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 such as hydrocortisone (a glucocorticoid).[3][4]
More information Compound, PRTooltip Progesterone receptor ...
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. |
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Quick facts Clinical data, Trade names ...
Epiestriol |
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| Trade names | Actriol, Arcagynil, Klimadoral |
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| Other names | Epioestriol; 16β-Epiestriol; 16-Epiestriol; 16β-Hydroxy-17β-estradiol |
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Routes of
administration | By mouth |
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| Drug class | Estrogen |
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(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
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| ChEMBL | |
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| CompTox Dashboard (EPA) | |
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| ECHA InfoCard | 100.008.126 |
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| Formula | C18H24O3 |
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| Molar mass | 288.387 g·mol−1 |
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| 3D model (JSmol) | |
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CC12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O
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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
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