2-Methoxyestradiol

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2-Methoxyestradiol
2-Methoxyestradiol.svg
Systematic (IUPAC) name
(8R,9S,13S,14S,17S)-2-methoxy-
13-methyl-6,7,8,9,11,12,14,15,16,17-
decahydrocyclopenta[a]phenanthrene-3,17-diol
Clinical data
Legal status ?
Identifiers
CAS number 362-07-2 N
ATC code ?
PubChem CID 66414
ChemSpider 59788 YesY
UNII 6I2QW73SR5 YesY
ChEBI CHEBI:28955 YesY
ChEMBL CHEMBL299613 YesY
Chemical data
Formula C19H26O3 
Mol. mass 302.408 g/mol
 N (what is this?)  (verify)

2-Methoxyestradiol (2ME2) 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.[citation needed]

2ME2 is derived from estrogen, although it binds poorly to known estrogen receptors.[3]

It induces apoptosis in some cancer cell lines.[4]

It has undergone Phase 1 clinical trials against breast cancer.[citation needed]

A phase II trial of 18 advanced ovarian cancer patients reported encouraging results in Oct 2007.[5]

Preclinical models also suggest that 2ME2 could also be effective against inflammatory diseases such as rheumatoid arthritis. Several studies have been conducted showing 2ME2 is a microtubule-inhibitor[6] and effective against prostate cancer in rodents.[citation needed]

The CAS name for 2ME2 is (17 beta)-2-methoxyestra-1,3,5(10)-triene-3,17-diol.

References[edit]

  1. ^ EntreMed's Product Information Site
  2. ^ 2-Methoxyestradiol: an endogenous antiangiogenic and antiproliferative drug candidate. Pribluda VS, et al. Cancer Metastasis Rev. 2000;19(1-2):173-9. Review.
  3. ^ Dose-response effects of 2-methoxyestradiol on estrogen target tissues in the ovariectomized rat. Sibonga JD et al. Endocrinology. 2003 Mar;144(3):785-92. PMID 12586754
  4. ^ LaValee et al. (2003). 2-Methoxyestradiol Up-Regulates Death Receptor 5 and Induces Apoptosis through Activation of the Extrinsic Pathway 63 (2). pp. 468–75. PMID 12543804. 
  5. ^ "EntreMed Presents Results for Panzem® NCD Phase 2 Ovarian Cancer Study". 
  6. ^ Lakhani, NJ; Sarkar, MA; Venitz, J; Figg, WD (2003). "2-Methoxyestradiol, a promising anticancer agent". Pharmacotherapy 23 (2): 165–72. doi:10.1592/phco.23.2.165.32088. PMID 12587805. 

External links[edit]