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MedKoo Cat#: 206464 | Name: ONO-5334
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

ONO-5334 is a potent and orally available inhibitor of cathepsin K (Ki values of 0.1 nM, 0.049 nM and 0.85 nM for human, rabbit and rat respectively). ONO-5334 improves bone strength by preferentially increasing cortical bone mass in ovariectomized rats. ONO-5334 inhibits N-terminal and C-terminal collagen crosslinks in serum and urine at similar plasma concentrations in postmenopausal women. ONO-5334 had entered clinical development for metabolic bone disorders with increased bone resorption, such as postmenopausal osteoporosis.

Chemical Structure

ONO-5334
ONO-5334
CAS#868273-90-9

Theoretical Analysis

MedKoo Cat#: 206464

Name: ONO-5334

CAS#: 868273-90-9

Chemical Formula: C21H34N4O4S

Exact Mass: 438.2301

Molecular Weight: 438.59

Elemental Analysis: C, 57.51; H, 7.81; N, 12.77; O, 14.59; S, 7.31

Price and Availability

Size Price Availability Quantity
2mg USD 305.00 2 Weeks
5mg USD 670.00 2 Weeks
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Related CAS #
No Data
Synonym
ONO-5334; ONO 5334; ONO5334.
IUPAC/Chemical Name
N-((S)-3-(2-((R,Z)-3,4-dimethylthiazolidin-2-ylidene)hydrazinyl)-2,3-dioxo-1-(tetrahydro-2H-pyran-4-yl)propyl)cycloheptanecarboxamide
InChi Key
BTZCSXIUAFVRTE-CHGLIHOBSA-N
InChi Code
InChI=1S/C21H34N4O4S/c1-14-13-30-21(25(14)2)24-23-20(28)18(26)17(15-9-11-29-12-10-15)22-19(27)16-7-5-3-4-6-8-16/h14-17H,3-13H2,1-2H3,(H,22,27)(H,23,28)/b24-21-/t14-,17+/m1/s1
SMILES Code
O=C(N/N=C1SC[C@@H](C)N\1C)C([C@@H](NC(C2CCCCCC2)=O)C3CCOCC3)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
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).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
ONO-5334 is a potent, selective and orally active cathepsin K inhibitor with Ki values of 0.10 nM, 0.049 nM and 0.85 nM for human, rabbit and rat cathepsin K.
In vitro activity:
In vitro experiments indicated that ONO-5334 is a potent inhibitor of cathepsin K with Ki value of 0.1 nM. ONO-5334 also inhibited human osteoclasts bone resorption in vitro at a concentration more than 100 fold lower than that of alendronate, a bisphosphonate. Reference: Bone. 2011 Dec;49(6):1351-6. https://pubmed.ncbi.nlm.nih.gov/21982869/
In vivo activity:
This study evaluated the long-term effects of the cathepsin K inhibitor ONO-5334 on bone mass and strength in ovariectomised (OVX) cynomolgus monkeys. Peripheral quantitative computed tomography (pQCT) analysis revealed that ONO-5334 increased not only trabecular bone mineral density (BMD) but also cortical BMD in the distal radius and the lumbar vertebra. ONO-5334 and ALN suppressed the deterioration of trabecular architecture by micro-CT analysis in the distal radius. Assessments of bone strength showed that ONO-5334 increased maximum load at the distal and midshaft radius. Reference: J Bone Miner Metab. 2019 Jul;37(4):636-647. https://pubmed.ncbi.nlm.nih.gov/30357565/

Preparing Stock Solutions

The following data is based on the product molecular weight 438.59 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Ochi Y, Yamada H, Mori H, Nakanishi Y, Nishikawa S, Kayasuga R, Kawada N, Kunishige A, Hashimoto Y, Tanaka M, Sugitani M, Kawabata K. Effects of ONO-5334, a novel orally-active inhibitor of cathepsin K, on bone metabolism. Bone. 2011 Dec;49(6):1351-6. doi: 10.1016/j.bone.2011.09.041. Epub 2011 Sep 18. PMID: 21982869. 2. Yamada H, Ochi Y, Mori H, Nishikawa S, Hashimoto Y, Tanaka M, Deacon S, Kawabata K. Cortical bone mineral density is increased by the cathepsin K inhibitor ONO-5334, which leads to a robust increase in bone strength: results from a 16-month study in ovariectomised cynomolgus monkeys. J Bone Miner Metab. 2019 Jul;37(4):636-647. doi: 10.1007/s00774-018-0968-2. Epub 2018 Oct 24. PMID: 30357565. 3. Ochi Y, Yamada H, Mori H, Nakanishi Y, Nishikawa S, Kayasuga R, Kawada N, Kunishige A, Hashimoto Y, Tanaka M, Sugitani M, Kawabata K. Effects of eight-month treatment with ONO-5334, a cathepsin K inhibitor, on bone metabolism, strength and microstructure in ovariectomized cynomolgus monkeys. Bone. 2014 Aug;65:1-8. doi: 10.1016/j.bone.2014.04.023. Epub 2014 Apr 27. PMID: 24784023.
In vitro protocol:
1. Ochi Y, Yamada H, Mori H, Nakanishi Y, Nishikawa S, Kayasuga R, Kawada N, Kunishige A, Hashimoto Y, Tanaka M, Sugitani M, Kawabata K. Effects of ONO-5334, a novel orally-active inhibitor of cathepsin K, on bone metabolism. Bone. 2011 Dec;49(6):1351-6. doi: 10.1016/j.bone.2011.09.041. Epub 2011 Sep 18. PMID: 21982869.
In vivo protocol:
1. Yamada H, Ochi Y, Mori H, Nishikawa S, Hashimoto Y, Tanaka M, Deacon S, Kawabata K. Cortical bone mineral density is increased by the cathepsin K inhibitor ONO-5334, which leads to a robust increase in bone strength: results from a 16-month study in ovariectomised cynomolgus monkeys. J Bone Miner Metab. 2019 Jul;37(4):636-647. doi: 10.1007/s00774-018-0968-2. Epub 2018 Oct 24. PMID: 30357565. 2. Ochi Y, Yamada H, Mori H, Nakanishi Y, Nishikawa S, Kayasuga R, Kawada N, Kunishige A, Hashimoto Y, Tanaka M, Sugitani M, Kawabata K. Effects of eight-month treatment with ONO-5334, a cathepsin K inhibitor, on bone metabolism, strength and microstructure in ovariectomized cynomolgus monkeys. Bone. 2014 Aug;65:1-8. doi: 10.1016/j.bone.2014.04.023. Epub 2014 Apr 27. PMID: 24784023.
1: Duong LT, Leung AT, Langdahl B. Cathepsin K Inhibition: A New Mechanism for the Treatment of Osteoporosis. Calcif Tissue Int. 2015 Sep 3. [Epub ahead of print] PubMed PMID: 26335104. 2: Tanaka M, Hashimoto Y, Hasegawa C. An oral cathepsin K inhibitor ONO-5334 inhibits N-terminal and C-terminal collagen crosslinks in serum and urine at similar plasma concentrations in postmenopausal women. Bone. 2015 Jul 16;81:178-185. doi: 10.1016/j.bone.2015.07.016. [Epub ahead of print] PubMed PMID: 26188109. 3: Gamsjäger M, Resch H. [Cathepsin K antagonists: preclinical and clinical data]. Wien Med Wochenschr. 2015 Feb;165(3-4):65-70. doi: 10.1007/s10354-014-0336-3. Epub 2015 Jan 9. German. PubMed PMID: 25572547. 4: Ochi Y, Yamada H, Mori H, Nakanishi Y, Nishikawa S, Kayasuga R, Kawada N, Kunishige A, Hashimoto Y, Tanaka M, Sugitani M, Kawabata K. Effects of eight-month treatment with ONO-5334, a cathepsin K inhibitor, on bone metabolism, strength and microstructure in ovariectomized cynomolgus monkeys. Bone. 2014 Aug;65:1-8. doi: 10.1016/j.bone.2014.04.023. Epub 2014 Apr 27. PubMed PMID: 24784023. 5: Hasegawa C, Kastrissios H, Monteleone J, Ohno T, Umemura T, Ohyama M, Nagase S, Small M, Deacon S, Ogawa M, Ieiri I. Modeling and simulation of bone mineral density response from a phase 2 study of ONO-5334, a new cathepsin K inhibitor, to support dose selection in osteoporosis. J Clin Pharmacol. 2014 Aug;54(8):937-48. doi: 10.1002/jcph.279. Epub 2014 Feb 28. PubMed PMID: 24615681. 6: Nagase S, Ohyama M, Hashimoto Y, Small M, Sharpe J, Manako J, Kuwayama T, Deacon S. Bone turnover markers and pharmacokinetics of a new sustained-release formulation of the cathepsin K inhibitor, ONO-5334, in healthy post-menopausal women. J Bone Miner Metab. 2015 Jan;33(1):93-100. doi: 10.1007/s00774-013-0558-2. Epub 2014 Jan 24. PubMed PMID: 24458199. 7: Ochi Y, Yamada H, Mori H, Kawada N, Kayasuga R, Nakanishi Y, Tanaka M, Imagawa A, Ohmoto K, Kawabata K. ONO-5334, a cathepsin K inhibitor, improves bone strength by preferentially increasing cortical bone mass in ovariectomized rats. J Bone Miner Metab. 2014 Nov;32(6):645-52. doi: 10.1007/s00774-013-0542-x. Epub 2013 Dec 8. PubMed PMID: 24317478. 8: Hasegawa C, Ohno T, Umemura T, Honda N, Ohyama M, Nagase S, Small M, Deacon S, Ogawa M, Ieiri I. Population pharmacokinetic and pharmacodynamic modeling of different formulations of ONO-5334, cathepsin K inhibitor, in Caucasian and Japanese postmenopausal females. J Clin Pharmacol. 2014 Jan;54(1):23-34. doi: 10.1002/jcph.186. Epub 2013 Oct 10. PubMed PMID: 24115072. 9: Tanaka M, Hashimoto Y, Sekiya N, Honda N, Deacon S, Yamamoto M. Effects of novel cathepsin K inhibitor ONO-5334 on bone resorption markers: a study of four sustained release formulations with different pharmacokinetic patterns. J Bone Miner Metab. 2014 Jul;32(4):447-54. doi: 10.1007/s00774-013-0517-y. Epub 2013 Oct 11. PubMed PMID: 24114194. 10: Engelke K, Nagase S, Fuerst T, Small M, Kuwayama T, Deacon S, Eastell R, Genant HK. The effect of the cathepsin K inhibitor ONO-5334 on trabecular and cortical bone in postmenopausal osteoporosis: the OCEAN study. J Bone Miner Res. 2014 Mar;29(3):629-38. doi: 10.1002/jbmr.2080. PubMed PMID: 24038152. 11: Eastell R, Nagase S, Small M, Boonen S, Spector T, Ohyama M, Kuwayama T, Deacon S. Effect of ONO-5334 on bone mineral density and biochemical markers of bone turnover in postmenopausal osteoporosis: 2-year results from the OCEAN study. J Bone Miner Res. 2014 Feb;29(2):458-66. doi: 10.1002/jbmr.2047. PubMed PMID: 23873670. 12: Nagase S, Hashimoto Y, Small M, Ohyama M, Kuwayama T, Deacon S. Serum and urine bone resorption markers and pharmacokinetics of the cathepsin K inhibitor ONO-5334 after ascending single doses in post menopausal women. Br J Clin Pharmacol. 2012 Dec;74(6):959-70. doi: 10.1111/j.1365-2125.2012.04307.x. PubMed PMID: 22533981; PubMed Central PMCID: PMC3522809. 13: Boonen S, Rosenberg E, Claessens F, Vanderschueren D, Papapoulos S. Inhibition of cathepsin K for treatment of osteoporosis. Curr Osteoporos Rep. 2012 Mar;10(1):73-9. doi: 10.1007/s11914-011-0085-9. Review. PubMed PMID: 22228398. 14: Ochi Y, Yamada H, Mori H, Nakanishi Y, Nishikawa S, Kayasuga R, Kawada N, Kunishige A, Hashimoto Y, Tanaka M, Sugitani M, Kawabata K. Effects of ONO-5334, a novel orally-active inhibitor of cathepsin K, on bone metabolism. Bone. 2011 Dec;49(6):1351-6. doi: 10.1016/j.bone.2011.09.041. Epub 2011 Sep 18. PubMed PMID: 21982869. 15: Wijkmans J, Gossen J. Inhibitors of cathepsin K: a patent review (2004 - 2010). Expert Opin Ther Pat. 2011 Oct;21(10):1611-29. doi: 10.1517/13543776.2011.616283. Review. PubMed PMID: 21923554. 16: Nagase S, Ohyama M, Hashimoto Y, Small M, Kuwayama T, Deacon S. Pharmacodynamic effects on biochemical markers of bone turnover and pharmacokinetics of the cathepsin K inhibitor, ONO-5334, in an ascending multiple-dose, phase 1 study. J Clin Pharmacol. 2012 Mar;52(3):306-18. doi: 10.1177/0091270011399080. Epub 2011 Jun 30. PubMed PMID: 21719717. 17: Eastell R, Nagase S, Ohyama M, Small M, Sawyer J, Boonen S, Spector T, Kuwayama T, Deacon S. Safety and efficacy of the cathepsin K inhibitor ONO-5334 in postmenopausal osteoporosis: the OCEAN study. J Bone Miner Res. 2011 Jun;26(6):1303-12. doi: 10.1002/jbmr.341. PubMed PMID: 21312264. 18: Manako J. [New approach for osteoporosis treatment: cathepsin K inhibitor, ONO-5334]. Clin Calcium. 2011 Jan;21(1):64-9. doi: CliCa11016469. Review. Japanese. PubMed PMID: 21187596. 19: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2010 Sep;32(7):517-48. doi: 10.1358/mf.2010.32.7.1549223. PubMed PMID: 21069103.

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