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Compound Detail

CHEMBL3183409

APALUTAMIDE
💊 Approved Drug
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💊 Approved Drug
CNC(=O)c1ccc(N2C(=S)N(c3cnc(C#N)c(C(F)(F)F)c3)C(=O)C23CCC3)cc1F

Basic Information

ChEMBL ID CHEMBL3183409
Name APALUTAMIDE
Phase Approved
Structure Type MOL
InChI Key HJBWBFZLDZWPHF-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Apalutamida Apalutamide Arn-509 Erleada JNJ-56021927
4
Targets
16
Activities
3
Assay Types
12
PK Parameters
20
Publications
5
Known Names
10
Indications
1
Mechanisms

Molecular Properties

477.4
MW (Da)
3.53
ALogP
5
HBA
1
HBD
89.3
PSA (Ų)
0.54
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2018
Availability Prescription
Chirality Achiral

Routes of Administration

Oral
USAN Stem -lutamide

Extended Properties

Molecular Formula C21H15F4N5O2S
MW 477.44
Aromatic Rings 2
Heavy Atoms 33
NP-Likeness -1.41

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Androgen Receptor antagonist ANTAGONIST Androgen receptor

Indications

Neoplasms Neoplasms Prostatic Neoplasms Prostatic Neoplasms Prostatic Neoplasms Prostatic Neoplasms Prostatic Neoplasms, Castration-Resistant Prostatic Neoplasms, Castration-Resistant Salivary Gland Neoplasms Liver Diseases

ATC Classification

L02BB05
apalutamide
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ENDOCRINE THERAPY

Activity Summary

IC50 11 meas. best 7.8
Ki 4 meas. best 7.46
Kd 1 meas. best 4.34

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Androgen receptor
CHEMBL1871
IC50 7.8 6.5611 16.0 9
Androgen receptor
CHEMBL1871
Ki 7.46 6.7767 34.7 3
LNCaP
CHEMBL612518
IC50 6.76 6.76 174.0 1
Androgen receptor
CHEMBL3072
Ki 5.84 5.84 1452.0 1
GABA-A receptor; anion channel
CHEMBL2093872
IC50 5.52 5.52 3000.0 1
Androgen receptor
CHEMBL1871
Kd 4.34 4.34 45180.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 61560.0 ng.hr.mL-1 Mus musculus
AUC 14752.0 ng.hr.mL-1 Rattus norvegicus
AUC 4494658.0 ng.hr.mL-1 Mus musculus
Cmax 6953.75 nM Mus musculus
Cmax 1981.4 nM Rattus norvegicus
Cmax 9069.2 nM Mus musculus
MRT 10.7 hr Rattus norvegicus
T1/2 5.9 hr Mus musculus
T1/2 7.4 hr Rattus norvegicus
Tmax 6.0 hr Mus musculus
Tmax 3.5 hr Rattus norvegicus
Tmax 4.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Androgen receptor IC50 = 16.0 nM 7.8 Antagonist activity at human androgen receptor expressed in HEK293 cells assesse... 30525603
Androgen receptor IC50 = 16.0 nM 7.8 Antagonist activity at AR in human LNCaP cells incubated for 24 hrs by Western b... 37948954
Androgen receptor IC50 = 16.25 nM 7.79 Displacement of [3H]-R1881 from AR in human LNCaP cells preincubated for 30 mins... 28478926
Androgen receptor Ki = 34.7 nM 7.46 Antagonist activity at androgen receptor (unknown origin) 26046313
Androgen receptor Ki = 93.0 nM 7.03 Inhibition of androgen receptor (unknown origin) 32911308
Androgen receptor IC50 = 160.0 nM 6.8 Antagonist activity at recombinant human AR expressed in HEK293 cells assessed a... 33095584
LNCaP IC50 = 174.0 nM 6.76 Antiproliferative activity against human LNCAP cells after 3 days 26046313
Androgen receptor IC50 = 200.0 nM 6.7 Inhibition of androgen receptor (unknown origin) 32911308
Androgen receptor IC50 = 348.9 nM 6.46 Binding affinity to androgen receptor LBD (unknown origin) incubated for 2 hrs b... 38385428
Androgen receptor Ki = 1452.0 nM 5.84 Displacement of [3H]-mibolerone from recombinant wild-type GST-tagged androgen r... 30525603
Androgen receptor Ki = 1452.0 nM 5.84 Displacement of [3H]-MIB from wild-type rat AR LBD measured after 16 hrs by scin... 33095584
GABA-A receptor; anion channel IC50 = 3000.0 nM 5.52 Binding affinity to GABA A receptor (unknown origin) 35786895
Androgen receptor IC50 = 3110.0 nM 5.51 Gal4-luciferase reporter assay: Briefly, the AR LBD is expressed as a fusion wit... -
Androgen receptor IC50 = 3280.0 nM 5.48 Gal4-luciferase reporter assay: Briefly, the AR LBD is expressed as a fusion wit... -
Androgen receptor IC50 = 19500.0 nM 4.71 mmTV-luciferase reporter assay: An AR-response element is contained within the m... -
Androgen receptor Kd = 45180.0 nM 4.34 Binding affinity to androgen receptor N-terminal domain (unknown origin) assesse... 38626524

Literature References

PubMed DOI Target Context # Activities
28478926 10.1016/j.bmcl.2017.04.071 Rattus norvegicus 5
36708680 10.1016/j.ejmech.2023.115110 ADMET 4
28478926 10.1016/j.bmcl.2017.04.071 Mus musculus 4
30525603 10.1021/acs.jmedchem.8b00973 Androgen receptor 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
36708680 10.1016/j.ejmech.2023.115110 Unchecked 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
32911308 10.1016/j.ejmech.2020.112667 Androgen receptor 2
33095584 10.1021/acs.jmedchem.0c00943 Androgen receptor 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
26046313 10.1016/j.ejmech.2015.05.039 Androgen receptor 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
30525603 10.1021/acs.jmedchem.8b00973 Unchecked 1
- 10.1101/2020.04.21.054387 SARS-CoV-2 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
34809430 10.1021/acs.jmedchem.1c01287 Unchecked 1
35786895 10.1021/acs.jmedchem.2c00716 GABA-A receptor; anion channel 1
34003642 10.1021/acs.jmedchem.0c02245 Cytochrome P450 3A4 1
38385428 10.1021/acs.jmedchem.3c01668 CWR22R 1
28478926 10.1016/j.bmcl.2017.04.071 Androgen receptor 1

Data from ChEMBL 36 via Core Engine