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2-Methoxyestradiol

2-Methoxyestradiol structure

CAS No:
362-07-2
Formula:
C19H26O3
Chemical Name:
2-Methoxyestradiol
Synonyms:
Estra-1,3,5(10)-triene-3,17-diol,2-methoxy-,(17β)-;Estra-1,3,5(10)-triene-3,17β-diol,2-methoxy-;Estradiol,2-methoxy-;(17β)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol;2-Methoxyestradiol;2-Methoxyestra-1,3,5(10)-triene-3,17β-diol;2-Hydroxyestradiol 2-methyl ether;NSC 659853;Panzem;2ME2;2-Methoxy-E2;916057-22-2
Categories:
Biochemical Engineering > Inhibitors

Description

2-Methoxyestradiol is an angiogenesis inhibitor and apoptosis inducer with potent antineoplastic activity. 2-Methoxyestradiol also destablize microtubules.

Solid

2-methoxy-17beta-estradiol is a 17beta-hydroxy steroid, being 17beta-estradiol methoxylated at C-2. It has a role as an antineoplastic agent, an antimitotic, a metabolite, a human metabolite, a mouse metabolite and an angiogenesis modulating agent. It is a 17beta-hydroxy steroid and a 3-hydroxy steroid. It derives from a 17beta-estradiol.|2-Methoxyestradiol (2ME2) is a drug that prevents the formation of new blood vessels that tumors need in order to grow (angiogenesis). It has undergone Phase 1 clinical trials against breast cancers and preclinical studies suggest that 2ME2 could also be effective against inflammatory diseases such as rheumatoid arthritis.|2-Methoxyestradiol 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. (NCI04)|A metabolite of estradiol that lacks estrogenic activity and inhibits TUBULIN polymerization. It has antineoplastic properties, including inhibition of angiogenesis and induction of APOPTOSIS.

2-Methoxyestradiol Basic Attributes

Molecular Weight：

302.41

Exact Mass：

302.41

UNII：

6I2QW73SR5

DSSTox ID：

DTXSID3040938

NCI Thesaurus Code：

C965

Characteristics

PSA：

49.7

XLogP3：

Appearance：

light yellow crystalline

Density：

1.2±0.1 g/cm3

Melting Point：

184-186 °C @ Solvent: Benzene

Boiling Point：

464.4°C at 760 mmHg

Flash Point：

234.7±28.7 °C

Refractive Index：

1.586

Water Solubility：

DMSO: 10 mg/mL

Storage Conditions：

−20°C

Safety Information

Packing level：

Ⅲ

Transport codes：

UN30779/PG3

wgk germany：

hazard class code：

23/24/25-36/37/38-48-61-60-46-45-51/53

safety instructions：

22-26-36/37/39-45-53-36-61

RTECS Number：

KG7537500

Marks：

T,Xi,N

Precautionary statement(s)：

P201-P261-P273-P280-P301 + P310-P305 + P351 + P338

Hazard Statements：

H301 + H311 + H331-H315-H319-H335-H350-H360-H372-H410

GHS Classification：

|Danger|H301+H311+H331 (92.68%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]|P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P311, P312, P314, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 41 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Protein Binding：

2ME2 was found to bind in decreasing order to plasma>albumin>alpha1-acid glycoprotein>sex-hormone-binding globulin. Plasma concentration-time profiles of total 2ME2 and unbound 2ME2 concentrations in a patient with cancer receiving 2ME2 as a single oral dose were parallel to each other. Thus, indicating that plasma protein binding is not an important consideration in pharmacokinetic monitoring of 2ME2.

Drug Information

Drug Indication：

For the treatment of breast cancer and inflammatory diseases such as rheumatoid arthritis.

Pharmacology：

2-Methoxyestradiol belongs to the family of drugs called angiogenesis inhibitors. It also acts as a vasodilator.

MeSH：

Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES. (See all compounds classified as Tubulin Modulators.)|Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

Metabolism/Metabolites：

In vivo metabolism, assessed using 24-h collections of urine from cancer patients treated with 2ME2 revealed that <0.01% of the total administered dose of 2ME2 is excreted unchanged in urine and about 1% excreted as glucuronides. Collectively, this suggests that glucuronidation and subsequent urinary excretion are elimination pathways for 2ME2.|2-O-methoxyestradiol has known human metabolites that include 2-Methoxy-estradiol-17beta 3-glucuronide.

Mechanism of Action：

2-Methoxyestradiol is an angiogenesis inhibitor, and has been shown to attack both tumor cells and their blood supply in preclinical testing. 2-methoxyestradiol is a naturally occurring estrogen metabolite but has no undesired estrogenic activity.

MeSH Entry Terms：

(17 beta)-2-methoxyestra-1,3,5(10)-triene-3,17-diol

2-Methoxyestradiol Use and Manufacturing

Uses

2-Methoxy 17β-Estradiol is a natural metabolite of 17β-Estradiol which is devoid of estrogenic activity. Inhibits cell proliferation and angiogenesis.2-Methoxy 17β-Estradiol binds to the colchicine binding site of tubulin, and has been suggested to function as a natural regulator of microtubule assembly and function.

Use Classification：

Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C18 steroids (estrogens) and derivatives [ST0201]

Computed Properties

Molecular Weight:302.4
XLogP3:4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:302.18819469
Monoisotopic Mass:302.18819469
Topological Polar Surface Area:49.7
Heavy Atom Count:22
Complexity:425
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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2-Methoxyestradiol

CAS No.: 362-07-2

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