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Compound Detail

CHEMBL254328

ABIRATERONE
🧪 Phase III
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🧪 Phase III
C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(c3cccnc3)=CC[C@@H]12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL254328
Name ABIRATERONE
Phase Phase III
Structure Type MOL
InChI Key GZOSMCIZMLWJML-VJLLXTKPSA-N
Therapeutic ✓ Yes

Known Names

Abiraterona Abiraterone CB 7598 CB-7598 NSC-741232 Zytiga
17
Targets
66
Activities
1
Assay Types
8
PK Parameters
20
Publications
6
Known Names
7
Indications
3
Mechanisms

Molecular Properties

349.5
MW (Da)
5.40
ALogP
2
HBA
1
HBD
33.1
PSA (Ų)
0.69
QED
1
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product First in Class
USAN Stem -terone

Extended Properties

Molecular Formula C24H31NO
MW 349.52
Aromatic Rings 1
Heavy Atoms 26
NP-Likeness 1.82

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cytochrome P450 17A1 inhibitor INHIBITOR Steroid 17-alpha-hydroxylase/17,20 lyase ✓ ✓
Androgen Receptor antagonist ANTAGONIST Androgen receptor ✓ ✓
Steroid 5-alpha-reductase inhibitor INHIBITOR Steroid 5-alpha-reductase ✓ ✓

Indications

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

ATC Classification

L02BX03
abiraterone
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ENDOCRINE THERAPY

Activity Summary

IC50 66 meas. best 8.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Steroid 17-alpha-hydroxylase/17,20 lyase
CHEMBL3522
 IC50 8.7 7.4296 2.0 26
Steroid 17-alpha-hydroxylase/17,20 lyase
CHEMBL4430
 IC50 7.9 7.5175 12.5 4
Steroid 21-hydroxylase
CHEMBL2759
 IC50 7.49 6.85 32.4 3
Cytochrome P450 3A4
CHEMBL340
 IC50 6.64 5.7483 230.0 6
Cytochrome P450 11B1, mitochondrial
CHEMBL1908
 IC50 5.79 5.79 1608.0 4
Cytochrome P450 11B2, mitochondrial
CHEMBL2722
 IC50 5.76 5.76 1750.0 3
LNCaP
CHEMBL612518
 IC50 5.57 5.525 2706.0 2
PC-3
CHEMBL390
 IC50 5.23 4.765 5940.0 4
MGC-803
CHEMBL3706566
 IC50 5.11 5.11 7720.0 1
CWR22R
CHEMBL612657
 IC50 5.04 5.04 9090.0 1
GES1
CHEMBL4296415
 IC50 4.88 4.88 13120.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.77 4.7225 16900.0 4
HeLa
CHEMBL399
 IC50 4.77 4.77 16900.0 1
T47D
CHEMBL614361
 IC50 4.46 4.46 34700.0 1
MCF7
CHEMBL387
 IC50 4.42 4.42 38200.0 1
HepG2
CHEMBL395
 IC50 4.22 4.22 59800.0 1
SK-OV-3
CHEMBL614925
 IC50 4.22 4.22 59500.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 4015.0 ng.hr.mL-1 Rattus norvegicus
CL 186.83 mL.min-1.kg-1 Rattus norvegicus
CL 54.95 uL.min-1.(10^6cells)-1 Homo sapiens
Cmax 1693.75 nM Rattus norvegicus
Cmax 90.0 nM Homo sapiens
T1/2 1.6 hr Rattus norvegicus
T1/2 0.01667 hr Homo sapiens
Tmax 2.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 2.0 nM 8.7 Inhibition of human recombinant CYP17A1 incubated for 5 mins in presence of NADP... 36070471
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 2.0 nM 8.7 Inhibition of recombinant human CYP17A1 using progesterone as substrate incubate... 37458396
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 2.9 nM 8.54 Ability to inhibit the C17,20-lyase enzyme by 50% using 17-alpha-hydroxyprogeste... 7608911
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 4.0 nM 8.4 Inhibition of human progesterone 17-alpha-hydroxylase. 9876107
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 4.0 nM 8.4 Ability to inhibit the Steroid 17-alpha-hydroxylase/17,20 lyase enzyme by 50%. 7608911
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 4.94 nM 8.31 Inhibition of C-terminal His-tagged recombinant human CYP17A1delta19H mutant exp... 29792703
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 5.0 nM 8.3 Irreversible inhibition of human cytochrome P450 17alpha -
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 9.4 nM 8.03 Inhibition of C-terminal His-tagged recombinant human CYP17A1delta19H mutant exp... 29792703
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 12.5 nM 7.9 Inhibition of Wistar rat testicular C17,20-lyase using [3H]17-hydroxyprogesteron... 24211641
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 12.5 nM 7.9 Inhibition of Wistar rat testicular C17,20-lyase assessed as androst-4-ene-3,17-... 27209562
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 24.7 nM 7.61 Inhibition of CYP17 in Sprague-Dawley rat testes microsomes using 17-alpha hydro... 28350999
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 29.0 nM 7.54 Inhibitory Activity Assay: The inhibition of CYP17A1 by the test compounds was e... -
Steroid 21-hydroxylase IC50 = 32.4 nM 7.49 Inhibition of C-terminal His-tagged recombinant human CYP21A2deltaH mutant expre... 29792703
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 35.8 nM 7.45 Inhibition of recombinant human CYP17 expressed in human A549 cell membranes usi... 28350999
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 48.0 nM 7.32 Inhibition of CYP17 (unknown origin) 27437082
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 72.0 nM 7.14 Inhibition of human CYP17 expressed in Escherichia coli 20684610
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 72.0 nM 7.14 Inhibition of human CYP17 expressed in Escherichia coli using progesterone subst... 22788843
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 72.0 nM 7.14 Inhibition of human recombinant CYP17 expressed in Escherichia coli coexpressing... 18672868
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 72.0 nM 7.14 Inhibition of human CYP17 expressed in Escherichia coli co-expressing rat NADPH-... 23363058
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 72.0 nM 7.14 Inhibition of human CYP17 expressed in Escherichia coli using 1,2[3H]-progestero... 23859149

Literature References

PubMed DOI Target Context # Activities
27209562 10.1016/j.ejmech.2016.05.006 NON-PROTEIN TARGET 12
35244402 10.1021/acs.jmedchem.1c02113 LNCaP 8
32847363 10.1021/acs.jmedchem.0c00939 CWR22R 6
38467086 10.1016/j.ejmech.2024.116296 B16 5
18061460 10.1016/j.bmc.2007.10.094 Rattus norvegicus 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
28350999 10.1016/j.ejmech.2017.03.037 Steroid 17-alpha-hydroxylase/17,20 lyase 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
18061460 10.1016/j.bmc.2007.10.094 Cytochrome P450 2B6 2
18061460 10.1016/j.bmc.2007.10.094 Cytochrome P450 2C19 2
18061460 10.1016/j.bmc.2007.10.094 Cytochrome P450 2C9 2
18024111 10.1016/j.bmcl.2007.10.079 Cytochrome P450 3A4 2
18024111 10.1016/j.bmcl.2007.10.079 Cytochrome P450 2C19 2
18024111 10.1016/j.bmcl.2007.10.079 Cytochrome P450 2C9 2
18024111 10.1016/j.bmcl.2007.10.079 Cytochrome P450 1A2 2
15828836 10.1021/jm040202w Unchecked 2
28350999 10.1016/j.ejmech.2017.03.037 Cytochrome P450 2D6 2
28350999 10.1016/j.ejmech.2017.03.037 Cytochrome P450 1A2 2
7608911 10.1021/jm00013a022 Steroid 17-alpha-hydroxylase/17,20 lyase 2
28350999 10.1016/j.ejmech.2017.03.037 Cytochrome P450 2C19 2

Data from ChEMBL 36 via Core Engine