Odanacatib (MK0822)

Alias: Odanacatib; MK 0822; MK0822; MK-0822
Cat No.:V0696 Purity: ≥98%
Odanacatib (also known as MK-0822) is a potent, selective, and neutral inhibitor of cathepsin K (human/rabbit) with the potential to be used for thetreatment for osteoporosis and bone metastasis.
Odanacatib (MK0822) Chemical Structure CAS No.: 603139-19-1
Product category: Cysteine Protease
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Odanacatib (also known as MK-0822) is a potent, neutral, and selective inhibitor of human/rabbit cathepsin K that may be applied to the management of bone metastases and osteoporosis. With IC50s of 0.2 nM/1 nM, it inhibits cathepsin K (human/rabbit) and shows good selectivity against off-target cathepsins B, L, and S. Odanacatib binds to cathepsin K specifically and inhibits its activity. This may reduce bone resorption, improve bone mineral density, and reverse osteoporotic changes. Approximately 16,000 postmenopausal osteoporosis patients are participating in a phase III trial to assess the potential of odanacatib to reduce fracture risk.

Biological Activity I Assay Protocols (From Reference)
Targets
Cathepsin K(human) (IC50 = 0.2 nM); Cathepsin K(human) (IC50 = 1 nM)
ln Vitro
Odanacatib exhibits strong cathepsin K inhibitory activity and selectivity in vitro, with IC50 values for human and rabbit cathepsin K of 0.2 nM and 1 nM, respectively. Additionally, with a corrected IC50 of 5 nM, odanacatib demonstrates comparable potencies in whole human cell enzyme occupancy assays.[1] Odanacatib reduces osteoclast (OC) resorption activity by blocking intracellular vesicular trafficking, according to a recent study.[2]
ln Vivo
Odanacatib (10 mg/kg) in preclinical rats shows good pharmacokinetics with low volume of distribution (Vdss: 1.1 L kg-1), half-life (T1/2: 6 hours), oral bioavailability (F: 8%), and clearance (Cl: 2 mL kg-1 min-1). Furthermore, in rat hepatocytes, odanacatib shows outstanding metabolic stability with a 96% recovery of the parent identity.[1] In ovariectomized (OVX) rabbits, odanacatib (ODN) administered orally reduces bone loss in a dose-dependent manner. Additionally, Odanacatib (9 µM/day) significantly raises the bone mineral density (BMD) of the femoral neck (10.8%), the greater trochanter (6.5%), and the proximal femur (7.8%).[3] Long-term administration of Odanacatib preserves the normal biomechanical characteristics of the spine in OVX nonhuman primates while effectively inhibiting bone turnover in estrogen-deficient, skeletally mature rhesus monkeys without lowering osteoclast frequency.[4]
Enzyme Assay
Odanacatib, also known as MK-0822, has been shown to exhibit high selectivity against off-target cathepsin B, L, and S. It is a potent, selective, and neutral inhibitor of cathepsin K (human/rabbit) with an IC50 of 0.2 nM/1 nM. Odanacatib binds to cathepsin K specifically and inhibits its activity. This may reduce bone resorption, improve bone mineral density, and reverse osteoporotic changes.
Cell Assay
In order to evaluate cell survival, 100 nM Odanacatib (ODN) or 7 ×104 differentiated osteoclast (OC) cells/cm2 are reseeded on slices of bovine bone. On days 2, 4, 6, and 12, bone slices are fixed without any media alterations. Samples are stained for both the OC number and TRAP activity.
Animal Protocol
Sixteen eight-month-old female Sprague-Dawley (SD) rats, weighing 385 ± 55 g, are provided with water and soft diet food on an as-needed basis in a temperature-controlled environment featuring regular 12-hour light and dark cycles. Four groups of four rats each are created by randomization: the sham group, the OVX + Veh group, the OVX + ODN-l group, and the OVX + ODN-h group. After implant insertion, OVX + ODN-l and OVX + ODN-h groups receive gavage once daily for eight weeks at concentrations of 1 mL/kg and 6 mL/kg, respectively, of odanacatib (ODN, 5 mg/mL). During the same period, a gavage containing 0.5% sodium carboxymethyl cellulose at a concentration of 6 mL/kg is administered to the OVX + Veh group. Following the administration of gavage, intravenous sodium pentobarbital injections are used to kill the rats in each group. Along with the surrounding bone, the implants are removed and preserved in 10% buffered formalin.
References

[1]. Bioorg Med Chem Lett . 2008 Feb 1;18(3):923-8.

[2]. Bone . 2011 Oct;49(4):623-35.

[3]. J Bone Miner Res . 2011 Feb;26(2):252-62.

[4]. J Bone Miner Res . 2012 Mar;27(3):509-23.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C25H27F4N3O3S
Molecular Weight
525.56
Exact Mass
525.17
Elemental Analysis
C, 57.13; H, 5.18; F, 14.46; N, 8.00; O, 9.13; S, 6.10
CAS #
603139-19-1
Appearance
white solid powder, m.p. = 223 - 224 oC
SMILES
CC(C)(C[C@@H](C(=O)NC1(CC1)C#N)N[C@@H](C2=CC=C(C=C2)C3=CC=C(C=C3)S(=O)(=O)C)C(F)(F)F)F
InChi Key
FWIVDMJALNEADT-SFTDATJTSA-N
InChi Code
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
Chemical Name
(2S)-N-(1-cyanocyclopropyl)-4-fluoro-4-methyl-2-[[(1S)-2,2,2-trifluoro-1-[4-(4-methylsulfonylphenyl)phenyl]ethyl]amino]pentanamide
Synonyms
Odanacatib; MK 0822; MK0822; MK-0822
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ~100 mg/mL (~190.3 mM)
Water: <1 mg/mL
Ethanol: <1 mg/mL
Solubility (In Vivo)
4% DMSO+corn oil: 5 mg/mL
 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.9027 mL 9.5137 mL 19.0273 mL
5 mM 0.3805 mL 1.9027 mL 3.8055 mL
10 mM 0.1903 mL 0.9514 mL 1.9027 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT00769418 Completed Drug: odanacatib
Drug: Comparator: Placebo
Osteoporosis Merck Sharp & Dohme LLC September 2004 Phase 1
NCT01068262 Completed Drug: Odanacatib
Drug: Comparator: Placebo
Osteoporosis Merck Sharp & Dohme LLC December 8, 2009 Phase 1
NCT01512693 Completed Drug: MK-0822 Hepatic Insufficiency Merck Sharp & Dohme LLC February 23, 2012 Phase 1
NCT01512667 Completed Drug: MK-0822 Renal Insufficiency Merck Sharp & Dohme LLC January 17, 2012 Phase 1
NCT00729183 Completed Drug: Odanacatib
Osteoporosis
Osteoporosis Merck Sharp & Dohme LLC October 2, 2008 Phase 3
Biological Data
  • Odanacatib (MK-0822)
    Validation of the rabbit ovariectomized (OVX) model using estradiol and alendronate (ALN) treatment.J Bone Miner Res.2011 Feb;26(2):252-62.
  • Odanacatib (MK-0822)
    Treatment with the cathepsin K inhibitors L-235 and odanacatib prevented bone loss in OVX rabbits.J Bone Miner Res.2011 Feb;26(2):252-62.
  • Odanacatib (MK-0822)
    Effects of the cathepsin K inhibitors L-235 and odanacatib compared with ALN on bone formation in lumbar vertebrae cancellous bone and central femoral endocortical bone in OVX rabbits treated for 27-weeks.J Bone Miner Res.2011 Feb;26(2):252-62.
  • Odanacatib (MK-0822)
    Correlation of ultimate load and BMC in the lumbar vertebrae and central femurs of OVX rabbits treated with ODN for 27 weeks.J Bone Miner Res.2011 Feb;26(2):252-62.
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