Demegestone

Source: Wikipedia, the free encyclopedia.
Demegestone
Progestin
ATC code
Pharmacokinetic data
BioavailabilityGood[2]
MetabolismHydroxylation, others[2]
Metabolites• 21-Hydroxydemegestone[2]
• Others[2]
ExcretionUrine[2]
Identifiers
  • (8S,13S,14S,17S)-17-acetyl-13,17-dimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
JSmol)
  • CC(=O)[C@]1(CC[C@@H]2[C@@]1(CCC3=C4CCC(=O)C=C4CC[C@@H]23)C)C
  • InChI=1S/C21H28O2/c1-13(22)20(2)11-9-19-18-6-4-14-12-15(23)5-7-16(14)17(18)8-10-21(19,20)3/h12,18-19H,4-11H2,1-3H3/t18-,19+,20-,21+/m1/s1
  • Key:JWAHBTQSSMYISL-MHTWAQMVSA-N

Demegestone, sold under the brand name Lutionex, is a

luteal insufficiency but is now no longer marketed.[3][4][5][6][7] It is taken by mouth.[2][1]

Demegestone is a progestin, or a

synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[6][2][8] It has no androgenic activity.[2]

Demegestone was first described in 1966 and was introduced for medical use in France in 1974.[3][4] It has only been marketed in France, and has since been discontinued in this country.[5][4]

Medical uses

Demegestone has been used to treat

oral contraceptive and treatment for infertility.[1][9][10]

Side effects

See also:
Progestin § Side effects

Pharmacology

Pharmacodynamics

Demegestone is a

hydroxylated metabolite, is a moderately potent progestogen (4 times the potency of progesterone) and a weak mineralocorticoid (2% of the potency of deoxycorticosterone).[2]

Relative affinities (%) of demegestone
Compound 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
Demegestone 230 1 0 5 1–2 ? ?
Notes: Values are percentages (%). Reference
CBGTooltip Corticosteroid-binding globulin. Sources: [13][15][16][17]

Pharmacokinetics

Demegestone has good

intravenous injection.[2] Demegestone and/or its metabolites are excreted, at least in part, in urine.[2]

Chemistry

See also: List of progestogens

Demegestone, also known as 17α-methyl-δ9-19-norprogesterone or as 17α-methyl-19-norpregna-4,9-diene-3,20-dione, is a

17α-methyl-19-norprogesterone.[3][4][6] Related derivatives of 17α-methyl-19-norprogesterone include promegestone and trimegestone.[3][6]

History

Demegestone was first described in the literature in 1964 and was introduced for medical use in 1974 in France.[3][4] It was developed by Roussel Uclaf.[4]

Society and culture

Generic names

Demegestone is the

INNTooltip International Nonproprietary Name.[3] It is also known by its developmental code name R-2453 or RU-2453.[3]

Brand names

Demegestone was marketed under the brand name Lutionex.[3][4]

Availability

Demegestone is no longer marketed and hence is no longer available in any country.[5] It was previously available in France.[5][4]

References

  1. ^
    PMID 12158578
    .
  2. ^
    ISSN 0022-4731
    .
  3. ^
    ISBN 978-1-4757-2085-3
    .
  4. ^
    ISBN 978-0-8155-1856-3
    .
  5. ^ a b c d "Demegestone". Micromedex.: [permanent dead link]
  6. ^
    S2CID 24616324
    .
  7. ^
    PMID 3194612
    .
  8. ^
    PMID 926114
    .
  9. ^ Hamada H, Nagao H, Toyoda H, Hayashi H, Akihiro L, Kotaki S (1970). "[Clinical observation on oral contraceptive effect by R-2453 (Abstracts of Papers Presented at Showa 44 in the field of gynecology])". Japanese Journal of Obstetrics and Gynecology-Acta Obstetrica et Gynaecologica Japonica. 22 (7): 753.
  10. ^ Levrier M (January 1979). "Treatment of Ovarian Sterility with Combined Moxestrol-Demegestone Preparation". Journal de Gynécologie Obstétrique et Biologie de la Reproduction. 8 (1). Paris, France: Masson Editeur: 89.
  11. ^ Rabe T, Goeckenjan M, Ahrendt HJ, Crosignani PG, Dinger JC, Mueck AO, et al. (October 2011). "Oral Contraceptive Pills: Combinations, Dosages and the Rationale behind 50 Years or Oral Hormonal Contraceptive Development" (PDF). Journal für Reproduktionsmedizinund Endokrinologie. 8 (1): 58–129.
  12. ISBN 978-1-349-81347-6
    .
  13. ^
    PMID 7382482
    .
  14. PMID 895725
    .
  15. PMID 7421203
    .
  16. S2CID 21336380
    .
  17. PMID 359134
    .