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2-Methoxyestradiol

Cayman Chemical Item Number 13021

NSC 659853; 2-ME2; Panzem; 2-Hydroxyestradiol 2-methyl ether (CAS 362-07-2)

2-Methoxyestradiol (CAS 362-07-2)

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Description

2-methoxy Estradiol (2-ME2) is a natural metabolite formed by CYP450-mediated hydroxylation followed by catechol-O-methyltransferase (COMT) methylation of estradiol. Administration of 2-hydroxy estradiol (2-HE2) to rats results in formation and clearance of 2-ME2 with t1/2 values of 7.9 and 24.9 minutes, respectively.1 2-ME2 exhibits no affinity for estrogen receptors. 2-ME2 has achieved considerable attention as an anti-cancer agent acting as an angiogenesis inhibitor via the HIF-1a pathway.2,3,4 The levels of COMT and 2-ME2 are significantly lower in women with severe pre-eclampsia.5

1 Zacharia, L.C., Piché, C.A., Fielding, R.M., et al. 2-hydroxyestradiol is a prodrug of 2-methoxyestradiol. J Pharmacol Exp Ther 309(3) 1093-1097 (2004).

2 Mooberry, S.L. New insights into 2-methoxyestradiol, a promising antiangiogenic and antitumor agent. Curr Opin Oncol 15 425-430 (2003).

3 Mooberry, S.L. Mechanism of action of 2-methoxyestradiol: New developments. Drug Resist Updat 6 355-361 (2003).

4 Becker, C.M., Rohwer, N., Funakoshi, T., et al. 2-methoxyestradiol inhibits hypoxia-inducible factor-1a and suppressess growth of lesions in a mouse model of endometriosis. Am J Pathol 172(2) 534-544 (2008).

5 Kanasaki, K., Palmsten, K., Sugimoto, H., et al. Deficiency in catechol-O-methyltransferase and 2-methoxyoestradiol is associated with pre-eclampsia. Nature 453 1117-1123 (2008).

Synonyms
  • NSC 659853
  • 2-ME2
  • Panzem
  • 2-Hydroxyestradiol 2-methyl ether
Formal Name 2-​methoxy-​estra-​1,​3,​5(10)-​triene-​3,​17β-​diol
CAS Number 362-07-2
Molecular Formula C19H26O3
Formula Weight 302.4
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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COc1cc2c(CCC3C2CC[C@]​2(C)​[C@@H]​(O)​CCC32)​cc1O

Background Reading

Becker, C.M., Rohwer, N., Funakoshi, T., et al. 2-methoxyestradiol inhibits hypoxia-inducible factor-1a and suppressess growth of lesions in a mouse model of endometriosis. Am J Pathol 172(2) 534-544 (2008).

Mooberry, S.L. Mechanism of action of 2-methoxyestradiol: New developments. Drug Resist Updat 6 355-361 (2003).

Mooberry, S.L. New insights into 2-methoxyestradiol, a promising antiangiogenic and antitumor agent. Curr Opin Oncol 15 425-430 (2003).

Zacharia, L.C., Piché, C.A., Fielding, R.M., et al. 2-hydroxyestradiol is a prodrug of 2-methoxyestradiol. J Pharmacol Exp Ther 309(3) 1093-1097 (2004).

Kanasaki, K., Palmsten, K., Sugimoto, H., et al. Deficiency in catechol-O-methyltransferase and 2-methoxyoestradiol is associated with pre-eclampsia. Nature 453 1117-1123 (2008).

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Size Price Quantity Subtotal
5 mg $24.00 $0.00
10 mg $46.00 $0.00
25 mg $108.00 $0.00
50 mg $192.00 $0.00
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Pricing updated 2012-05-26. Prices are subject to change without notice.

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