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Compound Detail

CHEMBL271227

ABIRATERONE ACETATE
💊 Approved Drug
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💊 Approved Drug
CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(c4cccnc4)=CC[C@@H]32)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL271227
Name ABIRATERONE ACETATE
Phase Approved
Structure Type MOL
InChI Key UVIQSJCZCSLXRZ-UBUQANBQSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL254328

Known Names

Abiraterone accord Abiraterone acetate Abiraterone acetate component of akeega Abiraterone krka Abiraterone mylan CB-7630 CB7630 NSC-748121 NSC-749227 Yonsa Zytiga
6
Targets
9
Activities
2
Assay Types
7
PK Parameters
20
Publications
11
Known Names
12
Indications
1
Mechanisms

Molecular Properties

391.6
MW (Da)
5.97
ALogP
3
HBA
0
HBD
39.2
PSA (Ų)
0.46
QED
1
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2011
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product First in Class Prodrug
USAN Stem -terone
USAN Year 2009

Extended Properties

Molecular Formula C26H33NO2
MW 391.56
Aromatic Rings 1
Heavy Atoms 29
NP-Likeness 1.71

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cytochrome P450 17A1 inhibitor INHIBITOR Steroid 17-alpha-hydroxylase/17,20 lyase ✓ ✓

Indications

Prostatic Neoplasms Prostatic Neoplasms Prostatic Neoplasms Prostatic Neoplasms Breast Neoplasms Adrenal Hyperplasia, Congenital Adrenal Hyperplasia, Congenital Salivary Gland Neoplasms Carcinoma, Non-Small-Cell Lung Liver Diseases Neoplasms Renal Insufficiency

Activity Summary

IC50 8 meas. best 8.6
EC50 1 meas. best 4.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Steroid 17-alpha-hydroxylase/17,20 lyase
CHEMBL3522
 IC50 8.6 7.985 2.5 4
Androgen receptor
CHEMBL1871
 EC50 4.77 4.77 17050.0 1
B16
CHEMBL381
 IC50 4.54 4.54 28740.0 1
T47D
CHEMBL614361
 IC50 4.46 4.46 34660.0 1
PC-3
CHEMBL390
 IC50 4.42 4.42 37610.0 1
SK-OV-3
CHEMBL614925
 IC50 4.29 4.29 51510.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 4015.0 ng.hr.mL-1 Rattus norvegicus
CL 186.67 mL.min-1.kg-1 Rattus norvegicus
Cmax 1511.9 nM Rattus norvegicus
Cmax 1739.2 nM Mus musculus
T1/2 1.6 hr Rattus norvegicus
Tmax 2.0 hr Rattus norvegicus
Tmax 4.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 2.5 nM 8.6 Inhibition of human CYP17A1 17-alpha hydroxylase activity 37948954
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 15.0 nM 7.82 Inhibition of human CYP17A1 17,20 lyase activity 37948954
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 17.0 nM 7.77 Ability to inhibit the C17,20-lyase enzyme by 50% using 17-alpha-hydroxyprogeste... 7608911
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 18.0 nM 7.75 Ability to inhibit the Steroid 17-alpha-hydroxylase/17,20 lyase enzyme by 50%. 7608911
Androgen receptor EC50 = 17050.0 nM 4.77 Antagonist activity at full length human androgen receptor expressed in mammalia... 28385503
B16 IC50 = 28740.0 nM 4.54 Antiproliferative activity against mouse B16 cells measured after 48 hrs by MTT ... 38467086
T47D IC50 = 34660.0 nM 4.46 Antiproliferative activity against human T47D cells assessed as inhibition of ce... 35244394
PC-3 IC50 = 37610.0 nM 4.42 Antiproliferative activity against human PC-3 cells assessed as inhibition of ce... 35244394
SK-OV-3 IC50 = 51510.0 nM 4.29 Antiproliferative activity against human SK-OV-3 cells assessed as inhibition of... 35244394

Literature References

PubMed DOI Target Context # Activities
38467086 10.1016/j.ejmech.2024.116296 Unchecked 12
18674917 10.1016/j.bmc.2008.07.011 Rattus norvegicus 11
38467086 10.1016/j.ejmech.2024.116296 B16 10
18061460 10.1016/j.bmc.2007.10.094 Rattus norvegicus 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
38467086 10.1016/j.ejmech.2024.116296 ADMET 3
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 Beta-2 adrenergic receptor 2
7608911 10.1021/jm00013a022 Steroid 17-alpha-hydroxylase/17,20 lyase 2
37468498 10.1038/s41467-023-40064-9 Glucocorticoid receptor 2
37468498 10.1038/s41467-023-40064-9 Peroxisome proliferator-activated receptor gamma 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 Vero C1008 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
24775307 10.1016/j.bmcl.2014.04.024 Hamster 2

Data from ChEMBL 36 via Core Engine