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Compound Detail

CHEMBL409

BICALUTAMIDE
💊 Approved Drug
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💊 Approved Drug
CC(O)(CS(=O)(=O)c1ccc(F)cc1)C(=O)Nc1ccc(C#N)c(C(F)(F)F)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL409
Name BICALUTAMIDE
Phase Approved
Structure Type MOL
InChI Key LKJPYSCBVHEWIU-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Bicalutamida Bicalutamide Calutide Casodex Cosudex ICI 176,334 ICI-176334 ICI176,334-1 Kalumid NSC-759816
381
Targets
803
Activities
4
Assay Types
23
PK Parameters
20
Publications
10
Known Names
19
Indications
1
Mechanisms

Molecular Properties

430.4
MW (Da)
2.88
ALogP
5
HBA
2
HBD
107.3
PSA (Ų)
0.56
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1995
Availability Prescription
Chirality Racemic

Routes of Administration

Oral
USAN Stem -lutamide
USAN Year 1994

Extended Properties

Molecular Formula C18H14F4N2O4S
MW 430.38
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness -1.64

Mechanism of Action

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

Indications

Carcinoma Neoplasms Breast Neoplasms Breast Neoplasms Breast Neoplasms Prostatic Neoplasms Prostatic Neoplasms Prostatic Neoplasms Prostatic Neoplasms, Castration-Resistant Severe Acute Respiratory Syndrome Severe Acute Respiratory Syndrome Fallopian Tube Neoplasms Gynecomastia Ovarian Neoplasms Peritoneal Neoplasms Puberty, Precocious Salivary Gland Neoplasms Urinary Bladder Neoplasms Urinary Bladder Neoplasms

ATC Classification

L02BB03
bicalutamide
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ENDOCRINE THERAPY

Activity Summary

IC50 774 meas. best 7.6
Ki 22 meas. best 7.96
EC50 6 meas. best 7.51
Kd 1 meas. best 4.75

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Androgen receptor
CHEMBL1871
 Ki 7.96 7.1856 11.0 18
Androgen receptor
CHEMBL3072
 Ki 7.85 6.8733 14.0 3
Androgen receptor
CHEMBL3072
 IC50 7.6 6.628 25.0 5
Androgen receptor
CHEMBL1871
 EC50 7.51 6.3817 31.0 6
Liver
CHEMBL613642
 IC50 7.31 7.31 48.9 1
Androgen receptor
CHEMBL1871
 IC50 7.27 6.5572 54.0 54
LNCaP
CHEMBL612518
 IC50 6.8 5.0786 160.0 14
Unchecked
CHEMBL612545
 IC50 6.8 6.415 160.0 2
Androgen receptor
CHEMBL3056
 IC50 6.72 6.1367 190.0 3
HT-3
CHEMBL1075470
 IC50 6.14 6.14 731.3 1
PC-3
CHEMBL390
 IC50 5.89 4.87 1300.0 6
Progesterone receptor
CHEMBL208
 IC50 5.74 5.74 1819.0 1
CCF-STTG1
CHEMBL1075419
 IC50 5.31 5.31 4929.3 1
Progesterone receptor
CHEMBL3456
 IC50 5.25 5.25 5600.0 2
SCC-25
CHEMBL614901
 IC50 5.22 5.22 6086.6 1
MKN-45
CHEMBL614354
 IC50 5.16 5.16 6960.5 1
Progesterone receptor
CHEMBL2596
 Ki 5.14 5.14 7200.0 1
ES5
CHEMBL2366312
 IC50 5.07 5.07 8611.5 1
SK-MEL3
CHEMBL614920
 IC50 5.0 5.0 10096.4 1
NOS-1
CHEMBL2366141
 IC50 4.95 4.95 11291.8 1
CAMA-1
CHEMBL1075416
 IC50 4.91 4.91 12392.6 1
LB1047-RCC
CHEMBL2366136
 IC50 4.91 4.91 12253.0 1
SAS
CHEMBL1075569
 IC50 4.88 4.88 13308.1 1
NCI-H2228
CHEMBL1075536
 IC50 4.86 4.86 13753.1 1
NCI-H187
CHEMBL2366276
 IC50 4.78 4.78 16661.6 1
BFTC-905
CHEMBL1075396
 IC50 4.76 4.76 17485.7 1
Albumin
CHEMBL3253
 Kd 4.75 4.75 18000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.75 4.3675 18000.0 4
DU-145
CHEMBL613508
 IC50 4.75 4.3214 18000.0 7
G-361
CHEMBL614036
 IC50 4.75 4.75 17826.0 1
SW780
CHEMBL1075595
 IC50 4.74 4.74 18415.0 1
BB49-HNC
CHEMBL2366295
 IC50 4.72 4.72 18953.2 1
AU565
CHEMBL1075393
 IC50 4.71 4.71 19740.2 1
KALS-1
CHEMBL2366155
 IC50 4.71 4.71 19663.5 1
NCI-H2087
CHEMBL1075532
 IC50 4.68 4.68 21059.1 1
RVH-421
CHEMBL1075567
 IC50 4.67 4.67 21579.5 1
KU-19-19
CHEMBL1075483
 IC50 4.66 4.66 22024.2 1
SK-CO-1
CHEMBL1075576
 IC50 4.66 4.66 21887.2 1
RO82-W-1
CHEMBL1075565
 IC50 4.64 4.64 23131.8 1
NB6
CHEMBL2366318
 IC50 4.64 4.64 22913.5 1
CTB-1
CHEMBL2366344
 IC50 4.61 4.61 24553.6 1
SW48
CHEMBL614055
 IC50 4.61 4.61 24654.6 1
TCC-SUP
CHEMBL615010
 IC50 4.61 4.61 24723.2 1
DK-MG
CHEMBL1075433
 IC50 4.6 4.6 24891.7 1
ST486
CHEMBL2366293
 IC50 4.59 4.59 25746.4 1
H4
CHEMBL1075452
 IC50 4.57 4.57 26945.8 1
SBC-1
CHEMBL2366327
 IC50 4.55 4.55 28350.7 1
HCC1954
CHEMBL1075459
 IC50 4.54 4.54 28752.5 1
OAW-42
CHEMBL1075554
 IC50 4.54 4.54 28719.5 1
CAS-1
CHEMBL2366100
 IC50 4.54 4.54 28629.4 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 46862.0 ng.hr.mL-1 Rattus norvegicus
AUC 52523.0 ng.hr.mL-1 Rattus norvegicus
AUC 10597.0 ng.hr.mL-1 Rattus norvegicus
AUC 338278.68 ng.hr.mL-1 Mus musculus
AUC - - Mus musculus
AUC 216201.39 ng.hr.mL-1 Homo sapiens
CL 0.945 mL.min-1.kg-1 Rattus norvegicus
CL 0.84 mL.min-1.kg-1 Rattus norvegicus
CL 3.75 mL.min-1.kg-1 Rattus norvegicus
CL 0.32 L/hr Homo sapiens
Cmax 3278.5 nM Rattus norvegicus
Cmax 4630.79 nM Rattus norvegicus
Cmax 745.85 nM Rattus norvegicus
Cmax 110000.0 nM Mus musculus
Cmax 1784.47 nM Homo sapiens
Cmax 1970.0 nM Homo sapiens
Css 8.939 mcg/mL Homo sapiens
T1/2 22.3 hr Rattus norvegicus
T1/2 23.4 hr Rattus norvegicus
T1/2 27.8 hr Rattus norvegicus
T1/2 139.2 hr Homo sapiens
Tmax 0.5 hr Mus musculus
Tmax 31.3 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Androgen receptor Ki = 11.0 nM 7.96 Binding affinity to Androgen receptor (unknown origin) assessed as inhibition co... 35063736
Androgen receptor Ki = 14.0 nM 7.85 Inhibition of rat AR 16420057
Androgen receptor Ki = 19.0 nM 7.72 Inhibition of human AR 16420057
Androgen receptor IC50 = 25.0 nM 7.6 Displacement of [3H]testosterone from androgen receptor in Sprague-Dawley rat pr... 21944856
Androgen receptor EC50 = 31.0 nM 7.51 Displacement of [3H]R1881 from AR in human MDA-MB-453 cells 23713567
Androgen receptor Ki = 35.0 nM 7.46 Inhibition of [3H]-DHT binding to T877A androgen receptor of LNCaP cells 15603960
Androgen receptor Ki = 35.0 nM 7.46 Binding affinity for mutant T877A Androgen receptor in human LNCaP cells 15603938
Androgen receptor Ki = 40.0 nM 7.4 Androgen Receptor Binding Assay: Androgen receptor (AR) binding affinities of te... -
Liver IC50 = 48.9 nM 7.31 Induction of mitochondrial dysfunction in Sprague-Dawley rat liver mitochondria ... 24799086
Androgen receptor IC50 = 54.0 nM 7.27 Displacement of [3H]testosterone from Sprague-Dawley rat AR by liquid scintillat... 21349712
Androgen receptor IC50 = 54.0 nM 7.27 Displacement of [17-alpha-methyl-3H]-mibolerone from human androgen receptor exp... 22094279
Androgen receptor IC50 = 54.0 nM 7.27 Displacement of [17-alpha-methyl-3H]mibolerone from androgen receptor expressed ... 22391033
Androgen receptor IC50 = 54.0 nM 7.27 Inhibition of wild type Androgen receptor (unknown origin) expressed in Freestyl... 23199477
Androgen receptor Ki = 64.0 nM 7.19 Inhibition of [3H]DHT binding to androgen receptor of MDA-453 cells 15603960
Androgen receptor Ki = 64.0 nM 7.19 Binding affinity for androgen receptor in human MDA-453 cells 15603938
Androgen receptor Ki = 65.0 nM 7.19 Displacement of [3H]DHT from androgen receptor of human MDA-453 cells 15546739
Androgen receptor Ki = 64.0 nM 7.19 Displacement of [3H]DHT from human androgen receptor in MDA453 cells 18291644
Androgen receptor Ki = 64.0 nM 7.19 Displacement of [3H]-DHT from androgen receptor in human MDA-MB-453 cells after ... 26288692
Androgen receptor Ki = 64.0 nM 7.19 Displacement of [3H]DHT from AR in human MDA-MB-453 cells 20584610
Androgen receptor Ki = 82.0 nM 7.09 Binding affinity against Androgen receptor transfected into COS cells 9871534

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 87
31158845 10.1038/s41586-019-1291-3 ADMET 65
16472241 10.2174/1570163043334794 Hepatotoxicity 18
16420057 10.1021/jm050293c Rattus norvegicus 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
22094279 10.1016/j.bmc.2011.10.067 Androgen receptor 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
18442912 10.1016/j.bmcl.2008.03.085 Androgen receptor 7
3361581 10.1021/jm00400a011 Rattus norvegicus 6
23199477 10.1016/j.bmc.2012.11.001 Androgen receptor 6
22391033 10.1016/j.bmc.2012.02.005 Androgen receptor 6
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 6
22175694 10.1021/jm2015292 Androgen receptor 6
15603938 10.1016/j.bmcl.2004.10.085 Androgen receptor 5
15603960 10.1016/j.bmcl.2004.10.051 Androgen receptor 5
22094279 10.1016/j.bmc.2011.10.067 NON-PROTEIN TARGET 5
20381361 10.1016/j.bmc.2010.03.036 Androgen receptor 5
10230628 10.1016/s0960-894x(99)00118-3 Androgen receptor 5
9871534 10.1016/s0960-894x(98)00107-3 Androgen receptor 5

Data from ChEMBL 36 via Core Engine