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ARD-2585 - CAS 2757422-79-8

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ARD-2585 is an exceptionally potent and orally active PROTAC degrader of androgen receptor for the treatment of advanced prostate cancer.

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Molecular Formula

C41H43ClN8O5

Molecular Weight

763.28

ARD-2585

- Specification
  - Solubility
    
    Soluble in DMSO
    
    Storage
    
    Store at -20°C
    
    IUPAC Name
    
    N-[(1r,4r)-4-(3-chloro-4-cyano-N-methylanilino)cyclohexyl]-4-[4-[1-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl]azetidin-3-yl]piperazin-1-yl]benzamide
    
    Synonyms
    
    Benzamide, N-[trans-4-[(3-chloro-4-cyanophenyl)methylamino]cyclohexyl]-4-[4-[1-[2-(2,6-dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl]-3-azetidinyl]-1-piperazinyl]-; N-((1r,4r)-4-((3-chloro-4-cyanophenyl)(methyl)amino)cyclohexyl)-4-(4-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)azetidin-3-yl)piperazin-1-yl)benzamide; N-[trans-4-[(3-Chloro-4-cyanophenyl)methylamino]cyclohexyl]-4-[4-[1-[2-(2,6-dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl]-3-azetidinyl]-1-piperazinyl]benzamide; ARD 2585; ARD2585
- Properties
  - Boiling Point
    
    1032.7±65.0°C at 760 Torr
    
    Density
    
    1.46±0.1 g/cm3
    
    InChI Key
    
    LUCHABJUYSYJAT-RVWRWSNSNA-N
    
    InChI
    
    InChI=1S/C41H43ClN8O5/c1-46(30-9-4-26(22-43)35(42)21-30)28-10-5-27(6-11-28)44-38(52)25-2-7-29(8-3-25)47-16-18-48(19-17-47)32-23-49(24-32)31-12-13-33-34(20-31)41(55)50(40(33)54)36-14-15-37(51)45-39(36)53/h2-4,7-9,12-13,20-21,27-28,32,36H,5-6,10-11,14-19,23-24H2,1H3,(H,44,52)(H,45,51,53)/t27-,28-,36?
    
    Canonical SMILES
    
    N#CC1=CC=C(C=C1Cl)N(C)C2CCC(NC(=O)C3=CC=C(C=C3)N4CCN(CC4)C5CN(C6=CC=C7C(=O)N(C(=O)C7=C6)C8C(=O)NC(=O)CC8)C5)CC2
- Reference Reading
  - 1. Discovery of ARD-2585 as an Exceptionally Potent and Orally Active PROTAC Degrader of Androgen Receptor for the Treatment of Advanced Prostate Cancer
    
    Hoda Metwally,Bukeyan Miao,Weiguo Xiang,Aleksas Matvekas,Miao He,Bo Wen,Lu Wang,Yu Wang,Paul D Kirchhoff,Duxin Sun,Shaomeng Wang,Xin Han,Lijie Zhao,Chong Qin,Donna McEachern J Med Chem . 2021 Sep 23;64(18):13487-13509. doi: 10.1021/acs.jmedchem.1c00900.
    
    We report herein the discovery of exceptionally potent and orally bioavailable PROTAC AR degraders with ARD-2585 being the most promising compound. ARD-2585 achieves DC50values of ≤0.1 nM in the VCaP cell line with AR gene amplification and in the LNCaP cell line carrying an AR mutation. It potently inhibits cell growth with IC50values of 1.5 and 16.2 nM in the VCaP and LNCaP cell lines, respectively, and achieves excellent pharmacokinetics and 51% of oral bioavailability in mice. It is more efficacious than enzalutamide in inhibition of VCaP tumor growth and does not cause any sign of toxicity in mice. ARD-2585 is a promising AR degrader for extensive investigations for the treatment of advanced prostate cancer.

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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳

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