Dydrogesterone

Not to be confused with Retroprogesterone.
Dydrogesterone
Clinical data
Trade namesDuphaston, others[1]
Other namesIsopregnenone; Dehydroprogesterone; Didrogesteron; 6-Dehydroretroprogesterone; 9β,10α-Pregna-4,6-diene-3,20-dione; NSC-92336[2][3]
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth
Drug classProgestogen; Progestin
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability28%[4][5]
Protein binding? (probably to albumin)[6][7]
MetabolismHepatic: AKR1C1, AKR1C3, CYP3A4[10][8]
Metabolites20α-DHDTooltip 20α-Dihydrodydrogesterone (exclusively via AKR1C1 and AKRC13)[8]
Elimination half-lifeParent: 5–7 hours[9]
Metabolite: 14–17 hours[9]
ExcretionUrine
Identifiers
IUPAC name
  • (8S,9R,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.005.280
Chemical and physical data
FormulaC21H28O2
Molar mass312.453 g·mol−1
3D model (JSmol)
Melting point144 °C (291 °F)
Boiling point463 °C (865 °F)
Solubility in waterInsoluble mg/mL (20 °C)
SMILES
  • O=C4\C=C3\C=C/[C@@H]1[C@@H](CC[C@@]2([C@@H](C(=O)C)CC[C@@H]12)C)[C@]3(C)CC4
InChI
  • InChI=1S/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4-5,12,16-19H,6-11H2,1-3H3/t16-,17+,18-,19+,20+,21+/m0/s1 Y
  • Key:JGMOKGBVKVMRFX-HQZYFCCVSA-N Y
  (verify)

Dydrogesterone, sold under the brand name Duphaston among others,[1] is a progestin medication which is used for a variety of indications, including threatened or recurrent miscarriage during pregnancy, dysfunctional bleeding, infertility due to luteal insufficiency, dysmenorrhea, endometriosis, secondary amenorrhea, irregular cycles, premenstrual syndrome, and as a component of menopausal hormone therapy.[7] It is taken by mouth.[7]

Side effects of dydrogesterone include menstrual irregularities, headache, nausea, breast tenderness, and others.[11][12] Dydrogesterone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[7][13] The medication is an atypical progestogen and does not inhibit ovulation.[7][14] It has weak antimineralocorticoid activity and no other important hormonal activity.[7][13]

Dydrogesterone was developed in the 1950s and introduced for medical use in 1961.[15] It is available widely throughout Europe, no longer available in the United Kingdom, since 2008 and is also marketed in Australia and elsewhere in the world.[3][15] The medication was previously available in the United States,[15] but it has been discontinued in that country.[16]

  1. ^ a b "Dydrogesterone international brands". Drugs.com. Archived from the original on 29 November 2020. Retrieved 29 November 2020.
  2. ^ Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
  3. ^ a b Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference Femoston-Label was invoked but never defined (see the help page).
  5. ^ Schindler AE (2015). "Pharmacology of Progestogens". Progestogens in Obstetrics and Gynecology. Springer. pp. 33–40. doi:10.1007/978-3-319-14385-9_2. ISBN 978-3-319-14384-2. S2CID 85844034.
  6. ^ Howard J.A. Carp, MB, BS, FRCOG (9 April 2015). Progestogens in Obstetrics and Gynecology. Springer. pp. 33, 38. ISBN 978-3-319-14385-9.
  7. ^ a b c d e f Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  8. ^ a b Beranič N, Gobec S, Rižner TL (May 2011). "Progestins as inhibitors of the human 20-ketosteroid reductases, AKR1C1 and AKR1C3". Chemico-Biological Interactions. 191 (1–3): 227–33. Bibcode:2011CBI...191..227B. doi:10.1016/j.cbi.2010.12.012. PMID 21182831.
  9. ^ a b Bińkowska M, Woroń J (June 2015). "Progestogens in menopausal hormone therapy". Przeglad Menopauzalny = Menopause Review. 14 (2): 134–43. doi:10.5114/pm.2015.52154. PMC 4498031. PMID 26327902.
  10. ^ Olbrich M, Weigl K, Kahler E, Mihara K (October 2016). "Dydrogesterone metabolism in human liver by aldo-keto reductases and cytochrome P450 enzymes". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 46 (10): 868–74. doi:10.3109/00498254.2015.1134852. PMID 26796435. S2CID 22311056.
  11. ^ Cite error: The named reference MishellKirschbaum1990 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference Femoston-NHS was invoked but never defined (see the help page).
  13. ^ a b Schindler AE (December 2009). "Progestational effects of dydrogesterone in vitro, in vivo and on the human endometrium". Maturitas. 65 (Suppl 1): S3-11. doi:10.1016/j.maturitas.2009.10.011. PMID 19969432.
  14. ^ Tausk MA (1972). "Pharmacology of the Endocrine System and Related Drugs: Progesterone, Progestational Drugs and Antifertility Drugs". International Encyclopaedia of Pharmacology and Therapeutics. 48: 19, 220, 278, 285, 481.
  15. ^ a b c William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1411–. ISBN 978-0-8155-1856-3.
  16. ^ Manu P (28 July 2000). The Pharmacotherapy of Common Functional Syndromes: Evidence-Based Guidelines for Primary Care Practice. CRC Press. pp. 235–. ISBN 978-0-7890-0588-5. The drug is not available for clinical use in the United States.
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