WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 202440
CAS#: 362505-84-8
Description: Relacatib, also known as SB-462795 and GSK462795;, is a potent and orally bioavailable small molecule inhibitor of cathepsin K that inhibits bone resorption both in vitro in human tissue and in vivo in cynomolgus monkeys. SB-462795 is a potent inhibitor of human cathepsins K, L, and V (K(i, app)=41, 68, and 53 pM, respectively) that exhibits 39-300-fold selectivity over other cathepsins. SB-462795 inhibited endogenous cathepsin K in situ in human osteoclasts and human osteoclast-mediated bone resorption with IC50 values of approximately 45 nM and approximately 70 nM, respectively.
MedKoo Cat#: 202440
Name: Relacatib
CAS#: 362505-84-8
Chemical Formula: C27H32N4O6S
Exact Mass: 540.20426
Molecular Weight: 540.63
Elemental Analysis: C, 59.98; H, 5.97; N, 10.36; O, 17.76; S, 5.93
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Synonym: SB462795; SB-462795; SB 462795; GSK462795; GSK-462795; GSK 462795; D06634
IUPAC/Chemical Name: N-((S)-4-methyl-1-(((4S,7R)-7-methyl-3-oxo-1-(pyridin-2-ylsulfonyl)azepan-4-yl)amino)-1-oxopentan-2-yl)benzofuran-2-carboxamide.
InChi Key: BWYBBMQLUKXECQ-GIVPXCGWSA-N
InChi Code: InChI=1S/C27H32N4O6S/c1-17(2)14-21(30-27(34)24-15-19-8-4-5-9-23(19)37-24)26(33)29-20-12-11-18(3)31(16-22(20)32)38(35,36)25-10-6-7-13-28-25/h4-10,13,15,17-18,20-21H,11-12,14,16H2,1-3H3,(H,29,33)(H,30,34)/t18-,20+,21+/m1/s1
SMILES Code: O=C(C1=CC2=CC=CC=C2O1)N[C@@H](CC(C)C)C(N[C@@H]3C(CN(S(=O)(C4=NC=CC=C4)=O)[C@H](C)CC3)=O)=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
Shelf Life: >5 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
The following data is based on the product molecular weight 540.63 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.
| 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 |
1: Stroup GB, Kumar S, Jerome CP. Treatment with a potent cathepsin K inhibitor preserves cortical and trabecular bone mass in ovariectomized monkeys. Calcif Tissue Int. 2009 Oct;85(4):344-55. Epub 2009 Sep 10. PubMed PMID: 19763376.
2: Kadono Y, Tanaka S. [Prevention of joint destruction by osteoclast-targeting therapy in search of new tools, such as OPG or cathepsin K inhibitor]. Clin Calcium. 2009 Mar;19(3):387-93. Review. Japanese. PubMed PMID: 19252249.
3: Le Gall C, Bonnelye E, Clézardin P. Cathepsin K inhibitors as treatment of bone metastasis. Curr Opin Support Palliat Care. 2008 Sep;2(3):218-22. Review. PubMed PMID: 18685424.
4: Kamiya N, Suzuki H, Kawamura K, Imamoto T, Ichikawa T. [Bony lesion with prostate cancer]. Clin Calcium. 2008 Apr;18(4):431-7. Review. Japanese. PubMed PMID: 18379023.
5: Gauthier JY, Chauret N, Cromlish W, Desmarais S, Duong le T, Falgueyret JP, Kimmel DB, Lamontagne S, Léger S, LeRiche T, Li CS, Massé F, McKay DJ, Nicoll-Griffith DA, Oballa RM, Palmer JT, Percival MD, Riendeau D, Robichaud J, Rodan GA, Rodan SB, Seto C, Thérien M, Truong VL, Venuti MC, Wesolowski G, Young RN, Zamboni R, Black WC. The discovery of odanacatib (MK-0822), a selective inhibitor of cathepsin K. Bioorg Med Chem Lett. 2008 Feb 1;18(3):923-8. Epub 2008 Jan 15. PubMed PMID: 18226527.
6: Kumar S, Dare L, Vasko-Moser JA, James IE, Blake SM, Rickard DJ, Hwang SM, Tomaszek T, Yamashita DS, Marquis RW, Oh H, Jeong JU, Veber DF, Gowen M, Lark MW, Stroup G. A highly potent inhibitor of cathepsin K (relacatib) reduces biomarkers of bone resorption both in vitro and in an acute model of elevated bone turnover in vivo in monkeys. Bone. 2007 Jan;40(1):122-31. Epub 2006 Sep 7. PubMed PMID: 16962401.
7: Yamashita DS, Marquis RW, Xie R, Nidamarthy SD, Oh HJ, Jeong JU, Erhard KF, Ward KW, Roethke TJ, Smith BR, Cheng HY, Geng X, Lin F, Offen PH, Wang B, Nevins N, Head MS, Haltiwanger RC, Narducci Sarjeant AA, Liable-Sands LM, Zhao B, Smith WW, Janson CA, Gao E, Tomaszek T, McQueney M, James IE, Gress CJ, Zembryki DL, Lark MW, Veber DF. Structure activity relationships of 5-, 6-, and 7-methyl-substituted azepan-3-one cathepsin K inhibitors. J Med Chem. 2006 Mar 9;49(5):1597-612. PubMed PMID: 16509577.
Relacatib (SB-462795) is a high-potency inhibitor of cathepsin K with demonstrated antiresorptive activity in normal and ovariectomized monkeys. Studies in ovariectomized monkeys also demonstrated a greater stimulatory effect on cortical bone compared to alendronate, with significant improvements in bone mineral density and bone mineral content compared with vehicle-treated controls. Studies in monkeys indicate site-specific differences between alendronate and relacatib which may translate into differential efficacy. (from drugs of the future)
