Norgestrienone Explained

Norgestrienone, sold under the brand names Ogyline, Planor, and Miniplanor, is a progestin medication which has been used in birth control pills, sometimes in combination with ethinylestradiol.[1] [2] [3] [4] [5] It was developed by Roussel Uclaf and has been registered for use only in France.[6] Under the brand name Planor, it has been marketed in France as 2 mg norgestrienone and 50 μg ethinylestradiol tablets.[7] It is taken by mouth.

Norgestrienone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has some androgenic activity.[8]

Norgestrienone was first described in the literature in 1965. It is sometimes referred to as a "second-generation" progestin. Norgestrienone is no longer available.

Medical uses

Norgestrienone was used in hormonal contraception to prevent pregnancy. It has typically been used as an oral contraceptive at a dosage of 2 mg/day in combination with ethinylestradiol and 350 μ/day when used alone.

Pharmacology

Pharmacodynamics

Norgestrienone has been found to possess similar affinity for the progesterone receptor and androgen receptor,[9] and in accordance, has some androgenic activity.[10] [11] [12] The androgenic activity of norgestrienone is greater than that of other 19-nortestosterone derivatives due to the presence of the C9(11) double bond, which enhances said activity. The ratio of progestogenic to androgenic activity appears to be much lower for norgestrienone that it is for other 19-nortestosterone progestins such as norethisterone and levonorgestrel. Gestrinone, the 18-methyl analogue of norgestrienone, has even greater androgenic activity than norgestrienone, as this modification increases androgenic activity similarly.

Relative affinities (%) of norgestrienone and related steroids
Compound
155–156 43–45 <0.1 2.7–2.8 0.2 ? ?
Norgestrienone 63–65 70 <0.1 11 1.8 ? ?
170 84–87 <0.1 14 0.6–0.9 ? ?
75–76 83–85 <0.1, 3–10 77 3.2 ? ?
Notes: Values are percentages (%). Reference ligands (100%) were progesterone for the, testosterone for the, for the, for the, aldosterone for the, for, and cortisol for . Sources: [13] [14] [15] [16]

Pharmacokinetics

The metabolism of norgestrienone in humans has been studied.[17]

Chemistry

See also: List of progestogens and List of androgens/anabolic steroids.

Norgestrienone, also known as 17α-ethynyl-19-nor-δ9,11-testosterone or as 17α-ethynylestra-4,9,11-trien-17β-ol-3-one, as well as δ9,11-norethisterone or 17α-ethynyltrienolone (17α-ethynyltrenbolone), is a synthetic estrane steroid and a derivative of testosterone and 19-nortestosterone.[18] It is structurally related to the anabolic steroid trenbolone (19-nor-δ9,11-testosterone; the non-17α-ethynylated analogue of norgestrienone), the progestogenic and androgenic steroid gestrinone (the 13β-ethyl variant or 18-methyl derivative of norgestrienone), and the anabolic steroid tetrahydrogestrinone (the 18-methyl and 17α-ethyl variant of norgestrienone).[19]

History

Norgestrienone was first described in the literature in 1965. It is sometimes referred to as a "second-generation" progestin based on its time of introduction.[20]

Society and culture

Generic names

Norgestrienone is the generic name of the drug and its . It is also known by its developmental code names RU-2010 and A-301.

Brand names

Norgestrienone has been marketed under the brand names Ogyline, Planor, and Miniplanor.

Availability

Norgestrienone is no longer marketed and hence is no longer available in any country. It was previously used in France. The medication was never marketed in the United States.[21]

Research

Norgestrienone has been studied for use in male hormonal contraception.[22]

Notes and References

  1. Book: Elks J . The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014. Springer. 978-1-4757-2085-3. 887–.
  2. Book: Morton IK, Hall JM . Concise Dictionary of Pharmacological Agents: Properties and Synonyms. 6 December 2012. Springer Science & Business Media. 978-94-011-4439-1. 202–.
  3. Diaz S, Pavez M, Quinteros E, Diaz J, Robertson DN, Croxatto HB . Clinical trial with subdermal implants containing norgestrienone . Contraception . 18 . 4 . 429–440 . October 1978 . 720075 . 10.1016/0010-7824(78)90027-6 .
  4. Book: Index Nominum 2000: International Drug Directory. January 2000. Taylor & Francis. 978-3-88763-075-1. 751–.
  5. Book: Sweetman SC . Sex hormones and their modulators . Martindale: The Complete Drug Reference . 36th . 2009 . 2122 . Pharmaceutical Press . London. 978-0-85369-840-1. https://www.medicinescomplete.com/. Norgestrienone is a progestogen structurally related to norethisterone that has been used as an oral contraceptive. Typical doses have been 2 mg daily with an oestrogen, and 350 micrograms daily when used alone..
  6. Book: McGuire JL . Pharmaceuticals, 4 Volume Set. 2000. Wiley. 978-3-527-29874-7. 1580,1599.
  7. Book: IARC Working Group on the Evaluation of Carcinogenic Risks to Humans. World Health Organization. International Agency for Research on Cancer. Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy. 2007. World Health Organization. 978-92-832-1291-1. 455–.
  8. Rozenbaum H . Relationships between chemical structure and biological properties of progestogens . American Journal of Obstetrics and Gynecology . 142 . 6 Pt 2 . 719–724 . March 1982 . 7065053 . 10.1016/S0002-9378(16)32477-2 .
  9. Loughney DA, Schwender CF . A comparison of progestin and androgen receptor binding using the CoMFA technique . Journal of Computer-Aided Molecular Design . 6 . 6 . 569–581 . December 1992 . 1291626 . 10.1007/bf00126215 . 22004130 . 1992JCAMD...6..569L .
  10. Book: Axelrod J . Biochemical Actions of Hormones. 1 January 1982. Academic Press. 978-0-12-452809-3.
  11. Book: Lauritzen C, Studd JW . Current Management of the Menopause. 22 June 2005. CRC Press. 978-0-203-48612-2. 45–.
  12. Book: Di Giulio RT, Monosson E . Interconnections Between Human and Ecosystem Health . 6 December 2012. Springer Science & Business Media. 978-94-009-1523-7. 60–.
  13. Delettré J, Mornon JP, Lepicard G, Ojasoo T, Raynaud JP . Steroid flexibility and receptor specificity . Journal of Steroid Biochemistry . 13 . 1 . 45–59 . January 1980 . 7382482 . 10.1016/0022-4731(80)90112-0 .
  14. Raynaud JP, Bouton MM, Moguilewsky M, Ojasoo T, Philibert D, Beck G, Labrie F, Mornon JP . 6 . Steroid hormone receptors and pharmacology . Journal of Steroid Biochemistry . 12 . 143–157 . January 1980 . 7421203 . 10.1016/0022-4731(80)90264-2 .
  15. Ojasoo T, Raynaud JP, Doé JC . Affiliations among steroid receptors as revealed by multivariate analysis of steroid binding data . The Journal of Steroid Biochemistry and Molecular Biology . 48 . 1 . 31–46 . January 1994 . 8136304 . 10.1016/0960-0760(94)90248-8 . 21336380 .
  16. Book: Raynaud J, Ojasoo T, Bouton M, Philibert D . Drug Design . 1979 . 169–214 . 10.1016/B978-0-12-060308-4.50010-X . https://books.google.com/books?id=bhAlBQAAQBAJ&pg=PA169. 9781483216102 . Receptor Binding as a Tool in the Development of New Bioactive Steroids. Medicinal Chemistry: A Series of Monographs . 11 . Academic Press .
  17. Raynaud JP . Metabolism of contraceptive steroids in man. . Excerpta Medica International Congress Series . 1970 . 219 . 915–922 . https://web.archive.org/web/20180329184746/https://www.popline.org/node/480947 . 29 March 2018 .
  18. Book: Lavery JP, Sanfilippo JS . Pediatric and Adolescent Obstetrics and Gynecology. 6 December 2012. Springer Science & Business Media. 978-1-4612-5064-7. 236–.
  19. Book: Gomel V, Brill A . Reconstructive and Reproductive Surgery in Gynecology. 27 September 2010. CRC Press. 978-1-84184-757-3. 90–.
  20. Weiss G . Risk of venous thromboembolism with third-generation oral contraceptives: A review . American Journal of Obstetrics and Gynecology . 180 . 2 Pt 2 . 295–301 . February 1999 . 9988833 . 10.1016/S0002-9378(99)70721-0 .
  21. Book: Lednicer D . Strategies for Organic Drug Synthesis and Design. 4 March 2009. John Wiley & Sons. 978-0-470-39959-0. 134–.
  22. Schearer SD . The use of progestins and androgens as a male contraceptive. Hormonal control of male fertility. . DHEW Publication No.(NIH). . 1978 . 78–1097 . https://web.archive.org/web/20180329184345/https://www.popline.org/node/443605 . 29 March 2018 .

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