Crizotinib

Crizotinib
Clinical data
Trade names	Xalkori, others
Other names	PF-02341066; 1066
AHFS/Drugs.com	Monograph
MedlinePlus	a612018
License data	US DailyMed: Crizotinib;
Pregnancy; category	AU: D;
Routes of; administration	By mouth
ATC code	L01ED01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	43%
Protein binding	91%
Metabolism	Liver (CYP3A4/CYP3A5-mediated)
Elimination half-life	42 hours
Excretion	Faeces (63%), urine (22%)
Identifiers
	IUPAC name 3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine;
CAS Number	877399-52-5 ;
PubChem CID	11626560;
IUPHAR/BPS	4903;
DrugBank	DB08700 ;
ChemSpider	9801307 ;
UNII	53AH36668S;
KEGG	D09731 ;
ChEBI	CHEBI:64310 ;
ChEMBL	ChEMBL601719 ;
PDB ligand	VGH (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID701009329 ;
ECHA InfoCard	100.166.440
Chemical and physical data
Formula	C21H22Cl2FN5O
Molar mass	450.34 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1(=C(C=CC(=C1[C@H](OC2=C(N=CC(=C2)C3=C[N](N=C3)C4CCNCC4)N)C)Cl)F)Cl;
	InChI InChI=1S/C21H22Cl2FN5O/c1-12(19-16(22)2-3-17(24)20(19)23)30-18-8-13(9-27-21(18)25)14-10-28-29(11-14)15-4-6-26-7-5-15/h2-3,8-12,15,26H,4-7H2,1H3,(H2,25,27)/t12-/m1/s1 ; Key:KTEIFNKAUNYNJU-GFCCVEGCSA-N ;
	(what is this?) (verify)

Crizotinib, sold under the brand name Xalkori among others, is an anti-cancer medication used for the treatment of non-small cell lung carcinoma (NSCLC).^[2]^[3]^[4]^[5] Crizotinib inhibits the c-Met/Hepatocyte growth factor receptor (HGFR) tyrosine kinase, which is involved in the oncogenesis of a number of other histological forms of malignant neoplasms.^[6] It also acts as an ALK (anaplastic lymphoma kinase) and ROS1 (c-ros oncogene 1) inhibitor.^[7]^[8]^[9]

^ "Prescription medicines and biologicals: TGA annual summary 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 31 March 2024.
^ ^a ^b "Xalkori- crizotinib capsule". DailyMed. Archived from the original on 9 October 2021. Retrieved 18 April 2021.
^ ^a ^b "Xalkori EPAR". European Medicines Agency (EMA). 17 September 2018. Archived from the original on 19 April 2021. Retrieved 18 April 2021.
^ "Drug Approval Package: Xalkori Capsules (crizotinib) NDA #202570". U.S. Food and Drug Administration (FDA). 27 September 2011. Archived from the original on 7 April 2021. Retrieved 18 April 2021.
^ "Summary Review for Regulatory Action" (PDF). U.S. Food and Drug Administration (FDA). 26 August 2011. Archived from the original (PDF) on 6 April 2021. Retrieved 19 April 2021.
^ Clinical trial number NCT00585195 for "A Study Of Oral PF-02341066, A c-Met/Hepatocyte Growth Factor Tyrosine Kinase Inhibitor, In Patients With Advanced Cancer" at ClinicalTrials.gov
^ Forde PM, Rudin CM (June 2012). "Crizotinib in the treatment of non-small-cell lung cancer". Expert Opinion on Pharmacotherapy. 13 (8): 1195–201. doi:10.1517/14656566.2012.688029. PMID 22594847. S2CID 23715951.
^ Roberts PJ (2013). "Clinical use of crizotinib for the treatment of non-small cell lung cancer". Biologics: Targets and Therapy. 7: 91–101. doi:10.2147/BTT.S29026. PMC 3643289. PMID 23671386.
^ Sahu A, Prabhash K, Noronha V, Joshi A, Desai S (April 2013). "Crizotinib: A comprehensive review". South Asian Journal of Cancer. 2 (2): 91–7. doi:10.4103/2278-330X.110506 (inactive 11 July 2025). PMC 3876666. PMID 24455567.{{cite journal}}: CS1 maint: DOI inactive as of July 2025 (link)

[1] "Prescription medicines and biologicals: TGA annual summary 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 31 March 2024.

[Xalkori_FDA_label-2] "Xalkori- crizotinib capsule". DailyMed. Archived from the original on 9 October 2021. Retrieved 18 April 2021.

[Xalkori_EPAR-3] "Xalkori EPAR". European Medicines Agency (EMA). 17 September 2018. Archived from the original on 19 April 2021. Retrieved 18 April 2021.

[FDA_approval_package-4] "Drug Approval Package: Xalkori Capsules (crizotinib) NDA #202570". U.S. Food and Drug Administration (FDA). 27 September 2011. Archived from the original on 7 April 2021. Retrieved 18 April 2021.

[5] "Summary Review for Regulatory Action" (PDF). U.S. Food and Drug Administration (FDA). 26 August 2011. Archived from the original (PDF) on 6 April 2021. Retrieved 19 April 2021.

[TrialNCT00585195-6] Clinical trial number NCT00585195 for "A Study Of Oral PF-02341066, A c-Met/Hepatocyte Growth Factor Tyrosine Kinase Inhibitor, In Patients With Advanced Cancer" at ClinicalTrials.gov

[pmid22594847-7] Forde PM, Rudin CM (June 2012). "Crizotinib in the treatment of non-small-cell lung cancer". Expert Opinion on Pharmacotherapy. 13 (8): 1195–201. doi:10.1517/14656566.2012.688029. PMID 22594847. S2CID 23715951.

[pmid23671386-8] Roberts PJ (2013). "Clinical use of crizotinib for the treatment of non-small cell lung cancer". Biologics: Targets and Therapy. 7: 91–101. doi:10.2147/BTT.S29026. PMC 3643289. PMID 23671386.

[pmid24455567-9] Sahu A, Prabhash K, Noronha V, Joshi A, Desai S (April 2013). "Crizotinib: A comprehensive review". South Asian Journal of Cancer. 2 (2): 91–7. doi:10.4103/2278-330X.110506 (inactive 11 July 2025). PMC 3876666. PMID 24455567.{{cite journal}}: CS1 maint: DOI inactive as of July 2025 (link)

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