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Compound Detail

CHEMBL1082407

ENZALUTAMIDE
💊 Approved Drug
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💊 Approved Drug
CNC(=O)c1ccc(N2C(=S)N(c3ccc(C#N)c(C(F)(F)F)c3)C(=O)C2(C)C)cc1F
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1082407
Name ENZALUTAMIDE
Phase Approved
Structure Type MOL
InChI Key WXCXUHSOUPDCQV-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Enzalutamida Enzalutamide Mdv 3100 MDV-3100 MDV3100 Xtandi
15
Targets
179
Activities
4
Assay Types
10
PK Parameters
20
Publications
6
Known Names
20
Indications
1
Mechanisms

Molecular Properties

464.4
MW (Da)
3.99
ALogP
4
HBA
1
HBD
76.4
PSA (Ų)
0.55
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2012
Availability Prescription
Chirality Achiral

Routes of Administration

Oral
USAN Stem -lutamide
USAN Year 2012

Extended Properties

Molecular Formula C21H16F4N4O2S
MW 464.44
Aromatic Rings 2
Heavy Atoms 32
NP-Likeness -1.50

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 Breast Neoplasms Breast Neoplasms Adenocarcinoma Carcinoma Carcinoma, Hepatocellular Endometrial Neoplasms Lymphoma, Mantle-Cell Ovarian Neoplasms Severe Acute Respiratory Syndrome Triple Negative Breast Neoplasms Urinary Bladder Neoplasms Uterine Neoplasms Kidney Diseases

ATC Classification

L02BB04
enzalutamide
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ENDOCRINE THERAPY

Activity Summary

IC50 154 meas. best 7.85
Ki 13 meas. best 7.77
EC50 9 meas. best 7.31
Kd 3 meas. best 5.19

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Androgen receptor
CHEMBL1871
 IC50 7.85 6.5854 14.0 41
Androgen receptor
CHEMBL1871
 Ki 7.77 6.065 17.0 10
LNCaP
CHEMBL612518
 IC50 7.6 5.5776 25.0 33
Androgen receptor
CHEMBL1871
 EC50 7.31 6.28 49.0 9
VCaP
CHEMBL4296508
 IC50 7.06 5.6575 87.4 12
Unchecked
CHEMBL612545
 IC50 7.0 5.6875 100.0 12
Prostate-specific antigen
CHEMBL2099
 IC50 6.89 6.89 130.0 1
Androgen receptor
CHEMBL3072
 IC50 6.53 6.1825 294.0 4
GABA-A receptor; anion channel
CHEMBL2093872
 IC50 5.52 5.42 3000.0 2
Androgen receptor
CHEMBL3072
 Ki 5.44 5.44 3641.0 2
Androgen receptor
CHEMBL1871
 Kd 5.19 4.795 6520.0 2
CWR22R
CHEMBL612657
 IC50 5.01 4.4984 9700.0 19
Glucocorticoid receptor
CHEMBL2034
 Ki 4.85 4.85 14000.0 1
PC-3
CHEMBL390
 IC50 4.82 4.4333 15070.0 6
L02
CHEMBL4296457
 IC50 4.77 4.77 17100.0 2
LNCaP C4-2B
CHEMBL4296461
 IC50 4.75 4.6771 17960.0 7
Glucocorticoid receptor
CHEMBL2034
 IC50 4.54 4.54 29000.0 1
DU-145
CHEMBL613508
 IC50 4.49 4.385 32270.0 10
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.49 4.385 32270.0 2
GES1
CHEMBL4296415
 IC50 4.01 4.01 96890.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 6.0 mL.min-1.kg-1 Homo sapiens
CL 1.438 mL.min-1.kg-1 Homo sapiens
CL 4.3 mL.min-1.kg-1 Homo sapiens
CL 86.3 ml/min Homo sapiens
CL 1.1 mL.min-1.g-1 Mus musculus
T1/2 10.04 hr Homo sapiens
T1/2 10.04 hr Homo sapiens
T1/2 6.69 hr Homo sapiens
T1/2 10.04 hr Homo sapiens
T1/2 20.71 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Androgen receptor IC50 = 14.0 nM 7.85 Inhibition of AR transcriptional activity in human LNCaP cells harboring ARR2PB-... 34809430
Androgen receptor Ki = 17.0 nM 7.77 Binding affinity to wild-type androgen receptor in human LNCaP cells assessed as... 33470111
Androgen receptor IC50 = 21.0 nM 7.68 Displacement of [18F]-FDHT from androgen receptor in human LNCAP/AR cells 27717544
Androgen receptor IC50 = 25.0 nM 7.6 Antagonist activity at androgen receptor (unknown origin) in human LNCap-ARR2PB-... 36154033
LNCaP IC50 = 25.0 nM 7.6 Cytotoxicity against AR-positive human LNCaP cells assessed as inhibition of cel... 30629437
Androgen receptor Ki = 28.2 nM 7.55 Antagonist activity at androgen receptor (unknown origin) 26046313
Androgen receptor IC50 = 36.0 nM 7.44 Antagonist activity at AR in human LNCaP cells incubated for 24 hrs by Western b... 37948954
LNCaP IC50 = 36.0 nM 7.44 Antiproliferative activity against human LNCaP cells 35786895
Androgen receptor IC50 = 36.0 nM 7.44 Antagonist activity at androgen receptor in human LNCaP cells transfected with A... 32114360
Androgen receptor IC50 = 38.0 nM 7.42 Displacement of [3H]methyltrienolone from wild-type androgen receptor in human L... 33470111
Androgen receptor EC50 = 49.0 nM 7.31 Displacement of [3H]R1881 from AR in human MDA-MB-453 cells 23713567
Androgen receptor IC50 = 50.0 nM 7.3 Inhibition of full length AR transcriptional activity in human LNCAP cells harbo... 30193215
LNCaP IC50 = 52.0 nM 7.28 Cytotoxicity against AR-positive human LNCaP cells assessed as inhibition of cel... 36960664
Androgen receptor EC50 = 61.8 nM 7.21 Agonist activity at VP16-AR F877L mutant (unknown origin) transfected in human H... 33470111
Androgen receptor IC50 = 70.0 nM 7.16 Antagonist activity against human androgen receptor expressed in human LNCap cel... 35077161
Androgen receptor IC50 = 75.0 nM 7.12 Antagonist activity at androgen receptor in human LNCaP cells harboring eGFP/ARR... 34661404
Androgen receptor IC50 = 80.0 nM 7.1 Binding affinity to GST-tagged AR ligand binding domain (unknown origin) measure... 34809430
Androgen receptor Ki = 86.0 nM 7.07 Inhibition of androgen receptor (unknown origin) 32911308
VCaP IC50 = 87.4 nM 7.06 Cytotoxicity against AR-positive human VCaP cells assessed as inhibition of cell... 30629437
Androgen receptor IC50 = 90.0 nM 7.05 Inhibition of R1881-induced full length AR transcriptional activity in human LNC... 30193215

Literature References

PubMed DOI Target Context # Activities
33470111 10.1021/acs.jmedchem.0c01563 Androgen receptor 22
35077161 10.1021/acs.jmedchem.1c01938 Unchecked 19
31288149 10.1016/j.ejmech.2019.07.001 LNCaP 13
31288149 10.1016/j.ejmech.2019.07.001 DU-145 13
31288149 10.1016/j.ejmech.2019.07.001 VCaP 13
31288149 10.1016/j.ejmech.2019.07.001 CWR22R 13
28953875 10.1038/nature24028 Androgen receptor 12
32847363 10.1021/acs.jmedchem.0c00939 CWR22R 10
38530938 10.1021/acs.jmedchem.3c01789 Unchecked 9
28011219 10.1016/j.bmcl.2016.12.022 LNCaP 8
33095584 10.1021/acs.jmedchem.0c00943 Androgen receptor 7
30525603 10.1021/acs.jmedchem.8b00973 Androgen receptor 7
37458396 10.1021/acs.jmedchem.3c00880 Androgen receptor 7
34269581 10.1021/acs.jmedchem.1c00439 Androgen receptor 7
30193215 10.1016/j.ejmech.2018.08.059 Androgen receptor 6
36493620 10.1016/j.ejmech.2022.114999 Unchecked 6
38033250 10.1021/acs.jmedchem.3c01626 DU-145 6
34422225 10.1021/acsmedchemlett.1c00032 Androgen receptor 6
35077161 10.1021/acs.jmedchem.1c01938 Androgen receptor 5
25121586 10.1021/jm5005122 LNCaP 5

Data from ChEMBL 36 via Core Engine