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Compound Detail

CHEMBL1274

NILUTAMIDE
💊 Approved Drug
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💊 Approved Drug
CC1(C)NC(=O)N(c2ccc([N+](=O)[O-])c(C(F)(F)F)c2)C1=O

Basic Information

ChEMBL ID CHEMBL1274
Name NILUTAMIDE
Phase Approved
Structure Type MOL
InChI Key XWXYUMMDTVBTOU-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Anadron Nilandron Nilutamida Nilutamide NSC-758683 RU 23908 RU-23908
3
Targets
6
Activities
1
Assay Types
2
PK Parameters
20
Publications
7
Known Names
5
Indications
1
Mechanisms

Molecular Properties

317.2
MW (Da)
2.45
ALogP
4
HBA
1
HBD
92.5
PSA (Ų)
0.51
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1996
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning
USAN Stem -lutamide
USAN Year 1995

Extended Properties

Molecular Formula C12H10F3N3O4
MW 317.22
Aromatic Rings 1
Heavy Atoms 22
NP-Likeness -1.46

Mechanism of Action

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

Indications

Neoplasms Prostatic Neoplasms Prostatic Neoplasms Prostatic Neoplasms Prostatic Neoplasms, Castration-Resistant

ATC Classification

L02BB02
nilutamide
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ENDOCRINE THERAPY

Drug Warnings

Black Box Warning
respiratory toxicity
Country: United States

Activity Summary

IC50 6 meas. best 8.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Androgen receptor
CHEMBL1871
IC50 8.05 6.905 9.0 4
ZR-75-1
CHEMBL614393
IC50 7.12 7.12 75.0 1
T47D
CHEMBL614361
IC50 7.06 7.06 87.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 7.0 mL.min-1.g-1 Homo sapiens
CL 7.0 mL.min-1.g-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
37468498 10.1038/s41467-023-40064-9 Androgen receptor 4
27933964 10.1021/acs.jmedchem.6b01410 No relevant target 3
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 3
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Sodium-dependent dopamine transporter 2
22931300 10.1021/tx300075j Liver microsomes 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2

Data from ChEMBL 36 via Core Engine