Lynestrenol

Source: Wikipedia, the free encyclopedia.
Lynestrenol
Progestin
ATC code
)
Identifiers
  • (8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
JSmol)
  • C#C[C@]2(O)CC[C@H]1[C@H]4[C@H](CC[C@@]12C)[C@@H]3\C(=C/CCC3)CC4
  • InChI=1S/C20H28O/c1-3-20(21)13-11-18-17-9-8-14-6-4-5-7-15(14)16(17)10-12-19(18,20)2/h1,6,15-18,21H,4-5,7-13H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1 checkY
  • Key:YNVGQYHLRCDXFQ-XGXHKTLJSA-N checkY
  (verify)

Lynestrenol, sold under the brand names Exluton and Ministat among others, is a

gynecological disorders.[2][3][4] The medication is available both alone and in combination with an estrogen.[3][5][6] It is taken by mouth.[7][8]

Lynestrenol is a progestin, or a

hormonal activity.[9][10] The medication is a prodrug of norethisterone in the body, with etynodiol occurring as an intermediate.[10][11][12]

Lynestrenol was discovered in the late 1950s and was introduced for medical use in 1961.[13][14] It has mostly been used in Europe and elsewhere in the world and was never marketed in the United States.[6][15][16][17]

Medical uses

Lynestrenol is used as a component of

gynecological disorders such as menstrual disorders.[4]

Side effects

Main articles:
Progestin § Side effects

Pharmacology

Norethisterone (3-ketolynestrenol), the active metabolite of lynestrenol.

Lynestrenol itself does not bind to the

hydroxyl group to form norethisterone.[11]

The

elimination half-life being 16 or 17 hours.[citation needed
]

The pharmacokinetics of lynestrenol have been reviewed.[18]

Relative affinities (%) of norethisterone, metabolites, and prodrugs
Compound Typea PRTooltip Progesterone receptor ARTooltip Androgen receptor ERTooltip Estrogen receptor GRTooltip Glucocorticoid receptor MRTooltip Mineralocorticoid receptor SHBGTooltip Sex hormone-binding globulin
CBG
Tooltip Corticosteroid binding globulin
Norethisterone – 67–75 15 0 0–1 0–3 16 0
5α-Dihydronorethisterone Metabolite 25 27 0 0 ? ? ?
3α,5α-Tetrahydronorethisterone Metabolite 1 0 0–1 0 ? ? ?
3α,5β-Tetrahydronorethisterone Metabolite ? 0 0 ? ? ? ?
3β,5α-Tetrahydronorethisterone Metabolite 1 0 0–8 0 ? ? ?
Ethinylestradiol Metabolite 15–25 1–3 112 1–3 0 0.18 0
Norethisterone acetate Prodrug 20 5 1 0 0 ? ?
Norethisterone enanthate Prodrug ? ? ? ? ? ? ?
Noretynodrel Prodrug 6 0 2 0 0 0 0
Etynodiol Prodrug 1 0 11–18 0 ? ? ?
Etynodiol diacetate Prodrug 1 0 0 0 0 ? ?
Lynestrenol Prodrug 1 1 3 0 0 ? ?
Notes: Values are percentages (%). Reference
CBGTooltip Corticosteroid-binding globulin. Footnotes: a = Active or inactive metabolite, prodrug
, or neither of norethisterone. Sources: See template.

Chemistry

See also:
List of androgens/anabolic steroids

Lynestrenol, also known as 17α-ethynyl-3-desoxy-19-nortestosterone or as 17α-ethynylestr-4-en-17β-ol, is a

hydroxyl group at the C3 position, respectively.[11]

Synthesis

Chemical syntheses of lynestrenol have been published.[2][18]

In another approach to analogues,

17-ketone
leads to the orally active progestin (6).

Lynestrenol synthesis:[20][21]

History

Lynestrenol was developed by the

pharmaceutical company Organon in the late 1950s and was introduced for medical use in 1961.[13][14] It received a Dutch patent for lynestrenol in 1957,[13] and lynestrenol subsequently became a component of Lyndiol, the first Dutch contraceptive pill, in 1962.[1][13][14] Around this time, pre- and post-marketing clinical trials of lynestrenol were conducted, and in 1965, a study consisting of 200 Dutch women was published.[13] Lynestrenol was approved, in the United Kingdom, in combination with mestranol in 1963 and in combination with ethinylestradiol in 1969.[16]

Society and culture

Generic names

Lynestrenol is the

INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, BANTooltip British Approved Name, and JANTooltip Japanese Accepted Name, while lynestrénol is its DCFTooltip Dénomination Commune Française and linestrenolo is its DCITTooltip Denominazione Comune Italiana.[2][3][4][6] Lynoestrenol was formerly the BANTooltip British Approved Name of the drug, but it was eventually changed to lynestrenol.[2][3][4][6]

Brand names

Lynestrenol has been marketed alone as Exluton, Exlutona, and Orgametril, in combination with mestranol as Anacyclin, Lyndiol, Lyndiol 1, Lyndiol 2.5, Nonovul, and Noracycline, and in combination with ethinylestradiol as Anacyclin, Fysioquens, Minilyn, and Ministat, among other formulations and brand names.[5][22]

Availability

Lynestrenol has been used mainly in Europe[15] and is also marketed elsewhere throughout the world.[6] The drug was never marketed in the United States.[16][17]

References

  1. ^
    ISBN 978-92-1-130230-1
    .
  2. ^
    ISBN 978-1-4757-2085-3
    .
  3. ^
    ISBN 978-3-88763-075-1
    .
  4. ^
    ISBN 978-94-011-4439-1
    .
  5. ^
    ISBN 978-3-7692-2114-5
    .
  6. ^ a b c d e "Lynestreno". Drugs.com l.
  7. ^
    S2CID 10774483
    .
  8. ^
    S2CID 10809537
    .
  9. ^
    PMID 19434889
    .
  10. ^
    S2CID 24616324
    .
  11. ^
    S2CID 27018468
    .
  12. ^
    PMID 2256526
    .
  13. ^
    ISBN 90-420-1577-2
    .
  14. ^
    ISBN 978-0-8103-7177-4
    . LYNESTRENOL Countries Where Available and Release Dates: Austria; Belgium (1961); Finland (1972); France (1970); Federal Republic of Germany (1962); Mexico (1973); Netherlands (1962); Republic of South Africa (1974); Spain (1971); Sweden (1964); Switzerland.
  15. ^
    ISBN 978-0-08-053620-0
    .
  16. ^ a b c Gelijns A (1991). Innovation in Clinical Practice: The Dynamics of Medical Technology Development. National Academies. pp. 167–. NAP:13513.
  17. ^ a b "Drugs@FDA: FDA-Approved Drugs".
  18. ^
    ISBN 978-3-642-99941-3
    .
  19. S2CID 44601264
    .
  20. ^ de Winter MS, Siegmann CM, Szpilfogel SA (1959). 17-Alkylated 3-deoxo-19-nortestosterones. Chem. Ind (Report). p. 905.
  21. ^ "Cingestol | C20H28O". ChemSpider.
  22. ^ Kolbe HK, Bergman RF (April 1976). Population/fertility control thesaurus. Population Information Program, Science Communication Division (Report). Department of Medical and Public Affairs, George Washington University.