2-methoxyestradiol
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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.


Chemical Structure

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2-methoxyestradiol
CAS# 362-07-2

Theoretical Analysis

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

Price and Availability

Size Price Availability Quantity
500.0mg USD 150.0 Same day
1.0g USD 250.0 Same day
2.0g USD 450.0 Same day
5.0g USD 950.0 Same day
10.0g USD 1750.0 Same day
100.0g USD 9850.0 2 Weeks
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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

Biological target: 2-Methoxyestradiol (2-ME2) is an apoptosis inducer and an angiogenesis inhibitor with potent antineoplastic activity.
In vitro activity: BG1 cells transfected with PKCδWT, PKCδDN or pGFP (mock) were treated with 10 μM 2MeOE2 (2-methoxyestradiol) for 24 h. Western blots demonstrated that 2MeOE2 treatment of BG1 cells transfected with PKCδWT resulted in a significantly higher amount of cleaved caspase-3, phosphorylated p38 MAPK and phH2Bser14 expression compared to untransfected and mock transfected BG1 cells. Notably, 2MeOE2 treatment of the PKCδDN -transfected cells did not alter cleavage of caspase-3, phosphorylation of p38 MAPK or phH2Bser14 expression compared to the untransfected and mock (Figure 3B). Reference: Oncotarget. 2020 Oct 6; 11(40): 3646–3659. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7546757/
In vivo activity: Compared to rats subjected to IR injury, rats pretreated with 2ME (2-methoxyestradiol) exhibited significantly attenuated IR-induced lung edema in a dose-dependent manner (Figures 1A–E and Supplementary Figures 3B–F). However, the addition of the anti-AnxA1 antibody or BOC2 significantly blocked the protective effects of 2ME on IR-induced lung edema. There was no statistically significant difference in the perfusate pH and PaCO2 levels between groups. Compared with the vehicle control, IR injury significantly increased the difference between final PaO2 and baseline PaO2 levels. The 2ME pretreatment significantly reduced the PaO2 difference in the IR group (Supplementary Table 1). Reference: Front Immunol. 2021; 12: 596376. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8007881/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 48.78 161.3
DMF 30.0 99.2
DMF:PBS (pH 7.2) (1:1) 0.5 1.65
Ethanol 1.0 3.31

Preparing Stock Solutions

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.

Recalculate based on batch purity %
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
Formulation protocol: 1. Löhndorf A, Hosang L, Dohle W, Odoardi F, Waschkowski SA, Rosche A, Bauche A, Winzer R, Tolosa E, Windhorst S, Marry S, Flügel A, Potter BVL, Diercks BP, Guse AH. 2-Methoxyestradiol and its derivatives inhibit store-operated Ca2+ entry in T cells: Identification of a new and potent inhibitor. Biochim Biophys Acta Mol Cell Res. 2021 May;1868(6):118988. doi: 10.1016/j.bbamcr.2021.118988. Epub 2021 Feb 10. PMID: 33581218; PMCID: PMC8062851. 2. Pal P, Hales K, Hales DB. The pro-apoptotic actions of 2-methoxyestradiol against ovarian cancer involve catalytic activation of PKCδ signaling. Oncotarget. 2020 Oct 6;11(40):3646-3659. doi: 10.18632/oncotarget.27760. PMID: 33088425; PMCID: PMC7546757. 3. Tofovic SP, Zhang X, Jones TJ, Petruševska G. 2-Methoxyestradiol Attenuates the Development and Retards the Progression of Hypoxia-And Alpha-Naphthylthiourea-Induced Pulmonary Hypertension. Pril (Makedon Akad Nauk Umet Odd Med Nauki). 2021 Apr 23;42(1):41-51. doi: 10.2478/prilozi-2021-0003. PMID: 33894125. 4. Liao WI, Wu SY, Tsai SH, Pao HP, Huang KL, Chu SJ. 2-Methoxyestradiol Protects Against Lung Ischemia/Reperfusion Injury by Upregulating Annexin A1 Protein Expression. Front Immunol. 2021 Mar 16;12:596376. doi: 10.3389/fimmu.2021.596376. PMID: 33796096; PMCID: PMC8007881.
In vitro protocol: 1. Löhndorf A, Hosang L, Dohle W, Odoardi F, Waschkowski SA, Rosche A, Bauche A, Winzer R, Tolosa E, Windhorst S, Marry S, Flügel A, Potter BVL, Diercks BP, Guse AH. 2-Methoxyestradiol and its derivatives inhibit store-operated Ca2+ entry in T cells: Identification of a new and potent inhibitor. Biochim Biophys Acta Mol Cell Res. 2021 May;1868(6):118988. doi: 10.1016/j.bbamcr.2021.118988. Epub 2021 Feb 10. PMID: 33581218; PMCID: PMC8062851. 2. Pal P, Hales K, Hales DB. The pro-apoptotic actions of 2-methoxyestradiol against ovarian cancer involve catalytic activation of PKCδ signaling. Oncotarget. 2020 Oct 6;11(40):3646-3659. doi: 10.18632/oncotarget.27760. PMID: 33088425; PMCID: PMC7546757.
In vivo protocol: 1. Tofovic SP, Zhang X, Jones TJ, Petruševska G. 2-Methoxyestradiol Attenuates the Development and Retards the Progression of Hypoxia-And Alpha-Naphthylthiourea-Induced Pulmonary Hypertension. Pril (Makedon Akad Nauk Umet Odd Med Nauki). 2021 Apr 23;42(1):41-51. doi: 10.2478/prilozi-2021-0003. PMID: 33894125. 2. Liao WI, Wu SY, Tsai SH, Pao HP, Huang KL, Chu SJ. 2-Methoxyestradiol Protects Against Lung Ischemia/Reperfusion Injury by Upregulating Annexin A1 Protein Expression. Front Immunol. 2021 Mar 16;12:596376. doi: 10.3389/fimmu.2021.596376. PMID: 33796096; PMCID: PMC8007881.

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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.



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 .