BICALUTAMIDE

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category Free-form
ATC L02BB03
UNII A0Z3NAU9DP
EPA CompTox DTXSID2022678

Structure

InChI Key LKJPYSCBVHEWIU-UHFFFAOYSA-N
Smiles CC(O)(CS(=O)(=O)c1ccc(F)cc1)C(=O)Nc1ccc(C#N)c(C(F)(F)F)c1
InChI
InChI=1S/C18H14F4N2O4S/c1-17(26,10-29(27,28)14-6-3-12(19)4-7-14)16(25)24-13-5-2-11(9-23)15(8-13)18(20,21)22/h2-8,26H,10H2,1H3,(H,24,25)

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H14F4N2O4S
Molecular Weight 430.38
AlogP 2.88
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 5.0
Polar Surface Area 107.26
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 29.0

Bioactivity

Mechanism of Action Action Reference
Androgen Receptor antagonist ANTAGONIST DailyMed
Protein: Androgen Receptor
Description: Androgen receptor
Organism : Homo sapiens
P10275 ENSG00000169083
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- - - - 7
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 3
- 5600-5600 - 7200 -
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
31-4300 54-44260 - 19-160 16-84
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 29300-79600 - - -
Assay Description Organism Bioactivity Reference
In vitro antagonistic activity against human androgen receptor (hAR) expressed in CV-1 cells Homo sapiens 157.0 nM
Antagonistic activity (IC50) against human androgen receptor (hAR) in co-transfected CV-1 cell None 157.0 nM
Antagonistic activity against human androgen receptor (hAR) in co-transfected CV-1 cells. None 157.0 nM
In vitro agonistic activity against human androgen receptor (hAR) expressed in CV-1 cells; not active Homo sapiens 10.0 nM
In vitro binding affinity at human androgen receptor transfected into COS cells. None 117.0 nM
Inhibitory concentration against human androgen receptor (AR) dependent transcriptional activity in co-transfected mammalian CV-1 cells None 338.0 nM
Binding affinity against Androgen receptor transfected into COS cells None 82.0 nM
Binding affinity for human androgen receptor transfected into mammalian COS-1 cells None 117.0 nM
Binding affinity for human androgen receptor in transiently-transfected COS-1 cells. None 117.0 nM
In vivo binding affinity for rat ventral prostate androgen receptor by displacement of [3H]R-1881 Rattus norvegicus 330.0 nM
Binding affinity for androgen receptor in human MDA-453 cells Homo sapiens 64.0 nM
Inhibition of [3H]DHT binding to androgen receptor of MDA-453 cells Homo sapiens 64.0 nM
Inhibition of [3H]-DHT binding to T877A androgen receptor of LNCaP cells Homo sapiens 35.0 nM
Displacement of [3H]DHT from androgen receptor of human MDA-453 cells Homo sapiens 65.0 nM
Inhibition of androgen receptor in human MDA-453 cells Homo sapiens 173.0 nM
Displacement of [3H]R-1881 from Androgen receptor of LNCaP cells Homo sapiens 940.0 nM
In vitro antagonistic activity against androgen receptor of MDA-453 cells Homo sapiens 170.0 nM
In vitro antagonistic activity against mutant androgen receptor of LNCap cells Homo sapiens 400.0 nM
Inhibition of human androgen receptor of breast carcinoma MDA-453 cells in reporter gene assay Homo sapiens 173.0 nM
Inhibition of T877A androgen receptor of human prostate cancer cells in reporter gene assay Homo sapiens 400.0 nM
Inhibition of androgen dependent human prostate cancer cell MDA-MB-PCa2b proliferation Homo sapiens 725.0 nM
Inhibition of L701H/T877A mutant androgen receptor of human prostate cancer MDAMB-PCa2b cell proliferation Homo sapiens 725.0 nM
Binding affinity for mutant T877A Androgen receptor in human LNCaP cells Homo sapiens 35.0 nM
Inhibition of mutant T877A Androgen receptor in human LNCaP cells Homo sapiens 400.0 nM
Inhibition of AR mediated transcriptional activation using reporter assay Homo sapiens 890.0 nM
Effect on ventral prostate weight with reference to control in Wistar rat at 10 mg/kg/day, po Rattus norvegicus 45.0 %
Inhibition of human AR Homo sapiens 19.0 nM
Inhibition of rat AR Rattus norvegicus 14.0 nM
Inhibition of rat AR-mediated reporter gene expression in COS7 cells Rattus norvegicus 850.0 nM
Inhibition of prostate weight in Sprague-Dawley rat at 2 mg/day, po relative to control Rattus norvegicus 70.0 %
Inhibition of seminal vesicle weight in Sprague-Dawley rat at 2 mg/day, po relative to control Rattus norvegicus 80.0 %
Displacement of [3H]mibolerone from androgen receptor expressed in CHOK1 cells Homo sapiens 200.0 nM
Antagonist activity at androgen receptor expressed in HeLa cells assessed as inhibition of dihydrotestosterone-induced transcriptional activity by reporter gene assay Homo sapiens 140.0 nM
Antagonist activity at human androgen receptor expressed in CV1 cells Homo sapiens 162.0 nM
Binding affinity to human androgen receptor expressed in CV1 cells Homo sapiens 151.0 nM
Inhibition of testoterone-induced prostate weight in castrated immature Sprague-Dawley rat at 2 mg/day relative to control Rattus norvegicus 70.0 %
Displacement of [3H]mibolerone from human androgen receptor expressed in CHOK1 cells Homo sapiens 200.0 nM
Antagonist activity at human androgen receptor expressed in HeLa cells assessed as inhibition of dihydrotestosterone induced transcriptional activity by reporter gene assay Homo sapiens 140.0 nM
Inhibition of prostate weight in testosterone treated castrated immature Sprague-Dawley rat at 2 mg/day Rattus norvegicus 70.0 %
Displacement of [3H]DHT from human androgen receptor in MDA453 cells Homo sapiens 64.0 nM
Antagonist activity at human androgen receptor in MDA453 cells by alkaline phosphatase reporter gene assay Homo sapiens 173.0 nM
Antagonist activity at human androgen receptor african green monkey CV1 cells by cotransfection assay Homo sapiens 162.0 nM
Binding affinity to human androgen receptor expressed in monkey COS7 cells by whole cell binding assay Homo sapiens 151.0 nM
Activity at androgen receptor in human Saos2 cells assessed as IL6 repression Homo sapiens 232.0 nM
Antagonist activity at human androgen receptor in CV1 cells by transcriptional activation assay Homo sapiens 162.0 nM
Displacement of [3H]DHT from human Androgen receptor in human MDA-MB-453 cells Homo sapiens 151.0 nM
Displacement of [3H]mibolerone from human AR expressed in CHO-K1 cells after 2 hrs by scintillation counting Homo sapiens 200.0 nM
Antagonist activity at AR in bicalutamide-resistant human LNCAP cells assessed as effect on cell proliferation after 6 days Homo sapiens 550.0 nM
Displacement of [3H]DHT from AR in human MDA-MB-453 cells Homo sapiens 64.0 nM
Antagonist activity at human wild type AR expressed in human MDA-MB-435 cells by transactivation assay Homo sapiens 173.0 nM
Antagonist activity at wild type human AR expressed in human LNCAP cells by transactivation assay Homo sapiens 400.0 nM
Antagonist activity at human androgen receptor expressed in human CV1 cells assessed as inhibition of receptor-mediated transactivation by MMTV-luciferase reporter gene assay Homo sapiens 300.0 nM
Antiandrogen activity against androgen receptor in androgen-dependent mouse SC3 cells assessed as inhibition of testosterone-induced cell proliferation by WST1 assay Mus musculus 670.0 nM
Antagonist activity at human AR expressed in human HeLa cells co-transfected with MMTV-Luc-Hyg after 48 hrs by transient-luciferase reporter gene assay Homo sapiens 200.0 nM
Antagonist activity at AR in human bicalutamide-resistant LNCAP cells assessed as inhibition of cell proliferation after 6 days Homo sapiens 600.0 nM
Inhibition of human ERG at 10 uM by whole cell patch-clamp technique Homo sapiens 7.4 %
Displacement of [3H]testosterone from Sprague-Dawley rat AR by liquid scintillation counting Rattus norvegicus 54.0 nM
Antagonist activity at androgen receptor T877A mutant expressed in african green monkey CV1 cells assessed as inhibition of dihydrotestosterone-induced transcriptional activity at 1 to 1000 nM by luciferase reporter gene assay None 84.0 %
Displacement of [3H]testosterone from androgen receptor in Sprague-Dawley rat prostate gland after 2 hrs by liquid scintillation counting Rattus norvegicus 25.0 nM
Antagonist activity at human AR overexpressed in human LNCAP cells at 1 uM by luciferase reporter gene assay in the presence of agonist R1881 Homo sapiens 72.0 %
Antitumor activity against human LNCAP cells xenografted in athymic nude Harlan Sprague-Dawley mouse assessed as tumor volume inhibition at 10 mg/kg, po administered once daily for 5 weeks measured after 5 weeks relative to vehicle treated control Homo sapiens 41.0 %
Displacement of [17-alpha-methyl-3H]-mibolerone from human androgen receptor expressed in HEK293 derived FreeStyle293F cells after 3 hrs Homo sapiens 54.0 nM
Displacement of [17-alpha-methyl-3H]-mibolerone from human androgen receptor T877A mutant expressed in HEK293 derived FreeStyle293F cells after 3 hrs Homo sapiens 120.0 nM
Antagonist activity at human androgen receptor expressed in COS7 cells assessed as inhibition of DHT-induced luciferase activity after 24 hrs by reporter gene assay Homo sapiens 330.0 nM
Antagonist activity at human androgen receptor T877A mutant expressed in COS7 cells assessed as inhibition of DHT-induced luciferase activity after 24 hrs by reporter gene assay Homo sapiens 470.0 nM
Agonist activity at human androgen receptor W741C mutant expressed in COS7 cells assessed as luciferase activity after 24 hrs by reporter gene assay Homo sapiens 180.0 nM
Displacement of [17-alpha-methyl-3H]mibolerone from androgen receptor expressed in HEK293 cells after 3 hrs None 54.0 nM
Displacement of [17-alpha-methyl-3H]mibolerone from androgen receptor T877A mutant expressed in HEK293 cells after 3 hrs None 120.0 nM
Antagonist activity at androgen receptor expressed in Cos7 cells assessed as inhibition of dihydrotestosterone-induced luciferase activity after 24 hrs by reporter gene assay None 330.0 nM
Antagonist activity at androgen receptor T877A mutant expressed in Cos7 cells assessed as inhibition of dihydrotestosterone-induced luciferase activity after 24 hrs by reporter gene assay None 470.0 nM
Antagonist activity at Androgen receptor T877A mutant (unknown origin) expressed in human Cos-7 cells co-expressing pGL3-MMTV-luc vector assessed as luciferase activity by reporter gene assay Homo sapiens 470.0 nM
Antagonist activity at wild type Androgen receptor (unknown origin) expressed in human Cos-7 cells co-expressing pGL3-MMTV-luc vector assessed as luciferase activity by reporter gene assay Homo sapiens 330.0 nM
Inhibition of Androgen receptor T877A mutant (unknown origin) expressed in Freestyle293F cells Homo sapiens 120.0 nM
Inhibition of wild type Androgen receptor (unknown origin) expressed in Freestyle293F cells Homo sapiens 54.0 nM
SANGER: Inhibition of human HT-3 cell growth in a cell viability assay. Homo sapiens 731.34 nM
Displacement of [3H]R1881 from AR in human MDA-MB-453 cells Homo sapiens 31.0 nM
Inhibition of androgen receptor in human LNCAP cells after 1 day by luciferase reporter gene assay Homo sapiens 270.0 nM
Antagonist activity at androgen receptor T877A mutant (unknown origin) expressed in human LNCAP cells assessed as inhibition of DHT-induced cell growth after 6 days by WST-8 assay Homo sapiens 940.0 nM
Antagonist activity at androgen receptor in human LNCAP cells assessed as inhibition of androgen-stimulated cell growth at 20 uM measured every 3 days relative to dihydrotestosterone Homo sapiens 28.0 %
Antagonist activity at androgen receptor in human LNCAP cells assessed as inhibition of androgen-stimulated cell growth at 40 uM measured every 3 days relative to dihydrotestosterone Homo sapiens 33.0 %
Antagonist activity against pSG5-tagged human androgen receptor expressed in COS1 cells assessed as reduction in receptor-mediated transcriptional activity by AR-regulated rat probasin promoter fragment driven firefly luciferase reporter assay Homo sapiens 86.9 nM
Displacement of [3H]R1881 from pSG5-tagged human androgen receptor expressed in COS1 cells assessed as relative binding inhibition Homo sapiens 86.9 nM
Antagonist activity against pSG5-tagged human androgen receptor expressed in COS1 cells assessed as receptor-mediated testosterone-induced transcriptional activity at 10 uM by AR-regulated rat probasin promoter fragment driven firefly luciferase reporter assay (Rvb = 100 +/- 5.7%) Homo sapiens 15.5 %
Displacement of [3H]R1881 from androgen receptor in human LNCAP cells Homo sapiens 971.0 nM
Antiproliferative activity against human LNCAP cells after 3 days Homo sapiens 732.7 nM
Antagonist activity at androgen receptor (unknown origin) Homo sapiens 160.2 nM
Displacement of [3H]-DHT from androgen receptor in human MDA-MB-453 cells after 90 mins by TopCount analysis Homo sapiens 64.0 nM
Antagonist activity at androgen receptor in human MDA-MB-453 cells assessed as inhibition of DHT-induced PSA expression by alkaline phosphatase reporter gene assay Homo sapiens 173.0 nM
Reporter Assay: The compounds were subjected to tests using an artificial AR response reporter system in a hormone refractory prostate cancer cell line. In this system, the prostate cancer LNCaP cells were engineered to stably express about 5-fold higher level of AR than endogenous level. The exogenous AR has similar properties to endogenous AR in that both are stabilized by a synthetic androgen R1881. The AR-over expressed cells were also engineered to stably incorporate an AR response reporter and the reporter activity of these cells shows features of hormone refractory prostate cancer. Homo sapiens 889.0 nM
Induction of mitochondrial dysfunction in Sprague-Dawley rat liver mitochondria assessed as inhibition of mitochondrial respiration per mg mitochondrial protein measured for 20 mins by A65N-1 oxygen probe based fluorescence assay Rattus norvegicus 48.9 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus -1.51 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 6.59 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 7.16 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 4.08 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 15.75 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans -0.48 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -5.03 %
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 -1.9 %
Antagonist activity at GAL4-DBD fused rat androgen receptor expressed in UAS-bla 293 cells assessed as reduction in R1881-induced activation at 10 uM incubated for 16 hrs followed by fluorescence substrate addition and measured after 2 hrs by beta lactamase reporter gene assay relative to control Rattus norvegicus 83.0 %
Antagonist activity at GAL4-DBD fused rat androgen receptor expressed in UAS-bla 293 cells assessed as reduction in R1881-induced activation incubated for 16 hrs followed by fluorescence substrate addition and measured after 2 hrs by beta lactamase reporter gene assay Rattus norvegicus 490.0 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 5.174 %
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 -0.13 % 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 -0.13 %
Inhibition of [3H] MIB binding to rat prostate androgen receptor LBD by competitive binding assay Rattus norvegicus 509.0 nM
Antagonist activity at human androgen receptor expressed in HEK-293 cells harboring GRE-LUC and CMV-renilla luciferase assessed as inhibition of transactivation incubated for 24 hrs in presence of R1881 by dual luciferase assay Homo sapiens 248.0 nM

Environmental Exposure

Environmental Exposure Map
Countries
Sweden

Cross References

Resources Reference
ChEBI 144093
ChEMBL CHEMBL409
DrugBank DB01128
DrugCentral 367
FDA SRS A0Z3NAU9DP
Human Metabolome Database HMDB0015260
Guide to Pharmacology 2863
PDB 198
PharmGKB PA164746255
PubChem 2375
SureChEMBL SCHEMBL3611
ZINC ZINC00538564
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