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Epiestriol

From Wikipedia, the free encyclopedia
Chemical compound
Not to be confused withepisterol.
For other uses, seeepiestriol (set index).
Pharmaceutical compound
Epiestriol
Clinical data
Trade namesActriol, Arcagynil, Klimadoral
Other namesEpioestriol; 16β-Epiestriol; 16-Epiestriol; 16β-Hydroxy-17β-estradiol
Routes of
administration
By mouth
Drug classEstrogen
Identifiers
  • (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
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.008.126Edit this at Wikidata
Chemical and physical data
FormulaC18H24O3
Molar mass288.387 g·mol−1
3D model (JSmol)
  • CC12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O
  • 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 namesActriol,Arcagynil,Klimadoral), orepioestriol (BANTooltip British Approved Name), also known as16β-epiestriol or simply16-epiestriol, as well as16β-hydroxy-17β-estradiol, is a minor and weakendogenousestrogen, and the 16β-epimer ofestriol (which is 16α-hydroxy-17β-estradiol).[1][2] Epiestriol is (or has previously been) used clinically in the treatment ofacne.[1] In addition to its estrogenic actions, epiestriol has been found to possess significantanti-inflammatory properties withoutglycogenic activity orimmunosuppressive effects, an interesting finding that is in contrast to conventional anti-inflammatory steroids such ashydrocortisone (aglucocorticoid).[3][4]

Relative affinities (%) of epiestriol and related steroids[5][6][7][8]
CompoundPRTooltip Progesterone receptorARTooltip Androgen receptorERTooltip Estrogen receptorGRTooltip Glucocorticoid receptorMRTooltip Mineralocorticoid receptorSHBGTooltip Sex hormone-binding globulinCBGTooltip Corticosteroid binding globulin
Estradiol2.67.91000.60.138.7<0.1
Alfatradiol<1<115<1<1??
Estriol<1<115<1<1??
16β-Epiestriol<1<120<1<1??
17α-Epiestriol<1<131<1<1??
Values are percentages (%). Referenceligands (100%) wereprogesterone for thePRTooltip progesterone receptor,testosterone for theARTooltip androgen receptor,E2 for theERTooltip estrogen receptor,DEXATooltip dexamethasone for theGRTooltip glucocorticoid receptor,aldosterone for theMRTooltip mineralocorticoid receptor,DHTTooltip dihydrotestosterone forSHBGTooltip sex hormone-binding globulin, andcortisol forCBGTooltip Corticosteroid-binding globulin.

See also

[edit]

References

[edit]
  1. ^abElks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 899–.ISBN 978-1-4757-2085-3.
  2. ^Labhart A (6 December 2012).Clinical Endocrinology: Theory and Practice. Springer Science & Business Media. pp. 522–.ISBN 978-3-642-96158-8.
  3. ^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.
  4. ^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.
  5. ^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.
  6. ^Ojasoo T, Raynaud JP (November 1978)."Unique steroid congeners for receptor studies".Cancer Research.38 (11 Pt 2):4186–98.PMID 359134.
  7. ^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.
  8. ^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.
Precursors
Corticosteroids
Glucocorticoids
Mineralocorticoids
Sex steroids
Androgens
Estrogens
Progestogens
Neurosteroids
Others
Acne-treating agents (D10)
Antibacterial
Keratolytic
Anti-inflammatory
Antibiotics
Hormonal
Retinoids
Other
Combinations
Estrogens
ERTooltip Estrogen receptor agonists
Progonadotropins
Antiestrogens
ERTooltip Estrogen receptor antagonists
(incl.SERMsTooltip selective estrogen receptor modulators/SERDsTooltip selective estrogen receptor downregulators)
Aromatase inhibitors
Antigonadotropins
Others
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown


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