Odanacatib

Odanacatib (INN;[1] codenamed MK-0822) is an investigational treatment for osteoporosis and bone metastasis.[2] It is an inhibitor of cathepsin K,[3] an enzyme involved in bone resorption.

Odanacatib

Clinical data
Other names	(2S)-N-(1-Cyanocyclopropyl)-4-fluoro-4-methyl-2-{[(1S)-2,2,2-trifluoro-1-{4'-(methanesulfonyl)-[1,1'-biphenyl]-4-yl}ethyl]amino}pentanamide
Routes of administration	By mouth
ATC code	None
Legal status
Legal status	Development terminated
Identifiers
IUPAC name N-(1-Cyanocyclopropyl)-4-fluoro-N^2-{(1S)-2,2,2-trifluoro-1-[4'-(methylsulfonyl)biphenyl-4-yl]ethyl}-L-leucinamide
CAS Number	603139-19-1
PubChem CID	10152654
IUPHAR/BPS	6478
ChemSpider	8328162
UNII	N673F6W2VH
KEGG	D08955
ChEMBL	ChEMBL481611
CompTox Dashboard (EPA)	DTXSID40209075
ECHA InfoCard	100.207.747
Chemical and physical data
Formula	C25H27F4N3O3S
Molar mass	525.56 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC(C)(CC(C(=O)NC1(CC1)C#N)NC(C2=CC=C(C=C2)C3=CC=C(C=C3)S(=O)(=O)C)C(F)(F)F)F
InChI 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 Key:FWIVDMJALNEADT-SFTDATJTSA-N
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The drug was developed by Merck & Co. The phase III clinical trial for this medicine was stopped early after a review showed it was highly effective and had a good safety profile. Merck announced in 2014 that it would apply for regulatory approval in 2015.[4]

In 2016, Merck discontinued development of odanacatib and announced it would not seek regulatory approval after analysis discovered an increased risk of stroke.[5]

This drug was developed at Merck Frosst in Montreal.

References

1. "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary names: List 60" (PDF). World Health Organization. 2008. p. 239. Retrieved 11 November 2016.
2. Le Gall, C. L.; Bonnelye, E.; Clézardin, P. (2008). "Cathepsin K inhibitors as treatment of bone metastasis". Current Opinion in Supportive and Palliative Care. 2 (3): 218–22. doi:10.1097/SPC.0b013e32830baea9. PMID 18685424. S2CID 5834581.
3. Gauthier JY, Chauret N, Cromlish W, et al. (February 2008). "The discovery of odanacatib (MK-0822), a selective inhibitor of cathepsin K". Bioorg. Med. Chem. Lett. 18 (3): 923–8. doi:10.1016/j.bmcl.2007.12.047. PMID 18226527.
4. https://www.reuters.com/article/2014/09/15/us-merck-osteoporosis-idUSKBN0HA1Y820140915
5. "Merck Provides Update on Odanacatib Development Program". Business Wire. 2016-09-02. Archived from the original on 2016-09-03. Retrieved 2016-09-30.