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Odanacatib

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Chemical compound Pharmaceutical compound
Odanacatib
Clinical data
Other names(2S)-N-(1-Cyanocyclopropyl)-4-fluoro-4-methyl-2-{-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-{(1S)-2,2,2-trifluoro-1-ethyl}-L-leucinamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.207.747 Edit this at Wikidata
Chemical and physical data
FormulaC25H27F4N3O3S
Molar mass525.56 g·mol
3D model (JSmol)
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
  (what is this?)  (verify)

Odanacatib (INN; 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.

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.

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

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). WHO Drug Information. 33 (3). World Health Organization: 239. 2008. Archived from the original (PDF) on 26 October 2013. Retrieved 11 November 2016.
  2. 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.
  3. 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.
  4. Pierson R (15 September 2014). "Merck osteoporosis drug passes trial, but side effects hover". Reuters. Archived from the original on 2021-07-11.
  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.
Drugs for treatment of bone diseases (M05)
Bisphosphonates
Bone morphogenetic proteins
Other
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