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). 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	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.

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