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 such as hydrocortisone (a glucocorticoid).[3][4]
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Clinical data | |
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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 | |
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ECHA InfoCard | 100.008.126 |
Chemical and physical data | |
Formula | C18H24O3 |
Molar mass | 288.387 g·mol−1 |
3D model (JSmol) | |
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Compound | PR | AR | ER | GR | MR | SHBG | CBG | ||
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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
editReferences
edit- ^ 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.