2-Methoxyestrone

2-Methoxyestrone
Names
	IUPAC name (8R,9S,13S,14S)-3-Hydroxy-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
	Other names 2-ME1; 2-MeOE1; 2-MeO-E1; 2-Hydroxyestrone 2-methyl ether; 2-Methoxyestra-1,3,5(10)-trien-3-ol-17-one; 2-Methoxy-3-hydroxyestra-1,3,5(10)-trien-17-one
Identifiers
CAS Number	362-08-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:1189;
ChEMBL	ChEMBL425194;
ChemSpider	389515;
ECHA InfoCard	100.006.042
KEGG	C05299;
PubChem CID	440624;
UNII	SJ5857RRL3;
CompTox Dashboard (EPA)	DTXSID90861900 ;
	InChI InChI=1S/C19H24O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,20H,3-8H2,1-2H3/t12-,13+,15-,19-/m0/s1 Key: WHEUWNKSCXYKBU-QPWUGHHJSA-N;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=CC(=C(C=C34)OC)O;
Properties
Chemical formula	C19H24O3
Molar mass	300.398 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

2-Methoxyestrone (2-ME1) is an endogenous, naturally occurring methoxylated catechol estrogen and metabolite of estrone that is formed by catechol O-methyltransferase via the intermediate 2-hydroxyestrone.[1][2][3] Unlike estrone but similarly to 2-hydroxyestrone and 2-methoxyestradiol, 2-methoxyestrone has very low affinity for the estrogen receptor and lacks significant estrogenic activity.[4]

Selected biological properties of endogenous estrogens in rats
Estrogen	ER RBA (%)	Uterine weight (%)	Uterotrophy	LH levels (%)	SHBG RBA (%)
Control	–	100	–	100	–
Estradiol	100	506 ± 20	+++	12–19	100
Estrone	11 ± 8	490 ± 22	+++	?	20
Estriol	10 ± 4	468 ± 30	+++	8–18	3
Estetrol	0.5 ± 0.2	?	Inactive	?	1
17α-Estradiol	4.2 ± 0.8	?	?	?	?
2-Hydroxyestradiol	24 ± 7	285 ± 8	+^b	31–61	28
2-Methoxyestradiol	0.05 ± 0.04	101	Inactive	?	130
4-Hydroxyestradiol	45 ± 12	?	?	?	?
4-Methoxyestradiol	1.3 ± 0.2	260	++	?	9
4-Fluoroestradiol^a	180 ± 43	?	+++	?	?
2-Hydroxyestrone	1.9 ± 0.8	130 ± 9	Inactive	110–142	8
2-Methoxyestrone	0.01 ± 0.00	103 ± 7	Inactive	95–100	120
4-Hydroxyestrone	11 ± 4	351	++	21–50	35
4-Methoxyestrone	0.13 ± 0.04	338	++	65–92	12
16α-Hydroxyestrone	2.8 ± 1.0	552 ± 42	+++	7–24	<0.5
2-Hydroxyestriol	0.9 ± 0.3	302	+^b	?	?
2-Methoxyestriol	0.01 ± 0.00	?	Inactive	?	4
Notes: Values are mean ± SD or range. ER RBA = Relative binding affinity to estrogen receptors of rat uterine cytosol. Uterine weight = Percentage change in uterine wet weight of ovariectomized rats after 72 hours with continuous administration of 1 μg/hour via subcutaneously implanted osmotic pumps. LH levels = Luteinizing hormone levels relative to baseline of ovariectomized rats after 24 to 72 hours of continuous administration via subcutaneous implant. Footnotes: ^a = Synthetic (i.e., not endogenous). ^b = Atypical uterotrophic effect which plateaus within 48 hours (estradiol's uterotrophy continues linearly up to 72 hours). Sources: See template.

References

http://www.hmdb.ca/metabolites/hmdb00010
Hemnes AR (16 December 2015). Gender, Sex Hormones and Respiratory Disease: A Comprehensive Guide. Humana Press. pp. 32–. ISBN 978-3-319-23998-9.
Lauritzen C, Studd JW (22 June 2005). Current Management of the Menopause. CRC Press. pp. 378–379. ISBN 978-0-203-48612-2.
Bhavnani BR, Nisker JA, Martin J, Aletebi F, Watson L, Milne JK (2000). "Comparison of pharmacokinetics of a conjugated equine estrogen preparation (premarin) and a synthetic mixture of estrogens (C.E.S.) in postmenopausal women". Journal of the Society for Gynecologic Investigation. 7 (3): 175–83. doi:10.1016/s1071-5576(00)00049-6. PMID 10865186.

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