GALETERONE

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Synonyms
Status
Molecule Category UNKNOWN
UNII WA33E149SW

Structure

InChI Key PAFKTGFSEFKSQG-PAASFTFBSA-N
Smiles C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(n3cnc4ccccc43)=CC[C@@H]12
InChI
InChI=1S/C26H32N2O/c1-25-13-11-18(29)15-17(25)7-8-19-20-9-10-24(26(20,2)14-12-21(19)25)28-16-27-22-5-3-4-6-23(22)28/h3-7,10,16,18-21,29H,8-9,11-15H2,1-2H3/t18-,19-,20-,21-,25-,26-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C26H32N2O
Molecular Weight 388.56
AlogP 5.81
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 1.0
Polar Surface Area 38.05
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 29.0

Bioactivity

Mechanism of Action Action Reference
Androgen Receptor antagonist ANTAGONIST PubMed PubMed Other
Protein: Cytochrome P450 17A1
Description: Steroid 17-alpha-hydroxylase/17,20 lyase
Organism : Homo sapiens
P05093 ENSG00000148795
Protein: Androgen Receptor
Description: Androgen receptor
Organism : Homo sapiens
P10275 ENSG00000169083
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 17 Cytochrome P450 family 17A Cytochrome P450 17A1
- 28-752 - - 50
Enzyme Cytochrome P450 Cytochrome P450 family 21 Cytochrome P450 family 21A Cytochrome P450 21A2
- 77 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 4
405-845 - - - 50-65
Assay Description Organism Bioactivity Reference
Inhibition of DHT-mediated AR transactivation in human LNCaP cells at 10 uM after 18 hrs by luciferase reporter gene assay relative to control Homo sapiens 65.0 %
Displacement of [3H]R1881 from AR in human LNCaP cells after 2 hrs by scintillation counting analysis Homo sapiens 670.0 nM
Inhibition of human truncated CYP17A1 expressed in Escherichia coli Homo sapiens 752.0 nM
Inhibition of human CYP17 expressed in Escherichia coli Homo sapiens 300.0 nM
Displacement of [3H]R1881 from androgen receptor in human LNCAP cells Homo sapiens 845.0 nM
Displacement of [3H]R1881 from androgen receptor in human PC3 cells Homo sapiens 405.0 nM
Antitumor activity against human LAPC4 cells xenografted in SCID mouse assessed as reduction in tumor volume at 0.15 mmol/kg, sc dosed twice daily starting 1 day after tumor cell inoculation and measured after 16 weeks of treatment Homo sapiens 93.8 %
Antitumor activity against human LAPC4 cells xenografted in SCID mouse assessed as regression of tumor volume at 0.13 mmol/kg, sc dosed twice daily Homo sapiens 26.55 %
Antitumor activity against human LAPC4 cells xenografted in SCID mouse with castration assessed as regression of tumor volume at 0.13 mmol/kg, sc dosed twice daily Homo sapiens 60.67 %
Inhibition of C-terminal His-tagged recombinant human CYP17A1delta19H mutant expressed in Escherichia coli DH5alpha assessed as decrease in progesterone hydroxylation preincubated for 3 mins followed by NADPH addition measured after 10 mins in presence of cytochrome p450 reductase by LC-MS/MS method Homo sapiens 28.1 nM
Inhibition of C-terminal His-tagged recombinant human CYP21A2deltaH mutant expressed in Escherichia coli DH5alpha assessed as decrease in progesterone hydroxylation preincubated for 3 mins followed by NADPH addition measured after 10 mins in presence of cytochrome p450 reductase by LC-MS/MS method Homo sapiens 77.2 nM
Inhibition of human membrane bound C-terminal His4-tagged CYP17A1 delta19H mutant assessed as reduction in progesterone hydroxylation preincubated for 3 mins followed by NADPH addition measured after 10 mins in presence of NADPH-cytochrome p450 reductase by HPLC method Homo sapiens 282.0 nM
Inhibition of human membrane bound C-terminal His4-tagged CYP21A2 delta19H mutant assessed as reduction in progesterone hydroxylation measured after 10 mins in presence of NADPH/NADPH-cytochrome p450 reductase by GC/MS method Homo sapiens 248.0 nM
Inhibition of C-myc/DDK tagged human CYP17A1 expressed in HEK293T cells assessed as reduction in formation of 17-OHP at 10 uM incubated for 30 mins by LC-MS/MS analysis Homo sapiens 50.0 %
Inhibition of R1881 induced-AR transcriptional activity in AR-positive human 22Rv1 cells harboring ARE14 construct at 10 uM after 24 hrs by luciferase assay relative to control Homo sapiens 50.0 %
Inhibition of CYP17 (unknown origin) Homo sapiens 140.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 10.02 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.18 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.18 %

Cross References

Resources Reference
ChEMBL CHEMBL2105738
DrugBank DB12415
FDA SRS WA33E149SW
Guide to Pharmacology 8638
PDB TOK
PubChem 11188409
SureChEMBL SCHEMBL939234
ZINC ZINC000006718442
CONTENTS