Odanacatib

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-N2-{(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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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.

This drug article relating to the musculoskeletal system is a stub. You can help Wikipedia by expanding it.

[INN-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.

[pmid18226527-3] 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.

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v t e Drugs for treatment of bone diseases (M05)
Bisphosphonates	Nitrogenous Alendronic acid Ibandronic acid Incadronic acid Minodronic acid Neridronic acid Pamidronic acid Risedronic acid Zoledronic acid Non-nitrogenous Etidronic acid Clodronic acid Tiludronic acid
Bone morphogenetic proteins	Dibotermin alfa Eptotermin alfa
Other	Resorption inhibitor Ipriflavone Aluminium chlorohydrate Dual action bone agent Strontium ranelate RANKL inhibitor Denosumab Sclerostin inhibitor Romosozumab Cathepsin K inhibitor Odanacatib Parathyroid hormone-related protein analogues Abaloparatide Teriparatide Calcitonin Calcium Vitamin D