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    Chemistry

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    Also known as: Arv-766, 2750830-09-0, Arv766, 4-(4-((1-(4-((trans-3-(4-cyano-3-methoxyphenoxy)-2,2,4,4-tetramethylcyclobutyl)carbamoyl)phenyl)piperidin-4-yl)methyl)piperazin-1-yl)-n-((s)-2,6-dioxopiperidin-3-yl)-2-fluorobenzamide, Luxdegalutamide [inn], 5bd7r933pv
    Molecular Formula
    C45H54FN7O6
    Molecular Weight
    808.0  g/mol
    InChI Key
    RDPPBRKNBBXPNZ-PJXMSJPKSA-N
    FDA UNII
    5BD7R933PV
    Luxdegalutamide
    Luxdegalutamide is an orally bioavailable androgen receptor (AR)-targeted protein degrader, composed of an AR ligand attached to an E3 ligase recognition moiety and utilizing the proteolysis targeting chimera (PROTAC) technology, with potential antineoplastic activity. Upon oral administration, luxdegalutamide targets and binds to the AR ligand binding domain on the AR. E3 ligase is then recruited to the AR by the E3 ligase recognition moiety of luxdegalutamide and the AR is tagged by ubiquitin. This causes ubiquitination and degradation of AR by the proteasome, and prevents the expression of AR target genes and halts AR-mediated signaling. This inhibits the proliferation of AR-overexpressing tumor cells. In addition, the degradation of the AR releases luxdegalutamide, allowing it to bind to additional AR. AR plays a key role in the proliferation of castration-resistant prostate cancer cells (CRPC). Luxdegalutamide may degrade resistance-driving point mutations of AR, including the L702H mutation associated with treatments including abiraterone.
    1 2D Structure

    Luxdegalutamide

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[4-[[1-[4-[[3-(4-cyano-3-methoxyphenoxy)-2,2,4,4-tetramethylcyclobutyl]carbamoyl]phenyl]piperidin-4-yl]methyl]piperazin-1-yl]-N-[(3S)-2,6-dioxopiperidin-3-yl]-2-fluorobenzamide
    2.1.2 InChI
    InChI=1S/C45H54FN7O6/c1-44(2)42(45(3,4)43(44)59-33-12-8-30(26-47)37(25-33)58-5)50-39(55)29-6-9-31(10-7-29)52-18-16-28(17-19-52)27-51-20-22-53(23-21-51)32-11-13-34(35(46)24-32)40(56)48-36-14-15-38(54)49-41(36)57/h6-13,24-25,28,36,42-43H,14-23,27H2,1-5H3,(H,48,56)(H,50,55)(H,49,54,57)/t36-,42?,43?/m0/s1
    2.1.3 InChI Key
    RDPPBRKNBBXPNZ-PJXMSJPKSA-N
    2.1.4 Canonical SMILES
    CC1(C(C(C1OC2=CC(=C(C=C2)C#N)OC)(C)C)NC(=O)C3=CC=C(C=C3)N4CCC(CC4)CN5CCN(CC5)C6=CC(=C(C=C6)C(=O)NC7CCC(=O)NC7=O)F)C
    2.1.5 Isomeric SMILES
    CC1(C(C(C1OC2=CC(=C(C=C2)C#N)OC)(C)C)NC(=O)C3=CC=C(C=C3)N4CCC(CC4)CN5CCN(CC5)C6=CC(=C(C=C6)C(=O)N[C@H]7CCC(=O)NC7=O)F)C
    2.2 Other Identifiers
    2.2.1 UNII
    5BD7R933PV
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Arv-766

    2. 2750830-09-0

    3. Arv766

    4. 4-(4-((1-(4-((trans-3-(4-cyano-3-methoxyphenoxy)-2,2,4,4-tetramethylcyclobutyl)carbamoyl)phenyl)piperidin-4-yl)methyl)piperazin-1-yl)-n-((s)-2,6-dioxopiperidin-3-yl)-2-fluorobenzamide

    5. Luxdegalutamide [inn]

    6. 5bd7r933pv

    7. Schembl23536786

    8. Schembl23594097

    9. Gtpl12624

    10. Ex-a7714

    11. Nsc847604

    12. At41584

    13. Nsc-847604

    14. Ts-09678

    15. Hy-153342

    16. Cs-0693933

    17. 4-[4-[[1-[4-[[[trans-3-(4-cyano-3-methoxyphenoxy)-2,2,4,4-tetramethylcyclobutyl]a Mino]carbonyl]phenyl]-4-piperidinyl]methyl]-1-piperazinyl]-n-[(3s)-2,6-dioxo-3-piperidinyl]-2-fluoro-benzamide

    18. 4-[4-[[1-[4-[[[trans-3-(4-cyano-3-methoxyphenoxy)-2,2,4,4-tetramethylcyclobutyl]amino]carbonyl]phenyl]-4-piperidinyl]methyl]-1-piperazinyl]-n-[(3s)-2,6-dioxo-3-piperidinyl]-2-fluorobenzamide

    19. Benzamide, 4-[4-[[1-[4-[[[trans-3-(4-cyano-3-methoxyphenoxy)-2,2,4,4-tetramethylcyclobutyl]amino]carbonyl]phenyl]-4-piperidinyl]methyl]-1-piperazinyl]-n-[(3s)-2,6-dioxo-3-piperidinyl]-2-fluoro-

    2.4 Create Date
    2021-08-21
    3 Chemical and Physical Properties
    Molecular Weight 808.0 g/mol
    Molecular Formula C45H54FN7O6
    XLogP35.9
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count11
    Exact Mass g/mol
    Monoisotopic Mass g/mol
    Topological Polar Surface Area156
    Heavy Atom Count59
    Formal Charge0
    Complexity1550
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1

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    Arvinas Partners with Novartis On Global License for PROTAC® ARV-766

    Details:

    Novartis obtains worldwide development & commercialization rights to ARV-766, Arvinas’ 2nd-generation PROTAC androgen receptor degrader for prostate cancer, including its preclinical AR-V7 program.


    Lead Product(s): Luxdegalutamide,Abiraterone Acetate

    Therapeutic Area: Oncology Brand Name: ARV-766

    Study Phase: Phase I/ Phase IIProduct Type: Small molecule

    Sponsor: Novartis Pharmaceuticals Corporation

    Deal Size: $1,160.0 million Upfront Cash: $150.0 million

    Deal Type: Licensing Agreement April 11, 2024

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    Lead Product(s) : Luxdegalutamide,Abiraterone Acetate

    Therapeutic Area : Oncology

    Highest Development Status : Phase I/ Phase II

    Partner/Sponsor/Collaborator : Novartis Pharmaceuticals Corporation

    Deal Size : $1,160.0 million

    Deal Type : Licensing Agreement

    DEALS_DEV arrow-down

    Arvinas Partners with Novartis On Global License for PROTAC® ARV-766

    Details : Novartis obtains worldwide development & commercialization rights to ARV-766, Arvinas’ 2nd-generation PROTAC androgen receptor degrader for prostate cancer, including its preclinical AR-V7 program.

    Brand Name : ARV-766

    Molecule Type : Small molecule

    Upfront Cash : $150.0 million

    April 11, 2024

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    Arvinas Announces Interim Data from the ARV-766 Phase 1/2 Dose Escalation and Expansion Trial Showing Promising Signals of Efficacy in Late-line mCRPC, ...

    Details:

    ARV-766 is an investigational orally bioavailable PROTAC® protein degrader designed to degrade all clinically relevant resistance-driving point mutations of the androgen receptor (AR) and which being investigated forLate-line mCRPC.


    Lead Product(s): Luxdegalutamide

    Therapeutic Area: Oncology Brand Name: ARV-766

    Study Phase: Phase I/ Phase IIProduct Type: Small molecule

    Sponsor: Not Applicable

    Deal Size: Not Applicable Upfront Cash: Not Applicable

    Deal Type: Not Applicable June 08, 2023

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    Arvinas

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    Lead Product(s) : Luxdegalutamide

    Therapeutic Area : Oncology

    Highest Development Status : Phase I/ Phase II

    Partner/Sponsor/Collaborator : Not Applicable

    Deal Size : Not Applicable

    Deal Type : Not Applicable

    DEALS_DEV arrow-down

    Arvinas Announces Interim Data from the ARV-766 Phase 1/2 Dose Escalation and Expansion Trial Show...

    Details : ARV-766 is an investigational orally bioavailable PROTAC® protein degrader designed to degrade all clinically relevant resistance-driving point mutations of the androgen receptor (AR) and which being investigated forLate-line mCRPC.

    Brand Name : ARV-766

    Molecule Type : Small molecule

    Upfront Cash : Not Applicable

    June 08, 2023

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