WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 201830
CAS#: 362-07-2
Description: 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
Appearance: white solid powder
Purity: >98% (or refer to the Certificate of Analysis)
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).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 302.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Perez-Sepulveda A, España-Perrot PP, Norwitz ER, Illanes SE. Metabolic pathways involved in 2-methoxyestradiol synthesis and their role in preeclampsia. Reprod Sci. 2013 Sep;20(9):1020-9. doi: 10.1177/1933719113477483. Epub 2013 Mar 1. Review. PubMed PMID: 23456663; PubMed Central PMCID: PMC3745713.
2: Machado-Linde F, Pelegrin P, Sanchez-Ferrer ML, Leon J, Cascales P, Parrilla JJ. 2-methoxyestradiol in the pathophysiology of endometriosis: focus on angiogenesis and therapeutic potential. Reprod Sci. 2012 Oct;19(10):1018-29. doi: 10.1177/1933719112446080. Epub 2012 Aug 8. Review. PubMed PMID: 22875846.
3: Peyrat JF, Brion JD, Alami M. Synthetic 2-methoxyestradiol derivatives: structure-activity relationships. Curr Med Chem. 2012;19(24):4142-56. Review. PubMed PMID: 22709003.
4: Verenich S, Gerk PM. Therapeutic promises of 2-methoxyestradiol and its drug disposition challenges. Mol Pharm. 2010 Dec 6;7(6):2030-9. doi: 10.1021/mp100190f. Epub 2010 Oct 21. Review. PubMed PMID: 20831190; PubMed Central PMCID: PMC3059899.
5: Mueck AO, Seeger H. 2-Methoxyestradiol--biology and mechanism of action. Steroids. 2010 Oct;75(10):625-31. doi: 10.1016/j.steroids.2010.02.016. Epub 2010 Mar 7. Review. PubMed PMID: 20214913.
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.
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 .
