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Compound Detail

CHEMBL1921976

ORTERONEL
🧪 Phase III
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🧪 Phase III
CNC(=O)c1ccc2cc([C@@]3(O)CCn4cncc43)ccc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1921976
Name ORTERONEL
Phase Phase III
Structure Type MOL
InChI Key OZPFIJIOIVJZMN-SFHVURJKSA-N

Known Names

Orteronel TAK-700
5
Targets
10
Activities
2
Assay Types
0
PK Parameters
16
Publications
2
Known Names
4
Indications
1
Mechanisms

Molecular Properties

307.4
MW (Da)
2.04
ALogP
4
HBA
2
HBD
67.2
PSA (Ų)
0.76
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Year 2011

Extended Properties

Molecular Formula C18H17N3O2
MW 307.35
Aromatic Rings 3
Heavy Atoms 23
NP-Likeness -0.23

Mechanism of Action

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

Indications

Prostatic Neoplasms, Castration-Resistant Breast Neoplasms Neoplasms Prostatic Neoplasms

Activity Summary

IC50 9 meas. best 8.4
Kd 1 meas. best 7.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Steroid 21-hydroxylase
CHEMBL2759
 IC50 8.4 6.855 4.0 2
Steroid 17-alpha-hydroxylase/17,20 lyase
CHEMBL3522
 IC50 8.4 7.005 4.0 4
Steroid 17-alpha-hydroxylase/17,20 lyase
CHEMBL3522
 Kd 7.4 7.4 40.0 1
Steroid 17-alpha-hydroxylase/17,20 lyase
CHEMBL4430
 IC50 7.32 7.32 48.0 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 4.85 4.85 14000.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 4.55 4.55 28000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 4.0 nM 8.4 Enzyme Activity Assay: Complementary assays were utilized for the quantitative c... -
Steroid 21-hydroxylase IC50 = 4.0 nM 8.4 Enzyme Activity Assay: Complementary assays were utilized for the quantitative c... -
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 19.0 nM 7.72 Inhibition of 17,20-lyase of recombinant human CYP17A1 using [1,2-3H]-17a-hydrox... 21978946
Steroid 17-alpha-hydroxylase/17,20 lyase Kd = 40.0 nM 7.4 Binding affinity human CYP17A1 32223238
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 48.0 nM 7.32 Inhibition of 17,20-lyase activity of Sprague-Dawley rat testicular microsomal C... 21978946
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 270.0 nM 6.57 Inhibition of human CYP17A1 32223238
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 4730.0 nM 5.33 Inhibition of human membrane bound C-terminal His4-tagged CYP17A1 delta19H mutan... -
Steroid 21-hydroxylase IC50 = 4870.0 nM 5.31 Inhibition of human membrane bound C-terminal His4-tagged CYP21A2 delta19H mutan... -
Cytochrome P450 2C19 IC50 = 14000.0 nM 4.85 Inhibition of human B-lymphoblastoid cell microsomal CYP2C19 assessed as (S)-mep... 21978946
Cytochrome P450 1A2 IC50 = 28000.0 nM 4.55 Inhibition of human B-lymphoblastoid cell microsomal CYP1A2 assessed as 7-ethoxy... 21978946

Literature References

PubMed DOI Target Context # Activities
32223238 10.1021/acs.jmedchem.9b01849 Steroid 17-alpha-hydroxylase/17,20 lyase 17
21978946 10.1016/j.bmc.2011.08.066 Cynomolgus monkey 8
21978946 10.1016/j.bmc.2011.08.066 Steroid 17-alpha-hydroxylase/17,20 lyase 2
21978946 10.1016/j.bmc.2011.08.066 Cytochrome P450 3A4 2
21978946 10.1016/j.bmc.2011.08.066 Cytochrome P450 2C9 2
21978946 10.1016/j.bmc.2011.08.066 Unchecked 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
21978946 10.1016/j.bmc.2011.08.066 ADMET 1
21978946 10.1016/j.bmc.2011.08.066 Cytochrome P450 1A2 1
21978946 10.1016/j.bmc.2011.08.066 Cytochrome P450 2A6 1
21978946 10.1016/j.bmc.2011.08.066 Cytochrome P450 2B6 1
21978946 10.1016/j.bmc.2011.08.066 Cytochrome P450 2C8 1
21978946 10.1016/j.bmc.2011.08.066 Cytochrome P450 2C19 1
21978946 10.1016/j.bmc.2011.08.066 Cytochrome P450 2D6 1
21978946 10.1016/j.bmc.2011.08.066 Cytochrome P450 2E1 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1

Data from ChEMBL 36 via Core Engine