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    Technical details about Proxalutamide, learn more about the structure, uses, toxicity, action, side effects and more

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    Proxalutamide

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    DIGITAL CONTENT

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    2D Structure
    1. Also known as: 1398046-21-3, Pruxelutamide, Gt-0918, Proxalutamide [who-dd], Qx6o64gp40, 4-(4,4-dimethyl-3-(6-(3-(2-oxazolyl)propyl)-3-pyridinyl)-5-oxo-2-thioxo-1-imidazolidinyl)-3-fluoro-2-(trifluoromethyl)-benzonitrile
    Molecular Formula
    C24H19F4N5O2S
    Molecular Weight
    517.5  g/mol
    InChI Key
    KCBJGVDOSBKVKP-UHFFFAOYSA-N
    FDA UNII
    QX6O64GP40
    Proxalutamide is an orally bioavailable androgen receptor (AR) antagonist with potential antineoplastic activity. Upon oral administration, proxalutamide binds to AR in target tissues, inhibits androgen-induced receptor activation, and facilitates the formation of inactive complexes that cannot translocate to the nucleus. This prevents binding to and transcription of AR-responsive genes that regulate prostate cancer cell proliferation. In addition, proxalutamide induces AR downregulation, thereby further preventing AR-mediated signaling. This ultimately leads to an inhibition of growth in AR-expressing prostate cancer cells. AR is overexpressed in prostate cancer and plays a key role in prostate cancer cell proliferation.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[4,4-dimethyl-3-[6-[3-(1,3-oxazol-2-yl)propyl]pyridin-3-yl]-5-oxo-2-sulfanylideneimidazolidin-1-yl]-3-fluoro-2-(trifluoromethyl)benzonitrile
    2.1.2 InChI
    InChI=1S/C24H19F4N5O2S/c1-23(2)21(34)32(17-9-6-14(12-29)19(20(17)25)24(26,27)28)22(36)33(23)16-8-7-15(31-13-16)4-3-5-18-30-10-11-35-18/h6-11,13H,3-5H2,1-2H3
    2.1.3 InChI Key
    KCBJGVDOSBKVKP-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1(C(=O)N(C(=S)N1C2=CN=C(C=C2)CCCC3=NC=CO3)C4=C(C(=C(C=C4)C#N)C(F)(F)F)F)C
    2.2 Other Identifiers
    2.2.1 UNII
    QX6O64GP40
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4-(4,4-dimethyl-3-(6-(3-(2-oxazolyl)propyl)-3-pyridinyl)-5-oxo-2-thioxo-1-imidazolidinyl)-3-fluoro-2-(trifluoromethyl)benzonitrile

    2. Gt 0918

    3. Gt-0918

    4. Gt0918

    2.3.2 Depositor-Supplied Synonyms

    1. 1398046-21-3

    2. Pruxelutamide

    3. Gt-0918

    4. Proxalutamide [who-dd]

    5. Qx6o64gp40

    6. 4-(4,4-dimethyl-3-(6-(3-(2-oxazolyl)propyl)-3-pyridinyl)-5-oxo-2-thioxo-1-imidazolidinyl)-3-fluoro-2-(trifluoromethyl)-benzonitrile

    7. 4-[4,4-dimethyl-3-[6-[3-(1,3-oxazol-2-yl)propyl]pyridin-3-yl]-5-oxo-2-sulfanylideneimidazolidin-1-yl]-3-fluoro-2-(trifluoromethyl)benzonitrile

    8. 4-(4,4-dimethyl-3-(6-(3-(oxazol-2-yl)propyl)pyridin-3-yl)-5-oxo-2-thioxoimidazolidin-1-yl)-3-fluoro-2-(trifluoromethyl)benzonitrile

    9. Unii-qx6o64gp40

    10. Pruxelutamide [inn]

    11. Chembl4594417

    12. Schembl12494226

    13. Gtpl11992

    14. Dtxsid901102678

    15. Ex-a5434

    16. Gt0918

    17. At29744

    18. Sb17303

    19. Hy-103184

    20. Cs-0025229

    21. Q27287540

    22. 4-(4,4-dimethyl-3-(6-(3-(oxazol-2-yl)propyl)pyridin-3-yl)-5-oxo-2-thioxoimidazolidin-1-yl)-3-fluoro-2-(trifluoromethyl) Benzonitrile

    2.4 Create Date
    2012-10-01
    3 Chemical and Physical Properties
    Molecular Weight 517.5 g/mol
    Molecular Formula C24H19F4N5O2S
    XLogP34.3
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count6
    Exact Mass517.11955869 g/mol
    Monoisotopic Mass517.11955869 g/mol
    Topological Polar Surface Area118 Ų
    Heavy Atom Count36
    Formal Charge0
    Complexity894
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 Mechanism of Action

    Proxalutamide is an antagonist at the androgen receptor which leads to inhibition of androgen-induced receptor activation and results in formation of inactive complexes that are not able to translocate to the nucleus. It also induces androgen receptor downregulation, furthering adrogen-induced receptor activation. This drug is being investigated for its potential antineoplastic activity and is being investigated specifically against prostate cancer and COVID-19.

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