defined (see the help page).
  9. ^ a b Cite error: The named reference MorganJones1959 was invoked but never defined (see the help page).
  10. ^ a b Cite error: The named reference Jucker2013 was invoked but never defined (see the help page).
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