Odanacatib

Chemical compound

None

Legal statusLegal status

Development terminated

Identifiers

IUPAC name

N-(1-Cyanocyclopropyl)-4-fluoro-N²-{(1S)-2,2,2-trifluoro-1-[4'-(methylsulfonyl)biphenyl-4-yl]ethyl}-L-leucinamide

CAS Number

603139-19-1^Y

PubChem CID

10152654

IUPHAR/BPS

6478

ChemSpider

8328162^N

UNII

N673F6W2VH

KEGG

D08955^N

ChEMBL

ChEMBL481611^N

CompTox Dashboard (EPA)

DTXSID40209075

ECHA InfoCard100.207.747

Chemical and physical dataFormulaC₂₅H₂₇F₄N₃O₃SMolar mass525.56 g·mol⁻¹3D 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^N
Key:FWIVDMJALNEADT-SFTDATJTSA-N^N

^NY (what is this?) (verify)

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.

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

^ "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary names: List 60" (PDF). WHO Drug Information. 33 (3). World Health Organization: 239. 2008. Archived from the original (PDF) on 26 October 2013. Retrieved 11 November 2016.
^ Le Gall C, Bonnelye E, Clézardin P (September 2008). "Cathepsin K inhibitors as treatment of bone metastasis". Current Opinion in Supportive and Palliative Care. 2 (3): 218–222. doi:10.1097/SPC.0b013e32830baea9. PMID 18685424. S2CID 5834581.
^ Gauthier JY, Chauret N, Cromlish W, Desmarais S, Duong LT, Falgueyret JP, et al. (February 2008). "The discovery of odanacatib (MK-0822), a selective inhibitor of cathepsin K". Bioorganic & Medicinal Chemistry Letters. 18 (3): 923–928. doi:10.1016/j.bmcl.2007.12.047. PMID 18226527.
^ Pierson R (15 September 2014). "Merck osteoporosis drug passes trial, but side effects hover". Reuters. Archived from the original on 2021-07-11.
^ "Merck Provides Update on Odanacatib Development Program". Business Wire. 2016-09-02. Archived from the original on 2016-09-03. Retrieved 2016-09-30.