Odanacatib (MK0822)
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 202062

CAS#: 603139-19-1

Description: Odanacatib, also known as MK-0822, 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. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).


Price and Availability

Size
Price

10mg
USD 90
100mg
USD 450
1g
USD 2950
Size
Price

25mg
USD 150
200mg
USD 850
2g
USD 4250
Size
Price

50mg
USD 250
500mg
USD 1650
5g
USD 6950

Odanacatib, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 202062
Name: Odanacatib (MK0822)
CAS#: 603139-19-1
Chemical Formula: C25H27F4N3O3S
Exact Mass: 525.17093
Molecular Weight: 525.56
Elemental Analysis: C, 57.13; H, 5.18; F, 14.46; N, 8.00; O, 9.13; S, 6.10


Synonym: MK0822; MK-0822; MK 0822; Odanacatib .

IUPAC/Chemical Name: (S)-N-(1-cyanocyclopropyl)-4-fluoro-4-methyl-2-(((S)-2,2,2-trifluoro-1-(4'-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethyl)amino)pentanamide

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

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


Technical Data

Appearance:
white solid powder, m.p. = 223 - 224 oC

Purity:
>98% (or refer to the Certificate of Analysis)

Safety Data Sheet (MSDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Odanacatib (pINN; codenamed MK-0822) is an investigational treatment for osteoporosis and bone metastasis. It is an inhibitor of cathepsin K,  an enzyme involved in bone resorption. It is being developed by Merck & Co. As of November 2009, Merck is conducting phase III clinical trials.
 
 


References

1: Chapurlat RD. Treatment of postmenopausal osteoporosis with odanacatib. Expert Opin Pharmacother. 2014 Jan 24. [Epub ahead of print] PubMed PMID: 24456412.

2: Odanacatib, a cathepsin K inhibitor, superior to alendronate. Bonekey Rep. 2013 Sep 4;2:426. doi: 10.1038/bonekey.2013.160. eCollection 2013. PubMed PMID: 24422127; PubMed Central PMCID: PMC3789222.

3: Retraction notice: Odanacatib for the treatment of postmenopausal osteoporosis. Expert Opin Pharmacother. 2014 Jan;15(1):151. doi: 10.1517/14656566.2014.868399. Epub 2013 Nov 30. PubMed PMID: 24289716.

4: Anderson MS, Gendrano IN, Liu C, Jeffers S, Mahon C, Mehta A, Mostoller K, Zajic S, Morris D, Lee J, Stoch SA. Odanacatib, a selective cathepsin K inhibitor, demonstrates comparable pharmacodynamics and pharmacokinetics in older men and postmenopausal women. J Clin Endocrinol Metab. 2013 Dec 20:jc20131688. [Epub ahead of print] PubMed PMID: 24276460.

5: Chapurlat RD. Odanacatib for the treatment of postmenopausal osteoporosis. Expert Opin Pharmacother. 2014 Jan;15(1):97-102. doi: 10.1517/14656566.2014.853038. Epub 2013 Oct 25. Retraction in: Expert Opin Pharmacother. 2014 Jan;15(1):151. PubMed PMID: 24156249.

6: Stoch SA, Witter R, Hrenuik D, Liu C, Zajic S, Mehta A, Chandler P, Morris D, Xue H, Denker A, Wagner JA. Odanacatib does not influence the single dose pharmacokinetics and pharmacodynamics of warfarin. J Popul Ther Clin Pharmacol. 2013;20(3):e312-20. Epub 2013 Oct 2. PubMed PMID: 24142206.

7: Jensen PR, Andersen TL, Pennypacker BL, Duong le T, Delaissé JM. The bone resorption inhibitors odanacatib and alendronate affect post-osteoclastic events differently in ovariectomized rabbits. Calcif Tissue Int. 2014 Feb;94(2):212-22. doi: 10.1007/s00223-013-9800-0. Epub 2013 Oct 2. PubMed PMID: 24085265.

8: Bonnick S, De Villiers T, Odio A, Palacios S, Chapurlat R, Dasilva C, Scott BB, Le Bailly De Tilleghem C, Leung AT, Gurner D. Effects of Odanacatib on BMD and Safety in the Treatment of Osteoporosis in Postmenopausal Women Previously Treated With Alendronate: A Randomized Placebo-Controlled Trial. J Clin Endocrinol Metab. 2013 Dec;98(12):4727-35. doi: 10.1210/jc.2013-2020. Epub 2013 Sep 24. PubMed PMID: 24064689.

9: Zerbini CA, McClung MR. Odanacatib in postmenopausal women with low bone mineral density: a review of current clinical evidence. Ther Adv Musculoskelet Dis. 2013 Aug;5(4):199-209. doi: 10.1177/1759720X13490860. PubMed PMID: 23904864; PubMed Central PMCID: PMC3728981.

10: Williams DS, McCracken PJ, Purcell M, Pickarski M, Mathers PD, Savitz AT, Szumiloski J, Jayakar RY, Somayajula S, Krause S, Brown K, Winkelmann CT, Scott BB, Cook L, Motzel SL, Hargreaves R, Evelhoch JL, Cabal A, Dardzinski BJ, Hangartner TN, Duong le T. Effect of odanacatib on bone turnover markers, bone density and geometry of the spine and hip of ovariectomized monkeys: a head-to-head comparison with alendronate. Bone. 2013 Oct;56(2):489-96. doi: 10.1016/j.bone.2013.06.008. Epub 2013 Jun 24. PubMed PMID: 23806798.

11: Cabal A, Jayakar RY, Sardesai S, Phillips EA, Szumiloski J, Posavec DJ, Mathers PD, Savitz AT, Scott BB, Winkelmann CT, Motzel S, Cook L, Hargreaves R, Evelhoch JL, Dardzinski BJ, Hangartner TN, McCracken PJ, Duong le T, Williams DS. High-resolution peripheral quantitative computed tomography and finite element analysis of bone strength at the distal radius in ovariectomized adult rhesus monkey demonstrate efficacy of odanacatib and differentiation from alendronate. Bone. 2013 Oct;56(2):497-505. doi: 10.1016/j.bone.2013.06.011. Epub 2013 Jun 20. PubMed PMID: 23791777.

12: Stoch SA, Witter R, Hreniuk D, Liu C, Zajic S, Mehta A, Brandquist C, Dempsey C, Degroot B, Stypinski D, Denker A, Wagner JA. Absence of clinically relevant drug-drug interaction between odanacatib and digoxin after concomitant administration. Int J Clin Pharmacol Ther. 2013 Aug;51(8):688-92. doi: 10.5414/CP201864. PubMed PMID: 23782582.

13: Nakamura T, Shiraki M, Fukunaga M, Tomomitsu T, Santora AC, Tsai R, Fujimoto G, Nakagomi M, Tsubouchi H, Rosenberg E, Uchida S. Effect of the cathepsin K inhibitor odanacatib administered once weekly on bone mineral density in Japanese patients with osteoporosis-a double-blind, randomized, dose-finding study. Osteoporos Int. 2014 Jan;25(1):367-76. doi: 10.1007/s00198-013-2398-2. Epub 2013 May 29. PubMed PMID: 23716037.

14: Brixen K, Chapurlat R, Cheung AM, Keaveny TM, Fuerst T, Engelke K, Recker R, Dardzinski B, Verbruggen N, Ather S, Rosenberg E, de Papp AE. Bone density, turnover, and estimated strength in postmenopausal women treated with odanacatib: a randomized trial. J Clin Endocrinol Metab. 2013 Feb;98(2):571-80. doi: 10.1210/jc.2012-2972. Epub 2013 Jan 21. PubMed PMID: 23337728.

15: Fratzl-Zelman N, Roschger P, Fisher JE, Duong le T, Klaushofer K. Effects of Odanacatib on bone mineralization density distribution in thoracic spine and femora of ovariectomized adult rhesus monkeys: a quantitative backscattered electron imaging study. Calcif Tissue Int. 2013 Mar;92(3):261-9. doi: 10.1007/s00223-012-9673-7. Epub 2012 Nov 23. PubMed PMID: 23179105.

16: Stoch SA, Zajic S, Stone JA, Miller DL, van Bortel L, Lasseter KC, Pramanik B, Cilissen C, Liu Q, Liu L, Scott BB, Panebianco D, Ding Y, Gottesdiener K, Wagner JA. Odanacatib, a selective cathepsin K inhibitor to treat osteoporosis: safety, tolerability, pharmacokinetics and pharmacodynamics--results from single oral dose studies in healthy volunteers. Br J Clin Pharmacol. 2013 May;75(5):1240-54. doi: 10.1111/j.1365-2125.2012.04471.x. PubMed PMID: 23013236; PubMed Central PMCID: PMC3635595.

17: Ng KW. Potential role of odanacatib in the treatment of osteoporosis. Clin Interv Aging. 2012;7:235-47. doi: 10.2147/CIA.S26729. Epub 2012 Jul 12. Review. PubMed PMID: 22866001; PubMed Central PMCID: PMC3410681.

18: Langdahl B, Binkley N, Bone H, Gilchrist N, Resch H, Rodriguez Portales J, Denker A, Lombardi A, Le Bailly De Tilleghem C, Dasilva C, Rosenberg E, Leung A. Odanacatib in the treatment of postmenopausal women with low bone mineral density: five years of continued therapy in a phase 2 study. J Bone Miner Res. 2012 Nov;27(11):2251-8. doi: 10.1002/jbmr.1695. PubMed PMID: 22777865.

19: Jayakar RY, Cabal A, Szumiloski J, Sardesai S, Phillips EA, Laib A, Scott BB, Pickarski M, Duong le T, Winkelmann CT, McCracken PJ, Hargreaves R, Hangartner TN, Williams DS. Evaluation of high-resolution peripheral quantitative computed tomography, finite element analysis and biomechanical testing in a pre-clinical model of osteoporosis: a study with odanacatib treatment in the ovariectomized adult rhesus monkey. Bone. 2012 Jun;50(6):1379-88. doi: 10.1016/j.bone.2012.03.017. Epub 2012 Mar 24. PubMed PMID: 22469953.

20: Khosla S. Odanacatib: location and timing are everything. J Bone Miner Res. 2012 Mar;27(3):506-8. doi: 10.1002/jbmr.1541. PubMed PMID: 22354850.