APALUTAMIDE

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Search structure


Trade Names	ERLEADA
Synonyms	ARN-509 Apalutamide Arn-509 Erleada JNJ-56021927
Status
Molecule Category	UNKNOWN
ATC	L02BB05
UNII	4T36H88UA7
EPA CompTox	DTXSID40241899


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	HJBWBFZLDZWPHF-UHFFFAOYSA-N
Smiles	CNC(=O)c1ccc(N2C(=S)N(c3cnc(C#N)c(C(F)(F)F)c3)C(=O)C23CCC3)cc1F
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)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C21H15F4N5O2S
Molecular Weight	477.44
AlogP	3.53
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	3.0
Polar Surface Area	89.33
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	33.0

Bioactivity

Mechanism of Action	Action	Reference
Androgen Receptor antagonist	ANTAGONIST	PubMed Other


Protein: Androgen Receptor Description: Androgen receptor Organism : Homo sapiens P10275 ENSG00000169083

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 4	-	16-200	-	35-1452	-

Assay Description	Organism	Bioactivity	Reference
Antiproliferative activity against human LNCAP cells after 3 days	Homo sapiens	174.0 nM
Antagonist activity at androgen receptor (unknown origin)	Homo sapiens	34.7 nM
Displacement of [3H]-R1881 from AR in human LNCaP cells preincubated for 30 mins followed by [3H]-R1881 addition measured after 30 mins by microbeta scintillation counter method	Homo sapiens	16.25 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-3.36 %
Antagonist activity at human androgen receptor expressed in HEK293 cells assessed as inhibition of R1881-induced receptor transactivation after 24 hrs by luciferase reporter gene assay	Homo sapiens	16.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-9.86 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.21 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.21 %
Antagonist activity at recombinant human AR expressed in HEK293 cells assessed as inhibition of R1881-induced transcriptional activity measured after 24 hrs by dual luciferase reporter gene assay	Homo sapiens	160.0 nM
Inhibition of androgen receptor (unknown origin)	Homo sapiens	93.0 nM		Inhibition of androgen receptor (unknown origin)	Homo sapiens	200.0 nM

Related Entries

Cross References

Resources	Reference
ChEMBL	CHEMBL3183409
DrugBank	DB11901
DrugCentral	5278
FDA SRS	4T36H88UA7
Guide to Pharmacology	9043
PubChem	24872560
SureChEMBL	SCHEMBL909297
ZINC	ZINC000043174901

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).