2-Methoxyestradiol
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| Synonyms | 2-Methoxyestra-1,3,5(10)-triene-3,17β-diol |
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100.164.606  |
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| Formula | C19H26O3 |
| Molar mass | 302.408 g/mol |
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2-Methoxyestradiol (2-ME2) is a natural metabolite of estradiol. As an experimental drug candidate, it is being developed under the tradename of Panzem.[1] It prevents the formation of new blood vessels that tumors need in order to grow (angiogenesis), hence it is an angiogenesis inhibitor.[2]
It also acts as a vasodilator.
2-ME2 is derived from estradiol, although it binds poorly (2000-fold lower activational potency) to known estrogen receptors.[3] However, 2-ME2 retains activity as a high-affinity agonist of the GPER (GPR30).[4]
It induces apoptosis in some cancer cell lines.[5]
It has undergone Phase 1 clinical trials against breast cancer.
A phase II trial of 18 advanced ovarian cancer patients reported encouraging results in October 2007.[6]
Preclinical models also suggest that 2-ME2 could also be effective against inflammatory diseases such as rheumatoid arthritis. Several studies have been conducted showing 2-ME2 is a microtubule-inhibitor[7] and effective against prostate cancer in rodents.
As of 2015, all clinical development of 2-ME2 has been suspended or discontinued.[8]
See also
References
- ↑ EntreMed's Product Information Site Archived May 4, 2005, at the Wayback Machine.
- ↑ Pribluda VS, Gubish ER, Lavallee TM, Treston A, Swartz GM, Green SJ (2000). "2-Methoxyestradiol: an endogenous antiangiogenic and antiproliferative drug candidate". Cancer Metastasis Reviews. 19 (1–2): 173–9. doi:10.1023/a:1026543018478. PMID 11191057.
- ↑ Sibonga JD, Lotinun S, Evans GL, Pribluda VS, Green SJ, Turner RT (March 2003). "Dose-response effects of 2-methoxyestradiol on estrogen target tissues in the ovariectomized rat". Endocrinology. 144 (3): 785–92. doi:10.1210/en.2002-220632. PMID 12586754.
- ↑ Thekkumkara T, Snyder R, Karamyan VT (2016). "Competitive Binding Assay for the G-Protein-Coupled Receptor 30 (GPR30) or G-Protein-Coupled Estrogen Receptor (GPER)". Methods in Molecular Biology. 1366: 11–7. doi:10.1007/978-1-4939-3127-9_2. PMID 26585123.
- ↑ LaVallee TM, Zhan XH, Johnson MS, Herbstritt CJ, Swartz G, Williams MS, Hembrough WA, Green SJ, Pribluda VS (January 2003). "2-methoxyestradiol up-regulates death receptor 5 and induces apoptosis through activation of the extrinsic pathway". Cancer Research. 63 (2): 468–75. PMID 12543804.
- ↑ "EntreMed Presents Results for Panzem® NCD Phase 2 Ovarian Cancer Study". Archived from the original on July 17, 2012.
- ↑ Lakhani NJ, Sarkar MA, Venitz J, Figg WD (February 2003). "2-Methoxyestradiol, a promising anticancer agent". Pharmacotherapy. 23 (2): 165–72. doi:10.1592/phco.23.2.165.32088. PMID 12587805.
- ↑ "2-Methoxyestradiol - CASI Pharmaceuticals". Adis Insight. Retrieved 2 March 2017.
External links
- Chemical Information and Structure from the Comparative Toxicogenomics Database
- 2-Methoxyestradiol 4 journal refs as URLs