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Odanacatib

Odanacatib structure

CAS No:
603139-19-1
Formula:
C25H27F4N3O3S
Chemical Name:
Odanacatib
Synonyms:
Pentanamide,N-(1-cyanocyclopropyl)-4-fluoro-4-methyl-2-[[(1S)-2,2,2-trifluoro-1-[4′-(methylsulfonyl)[1,1′-biphenyl]-4-yl]ethyl]amino]-,(2S)-;(2S)-N-(1-Cyanocyclopropyl)-4-fluoro-4-methyl-2-[[(1S)-2,2,2-trifluoro-1-[4′-(methylsulfonyl)[1,1′-biphenyl]-4-yl]ethyl]amino]pentanamide;Odanacatib;N1-[(1-Cyanocyclopropyl)-4-fluoro-N2-[(1S)-2,2,2-trifluoro-1-[4-methylsulfonyl]-1,1′-biphenyl-4-yl] ethyl]-L-leucinamide
Categories:
Biochemical Engineering > Inhibitors

Description

Odanacatib (MK-0822) is a potent and selective inhibitor of cathepsin K, with an IC50 of 0.2 nM for human cathepsin K.

Odanacatib is an inhibiter of cathepsin K which was originally developed be Merck & Co as a new treatment for osteoporosis. The drug made it to phase III trials before abandoned due to increased stroke.|Odanacatib is an inhibitor of cathepsin K with potential anti-osteoporotic activity. Odanacatib selectively binds to and inhibits the activity of cathepsin K, which may result in a reduction in bone resorption, improvement of bone mineral density, and a reversal in osteoporotic changes. Cathepsin K, a tissue-specific cysteine protease that catalyzes degradation of bone matrix proteins such as collagen I/II, elastin, and osteonectin plays an important role in osteoclast function and bone resorption.

Odanacatib Basic Attributes

Molecular Weight：

525.564

Exact Mass：

525.56

EC Number：

1533716-785-6

UNII：

N673F6W2VH

DSSTox ID：

DTXSID40209075

NCI Thesaurus Code：

C66981

Characteristics

PSA：

107

XLogP3：

4.1

Density：

1.4±0.1 g/cm3

Melting Point：

223-224 °C

Boiling Point：

681.6±55.0°C at 760 mmHg

Flash Point：

366.0±31.5 °C

Refractive Index：

1.563

Safety Information

Precautionary statement(s)：

P260, P264, P270, P314, P501

Hazard Statements：

H372

Toxicity

Toxicity Summary：

Odanacatib was found to increase the risk of stroke. No further toxicological studies have been performed.

Protein Binding：

97.5% bound to plasma proteins.

Drug Information

Drug Indication：

Investigated for use/treatment in osteoporosis.|Treatment of osteoporosis

Pharmacology：

Increases bone mineral density and reduces risk of fractures in osteoporosis.

Absorption：

Tmax of 2-6h. The absolute bioavailabilities observed with 30mg and 50 mg doses are 70% and 30% respectively. When taken with high fat meals the 50mg dose's bioavailability increases to 49% and tmax increases to 10.5h.|16.9% excreted in urine. 74.5% excreted in feces.|100L|Total clearance of 0.8L/h.

Metabolism/Metabolites：

The major metabolite is the product of hydroxylation by CYP3A4 and CYP2C8. This metabolite is active but is 25 times less effective at inhibiting cathepsin K than odanacatib. The other metabolites are produced through glutathione conjugation, hydrolysis, dealkylation, glucuronidation, oxidation, and cyclization.

Biological Half-Life：

Apparent half life observed to be 87.3-94.7h.

Mechanism of Action：

Odanacatib inhibits cathepsin K, likely by binding to its active site. Cathepsin K is a cysteine protease enzyme which is secreted by osteoclasts. Cathepsin K is responsible for the breakdown of collagen in the bone matrix as part of bone resorption. The inhibition of this enzyme results in decreased bone resorption without affecting bone deposition resulting in increased bone mineral density. This increased bone mineral density strengthens the bone which leads to fewer fractures in osteoporosis.

MeSH Entry Terms：

L-1037536

Odanacatib Use and Manufacturing

Use Classification：

Human Drugs -> EU pediatric investigation plans

Computed Properties

Molecular Weight:525.6
XLogP3:4.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:9
Exact Mass:525.17092555
Monoisotopic Mass:525.17092555
Topological Polar Surface Area:107
Heavy Atom Count:36
Complexity:934
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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