apalutamide   

GtoPdb Ligand ID: 9043

Synonyms: ARN-509 | ARN509 | Erleada® | JNJ-56021927
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].
2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
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)
InChI Key HJBWBFZLDZWPHF-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2018), EMA (2019))
IUPAC Name
4-[7-[6-cyano-5-(trifluoromethyl)pyridin-3-yl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-5-yl]-2-fluoro-N-methylbenzamide
International Nonproprietary Names
INN number INN
10118 apalutamide
Synonyms
ARN-509 | ARN509 | Erleada® | JNJ-56021927
Database Links
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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