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)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2018), EMA (2019))
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
10118 apalutamide
Synonyms Click here for help
ARN-509 | ARN509 | Erleada® | JNJ-56021927
Database Links Click here for help
CAS Registry No. 956104-40-8 (source: WHO INN record)
ChEMBL Ligand CHEMBL3183409
DrugCentral Ligand 5278
GtoPdb PubChem SID 315661128
PubChem CID 24872560
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