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    Elacestrant

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    2D Structure
    Also known as: 722533-56-4, Rad1901, Elacestrant [inn], Elacestrant [usan], Rad-1901, Er-306323
    Molecular Formula
    C30H38N2O2
    Molecular Weight
    458.6  g/mol
    InChI Key
    SIFNOOUKXBRGGB-AREMUKBSSA-N
    FDA UNII
    FM6A2627A8
    Elacestrant is an orally available, selective estrogen receptor degrader (SERD) and selective estrogen receptor modulator (SERM), with potential antineoplastic and estrogen-like activities. Upon oral administration of higher doses of elacestrant, this agent acts as a SERD, which binds to the estrogen receptor (ER) and induces a conformational change that results in the degradation of the receptor. This may inhibit the growth and survival of ER-expressing cancer cells. At lower doses of this agent, RAD1901 acts as a SERM and has estrogen-like effects in certain tissues, which can both reduce hot flashes and protect against bone loss. In addition, elacestrant is able to cross the blood-brain barrier (BBB).
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6R)-6-[2-[ethyl-[[4-[2-(ethylamino)ethyl]phenyl]methyl]amino]-4-methoxyphenyl]-5,6,7,8-tetrahydronaphthalen-2-ol
    2.1.2 InChI
    InChI=1S/C30H38N2O2/c1-4-31-17-16-22-6-8-23(9-7-22)21-32(5-2)30-20-28(34-3)14-15-29(30)26-11-10-25-19-27(33)13-12-24(25)18-26/h6-9,12-15,19-20,26,31,33H,4-5,10-11,16-18,21H2,1-3H3/t26-/m1/s1
    2.1.3 InChI Key
    SIFNOOUKXBRGGB-AREMUKBSSA-N
    2.1.4 Canonical SMILES
    CCNCCC1=CC=C(C=C1)CN(CC)C2=C(C=CC(=C2)OC)C3CCC4=C(C3)C=CC(=C4)O
    2.1.5 Isomeric SMILES
    CCNCCC1=CC=C(C=C1)CN(CC)C2=C(C=CC(=C2)OC)[C@@H]3CCC4=C(C3)C=CC(=C4)O
    2.2 Other Identifiers
    2.2.1 UNII
    FM6A2627A8
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (6r)-6-(2-(ethyl((4-(2-(ethylamino)ethyl)phenyl)methyl)amino)-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-ol

    2.3.2 Depositor-Supplied Synonyms

    1. 722533-56-4

    2. Rad1901

    3. Elacestrant [inn]

    4. Elacestrant [usan]

    5. Rad-1901

    6. Er-306323

    7. Fm6a2627a8

    8. (6r)-6-[2-[ethyl-[[4-[2-(ethylamino)ethyl]phenyl]methyl]amino]-4-methoxyphenyl]-5,6,7,8-tetrahydronaphthalen-2-ol

    9. (6r)-6-{2-[ethyl({4-[2-(ethylamino)ethyl]phenyl}methyl)amino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

    10. (2r)-2-(2-(ethyl-((4-(2-(ethylamino)ethyl)phenyl)methyl)amino)-4-methoxy-phenyl)tetralin-6-ol

    11. (6r)-6-(2-(ethyl((4-(2- (ethylamino)ethyl)phenyl)methyl)amino)-4-methoxyphenyl)- 5,6,7,8-tetrahydronaphthalen-2-ol

    12. 2-naphthalenol, 6-(2-(ethyl((4-(2-(ethylamino)ethyl)phenyl)methyl)amino)-4-methoxyphenyl)-5,6,7,8-tetrahydro-, (6r)-

    13. Elacestrant (usan/inn)

    14. Elacestrant [usan:inn]

    15. Elacestrant [who-dd]

    16. Schembl229431

    17. Unii-fm6a2627a8

    18. Chembl4297509

    19. Bdbm349630

    20. Dtxsid901045846

    21. Glxc-26208

    22. Ex-a5070

    23. Us10208011, Compound Rad-

    24. Mfcd30532693

    25. Who 10247

    26. Cs-6306

    27. Db06374

    28. Hy-19822

    29. D11671

    30. Q27278069

    31. (r)-6-(2-(ethyl(4-(2-(ethylamino)ethyl)benzyl)amino)-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-ol

    32. I0v

    2.4 Create Date
    2008-01-14
    3 Chemical and Physical Properties
    Molecular Weight 458.6 g/mol
    Molecular Formula C30H38N2O2
    XLogP36.3
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count10
    Exact Mass458.293328459 g/mol
    Monoisotopic Mass458.293328459 g/mol
    Topological Polar Surface Area44.7 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity578
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in menopause and female hormonal deficiencies/abnormalities.

    5 Pharmacology and Biochemistry
    5.1 Mechanism of Action

    RAD1901 is a novel selective estrogen receptor modulator(SERM). SERMs are small molecules that bind to and selectively modulate estrogen receptors. These molecules have the ability to stimulate or block estrogen's activity in different types of tissue, functioning as estrogen receptor agonists in some tissues and as estrogen receptor antagonists in others. RAD1901 has potential to reduce vasomotor symptoms, along with a simultaneous bone-protective effect, without stimulating breast or uterine tissues. RAD1901 is distinctive from other SERMs in its unique biological profile, combined with its significant ability to penetrate the blood-brain barrier, which enables RAD1901 to function as an estrogen agonist within the central nervous system and thereby relieve hot flashes.