2-Methoxyestradiol
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Grundinformationen
- CAS
362-07-2- Standard-SMILES
COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12- InChIKey
CQOQDQWUFQDJMK-SSTWWWIQSA-N- Summenformel
- C19H26O3
- Durchschnittliche Molmasse
- 302,4 g/mol
- Monoisotopische Masse
- 302,18819469
Überblick
2-methoxy-17beta-estradiol is a 17beta-hydroxy steroid, being 17beta-estradiol methoxylated at C-2. It has a role as a metabolite, an antineoplastic agent, an angiogenesis modulating agent, an antimitotic, a mouse metabolite and a human metabolite. It is a 17beta-hydroxy steroid and a 3-hydroxy steroid. It is functionally related to a 17beta-estradiol.
Namen und Bezeichner
- Bevorzugter Name
- 2-Methoxyestradiol
- IUPAC
- (8R,9S,13S,14S,17S)-2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
Namen und Synonyme
2-Methoxyestradiol362-07-2Panzem2-Methoxyestradiol-17beta2-ME22-Hydroxyestradol 2-methyl ether2ME22-methoxy-17beta-estradiol2-methoxyoestradiolNSC-659853(17beta)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol2-Methoxyestra-1,3,5(10)-triene-3,17beta-diol
Weitere Namen anzeigen
6I2QW73SR5DTXSID3040938Estra-1,3,5(10)-triene-3,17-diol, 2-methoxy-, (17beta)-2-methoxy-estra-1,3,5(10)-triene-3,17beta-diol(8R,9S,13S,14S,17S)-2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diolCHEBI:289552 Methoxyestradiol2 Methoxyoestradiol
Datenbank-Bezeichner
- CAS
362-07-2- PubChem CID
- 66414
- DTXSID
DTXSID3040938- ChEMBL
CHEMBL299613- ChEBI
CHEBI:28955- UNII
- 6I2QW73SR5
- EC Number
- 636-846-8
- Nikkaji
- J104.105C
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 4
- Polarare Oberfläche (TPSA)
- 49,7 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 22
- Formalladung
- 0
- Komplexität
- 425
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C18 steroids (estrogens) and derivatives [ST0201]
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point189 - 190 °C
Physical DescriptionSolid
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H301+H311+H331 (88.4%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P203, P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 43 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 3 (88.4%)
Chemie und Industrie
Pharmakologische Informationen
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.
Pharmacodynamics2-Methoxyestradiol belongs to the family of drugs called angiogenesis inhibitors. It also acts as a vasodilator.
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.
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.
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.
Tissue LocationsAdipose Tissue
Cellular LocationsExtracellular
Zugehörige Reaktionen
5
Notizen zur Verbindung
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