17α-Epiestriol

17α-Epiestriol
Names
	Preferred IUPAC name (1S,2R,3aS,3bR,9bS,11aS)-11a-Methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthrene-1,2,7-triol
	Other names 17-Epiestriol; 16α-Hydroxy-17α-estradiol; Estra-1,3,5(10)-triene-3,16α,17α-triol; 3,16α,17α-Trihydroxy-1,3,5(10)-estratriene
Identifiers
CAS Number	1228-72-4;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:42156;
ChEMBL	ChEMBL1232445;
ChemSpider	225189;
DrugBank	DB07702;
PubChem CID	256737;
UNII	4G7IHY560Z;
CompTox Dashboard (EPA)	DTXSID00858947 ;
	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-PNVOZDDCSA-N;
	SMILES CC12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O;
Properties
Chemical formula	C18H24O3
Molar mass	288.38136 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

17α-Epiestriol, or simply 17-epiestriol, also known as 16α-hydroxy-17α-estradiol or estra-1,3,5(10)-triene-3,16α,17α-triol, is a minor and weak endogenous estrogen, and the 17α-epimer of estriol (which is 16α-hydroxy-17β-estradiol).^[1]^[2]^[3] It is formed from 16α-hydroxyestrone.^[4]^[5] In contrast to other endogenous estrogens like estradiol, 17α-epiestriol is a selective agonist of the ERβ.^[6] It is described as a relatively weak estrogen, which is in accordance with its relatively low affinity for the ERα.^[7] 17α-Epiestriol has been found to be approximately 400-fold more potent than estradiol in inhibiting tumor necrosis factor α (TNFα)-induced vascular cell adhesion molecule 1 (VCAM-1) expression in vitro.^[8]

Relative affinities (%) of 17α-epiestriol and related steroids^[9]^[10]^[11]^[12]
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.

References[]

^ Tewari AK (5 April 2013). Prostate Cancer: A Comprehensive Perspective. Springer Science & Business Media. pp. 373–. ISBN 978-1-4471-2864-9.
^ Labhart A (6 December 2012). Clinical Endocrinology: Theory and Practice. Springer Science & Business Media. pp. 522–. ISBN 978-3-642-96158-8.
^ Assali NS (3 September 2013). The Maternal Organism. Elsevier. pp. 341–. ISBN 978-1-4832-6380-9.
^ Von Euler US (2 December 2012). Comparative Endocrinology. Elsevier Science. pp. 135–. ISBN 978-0-323-14609-8.
^ Tietz NW (1 August 1976). Fundamentals of clinical chemistry. Saunders. p. 773. ISBN 978-0-7216-8866-4.
^ Sherbet GV (26 July 2013). Therapeutic Strategies in Cancer Biology and Pathology. Elsevier. pp. 83–. ISBN 978-0-12-416590-8.
^ Dorfman RI (22 October 2013). Steroidal Activity in Experimental Animals and Man. Elsevier Science. pp. 13–. ISBN 978-1-4832-7299-3.
^ Mukherjee TK, Nathan L, Dinh H, Reddy ST, Chaudhuri G (April 2003). "17-epiestriol, an estrogen metabolite, is more potent than estradiol in inhibiting vascular cell adhesion molecule 1 (VCAM-1) mRNA expression". The Journal of Biological Chemistry. 278 (14): 11746–52. doi:10.1074/jbc.M207800200. PMID 12547825.
^ Raynaud, J.P.; Ojasoo, T.; Bouton, M.M.; 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.

This article about a steroid is a stub. You can help Wikipedia by .

This biochemistry article is a stub. You can help Wikipedia by .

[Tewari2013-1] Tewari AK (5 April 2013). Prostate Cancer: A Comprehensive Perspective. Springer Science & Business Media. pp. 373–. ISBN 978-1-4471-2864-9.

[Labhart2012-2] Labhart A (6 December 2012). Clinical Endocrinology: Theory and Practice. Springer Science & Business Media. pp. 522–. ISBN 978-3-642-96158-8.

[Assali2013-3] Assali NS (3 September 2013). The Maternal Organism. Elsevier. pp. 341–. ISBN 978-1-4832-6380-9.

[Euler2012-4] Von Euler US (2 December 2012). Comparative Endocrinology. Elsevier Science. pp. 135–. ISBN 978-0-323-14609-8.

[Tietz1976-5] Tietz NW (1 August 1976). Fundamentals of clinical chemistry. Saunders. p. 773. ISBN 978-0-7216-8866-4.

[Sherbet2013-6] Sherbet GV (26 July 2013). Therapeutic Strategies in Cancer Biology and Pathology. Elsevier. pp. 83–. ISBN 978-0-12-416590-8.

[Dorfman2013-7] Dorfman RI (22 October 2013). Steroidal Activity in Experimental Animals and Man. Elsevier Science. pp. 13–. ISBN 978-1-4832-7299-3.

[MukherjeeNathan2003-8] Mukherjee TK, Nathan L, Dinh H, Reddy ST, Chaudhuri G (April 2003). "17-epiestriol, an estrogen metabolite, is more potent than estradiol in inhibiting vascular cell adhesion molecule 1 (VCAM-1) mRNA expression". The Journal of Biological Chemistry. 278 (14): 11746–52. doi:10.1074/jbc.M207800200. PMID 12547825.

[RaynaudOjasoo1979-9] Raynaud, J.P.; Ojasoo, T.; Bouton, M.M.; 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.

[pmid359134-10] Ojasoo T, Raynaud JP (November 1978). "Unique steroid congeners for receptor studies". Cancer Research. 38 (11 Pt 2): 4186–98. PMID 359134.

[pmid3695484-11] 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.

[pmid7421203-12] 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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

17α-Epiestriol

See also[]

References[]