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Compound Detail

CHEMBL491

HYDROXYFLUTAMIDE
🧪 Phase II
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🧪 Phase II
CC(C)(O)C(=O)Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL491
Name HYDROXYFLUTAMIDE
Phase Phase II
Structure Type MOL
InChI Key YPQLFJODEKMJEF-UHFFFAOYSA-N

Known Names

.alpha.-hydroxyflutamide 2-hydroxyflutamide Hydroxy-flutamide Hydroxyflutamide
8
Targets
40
Activities
3
Assay Types
0
PK Parameters
20
Publications
4
Known Names
1
Indications

Molecular Properties

292.2
MW (Da)
2.32
ALogP
4
HBA
2
HBD
92.5
PSA (Ų)
0.66
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral
USAN Stem -lutamide

Extended Properties

Molecular Formula C11H11F3N2O4
MW 292.21
Aromatic Rings 1
Heavy Atoms 20
NP-Likeness -1.19

Indications

Prostatic Neoplasms, Castration-Resistant

Activity Summary

IC50 28 meas. best 7.82
Ki 11 meas. best 8.7
EC50 1 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Androgen receptor
CHEMBL1871
 Ki 8.7 7.7156 2.0 9
Androgen receptor
CHEMBL1871
 IC50 7.82 6.9111 15.0 18
T47D
CHEMBL614361
 IC50 7.35 7.35 45.0 1
Unchecked
CHEMBL612545
 Ki 7.3 7.3 50.1 1
Androgen receptor
CHEMBL3056
 IC50 7.28 6.6825 52.0 4
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.28 7.28 52.5 1
Unchecked
CHEMBL612545
 IC50 7.08 7.005 84.0 2
Unchecked
CHEMBL612545
 EC50 7.0 7.0 100.0 1
SC-3
CHEMBL614897
 IC50 6.62 6.62 240.0 1
Progesterone receptor
CHEMBL208
 IC50 5.7 5.7 2013.0 1
Androgen receptor
CHEMBL3072
 Ki 5.68 5.68 2100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Androgen receptor Ki = 2.0 nM 8.7 Inhibition of [3H]-DHT binding to T877A androgen receptor of LNCaP cells 15603960
Androgen receptor Ki = 2.0 nM 8.7 Binding affinity for mutant T877A Androgen receptor in human LNCaP cells 15603938
Androgen receptor Ki = 3.0 nM 8.52 Displacement of [3H]testosterone from human recombinant androgen receptor T877A ... 18571420
Androgen receptor IC50 = 15.0 nM 7.82 Antagonistic activity against human androgen receptor (hAR) in co-transfected CV... 9484511
Androgen receptor IC50 = 25.0 nM 7.6 Antagonist activity at androgen receptor ligand binding domain expressed in afri... 19863083
Androgen receptor IC50 = 26.0 nM 7.58 Antagonist activity at human androgen receptor in MDA453 cells by alkaline phosp... 18291644
Androgen receptor IC50 = 26.0 nM 7.58 Inhibition of human androgen receptor of breast carcinoma MDA-453 cells in repor... 15603960
Androgen receptor IC50 = 26.0 nM 7.58 Inhibition of androgen receptor in human MDA-453 cells 15603938
Androgen receptor Ki = 27.0 nM 7.57 Binding affinity for human androgen receptor in transiently-transfected COS-1 ce... 9484511
Androgen receptor IC50 = 31.0 nM 7.51 Antagonist activity at androgen receptor expressed in HeLa cells assessed as inh... 17064916
Androgen receptor IC50 = 31.0 nM 7.51 Antagonist activity at human androgen receptor expressed in HeLa cells assessed ... 17804229
Androgen receptor Ki = 34.0 nM 7.47 Binding affinity for human androgen receptor transfected into mammalian COS-1 ce... 10743937
Androgen receptor Ki = 43.0 nM 7.37 Inhibition of [3H]DHT binding to androgen receptor of MDA-453 cells 15603960
Androgen receptor Ki = 43.0 nM 7.37 Binding affinity for androgen receptor in human MDA-453 cells 15603938
Androgen receptor Ki = 43.0 nM 7.37 Displacement of [3H]DHT from human androgen receptor in MDA453 cells 18291644
Androgen receptor IC50 = 43.0 nM 7.37 Inhibitory concentration against human androgen receptor (AR) dependent transcri... 10743937
T47D IC50 = 45.0 nM 7.35 Antiproliferative activity against human T47D cells 35786895
Unchecked Ki = 50.12 nM 7.3 Binding affinity to androgen receptor in hamster DDT cells by scintillation coun... 19856921
Androgen receptor IC50 = 52.0 nM 7.28 In vitro inhibition of DHT (dihydrotestosterone) on proliferation of androgen-se... 7707319
NON-PROTEIN TARGET IC50 = 52.5 nM 7.28 Concentration required for inhibition of 5-alpha-Dihydrotestosterone (DHT) stimu... -

Literature References

PubMed DOI Target Context # Activities
15603938 10.1016/j.bmcl.2004.10.085 Androgen receptor 5
15603960 10.1016/j.bmcl.2004.10.051 Androgen receptor 5
18571420 10.1016/j.bmc.2008.05.063 Androgen receptor 4
26295173 10.1016/j.ejmech.2015.08.002 Androgen receptor 4
19856921 10.1021/jm901149c Unchecked 4
17804229 10.1016/j.bmcl.2007.07.090 Mus musculus 3
17804229 10.1016/j.bmcl.2007.07.090 Androgen receptor 3
17336533 10.1016/j.bmc.2007.02.007 Unchecked 3
17064916 10.1016/j.bmc.2006.09.072 Androgen receptor 3
24900588 10.1021/ml4001744 Androgen receptor 3
2374140 10.1021/jm00170a008 Androgen receptor 3
18472187 10.1016/j.ejmech.2008.03.020 NON-PROTEIN TARGET 3
10743937 10.1016/s0960-894x(00)00010-x Androgen receptor 3
9484511 10.1021/jm970699s Androgen receptor 3
1588549 10.1021/jm00088a001 Androgen receptor 3
22746350 10.1021/jm300233k Androgen receptor 3
18707892 10.1016/j.bmc.2008.07.055 Androgen receptor 2
1992146 10.1021/jm00105a067 No relevant target 2
1992146 10.1021/jm00105a067 Androgen receptor 2
19725582 10.1021/jm801218k Androgen receptor 2

Data from ChEMBL 36 via Core Engine