ODANACATIB

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Synonyms
Status
Molecule Category UNKNOWN
UNII N673F6W2VH
EPA CompTox DTXSID40209075

Structure

InChI Key FWIVDMJALNEADT-SFTDATJTSA-N
Smiles CC(C)(F)C[C@H](N[C@@H](c1ccc(-c2ccc(S(C)(=O)=O)cc2)cc1)C(F)(F)F)C(=O)NC1(C#N)CC1
InChI
InChI=1S/C25H27F4N3O3S/c1-23(2,26)14-20(22(33)32-24(15-30)12-13-24)31-21(25(27,28)29)18-6-4-16(5-7-18)17-8-10-19(11-9-17)36(3,34)35/h4-11,20-21,31H,12-14H2,1-3H3,(H,32,33)/t20-,21-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C25H27F4N3O3S
Molecular Weight 525.57
AlogP 4.63
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 9.0
Polar Surface Area 99.06
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 36.0

Bioactivity

Mechanism of Action Action Reference
Cathepsin K inhibitor INHIBITOR PubMed
Protein: Cathepsin K
Description: Cathepsin K
Organism : Homo sapiens
P43235 ENSG00000143387
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Protease Cysteine protease Cysteine protease CA clan Cysteine protease C1A family
- 0-0 - 0 19
Assay Description Organism Bioactivity Reference
Inhibition of humanized rabbit cathepsin K Homo sapiens 0.2 nM
Inhibition of cathepsin S None 60.0 nM
Inhibition of cathepsin F None 795.0 nM
Inhibition of cathepsin V None 762.0 nM
Inhibition of cathepsin C None 10.0 nM
Inhibition of cathepsin H None 10.0 nM
Inhibition of cathepsin Z None 10.0 nM
Inhibition of human cathepsin K Homo sapiens 0.2 nM
Inhibition of rabbit cathepsin K Oryctolagus cuniculus 1.0 nM
Inhibition of bone resorption in rabbit osteoclast Oryctolagus cuniculus 23.0 nM
Inhibition of cathepsin S in human ramos cells None 45.0 nM
Inhibition of MHC 2 invariant chain iip10 in mouse splenocytes Mus musculus 1.0 nM
Inhibition of humanized rabbit cathepsin K Homo sapiens 0.2 nM
Inhibition of humanized rabbit cathepsin K Homo sapiens 0.2 nM
Decrease in bone resorption assessed as corrected bone resorption measured as ratio of bone resorption IC50 x humanized rabbit cathepsin K IC50 to rabbit cathepsin K IC50 equation None 5.0 nM
Inhibition of cathepsin K None 0.2 nM
Inhibition of humanized rabbit cathepsin K Homo sapiens 0.2 nM
Ratio of product of IC50 for rabbit bone resorption and IC50 for humanized rabbit cathepsin K to IC50 for rabbit cathepsin K None 5.0 nM
Inhibition of human recombinant CatK assessed as suppression of enzyme-mediated Z-Phe-Arg-AMC cleavage incubated for 1 hrs by QFRET assay Homo sapiens 1.0 nM
Inhibition of human recombinant CatS assessed as suppression of enzyme-mediated Z-Val-Val-Arg-AMC cleavage by QFRET assay Homo sapiens 183.0 nM
Inhibition of osteoclastogenesis in human bone marrow-derived stem cells assessed as reduction of pit formation by measuring TRACP5b activity after 7 days by bone TRAP assay Homo sapiens 100.0 nM
Inhibition of cathepsin-k None 1.0 nM
Inhibition of human cathepsin K Homo sapiens 0.18 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 3.39 %
Inhibition of Trypanosoma cruzi cruzain using Z-Phe-Arg-7-amido-4-methylcoumarin as substrate preincubated for 2 mins followed by susbtrate addition by fluorescence based analysis Trypanosoma cruzi 125.89 nM
Inhibition of cathepsin K in mouse Primary chondrocytes derived after 2 passages at 0.1 to 1 uM using Z-GPR-4MbetaNA as substrate by fluorescence assay relative to control Mus musculus 19.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 21.11 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 4.464 %
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 -0.09 % 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 0.04 % 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 -0.09 % 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 0.04 %

Cross References

Resources Reference
ChEMBL CHEMBL481611
DrugBank DB06670
FDA SRS N673F6W2VH
Guide to Pharmacology 6478
PubChem 10152654
SureChEMBL SCHEMBL1496266
ZINC ZINC000042893657
CONTENTS