2-Methoxyestradiol

2-Methoxyestradiol

File: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
Identifiers
CAS Number	362-07-2 N
PubChem	CID: 66414
ChemSpider	59788 Y
UNII	6I2QW73SR5 Y
ChEBI	CHEBI:28955 Y
ChEMBL	CHEMBL299613 Y
Chemical data
Formula	C19H26O3
Molecular mass	302.408 g/mol
SMILES Oc1cc3c(cc1OC)[C@H]2CC[C@@]4([C@@H](O)CC[C@H]4[C@@H]2CC3)C
InChI InChI=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 Y Key:CQOQDQWUFQDJMK-SSTWWWIQSA-N Y
NY (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. It prevents the formation of new blood vessels that tumors need in order to grow (angiogenesis), hence it is an angiogenesis inhibitor.

It also acts as a vasodilator.

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

It induces apoptosis in some cancer cell lines.

It has undergone Phase 1 clinical trials against breast cancer.

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

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 and effective against prostate cancer in rodents.

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

External links

• Chemical Information and Structure from the Comparative Toxicogenomics Database
• 2-Methoxyestradiol 4 journal refs as URLs

• EntreMed's Product Information Site Archived May 4, 2005 at the Wayback Machine
• 2-Methoxyestradiol: an endogenous antiangiogenic and antiproliferative drug candidate. Pribluda VS, et al. Cancer Metastasis Rev. 2000;19(1-2):173-9. Review.
• 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