Gestodene

Gestodene
Clinical data
Trade namesFemodene, Femodette, Gynera, Harmonet, Meliane, Minesse, Minulet, others
Other namesGSD; SHB-331; δ15-Norgestrel; 15-Dehydronorgestrel; 17-hydroxy-18a-homo-19-nor-17α-pregna-4,15-dien-20-yn-3-one; 17α-Ethynyl-18-methyl-19-nor-δ15-testosterone; 17α-Ethynyl-18-methylestra-4,15-dien-17β-ol-3-one; 13β-Ethyl-18,19-dinor-17α-pregna-4,15-dien-20-yn-17β-ol-3-one
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • X
Routes of
administration		By mouth
Drug classProgestogen; Progestin
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability96% (87–111%)[1][2][3]
Protein binding98% (64% to SHBGTooltip sex hormone-binding globulin, 34% to albumin, 2% free)[4]
MetabolismLiver (reduction, hydroxylation)[4]
Elimination half-life12–15 hours[2][4]
ExcretionUrine
Identifiers
  • (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14-decahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.056.478 Edit this at Wikidata
Chemical and physical data
FormulaC21H26O2
Molar mass310.437 g·mol−1
3D model (JSmol)
Melting point197.9 °C (388.2 °F)
  • O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](/C=C\[C@]1(C#C)O)[C@@H]2CC3)CC)CC4
  • InChI=1S/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1 checkY
  • Key:SIGSPDASOTUPFS-XUDSTZEESA-N checkY
  (verify)

Gestodene, sold under the brand names Femodene and Minulet among others, is a progestin medication which is used in birth control pills for women.[5][6] It is also used in menopausal hormone therapy.[7] The medication is available almost exclusively in combination with an estrogen.[8] It is taken by mouth.[6][9]

Side effects of the combination of an estrogen and gestodene include menstrual irregularities, headaches, nausea, breast tenderness, mood changes, and others.[citation needed] Gestodene is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[10][11] It has weak androgenic activity, weak antimineralocorticoid activity, and weak glucocorticoid activity.[10][11]

Gestodene was discovered in 1975 and was introduced for medical use, specifically in birth control pills, in 1987.[4][12] It was subsequently introduced for use in menopausal hormone therapy as well.[7][8] Gestodene is sometimes referred to as a "third-generation" progestin.[13] It is marketed in birth control pills widely throughout the world, whereas it is available for use in menopausal hormone therapy only a few countries.[8][7] Gestodene is not approved in the United States.[14][15]

  1. ^ Cite error: The named reference Mishell1999 was invoked but never defined (see the help page).
  2. ^ a b Stanczyk FZ (2002). "Pharmacokinetics and potency of progestins used for hormone replacement therapy and contraception". Rev Endocr Metab Disord. 3 (3): 211–24. doi:10.1023/A:1020072325818. PMID 12215716. S2CID 27018468.
  3. ^ Fotherby K (August 1996). "Bioavailability of orally administered sex steroids used in oral contraception and hormone replacement therapy". Contraception. 54 (2): 59–69. doi:10.1016/0010-7824(96)00136-9. PMID 8842581.
  4. ^ a b c d Cite error: The named reference pmid8616979 was invoked but never defined (see the help page).
  5. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 595–. ISBN 978-1-4757-2085-3.
  6. ^ a b Morton IK, Hall JM (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 132–. ISBN 978-0-7514-0499-9.
  7. ^ a b c "Estradiol/gestodene - Bayer Healthcare Pharmaceuticals - AdisInsight". adisinsight.springer.com.
  8. ^ a b c Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  9. ^ Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  10. ^ a b Cite error: The named reference FuhrmannSlater1995 was invoked but never defined (see the help page).
  11. ^ a b Cite error: The named reference SchindlerCampagnoli2003 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference RunnebaumRabe2012 was invoked but never defined (see the help page).
  13. ^ Carp HJ (9 April 2015). Progestogens in Obstetrics and Gynecology. Springer. p. 112. ISBN 978-3-319-14385-9.
  14. ^ Becker KL (2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 1024–. ISBN 978-0-7817-1750-2.
  15. ^ Jiang Q, He W (25 May 2016). Benefit-Risk Assessment Methods in Medical Product Development: Bridging Qualitative and Quantitative Assessments. CRC Press. pp. 135–. ISBN 978-1-4822-5937-7.