apalutamide   Click here for help

GtoPdb Ligand ID: 9043

Synonyms: ARN-509 | ARN509 | Erleada® | JNJ-56021927
Approved drug
apalutamide is an approved drug (FDA (2018), EMA (2019))
Compound class: Synthetic organic
Comment: Apalutamide is a novel androgen receptor (AR) antagonist (antiandrogen) that is approved as a treatment for castration-resistant prostate cancer (CRPC) [3]. This compound (91) was discovered in a structure/activity relationship-guided medicinal chemistry program designed to identify antiandrogens devoid of agonistic activity in the setting of androgen receptor overexpression [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 121.42
Molecular weight 477.09
XLogP 2.86
No. Lipinski's rules broken 0
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Canonical SMILES CNC(=O)c1ccc(cc1F)N1C(=S)N(C(=O)C21CCC2)c1cnc(c(c1)C(F)(F)F)C#N
Isomeric SMILES CNC(=O)c1ccc(cc1F)N1C(=S)N(C(=O)C21CCC2)c1cnc(c(c1)C(F)(F)F)C#N
InChI InChI=1S/C21H15F4N5O2S/c1-27-17(31)13-4-3-11(8-15(13)22)30-19(33)29(18(32)20(30)5-2-6-20)12-7-14(21(23,24)25)16(9-26)28-10-12/h3-4,7-8,10H,2,5-6H2,1H3,(H,27,31)
Selectivity at nuclear hormone receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Androgen receptor Rn Antagonist Antagonist 7.0 pKi - 2
pKi 7.0 (Ki 9.3x10-8 M) [2]
Description: Binding affinity measured in competition with [3H]mibolerone using wtAR isolated from rat ventral prostates.
Androgen receptor Primary target of this compound Hs Antagonist Antagonist 6.7 – 6.9 pIC50 - 1-2
pIC50 6.9 (IC50 1.22x10-7 M) [1]
pIC50 6.7 (IC50 2x10-7 M) [2]
Description: Antagonism of testosterone-induced activation of wtAR determined using AR-HEK293 cells and a luciferase reporter system..