ARD-2585   Click here for help

GtoPdb Ligand ID: 11755

Synonyms: ARD2585 | compound 43 [PMID: 34473519]
Compound class: Synthetic organic
Comment: ARD-2585 is a highly potent and orally bioavailable PROTAC androgen receptor (AR) degrader molecule [1]. It was designed to reduce AR in metastatic castration-resistant prostate cancer (mCRPC), as an alternative mechanism to antagonising AR signaling with drugs such as enzalutamide and apalutamide. Structurally ARD-2585 is a bifunctional molecule that contains an AR antagonist ligand linked to a cereblon binding component, that targets the AR to the cereblon/cullin 4A E3 ligase complex for degradation. It shares structural similarities to ARV110, which was the first AR PROTAC to advance to clinical evaluation in humans.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 13
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 149.4
Molecular weight 762.3
XLogP 5.26
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES N#Cc1ccc(cc1Cl)N([C@@H]1CC[C@H](CC1)NC(=O)c1ccc(cc1)N1CCN(CC1)C1CN(C1)c1ccc2c(c1)C(=O)N(C2=O)C1CCC(=O)NC1=O)C
Isomeric SMILES Clc1c(C#N)ccc(N(C)[C@H]2CC[C@@H](CC2)NC(=O)c2ccc(N3CCN(C4CN(C4)c4cc5c(C(=O)N(C6C(=O)NC(=O)CC6)C5=O)cc4)CC3)cc2)c1
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?
InChI Key LUCHABJUYSYJAT-RVWRWSNSSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups PROTACs, molecular glues and other degraders
Synonyms Click here for help
ARD2585 | compound 43 [PMID: 34473519]
Database Links Click here for help
GtoPdb PubChem SID 458923790
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