Norgestrienone

Norgestrienone
Clinical data
Trade namesOgyline, Planor, Miniplanor
Other namesRU-2010; A-301; 17α-Ethynyltrienolone; 17α-Ethynyltrenbolone; Δ9,11-Norethisterone; 17α-Ethynylestra-4,9,11-trien-17β-ol-3-one
Routes of
administration		By mouth
Drug classProgestogen; Progestin; Androgen; Anabolic steroid
ATC code
Identifiers
  • (8S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.011.544 Edit this at Wikidata
Chemical and physical data
FormulaC20H22O2
Molar mass294.394 g·mol−1
3D model (JSmol)
  • O=C4\C=C3/C(=C2/C=C\[C@]1([C@@H](CC[C@]1(C#C)O)[C@@H]2CC3)C)CC4
  • InChI=1S/C20H22O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,8,10,12,17-18,22H,4-7,9,11H2,2H3/t17-,18+,19+,20+/m1/s1 checkY
  • Key:GVDMJXQHPUYPHP-FYQPLNBISA-N checkY
  (verify)

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.[4][5][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.[5]

Norgestrienone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[8] It has some androgenic activity.[9][10][11][12]

Norgestrienone was first described in the literature in 1965.[10] It is sometimes referred to as a "second-generation" progestin.[13] Norgestrienone is no longer available.[citation needed]

  1. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 887–. ISBN 978-1-4757-2085-3.
  2. ^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 202–. ISBN 978-94-011-4439-1.
  3. ^ Diaz S, Pavez M, Quinteros E, Diaz J, Robertson DN, Croxatto HB (October 1978). "Clinical trial with subdermal implants containing norgestrienone". Contraception. 18 (4): 429–440. doi:10.1016/0010-7824(78)90027-6. PMID 720075.
  4. ^ a b Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 751–. ISBN 978-3-88763-075-1.
  5. ^ a b c Sweetman SC, ed. (2009). "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. p. 2122. ISBN 978-0-85369-840-1. 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. ^ McGuire JL (2000). Pharmaceuticals, 4 Volume Set. Wiley. p. 1580,1599. ISBN 978-3-527-29874-7.
  7. ^ IARC Working Group on the Evaluation of Carcinogenic Risks to Humans; World Health Organization; International Agency for Research on Cancer (2007). Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy. World Health Organization. pp. 455–. ISBN 978-92-832-1291-1.
  8. ^ Cite error: The named reference pmid1291626 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference Axelrod1982 was invoked but never defined (see the help page).
  10. ^ a b Cite error: The named reference LauritzenStudd2005 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference GiulioMonosson2012 was invoked but never defined (see the help page).
  12. ^ Rozenbaum H (March 1982). "Relationships between chemical structure and biological properties of progestogens". American Journal of Obstetrics and Gynecology. 142 (6 Pt 2): 719–724. doi:10.1016/S0002-9378(16)32477-2. PMID 7065053.
  13. ^ Cite error: The named reference pmid9988833 was invoked but never defined (see the help page).