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Compound Detail

CHEMBL4865865

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CN1CCC(Oc2ccc(N3C(=S)N(c4cnc(C#N)c(C(F)(F)F)c4)C(=O)C34CCC4)cc2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4865865
Phase Preclinical
Structure Type MOL
InChI Key IZKSMIBPGSWAMO-UHFFFAOYSA-N
3
Targets
11
Activities
2
Assay Types
6
PK Parameters
7
Publications
0
Known Names

Molecular Properties

515.6
MW (Da)
4.51
ALogP
6
HBA
0
HBD
72.7
PSA (Ų)
0.56
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H24F3N5O2S
MW 515.56
Aromatic Rings 2
Heavy Atoms 36
NP-Likeness -0.88

Activity Summary

IC50 9 meas. best 7.72
Ki 2 meas. best 8.08

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Androgen receptor
CHEMBL1871
 Ki 8.08 8.08 8.4 1
Androgen receptor
CHEMBL1871
 IC50 7.72 7.0133 19.0 6
VCaP
CHEMBL4296508
 IC50 7.04 7.04 92.0 2
Glucocorticoid receptor
CHEMBL2034
 Ki 5.0 5.0 9900.0 1
Glucocorticoid receptor
CHEMBL2034
 IC50 4.7 4.7 20000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 9400.0 ng.hr.mL-1 Mus musculus
CL 4.12 mL.min-1.kg-1 Mus musculus
Cmax 980.0 nM Mus musculus
F 56.0 % Mus musculus
T1/2 1.552 hr Mus musculus
T1/2 46.4 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Androgen receptor Ki = 8.4 nM 8.08 Binding affinity to wild-type androgen receptor in human LNCaP cells assessed as... 33470111
Androgen receptor IC50 = 19.0 nM 7.72 Displacement of [3H]methyltrienolone from wild-type androgen receptor in human L... 33470111
VCaP IC50 = 92.0 nM 7.04 Antiproliferative activity against human VCaP cells expressing wild-type androge... 33470111
VCaP IC50 = 92.0 nM 7.04 Antiproliferative activity against human VCaP cells expressing wild type AR asse... 34422225
Androgen receptor IC50 = 98.0 nM 7.01 Antagonist activity at AR F877L mutant (unknown origin) transfected in human LNC... 33470111
Androgen receptor IC50 = 98.0 nM 7.01 Antagonist activity at AR F877L mutant (unknown origin) transfected in human LNC... 34422225
Androgen receptor IC50 = 127.0 nM 6.9 Antagonist activity at VP16-AR wild-type (unknown origin) transfected in human H... 33470111
Androgen receptor IC50 = 191.0 nM 6.72 Antagonist activity at AR wild-type (unknown origin) transfected in human LNCAP ... 33470111
Androgen receptor IC50 = 191.0 nM 6.72 Antagonist activity at wild type androgen receptor in castration-resistant human... 34422225
Glucocorticoid receptor Ki = 9900.0 nM 5.0 Binding affinity to glucocorticoid receptor in human IM-9 cells assessed as inhi... 33470111
Glucocorticoid receptor IC50 = 20000.0 nM 4.7 Displacement of [3H]dexamethasone from glucocorticoid receptor in human IM-9 cel... 33470111

Literature References

PubMed DOI Target Context # Activities
33470111 10.1021/acs.jmedchem.0c01563 Androgen receptor 30
33470111 10.1021/acs.jmedchem.0c01563 ADMET 22
34422225 10.1021/acsmedchemlett.1c00032 Androgen receptor 6
33470111 10.1021/acs.jmedchem.0c01563 Glucocorticoid receptor 2
33470111 10.1021/acs.jmedchem.0c01563 LNCaP 2
33470111 10.1021/acs.jmedchem.0c01563 VCaP 1
34422225 10.1021/acsmedchemlett.1c00032 VCaP 1

Data from ChEMBL 36 via Core Engine