Epiestriol

Epiestriol
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
	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	547-81-9;
PubChem CID	68929;
ChemSpider	62155;
UNII	8XZ32LI44K;
ChEMBL	ChEMBL1908074;
CompTox Dashboard (EPA)	DTXSID10894790 ;
ECHA InfoCard	100.008.126
Chemical and physical data
Formula	C18H24O3
Molar mass	288.387 g·mol−1
3D model (JSmol)	Interactive image;
	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;

Epiestriol (INNTooltip International Nonproprietary Name) (brand names Actriol, Arcagynil, Klimadoral), or epioestriol (BANTooltip British Approved Name), 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]
Compound	PRTooltip Progesterone receptor	ARTooltip Androgen receptor	ERTooltip Estrogen receptor	GRTooltip Glucocorticoid receptor	MRTooltip Mineralocorticoid receptor	SHBGTooltip Sex hormone-binding globulin	CBGTooltip Corticosteroid binding globulin
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 PRTooltip progesterone receptor, testosterone for the ARTooltip androgen receptor, E2 for the ERTooltip estrogen receptor, DEXATooltip dexamethasone for the GRTooltip glucocorticoid receptor, aldosterone for the MRTooltip mineralocorticoid receptor, DHTTooltip dihydrotestosterone for SHBGTooltip sex hormone-binding globulin, and cortisol for CBGTooltip Corticosteroid-binding globulin.

References

^ ^a ^b 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.
^ Labhart A (6 December 2012). Clinical Endocrinology: Theory and Practice. Springer Science & Business Media. pp. 522–. ISBN 978-3-642-96158-8.
^ 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.
^ 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.
^ 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.
^ Ojasoo T, Raynaud JP (November 1978). "Unique steroid congeners for receptor studies". Cancer Research. 38 (11 Pt 2): 4186–98. PMID 359134.
^ 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.
^ 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.