odanacatib

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 443444475

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

| image = Odanacatib corrected.svg

| width = 300

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status = Development terminated

| routes_of_administration = By mouth

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| IUPHAR_ligand = 6478

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 603139-19-1

| ATC_prefix = None

| ATC_suffix =

| ATC_supplemental =

| PubChem = 10152654

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = N673F6W2VH

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = D08955

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 481611

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 8328162

| chemical_formula =

| C=25 | H=27 | F=4 | N=3 | O=3 | S=1

| 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

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = FWIVDMJALNEADT-SFTDATJTSA-N

| synonyms = (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

}}

Odanacatib (INN;{{cite journal |title=International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary names: List 60 | journal = WHO Drug Information | volume = 33 | issue= 3 | date = 2008 |url=https://www.who.int/medicines/publications/druginformation/innlists/RL60.pdf | archive-url = https://web.archive.org/web/20131026150609/https://www.who.int/medicines/publications/druginformation/innlists/RL60.pdf | archive-date = 26 October 2013 |publisher=World Health Organization|access-date=11 November 2016|page=239 }} codenamed MK-0822) is an investigational treatment for osteoporosis and bone metastasis.{{cite journal | vauthors = Le Gall C, Bonnelye E, Clézardin P | title = Cathepsin K inhibitors as treatment of bone metastasis | journal = Current Opinion in Supportive and Palliative Care | volume = 2 | issue = 3 | pages = 218–222 | date = September 2008 | pmid = 18685424 | doi = 10.1097/SPC.0b013e32830baea9 | s2cid = 5834581 }} It is an inhibitor of cathepsin K,{{cite journal | vauthors = Gauthier JY, Chauret N, Cromlish W, Desmarais S, Duong LT, 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 | display-authors = 6 | title = The discovery of odanacatib (MK-0822), a selective inhibitor of cathepsin K | journal = Bioorganic & Medicinal Chemistry Letters | volume = 18 | issue = 3 | pages = 923–928 | date = February 2008 | pmid = 18226527 | doi = 10.1016/j.bmcl.2007.12.047 }} 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.{{cite web | vauthors = Pierson R | date = 15 September 2014 |title=Merck osteoporosis drug passes trial, but side effects hover |website=Reuters |archive-url=https://web.archive.org/web/20210711172651/https://www.reuters.com/article/us-merck-osteoporosis-idUSKBN0HA1Y820140915 |archive-date=2021-07-11 |url-status=live |url=https://www.reuters.com/article/us-merck-osteoporosis-idUSKBN0HA1Y820140915}}

In 2016, Merck discontinued development of odanacatib and announced it would not seek regulatory approval after analysis discovered an increased risk of stroke.{{cite news | url=http://www.businesswire.com/news/home/20160902005107/en/Merck-Update-Odanacatib-Development-Program | title=Merck Provides Update on Odanacatib Development Program | work=Business Wire | date=2016-09-02 | access-date=2016-09-30 | archive-url=https://web.archive.org/web/20160903172200/http://www.businesswire.com/news/home/20160902005107/en/Merck-Update-Odanacatib-Development-Program | archive-date=2016-09-03 | url-status=live}}

This drug was developed at Merck Frosst in Montreal.