Odanacatib: Difference between revisions

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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}}

	]

Latest revision as of 17:27, 28 October 2023

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	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
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; 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

"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.

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

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