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Revision as of 02:20, 7 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (changes to verified fields - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validation|Chem/Drugbo← Previous edit		Latest revision as of 17:27, 28 October 2023 edit undoBoghog (talk | contribs)Autopatrolled, Extended confirmed users, IP block exemptions, New page reviewers, Pending changes reviewers, Rollbackers, Template editors137,723 edits consistent citation formatting
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			{{Short description|Chemical compound}}
	{{drugbox
			{{Drugbox
	| Verifiedfields = changed		| Verifiedfields = changed
	| UNII_Ref = {{fdacite|changed|FDA}}		| Watchedfields = changed
		⚫	| verifiedrevid = 443444475
⚫	| UNII = N673F6W2VH
		⚫	| IUPAC_name = ''N''-(1-Cyanocyclopropyl)-4-fluoro-''N''<sup>2</sup>-<nowiki/>{(1''S'')-2,2,2-trifluoro-1-ethyl}-<small>L</small>-leucinamide
⚫	| verifiedrevid = 407876319
		⚫	| image = Odanacatib corrected.svg
⚫	| IUPAC_name = ''N''-(1-cyanocyclopropyl)-4-fluoro-''N''<sup>2</sup>-{(1''S'')-2,2,2-trifluoro-1-ethyl}-<small>L</small>-leucinamide
			| width = 300
⚫	| synonyms = <small>(2''S'')-''N''-(1-cyanocyclopropyl)-4-fluoro-4-methyl-2-{-4-yl}ethyl]amino}pentanamide</small>
⚫	| image = Odanacatib Structural Formulae V.1.svg
			<!--Clinical data-->
⚫	| CAS_number = 603139-19-1
			| tradename =
	| CAS_supplemental =
		⚫	| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫	| ATC_prefix = none
	| ATC_suffix =		| pregnancy_US = <!-- A / B/ C / D / X -->
		⚫	| pregnancy_category =
⚫	| ATC_supplemental =
	| PubChem = 10152654		| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
		⚫	| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
		⚫	| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
		⚫	| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
		⚫	| legal_status = Development terminated
		⚫	| routes_of_administration = ]
			<!--Pharmacokinetic data-->
		⚫	| bioavailability =
		⚫	| protein_bound =
		⚫	| metabolism =
		⚫	| elimination_half-life =
		⚫	| excretion =
			<!--Identifiers-->
			| 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_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank =		| DrugBank =
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| chemical_formula =
		⚫	| UNII = N673F6W2VH
⚫	| C=25 | H=27 | F=4 | N=3 | O=3 | S=1
			| KEGG_Ref = {{keggcite|changed|kegg}}
	| molecular_weight = 525.56 g/mol
			| KEGG = D08955
⚫	| 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
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
⚫	| bioavailability =
			| ChEMBL = 481611
⚫	| protein_bound =
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫	| metabolism =
			| ChemSpiderID = 8328162
⚫	| elimination_half-life =
⚫	| excretion =
			<!--Chemical data-->
⚫	| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
		⚫	| chemical_formula =
	| pregnancy_US = <!-- A / B / C / D / X -->
		⚫	| C=25 | H=27 | F=4 | N=3 | O=3 | S=1
⚫	| pregnancy_category=
		⚫	| 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
	| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫	| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
			| 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
⚫	| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫	| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
			| StdInChIKey = FWIVDMJALNEADT-SFTDATJTSA-N
⚫	| legal_status =
		⚫	| synonyms = <small>(2''S'')-''N''-(1-Cyanocyclopropyl)-4-fluoro-4-methyl-2-<nowiki/>{-4-yl}ethyl]amino}pentanamide</small>
⚫	| routes_of_administration = oral
	}}		}}
	'''Odanacatib''' (]; codenamed '''MK-0822''') is an investigational treatment for ] and ]<ref>{{pmid|18685424}}</ref>. It is an ] of ],<ref name="pmid18226527">{{cite journal |author=Gauthier JY, Chauret N, Cromlish W, ''et al.'' |title=The discovery of odanacatib (MK-0822), a selective inhibitor of cathepsin K |journal=Bioorg. Med. Chem. Lett. |volume=18 |issue=3 |pages=923–8 |year=2008 |month=February |pmid=18226527 |doi=10.1016/j.bmcl.2007.12.047 |url=}}</ref> an ] involved in ].
			'''Odanacatib''' (];<ref name="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 }}</ref> codenamed '''MK-0822''') is an investigational treatment for ] and ].<ref>{{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 }}</ref> It is an ] of ],<ref name="pmid18226527">{{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 }}</ref> an ] involved in ].
	It is being developed by ] {{As of|2009|11}}, Merck is conducting ].
			The drug was developed by ] The ] 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.<ref>{{cite web | vauthors = Pierson R | date = 15 September 2014 |title=Merck osteoporosis drug passes trial, but side effects hover |website=] |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}}</ref>
⚫	==References==
			In 2016, Merck discontinued development of odanacatib and announced it would not seek regulatory approval after analysis discovered an increased risk of ].<ref>{{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}}</ref>
			This drug was developed at Merck Frosst in ].
		⚫	== References ==
	{{Reflist}}		{{Reflist}}
	{{Drugs for treatment of bone diseases}}		{{Drugs for treatment of bone diseases}}
	]		]
	]		]
			]
			]
			]
			]
			]
	{{musculoskeletal-drug-stub}}		{{musculoskeletal-drug-stub}}
	]