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Compound Detail

CHEMBL481611

ODANACATIB
🧪 Phase III
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🧪 Phase III
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
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL481611
Name ODANACATIB
Phase Phase III
Structure Type MOL
InChI Key FWIVDMJALNEADT-SFTDATJTSA-N

Known Names

L-001037536 L-1037536 MK-0822 MK0822 Odanacatib
12
Targets
28
Activities
3
Assay Types
17
PK Parameters
20
Publications
5
Known Names
6
Indications
1
Mechanisms

Molecular Properties

525.6
MW (Da)
4.63
ALogP
5
HBA
2
HBD
99.1
PSA (Ų)
0.47
QED
1
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -catib
USAN Year 2007

Extended Properties

Molecular Formula C25H27F4N3O3S
MW 525.57
Aromatic Rings 2
Heavy Atoms 36
NP-Likeness -0.91

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cathepsin K inhibitor INHIBITOR Cathepsin K ✓ ✓

Indications

Breast Neoplasms Osteoporosis Osteoporosis, Postmenopausal Prostatic Neoplasms, Castration-Resistant Osteoarthritis Renal Insufficiency

Activity Summary

IC50 23 meas. best 9.7
Ki 4 meas. best 9.74
EC50 1 meas. best 5.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cathepsin K
CHEMBL268
 Ki 9.74 9.72 0.2 2
Cathepsin K
CHEMBL268
 IC50 9.7 9.5671 0.2 7
Cathepsin K
CHEMBL3349
 IC50 9.0 9.0 1.0 1
Splenocyte
CHEMBL612422
 IC50 9.0 9.0 1.0 1
Unchecked
CHEMBL612545
 IC50 8.3 7.355 5.0 4
Osteoclast
CHEMBL612548
 IC50 7.64 7.64 23.0 1
Cathepsin S
CHEMBL2954
 IC50 7.35 7.1033 45.0 3
Cruzipain
CHEMBL3563
 Ki 6.9 6.9 125.9 1
Cathepsin L2
CHEMBL3272
 IC50 6.12 6.12 762.0 1
Cathepsin F
CHEMBL2517
 IC50 6.1 6.1 795.0 1
Cathepsin B
CHEMBL4072
 IC50 5.99 5.985 1034.0 2
Procathepsin L
CHEMBL3837
 Ki 5.9 5.9 1258.9 1
Trypanosoma cruzi
CHEMBL368
 EC50 5.6 5.6 2511.9 1
Procathepsin L
CHEMBL3837
 IC50 5.52 5.42 2995.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 0.13 mL.min-1.kg-1 Canis lupus familiaris
CL 6.1 mL.min-1.kg-1 Macaca mulatta
CL 2.0 mL.min-1.kg-1 Rattus norvegicus
CL 2.0 mL.min-1.kg-1 Rattus norvegicus
F 8.0 % Rattus norvegicus
F 6.0 % Canis lupus familiaris
F 7.0 % Macaca mulatta
F 38.0 % Rattus norvegicus
F 100.0 % Canis lupus familiaris
F 8.0 % Rattus norvegicus
F 6.0 % Canis lupus familiaris
T1/2 6.0 hr Rattus norvegicus
T1/2 57.0 hr Canis lupus familiaris
T1/2 18.0 hr Macaca mulatta
T1/2 6.0 hr Rattus norvegicus
T1/2 6.0 hr Rattus norvegicus
T1/2 57.0 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cathepsin K Ki = 0.18 nM 9.74 Inhibition of human cathepsin K 29272750
Cathepsin K IC50 = 0.2 nM 9.7 Inhibition of humanized rabbit cathepsin K 18226527
Cathepsin K IC50 = 0.2 nM 9.7 Inhibition of human cathepsin K 18226527
Cathepsin K IC50 = 0.2 nM 9.7 Inhibition of humanized rabbit cathepsin K 19117756
Cathepsin K IC50 = 0.2 nM 9.7 Inhibition of humanized rabbit cathepsin K 20061146
Cathepsin K IC50 = 0.2 nM 9.7 Inhibition of cathepsin K 20218623
Cathepsin K IC50 = 0.2 nM 9.7 Inhibition of humanized rabbit cathepsin K 21232956
Cathepsin K Ki = 0.1995 nM 9.7 Binding affinity to human Cathepsin K assessed as inhibition constant 39002936
Cathepsin K IC50 = 1.0 nM 9.0 Inhibition of rabbit cathepsin K 18226527
Splenocyte IC50 = 1.0 nM 9.0 Inhibition of MHC 2 invariant chain iip10 in mouse splenocytes 18226527
Cathepsin K IC50 = 1.7 nM 8.77 Inhibition of Cathepsin K (unknown origin) assessed as inhibition of AFC release... 36270112
Unchecked IC50 = 5.0 nM 8.3 Decrease in bone resorption assessed as corrected bone resorption measured as ra... 20061146
Unchecked IC50 = 5.0 nM 8.3 Ratio of product of IC50 for rabbit bone resorption and IC50 for humanized rabbi... 21232956
Osteoclast IC50 = 23.0 nM 7.64 Inhibition of bone resorption in rabbit osteoclast 18226527
Cathepsin S IC50 = 45.0 nM 7.35 Inhibition of cathepsin S in human ramos cells 18226527
Cathepsin S IC50 = 60.0 nM 7.22 Inhibition of cathepsin S 18226527
Unchecked IC50 = 100.0 nM 7.0 Inhibition of osteoclastogenesis in human bone marrow-derived stem cells assesse... 22984809
Cruzipain Ki = 125.89 nM 6.9 Inhibition of Trypanosoma cruzi cruzain using Z-Phe-Arg-7-amido-4-methylcoumarin... 31561938
Cathepsin S IC50 = 183.0 nM 6.74 Inhibition of human recombinant CatS assessed as suppression of enzyme-mediated ... 22742641
Cathepsin L2 IC50 = 762.0 nM 6.12 Inhibition of cathepsin V 18226527

Literature References

PubMed DOI Target Context # Activities
20218623 10.1021/jm9018756 Unchecked 6
21232956 10.1016/j.bmcl.2010.12.070 Unchecked 5
20061146 10.1016/j.bmcl.2009.12.083 Unchecked 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
18226527 10.1016/j.bmcl.2007.12.047 Rhesus monkey 4
18226527 10.1016/j.bmcl.2007.12.047 Canis familiaris 4
18226527 10.1016/j.bmcl.2007.12.047 Rattus norvegicus 4
36270112 10.1016/j.bmc.2022.117053 Cathepsin K 3
18226527 10.1016/j.bmcl.2007.12.047 Cathepsin K 3
- 10.6019/CHEMBL3301361 ADMET 3
19117756 10.1016/j.bmcl.2008.12.053 Unchecked 3
30773420 10.1016/j.bmc.2019.02.003 Cathepsin K 2
18226527 10.1016/j.bmcl.2007.12.047 Hepatocyte 2
18226527 10.1016/j.bmcl.2007.12.047 ADMET 2
21232956 10.1016/j.bmcl.2010.12.070 Canis familiaris 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
18226527 10.1016/j.bmcl.2007.12.047 Cathepsin S 2
18226527 10.1016/j.bmcl.2007.12.047 Procathepsin L 2
19117756 10.1016/j.bmcl.2008.12.053 Rattus norvegicus 2
18226527 10.1016/j.bmcl.2007.12.047 Cathepsin B 2

Data from ChEMBL 36 via Core Engine