Epiestriol

Epiestriol (INN) (brand names Actriol, Arcagynil, Klimadoral), or epioestriol (BAN), also known as 16β-epiestriol or simply 16-epiestriol as well as 16β-hydroxy-17β-estradiol, is a minor and weak endogenous estrogen, and the 16β-epimer of estriol (which is 16α-hydroxy-17β-estradiol).[1][2] Epiestriol is (or has previously been) used clinically in the treatment of acne.[1] In addition to its estrogenic actions, epiestriol has been found to possess significant anti-inflammatory properties without glycogenic activity or immunosuppressive effects, an interesting finding that is in contrast to conventional anti-inflammatory steroids like hydrocortisone (a glucocorticoid).[3][4]

Relative affinities (%) of epiestriol and related steroids[5][6][7][8]
CompoundPRARERGRMRSHBGCBG
Estradiol2.67.91000.60.138.7<0.1
Alfatradiol<1<115<1<1 ? ?
Estriol<1<115<1<1 ? ?
16β-Epiestriol<1<120<1<1 ? ?
17α-Epiestriol<1<131<1<1 ? ?
Values are percentages (%). Reference ligands (100%) were progesterone for the PR, testosterone for the AR, E2 for the ER, DEXA for the GR, aldosterone for the MR, DHT for SHBG, and cortisol for CBG.
For other uses, see epiestriol (set index).
Epiestriol
Clinical data
Trade namesActriol, Arcagynil, Klimadoral
Other namesEpioestriol; 16β-Epiestriol; 16-Epiestriol; 16β-Hydroxy-17β-estradiol
Routes of
administration		By mouth
Drug classEstrogen
Identifiers
IUPAC name
  • (8R,9S,13S,14S,16S,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.008.126
Chemical and physical data
FormulaC18H24O3
Molar mass288.387 g·mol−1
3D model (JSmol)
SMILES
  • CC12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O
InChI
  • InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,17+,18+/m1/s1
  • Key:PROQIPRRNZUXQM-ZMSHIADSSA-N

See also

References
  1. 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.
  2. Labhart A (6 December 2012). Clinical Endocrinology: Theory and Practice. Springer Science & Business Media. pp. 522–. ISBN 978-3-642-96158-8.
  3. Latman NS, Kishore V, Bruot BC (June 1994). "16-epiestriol: an anti-inflammatory steroid without glycogenic activity". Journal of Pharmaceutical Sciences. 83 (6): 874–7. doi:10.1002/jps.2600830623. PMID 9120824.
  4. Miller E, Bates R, Bjorndahl J, Allen D, Burgio D, Bouma C, Stoll J, Latman N (November 1998). "16-Epiestriol, a novel anti-inflammatory nonglycogenic steroid, does not inhibit IFN-gamma production by murine splenocytes". Journal of Interferon & Cytokine Research. 18 (11): 921–5. doi:10.1089/jir.1998.18.921. PMID 9858313.
  5. Raynaud JP, Ojasoo T, Bouton MM, Philibert D (1979). "Receptor Binding as a Tool in the Development of New Bioactive Steroids". Drug Design. pp. 169–214. doi:10.1016/B978-0-12-060308-4.50010-X. ISBN 9780120603084.
  6. Ojasoo T, Raynaud JP (November 1978). "Unique steroid congeners for receptor studies". Cancer Research. 38 (11 Pt 2): 4186–98. PMID 359134.
  7. Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP (1987). "Towards the mapping of the progesterone and androgen receptors". Journal of Steroid Biochemistry. 27 (1–3): 255–69. doi:10.1016/0022-4731(87)90317-7. PMID 3695484.
  8. Raynaud JP, Bouton MM, Moguilewsky M, Ojasoo T, Philibert D, Beck G, Labrie F, Mornon JP (January 1980). "Steroid hormone receptors and pharmacology". Journal of Steroid Biochemistry. 12: 143–57. doi:10.1016/0022-4731(80)90264-2. PMID 7421203.


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