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Compound Detail

CHEMBL806

FLUTAMIDE
💊 Approved Drug
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💊 Approved Drug
CC(C)C(=O)Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL806
Name FLUTAMIDE
Phase Approved
Structure Type MOL
InChI Key MKXKFYHWDHIYRV-UHFFFAOYSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL491

Known Names

Chimax Drogenil Eulexin Flutamida Flutamide NSC-215876 SCH 13521 SCH-13521
17
Targets
48
Activities
3
Assay Types
30
PK Parameters
20
Publications
8
Known Names
8
Indications
1
Mechanisms

Molecular Properties

276.2
MW (Da)
3.21
ALogP
3
HBA
1
HBD
72.2
PSA (Ų)
0.68
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1989
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Prodrug
USAN Stem -lutamide
USAN Year 1975

Extended Properties

Molecular Formula C11H11F3N2O3
MW 276.21
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness -1.76

Mechanism of Action

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

Indications

Carcinoma Neoplasms Prostatic Neoplasms Prostatic Neoplasms Prostatic Neoplasms Prostatic Neoplasms, Castration-Resistant Ovarian Neoplasms Polycystic Ovary Syndrome

ATC Classification

L02BB01
flutamide
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ENDOCRINE THERAPY

Drug Warnings

Black Box Warning
hepatotoxicity
Country: United States
Black Box Warning
vascular toxicity
Country: United States
Black Box Warning
dermatological toxicity
Country: United States
Black Box Warning
immune system toxicity
Country: United States
Black Box Warning
nephrotoxicity
Country: United States

Activity Summary

IC50 34 meas. best 7.24
Ki 11 meas. best 7.26
EC50 3 meas. best 5.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Androgen receptor
CHEMBL1871
 Ki 7.26 6.1933 55.0 3
Liver
CHEMBL613642
 IC50 7.24 7.24 57.6 1
Androgen receptor
CHEMBL1871
 IC50 6.81 6.1567 154.0 6
Unchecked
CHEMBL612545
 Ki 6.4 6.3 398.1 2
Arylacetamide deacetylase
CHEMBL3509584
 Ki 6.22 5.535 600.0 2
SC-3
CHEMBL614897
 IC50 6.14 6.14 720.0 1
LNCaP
CHEMBL612518
 IC50 6.05 4.82 900.0 3
5-hydroxytryptamine receptor 4
CHEMBL5017
 Ki 5.65 5.65 2258.0 1
Cocaine esterase
CHEMBL3180
 Ki 5.64 5.64 2300.0 1
LNCaP
CHEMBL612518
 EC50 5.16 5.16 7000.0 2
5-hydroxytryptamine receptor 6
CHEMBL3371
 Ki 5.08 5.08 8271.0 1
Androgen receptor
CHEMBL3072
 Ki 5.05 5.05 8927.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.0 4.925 10000.0 4
Unchecked
CHEMBL612545
 IC50 4.96 4.95 10985.0 2
5-hydroxytryptamine receptor 4
CHEMBL5017
 IC50 4.87 4.87 13545.0 1
Androgen receptor
CHEMBL3072
 IC50 4.87 4.87 13390.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
 IC50 4.75 4.75 17814.0 1
Unchecked
CHEMBL612545
 EC50 4.7 4.7 19952.6 1
PC-3
CHEMBL390
 IC50 4.69 4.275 20300.0 4
U-251
CHEMBL615022
 IC50 4.66 4.66 22110.0 1
K562
CHEMBL385
 IC50 4.54 4.54 29200.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.3 4.2025 50000.0 4
COS-7
CHEMBL614564
 IC50 4.29 4.29 51510.0 1
Bile salt export pump
CHEMBL2073674
 IC50 4.1 4.1 78700.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 96.4 ng.hr.mL-1 Homo sapiens
AUC 96.4 ng.hr.mL-1 Homo sapiens
AUC 75.8 ng.hr.mL-1 Homo sapiens
AUC 5132.0 ng.hr.mL-1 Homo sapiens
AUC 5527.0 ng.hr.mL-1 Homo sapiens
AUC 5476.0 ng.hr.mL-1 Homo sapiens
AUC 5527.0 ng.hr.mL-1 Homo sapiens
AUC 59.8 ng.hr.mL-1 Homo sapiens
AUC 59.8 ng.hr.mL-1 Homo sapiens
AUC 32.5 ng.hr.mL-1 Homo sapiens
AUC 4663.0 ng.hr.mL-1 Homo sapiens
AUC 4993.0 ng.hr.mL-1 Homo sapiens
AUC 4928.0 ng.hr.mL-1 Homo sapiens
AUC 4993.0 ng.hr.mL-1 Homo sapiens
AUC 98.0 ng.hr.mL-1 Homo sapiens
AUC 98.0 ng.hr.mL-1 Homo sapiens
AUC 74.0 ng.hr.mL-1 Homo sapiens
AUC 6166.0 ng.hr.mL-1 Homo sapiens
AUC 6907.0 ng.hr.mL-1 Homo sapiens
AUC 6843.0 ng.hr.mL-1 Homo sapiens
AUC 6907.0 ng.hr.mL-1 Homo sapiens
AUC 107.0 ng.hr.mL-1 Homo sapiens
AUC 107.0 ng.hr.mL-1 Homo sapiens
AUC 79.0 ng.hr.mL-1 Homo sapiens
AUC 5821.0 ng.hr.mL-1 Homo sapiens
AUC 6499.0 ng.hr.mL-1 Homo sapiens
AUC 6435.0 ng.hr.mL-1 Homo sapiens
AUC 6499.0 ng.hr.mL-1 Homo sapiens
AUC 217.0 ng.hr.mL-1 Homo sapiens
AUC 217.0 ng.hr.mL-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Androgen receptor Ki = 55.0 nM 7.26 Binding affinity to androgen receptor (unknown origin) assessed as inhibition co... 37948954
Liver IC50 = 57.6 nM 7.24 Induction of mitochondrial dysfunction in Sprague-Dawley rat liver mitochondria ... 24799086
Androgen receptor IC50 = 154.0 nM 6.81 Inhibition of 1.0 nM [3H]mibolerone binding to human androgen receptor of PC3/AR... 14613328
Androgen receptor IC50 = 154.0 nM 6.81 Inhibition of [3H]mibolerone binding to human Androgen receptor of PC3/AR Cell L... 15509168
Unchecked Ki = 398.11 nM 6.4 Binding affinity to androgen receptor LBD T877A mutant in hamster DDT cells by s... 19856921
Androgen receptor IC50 = 580.0 nM 6.24 Antagonist activity at human androgen receptor expressed in mouse NIH3T3 cells a... 18707892
Arylacetamide deacetylase Ki = 600.0 nM 6.22 Inhibition of AADAC in human kidney microsome 22207054
Unchecked Ki = 630.96 nM 6.2 Binding affinity to androgen receptor in hamster DDT cells by scintillation coun... 19856921
SC-3 IC50 = 720.0 nM 6.14 Growth inhibition of mouse SC3 cells after 3 days by WST-8 assay 20521823
LNCaP IC50 = 900.0 nM 6.05 Anticancer activity against human LNCAP cells after 24 hrs by MTT assay in prese... 21600678
Androgen receptor IC50 = 1000.0 nM 6.0 Antagonist activity at AR in human MDA-kb2 cells co-transfected with MMTV-luc as... 20226658
Androgen receptor Ki = 1300.0 nM 5.89 Binding affinity against GST-hARLBD was measured in SC-3 cell by using [3H]testo... 12873487
Androgen receptor IC50 = 2000.0 nM 5.7 Antiandrogenic activity in human MDA-MB-453 cells expressing androgen receptor a... 19131248
5-hydroxytryptamine receptor 4 Ki = 2258.0 nM 5.65 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT4 radioligand binding (ligand: [... -
Cocaine esterase Ki = 2300.0 nM 5.64 Inhibition of human recombinant CES2 assessed as compound hydrolysis 22446520
Androgen receptor Ki = 3700.0 nM 5.43 Displacement of [3H]testosterone from wild type human androgen receptor 18571420
Androgen receptor IC50 = 4200.0 nM 5.38 Antagonist activity at wild type human recombinant androgen receptor assessed as... 18571420
LNCaP EC50 = 7000.0 nM 5.16 Cytotoxicity against human LNCAP cells assessed as reduction in cell viability a... -
LNCaP EC50 = 7000.0 nM 5.16 Cytotoxicity against human LNCAP cells after 24 hrs by MTT assay 28363155
5-hydroxytryptamine receptor 6 Ki = 8271.0 nM 5.08 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1446
- 10.6019/CHEMBL3885881 Rattus norvegicus 514
10073738 10.1046/j.1365-2125.1999.00831.x Homo sapiens 89
22207054 10.1124/dmd.111.043067 Arylacetamide deacetylase 34
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22446520 10.1124/dmd.112.044537 Cocaine esterase 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
10073738 10.1046/j.1365-2125.1999.00831.x ADMET 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
22446520 10.1124/dmd.112.044537 Arylacetamide deacetylase 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.1039/C6MD00426A Rattus norvegicus 7
20829430 10.1093/toxsci/kfq269 Bile salt export pump 6
3361581 10.1021/jm00400a011 Rattus norvegicus 6
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 5
22207054 10.1124/dmd.111.043067 ADMET 5
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 5
19856921 10.1021/jm901149c Unchecked 4
19734910 10.1038/nchembio.215 Plasmodium falciparum 4
32847363 10.1021/acs.jmedchem.0c00939 CWR22R 4

Data from ChEMBL 36 via Core Engine