2-methoxyestradiol, also known as 2-ME, is an orally bioavailable estradiol metabolite with potential antineoplastic activity. 2-Methoxyestradiol inhibits angiogenesis by reducing endothelial cell proliferation and inducing endothelial cell apoptosis. This agent also inhibits tumor cell growth by binding to tubulin, resulting in antimitotic activity, and by inducing caspase activation, resulting in cell cycle arrest in the G2 phase, DNA fragmentation, and apoptosis.

MedKoo Cat#: 201830 Name: 2-methoxyestradiol CAS#: 362-07-2 Chemical Formula: C19H26O3 Exact Mass: 302.18819 Molecular Weight: 302.41 Elemental Analysis: C, 75.46; H, 8.67; O, 15.87

Synonym: 2-ME; 2-Methoxy Estradiol. 2-methoxyestradiol; US brand name: Panzem. Abbreviation: 2-ME2.

IUPAC/Chemical Name: (8R,9S,13S,14S,17S)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

InChi Key: CQOQDQWUFQDJMK-SSTWWWIQSA-N

InChi Code: 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

SMILES Code: OC1=C(OC)C=C2[C@@]3([H])CC[C@]4(C)[C@@H](O)CC[C@@]4([H])[C@]3([H])CCC2=C1

Technical Data

Appearance: white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Certificate of Analysis: View CoA: current batch, Lot#TZC50323 View CoA: Previous batch, Lot#BCP20131130.

QC Data: View QC data: current batch, Lot#TZC50323 View QC data: previous batch, Lot#BCP20131130.

Safety Data Sheet (MSDS): View Material Safety Data Sheet (MSDS)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code: 293490

Additional Information

2-Methoxyestradiol (2ME2) is a drug that prevents the formation of new blood vessels that tumors need in order to grow (angiogenesis). It is derived from estrogen, although it binds poorly to known estrogen receptors, and belongs to the family of drugs called angiogenesis inhibitors. It has undergone Phase 1 clinical trials against breast cancers. Preclinical models also suggest that 2ME2 could also be effective against inflammatory diseases such as rheumatoid arthritis. The CAS name for 2ME2 is (17 beta)-2-methoxyestra-1,3,5(10)-triene-3,17-diol. It also acts as a vasodilator. Several studies have been conducted showing 2ME2 is a microtubule-inhibitor and effective against prostate cancer in rodents. see http://en.wikipedia.org/wiki/2-methoxyestradiol .    

References

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6: Dubey RK, Jackson EK. Potential vascular actions of 2-methoxyestradiol. Trends Endocrinol Metab. 2009 Oct;20(8):374-9. doi: 10.1016/j.tem.2009.04.007. Epub 2009 Sep 4. Review. PubMed PMID: 19734053; PubMed Central PMCID: PMC2761235.

7: Kirches E, Warich-Kirches M. 2-methoxyestradiol as a potential cytostatic drug in gliomas? Anticancer Agents Med Chem. 2009 Jan;9(1):55-65. Review. PubMed PMID: 19149482.

8: Dragun D, Haase-Fielitz A. Low catechol-O-methyltransferase and 2-methoxyestradiol in preeclampsia: more than a unifying hypothesis. Nephrol Dial Transplant. 2009 Jan;24(1):31-3. doi: 10.1093/ndt/gfn534. Epub 2008 Nov 27. Review. PubMed PMID: 19039028.

9: Sutherland TE, Anderson RL, Hughes RA, Altmann E, Schuliga M, Ziogas J, Stewart AG. 2-Methoxyestradiol--a unique blend of activities generating a new class of anti-tumour/anti-inflammatory agents. Drug Discov Today. 2007 Jul;12(13-14):577-84. Epub 2007 Jun 26. Review. PubMed PMID: 17631253.

10: Dantas AP, Sandberg K. Does 2-methoxyestradiol represent the new and improved hormone replacement therapy for atherosclerosis? Circ Res. 2006 Aug 4;99(3):234-7. Review. PubMed PMID: 16888248.