ODANACATIB

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H27F4N3O3S
Molecular Weight	525.559
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CC(C)(F)C[C@H](N[C@@H](C1=CC=C(C=C1)C2=CC=C(C=C2)S(C)(=O)=O)C(F)(F)F)C(=O)NC3(CC3)C#N

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

Description

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cathepsin K 4	Inhibitor 8,297

Conditions

Condition	Modality	Highest Phase	Product
Postmenopausal osteoporosis 59	Primary	Phase III 656	Unknown
Osteoporosis 97	Primary	Phase III 656	Unknown
Breast cancer 434	Primary	Phase III 656	Unknown
Osteoarthritis 157	Primary	Phase II 1,132	Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
183 nM	50 mg single, oral		ODANACATIB plasma	Homo sapiens
353.5 nM	100 mg single, oral		ODANACATIB plasma	Homo sapiens
477.3 nM	600 mg single, oral		ODANACATIB plasma	Homo sapiens
738.5 nM	200 mg single, oral		ODANACATIB plasma	Homo sapiens
630.4 nM	100 mg single, oral		ODANACATIB plasma	Homo sapiens
839.2 nM	300 mg single, oral		ODANACATIB plasma	Homo sapiens
154.7 nM	25 mg single, oral		ODANACATIB plasma	Homo sapiens
344.7 nM	25 mg single, oral		ODANACATIB plasma	Homo sapiens
56.2 nM	1 mg single, intravenous	ODANACATIB	ODANACATIB plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
3 μM × h	50 mg single, oral		ODANACATIB plasma	Homo sapiens
6.4 μM × h	100 mg single, oral		ODANACATIB plasma	Homo sapiens
9.4 μM × h	600 mg single, oral		ODANACATIB plasma	Homo sapiens
13.6 μM × h	200 mg single, oral		ODANACATIB plasma	Homo sapiens
11.3 μM × h	100 mg single, oral		ODANACATIB plasma	Homo sapiens
16.1 μM × h	300 mg single, oral		ODANACATIB plasma	Homo sapiens
3.2 μM × h	25 mg single, oral		ODANACATIB plasma	Homo sapiens
6.7 μM × h	25 mg single, oral		ODANACATIB plasma	Homo sapiens
2.7 μM × h	1 mg single, intravenous	ODANACATIB	ODANACATIB plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
78.8 h	50 mg single, oral		ODANACATIB plasma	Homo sapiens
96.7 h	25 mg single, oral		ODANACATIB plasma	Homo sapiens
59.2 h	600 mg single, oral		ODANACATIB plasma	Homo sapiens
50.5 h	200 mg single, oral		ODANACATIB plasma	Homo sapiens
48.2 h	100 mg single, oral		ODANACATIB plasma	Homo sapiens
62.6 h	300 mg single, oral		ODANACATIB plasma	Homo sapiens
104.4 h	1 mg single, intravenous	ODANACATIB	ODANACATIB plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
2.5%	25 mg single, oral		ODANACATIB plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
50 mg 1 times / week multiple, oral Studied dose	unhealthy, ADULT	Disc. AE: Myalgia...
300 mg 1 times / day multiple, oral Highest recorded dose	healthy	Other AEs: Abdominal pain, Application-site erosion...
50 mg 1 times / week multiple, oral Studied dose	unhealthy	Disc. AE: Basal cell carcinoma...

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AEs

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AE	Significance	Dose	Population
Myalgia	0.7% Disc. AE	50 mg 1 times / week multiple, oral Studied dose	unhealthy, ADULT
Application-site erythema	17.9%	300 mg 1 times / day multiple, oral Highest recorded dose	healthy
Abdominal pain	5.4%	300 mg 1 times / day multiple, oral Highest recorded dose	healthy
Application-site erosion	5.4%	300 mg 1 times / day multiple, oral Highest recorded dose	healthy
Pruritus	7.1%	300 mg 1 times / day multiple, oral Highest recorded dose	healthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737 inhibitor 1,587	inhibitor 1,767		inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 1,478 CYP1A2 1,524	CYP2C8 693 P-gp 1,537

Drug as perpetrator

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Target	Modality	Activity	Clinical evidence
CYP1A2 1,692	inhibitor 3,277	no	no (co-administration study)
CYP2C19 1,553	inhibitor 3,277	no	no (co-administration study)
CYP2C9 1,819	inhibitor 3,277	no	no (co-administration study)
CYP3A4 1,925	inhibitor 3,277	no	no (co-administration study)

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Drug as victim

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Target	Modality	Activity
CYP3A4 1,737	substrate 3,367	major
CYP2C8 693	substrate 3,367	minor
P-gp 1,537	substrate 3,367	yes

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
001 Chemical	DY105556	https://www.001chemical.com/chem/search?q=DY105556
1PlusChem LLC	1P003A9R	https://www.1pchem.com/search?query=1P003A9R
A2B Chem	AB52479	http://a2bchem.com/prod/AB52479
Aceschem	ACF023007	https://www.aceschem.com/catalog/search.do?q=ACF023007
AChemBlock	10356	http://www.achemblock.com/catalogsearch/result/?q=10356

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PubMed

Title	Date	PubMed
No data available in table

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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

Show entries

Name

Type

Language

ODANACATIB

Official Name

English

MK0822

Code

English

ODANACATIB [USAN]

Common Name

English

ODANACATIB [MI]

Common Name

English

ODANACATIB [MART.]

Common Name

English

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Classification Tree

Code System

Code

Agent Affecting Musculoskeletal System

NCI_THESAURUS

C67439

Enzyme Inhibitor

NCI_THESAURUS

C783

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Code System

Code

Type

Description

INN

8962

PRIMARY

SMS_ID

100000128030

PRIMARY

WIKIPEDIA

ODANACATIB

PRIMARY

DRUG BANK

DB06670

PRIMARY

CAS

603139-19-1

PRIMARY

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ACTIVE MOIETY


					N673F6W2VH

ODANACATIB

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator