U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H27F4N3O3S
Molecular Weight 525.5608
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ODANACATIB

SMILES

CC(C)(C[C@@]([H])(C(=NC1(CC1)C#N)O)N[C@@]([H])(c2ccc(cc2)-c3ccc(cc3)S(=O)(=O)C)C(F)(F)F)F

InChI

InChIKey=FWIVDMJALNEADT-SFTDATJTSA-N
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

HIDE SMILES / InChI

Molecular Formula C25H27F4N3O3S
Molecular Weight 525.5608
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18226527 | https://www.ncbi.nlm.nih.gov/pubmed/27681784

Odanacatib is a potent, selective, and neutral cathepsin K inhibitor, an enzyme involved in bone resorption. Merck & Co was developing odanacatib, a once-weekly, oral Odanacatib, for the treatment of postmenopausal osteoporosis and osteoporosis in men. Merck & Co. has discontinued development of its cathepsin K inhibitor odanacatib, citing an increased risk of cardiovascular events for the osteoporosis drug.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
839.2 nM
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: HIGH-FAT
154.7 nM
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
477.3 nM
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.76 nM
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: HIGH-FAT
2.23 nM
-0.01 mg single, oral
dose: -0.01 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: HIGH-FAT
353.5 nM
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
56.2 nM
1 mg single, intravenous
dose: 1 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: ODANACATIB
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
1.82 nM
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: HIGH-FAT
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
16.1 μM × h
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: HIGH-FAT
3.2 μM × h
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
9.4 μM × h
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.73 μM × h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: HIGH-FAT
2.11 μM × h
-0.01 mg single, oral
dose: -0.01 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: HIGH-FAT
6.4 μM × h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2.7 μM × h
1 mg single, intravenous
dose: 1 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: ODANACATIB
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
1.87 μM × h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: HIGH-FAT
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
62.6 h
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: HIGH-FAT
59.2 h
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
48.2 h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: HIGH-FAT
104.4 h
1 mg single, intravenous
dose: 1 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: ODANACATIB
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
50.5 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ODANACATIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: HIGH-FAT
Doses

Doses

DosePopulationAdverse events​
50 mg 1 times / week multiple, oral (unknown)
Studied dose
Dose: 50 mg, 1 times / week
Route: oral
Route: multiple
Dose: 50 mg, 1 times / week
Sources:
unhealthy, ADULT
n = 146
Health Status: unhealthy
Condition: osteoporosis
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 146
Sources:
Disc. AE: Myalgia...
AEs leading to
discontinuation/dose reduction:
Myalgia (0.7%)
Sources:
300 mg 1 times / day multiple, oral (starting)
Highest recorded dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
healthy
n = 56
Health Status: healthy
Sex: M+F
Food Status: FASTED
Population Size: 56
Sources:
Other AEs: Abdominal pain, Application-site erosion...
Other AEs:
Abdominal pain (5.4%)
Application-site erosion (5.4%)
Application-site erythema (17.9%)
Pruritus (7.1%)
Sources:
50 mg 1 times / week multiple, oral (unknown)
Studied dose
Dose: 50 mg, 1 times / week
Route: oral
Route: multiple
Dose: 50 mg, 1 times / week
Sources:
unhealthy
n = 28
Health Status: unhealthy
Condition: low bone mineral density
Sex: F
Food Status: UNKNOWN
Population Size: 28
Sources:
Disc. AE: Basal cell carcinoma...
AEs leading to
discontinuation/dose reduction:
Basal cell carcinoma (3.6%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Myalgia 0.7%
Disc. AE
50 mg 1 times / week multiple, oral (unknown)
Studied dose
Dose: 50 mg, 1 times / week
Route: oral
Route: multiple
Dose: 50 mg, 1 times / week
Sources:
unhealthy, ADULT
n = 146
Health Status: unhealthy
Condition: osteoporosis
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 146
Sources:
Application-site erythema 17.9%
300 mg 1 times / day multiple, oral (starting)
Highest recorded dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
healthy
n = 56
Health Status: healthy
Sex: M+F
Food Status: FASTED
Population Size: 56
Sources:
Abdominal pain 5.4%
300 mg 1 times / day multiple, oral (starting)
Highest recorded dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
healthy
n = 56
Health Status: healthy
Sex: M+F
Food Status: FASTED
Population Size: 56
Sources:
Application-site erosion 5.4%
300 mg 1 times / day multiple, oral (starting)
Highest recorded dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
healthy
n = 56
Health Status: healthy
Sex: M+F
Food Status: FASTED
Population Size: 56
Sources:
Pruritus 7.1%
300 mg 1 times / day multiple, oral (starting)
Highest recorded dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
healthy
n = 56
Health Status: healthy
Sex: M+F
Food Status: FASTED
Population Size: 56
Sources:
Basal cell carcinoma 3.6%
Disc. AE
50 mg 1 times / week multiple, oral (unknown)
Studied dose
Dose: 50 mg, 1 times / week
Route: oral
Route: multiple
Dose: 50 mg, 1 times / week
Sources:
unhealthy
n = 28
Health Status: unhealthy
Condition: low bone mineral density
Sex: F
Food Status: UNKNOWN
Population Size: 28
Sources:
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
yes (co-administration study)
Comment: Coadministration did not affect R( )- and S(-)-warfarin exposure.
no
yes (co-administration study)
Comment: Coadministration did not affect R( )- and S(-)-warfarin exposure.
no
yes (co-administration study)
Comment: Coadministration did not affect R( )- and S(-)-warfarin exposure.
no
yes (co-administration study)
Comment: Coadministration did not affect R( )- and S(-)-warfarin exposure.
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

Merck is conducting a long-term phase II trial that is assessing four different doses of odanacatib (3mg, 10mg, 25mg and 50mg once-weekly for 2 years) in women with postmenopausal osteoporosis (NCT00112437; EudraCT2005-001511-22). Results from this phase IIb study showed that odanacatib 50mg increased bone mineral density (BMD) from baseline, and was generally safe and well tolerated.
Route of Administration: Oral
1 nM odanacatib had suppressive effects on the expression levels of inflammatory cytokines in murine RAW 264.7 cells were cultured in the presence of the receptor activator of NF-kB and lipopolysaccharide
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:07:52 UTC 2021
Edited
by admin
on Sat Jun 26 13:07:52 UTC 2021
Record UNII
N673F6W2VH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ODANACATIB
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
ODANACATIB [WHO-DD]
Common Name English
MK0822
Code English
ODANACATIB [USAN]
Common Name English
ODANACATIB [MI]
Common Name English
ODANACATIB [MART.]
Common Name English
ODANACATIB [JAN]
Common Name English
MK-0822
Code English
ODANACATIB [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67439
Created by admin on Sat Jun 26 13:07:53 UTC 2021 , Edited by admin on Sat Jun 26 13:07:53 UTC 2021
NCI_THESAURUS C783
Created by admin on Sat Jun 26 13:07:53 UTC 2021 , Edited by admin on Sat Jun 26 13:07:53 UTC 2021
Code System Code Type Description
INN
8962
Created by admin on Sat Jun 26 13:07:53 UTC 2021 , Edited by admin on Sat Jun 26 13:07:53 UTC 2021
PRIMARY
WIKIPEDIA
ODANACATIB
Created by admin on Sat Jun 26 13:07:53 UTC 2021 , Edited by admin on Sat Jun 26 13:07:53 UTC 2021
PRIMARY
DRUG BANK
DB06670
Created by admin on Sat Jun 26 13:07:53 UTC 2021 , Edited by admin on Sat Jun 26 13:07:53 UTC 2021
PRIMARY
CAS
603139-19-1
Created by admin on Sat Jun 26 13:07:53 UTC 2021 , Edited by admin on Sat Jun 26 13:07:53 UTC 2021
PRIMARY
NCI_THESAURUS
C66981
Created by admin on Sat Jun 26 13:07:53 UTC 2021 , Edited by admin on Sat Jun 26 13:07:53 UTC 2021
PRIMARY
EPA CompTox
603139-19-1
Created by admin on Sat Jun 26 13:07:53 UTC 2021 , Edited by admin on Sat Jun 26 13:07:53 UTC 2021
PRIMARY
FDA UNII
N673F6W2VH
Created by admin on Sat Jun 26 13:07:53 UTC 2021 , Edited by admin on Sat Jun 26 13:07:53 UTC 2021
PRIMARY
ChEMBL
CHEMBL481611
Created by admin on Sat Jun 26 13:07:53 UTC 2021 , Edited by admin on Sat Jun 26 13:07:53 UTC 2021
PRIMARY
MESH
C527128
Created by admin on Sat Jun 26 13:07:53 UTC 2021 , Edited by admin on Sat Jun 26 13:07:53 UTC 2021
PRIMARY
MERCK INDEX
M8131
Created by admin on Sat Jun 26 13:07:53 UTC 2021 , Edited by admin on Sat Jun 26 13:07:53 UTC 2021
PRIMARY Merck Index
PUBCHEM
10152654
Created by admin on Sat Jun 26 13:07:53 UTC 2021 , Edited by admin on Sat Jun 26 13:07:53 UTC 2021
PRIMARY
EVMPD
SUB34600
Created by admin on Sat Jun 26 13:07:53 UTC 2021 , Edited by admin on Sat Jun 26 13:07:53 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SELECTIVE
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
EXCRETED UNCHANGED
URINE
TRANSPORTER -> SUBSTRATE
EXCRETED UNCHANGED
FECAL
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC ORAL ADMINISTRATION

SINGLE DOSE

Tmax PHARMACOKINETIC ORAL ADMINISTRATION

SINGLE DOSE