2-Methoxyestradiolのソースを表示

{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{distinguish|2-Methoxyestriol}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477213877
| IUPAC_name = (8''R'',9''S'',13''S'',14''S'',17''S'')-2-Methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[''a'']phenanthrene-3,17-diol
| image = 2-Methoxyestradiol.svg
| width = 250px

<!--Clinical data-->
| tradename = Panzem
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S8 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = 
| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 362-07-2
| ATC_prefix = 
| ATC_suffix = 
| PubChem = 66414
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 59788
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6I2QW73SR5
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28955
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 299613
| synonyms = 2-ME2; 2-MeO-E2; 2-MeOE2; 2-Hydroxyestradiol 2-methyl ether; 2-Methoxyestra-1,3,5(10)-triene-3,17β-diol

<!--Chemical data-->
| C=19 | H=26 | O=3 
| SMILES = Oc1cc3c(cc1OC)[C@H]2CC[C@@]4([C@@H](O)CC[C@H]4[C@@H]2CC3)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C19H26O3/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/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CQOQDQWUFQDJMK-SSTWWWIQSA-N
}}

'''2-Methoxyestradiol''' ('''2-ME2''', '''2-MeO-E2''') is a [[naturally occurring|natural]] [[metabolite]] of [[estradiol]] and [[2-hydroxyestradiol]] (2-OHE2). It is specifically the 2-[[methyl group|methyl]] [[ether]] of 2-hydroxyestradiol. 2-Methoxyestradiol prevents the formation of new [[blood vessel]]s that [[tumor]]s need in order to grow ([[angiogenesis]]), hence it is an [[angiogenesis inhibitor]].<ref>{{cite journal | vauthors = Pribluda VS, Gubish ER, Lavallee TM, Treston A, Swartz GM, Green SJ | title = 2-Methoxyestradiol: an endogenous antiangiogenic and antiproliferative drug candidate | journal = Cancer and Metastasis Reviews | volume = 19 | issue = 1–2 | pages = 173–179 | date = 2000 | pmid = 11191057 | doi = 10.1023/a:1026543018478 | s2cid = 20055299 }}</ref> It also acts as a [[vasodilator]]<ref>{{cite journal | vauthors = Koganti S, Snyder R, Thekkumkara T | title = Pharmacologic effects of 2-methoxyestradiol on angiotensin type 1 receptor down-regulation in rat liver epithelial and aortic smooth muscle cells | journal = Gender Medicine | volume = 9 | issue = 2 | pages = 76–93 | date = April 2012 | pmid = 22366193 | pmc = 3322289 | doi = 10.1016/j.genm.2012.01.008 }}</ref> and induces [[apoptosis]] in some [[cancer]] [[cell line]]s.<ref>{{cite journal | vauthors = LaVallee TM, Zhan XH, Johnson MS, Herbstritt CJ, Swartz G, Williams MS, Hembrough WA, Green SJ, Pribluda VS | title = 2-methoxyestradiol up-regulates death receptor 5 and induces apoptosis through activation of the extrinsic pathway | journal = Cancer Research | volume = 63 | issue = 2 | pages = 468–475 | date = January 2003 | pmid = 12543804 | url = http://cancerres.aacrjournals.org/content/63/2/468.long }}</ref> 2-Methoxyestradiol is derived from estradiol, although it interacts poorly with the [[estrogen receptor]]s (2,000-fold lower activational potency relative to estradiol).<ref>{{cite journal | vauthors = Sibonga JD, Lotinun S, Evans GL, Pribluda VS, Green SJ, Turner RT | title = Dose-response effects of 2-methoxyestradiol on estrogen target tissues in the ovariectomized rat | journal = Endocrinology | volume = 144 | issue = 3 | pages = 785–792 | date = March 2003 | pmid = 12586754 | doi = 10.1210/en.2002-220632 | doi-access = free }}</ref> However, it retains activity as a high-affinity [[agonist]] of the [[G protein-coupled estrogen receptor]] (GPER) (10&nbsp;nM, relative to 3–6&nbsp;nM for estradiol).<ref name="pmid26023144">{{cite journal | vauthors = Prossnitz ER, Arterburn JB | title = International Union of Basic and Clinical Pharmacology. XCVII. G Protein-Coupled Estrogen Receptor and Its Pharmacologic Modulators | journal = Pharmacological Reviews | volume = 67 | issue = 3 | pages = 505–540 | date = July 2015 | pmid = 26023144 | pmc = 4485017 | doi = 10.1124/pr.114.009712 }}</ref><ref name="ThekkumkaraSnyder2016">{{cite book | vauthors = Thekkumkara T, Snyder R, Karamyan VT | title = Estrogen Receptors | chapter = Competitive Binding Assay for the G-Protein-Coupled Receptor 30 (GPR30) or G-Protein-Coupled Estrogen Receptor (GPER) | series = Methods in Molecular Biology | volume = 1366 | pages = 11–7 | year = 2016 | publisher = Springer | pmid = 26585123 | doi = 10.1007/978-1-4939-3127-9_2 | isbn = 978-1-4939-3126-2 }}</ref>

{{Selected biological properties of endogenous estrogens in rats}}