Estrone (medication)

This article is about estrone as a medication. For its role as a hormone, see Estrone.

Estrone (medication)
Clinical data
Trade namesEstragyn, Kestrin, Theelin, many others
Other namesOestrone; E1; Follicular hormone; Folliculin; Folliculine; Follikulin; Theelin; Ketohydroxyestrin; Oxohydroxyestrin; 3-Hydroxyestra-1,3,5(10)-trien-17-one
Routes of
administration		Intramuscular injection, vaginal, by mouth (as E2/E1/E3Tooltip estradiol/estrone/estriol or as estrone sulfate)[1][2][3][4][5]
Drug classEstrogen
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: very low[6]
Protein binding96.0–98.0%:[5][7]
• Albumin: ~80%
• SHBG: ~16%
• Free: 2.0–4.0%
MetabolismLiver (via hydroxylation, sulfation, glucuronidation)[5]
Metabolites• Estradiol[5]
• Estrone sulfate[5]
• Estrone glucuronide[5]
• Others[5]
Elimination half-lifeIVTooltip Intravenous injection: 20–30 minutes[5]
ExcretionUrine[5]
Identifiers
  • (8R,9S,13S,14S)-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC18H22O2
Molar mass270.372 g·mol−1
3D model (JSmol)
Melting point254.5 °C (490.1 °F)
  • O=C4[C@]3(CC[C@@H]2c1ccc(O)cc1CC[C@H]2[C@@H]3CC4)C
  • InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1 ☒N
  • Key:DNXHEGUUPJUMQT-CBZIJGRNSA-N ☒N
  (verify)

Estrone (E1), sold under the brand names Estragyn, Kestrin, and Theelin among many others, is an estrogen medication and naturally occurring steroid hormone which has been used in menopausal hormone therapy and for other indications.[5][8][9][10][1][2] It has been provided as an aqueous suspension or oil solution given by injection into muscle and as a vaginal cream applied inside of the vagina.[1][2][3][4] It can also be taken by mouth as estradiol/estrone/estriol (brand name Hormonin) and in the form of prodrugs like estropipate (estrone sulfate; brand name Ogen) and conjugated estrogens (mostly estrone sulfate; brand name Premarin).[11][2][5]

Side effects of estrogens like estrone include breast tenderness, breast enlargement, headache, nausea, fluid retention, and edema, among others.[5] Estrone is a naturally occurring and bioidentical estrogen, or an agonist of the estrogen receptor, the biological target of estrogens like endogenous estradiol.[5] It is a relatively weak estrogen, with much lower activity than estradiol.[5] However, estrone is converted in the body into estradiol, which provides most or all of its estrogenic potency.[5][12] As such, estrone is a prodrug of estradiol.[5]

Estrone was first discovered in 1929, and was introduced for medical use shortly thereafter.[13][14][15] Although it has been used clinically in the past, estrone has largely been discontinued and is mostly no longer marketed.[9][16]

  1. ^ a b c Sweetman SC, ed. (2009). "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. p. 2101. ISBN 978-0-85369-840-1.
  2. ^ a b c d Guo JZ, Hahn DW, Wachter MP (2000). "Hormones, Estrogens and Antiestrogens". Kirk-Othmer Encyclopedia of Chemical Technology. Wiley. doi:10.1002/0471238961.05192018072115.a01. ISBN 0471238961.
  3. ^ a b Speroff L (2015). "Women's Hormonal Health Issues". In Speroff L (ed.). Blood and Marrow Transplant Handbook: Comprehensive Guide for Patient Care. pp. 341–354. doi:10.1007/978-3-319-13832-9_28. ISBN 978-3-319-13831-2.
  4. ^ a b Vuong LK (2006). "Gynecological Disorders". In Helms RA, Quan DJ (eds.). Textbook of Therapeutics: Drug and Disease Management. Lippincott Williams & Wilkins. pp. 397–. ISBN 978-0-7817-5734-8.
  5. ^ a b c d e f g h i j k l m n o p 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.
  6. ^ Cite error: The named reference MelmonCarruthers2000 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference JamesonGroot2010 was invoked but never defined (see the help page).
  8. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 899–. ISBN 978-1-4757-2085-3.
  9. ^ a b Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 407–. ISBN 978-3-88763-075-1.
  10. ^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 207–. ISBN 978-94-011-4439-1.
  11. ^ Quirk Jr JG, Wendel Jr GD (6 December 2012). "Biologic effects of natural and synthetic estrogens". In Buchsbaum HJ (ed.). The Menopause. Springer Science & Business Media. pp. 60, 62, 64. ISBN 978-1-4612-5525-3.
  12. ^ Cite error: The named reference FishmanMartucci1980 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference Bullough1995 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference pmid18744783 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference Watkins2007 was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).