Chemistry:Epiestriol
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Short description: Chemical compound
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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 |
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| Chemical and physical data | |
| Formula | C18H24O3 |
| Molar mass | 288.387 g·mol−1 |
| 3D model (JSmol) | |
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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 like hydrocortisone (a glucocorticoid).[3][4]
| 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
References
- ↑ 1.0 1.1 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 899–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA899.
- ↑ Clinical Endocrinology: Theory and Practice. Springer Science & Business Media. 6 December 2012. pp. 522–. ISBN 978-3-642-96158-8. https://books.google.com/books?id=DAgJCAAAQBAJ&pg=PA522.
- ↑ "16-epiestriol: an anti-inflammatory steroid without glycogenic activity". Journal of Pharmaceutical Sciences 83 (6): 874–7. June 1994. doi:10.1002/jps.2600830623. PMID 9120824.
- ↑ "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. November 1998. doi:10.1089/jir.1998.18.921. PMID 9858313.
- ↑ "Receptor Binding as a Tool in the Development of New Bioactive Steroids". Drug Design. 1979. pp. 169–214. doi:10.1016/B978-0-12-060308-4.50010-X. ISBN 9780120603084. https://books.google.com/books?id=bhAlBQAAQBAJ&pg=PA169.
- ↑ "Unique steroid congeners for receptor studies". Cancer Research 38 (11 Pt 2): 4186–98. November 1978. PMID 359134. http://cancerres.aacrjournals.org/content/38/11_Part_2/4186.short.
- ↑ "Towards the mapping of the progesterone and androgen receptors". Journal of Steroid Biochemistry 27 (1–3): 255–69. 1987. doi:10.1016/0022-4731(87)90317-7. PMID 3695484.
- ↑ "Steroid hormone receptors and pharmacology". Journal of Steroid Biochemistry 12: 143–57. January 1980. doi:10.1016/0022-4731(80)90264-2. PMID 7421203.
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