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Anti-acne preparations
Epiestriol
Другие языки:

Epiestriol

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Not to be confused with episterol.
For other uses, see epiestriol (set index).
Epiestriol
Epiestriol.svg
Clinical data
Trade names Actriol, Arcagynil, Klimadoral
Other names Epioestriol; 16β-Epiestriol; 16-Epiestriol; 16β-Hydroxy-17β-estradiol
Routes of
administration		 By mouth
Drug class Estrogen
Identifiers
  • (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 InfoCard 100.008.126
Chemical and physical data
Formula C18H24O3
Molar mass 288.387 g·mol−1
3D model (JSmol)
  • CC12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O
  • 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

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). Epiestriol is (or has previously been) used clinically in the treatment of acne. 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).

Relative affinities (%) of epiestriol and related steroids
Compound PR AR ER GR MR SHBG CBG
Estradiol 2.6 7.9 100 0.6 0.13 8.7 <0.1
Alfatradiol <1 <1 15 <1 <1 ? ?
Estriol <1 <1 15 <1 <1 ? ?
16β-Epiestriol <1 <1 20 <1 <1 ? ?
17α-Epiestriol <1 <1 31 <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.

See also



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