Canertinib

Canertinib
Names
	Preferred IUPAC name N-{4-(3-Chloro-4-fluoroanilino)-7-[3-(morpholin-4-yl)propoxy]quinazolin-6-yl}prop-2-enamide
	Other names CI-1033; PD-183805
Identifiers
CAS Number	267243-28-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:61399 ;
ChEMBL	ChEMBL31965 ; ChEMBL545315 ;
ChemSpider	137741 ;
IUPHAR/BPS	5675;
PubChem CID	156414;
UNII	C78W1K5ASF ;
CompTox Dashboard (EPA)	DTXSID8048943 ;
	InChI InChI=1S/C24H25ClFN5O3/c1-2-23(32)30-21-13-17-20(14-22(21)34-9-3-6-31-7-10-33-11-8-31)27-15-28-24(17)29-16-4-5-19(26)18(25)12-16/h2,4-5,12-15H,1,3,6-11H2,(H,30,32)(H,27,28,29) Key: OMZCMEYTWSXEPZ-UHFFFAOYSA-N ; InChI=1/C24H25ClFN5O3/c1-2-23(32)30-21-13-17-20(14-22(21)34-9-3-6-31-7-10-33-11-8-31)27-15-28-24(17)29-16-4-5-19(26)18(25)12-16/h2,4-5,12-15H,1,3,6-11H2,(H,30,32)(H,27,28,29) Key: OMZCMEYTWSXEPZ-UHFFFAOYAG;
	SMILES Fc1ccc(cc1Cl)Nc4ncnc3cc(OCCCN2CCOCC2)c(NC(=O)\C=C)cc34;
Properties
Chemical formula	C24H25ClFN5O3
Molar mass	485.94 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Canertinib (CI-1033) is an experimental drug candidate for the treatment of cancer. It is an irreversible tyrosine-kinase inhibitor with activity against EGFR (IC₅₀ 0.8 nM), HER-2 (IC₅₀ 19 nM) and ErbB-4 (IC₅₀ 7 nM).^[1]^[2] By 2015, Pfizer had discontinued development of the drug.^[3]

Canertinib has been reported as a substrate for the transporter protein OATP1B3. Interaction of canertinib with OATP1B3 may alter its hepatic disposition and can lead to transporter mediated drug-drug interactions.^[4] Canertinib is not an inhibitor of the OATP1B1 or OATP1B3 transporters.^[5]

References

^ Smaill, JB; Rewcastle, GW; Loo, JA; Greis, KD; Chan, OH; Reyner, EL; Lipka, E; Showalter, HD; et al. (2000). "Tyrosine kinase inhibitors. 17. Irreversible inhibitors of the epidermal growth factor receptor: 4-(phenylamino)quinazoline- and 4-(phenylamino)pyrido3,2-dpyrimidine-6-acrylamides bearing additional solubilizing functions". Journal of Medicinal Chemistry. 43 (7): 1380–97. doi:10.1021/jm990482t. PMID 10753475.
^ CI-1033 (Canertinib), Selleck Chemicals
^ "Canertinib - AdisInsight".
^ Khurana V, Minocha M, Pal D, Mitra AK (March 2014). "Role of OATP-1B1 and/or OATP-1B3 in hepatic disposition of tyrosine kinase inhibitors". Drug Metabol Drug Interact. 29 (3): 179–90. doi:10.1515/dmdi-2013-0062. PMC 4407685. PMID 24643910.
^ Khurana V, Minocha M, Pal D, Mitra AK (May 2014). "Inhibition of OATP-1B1 and OATP-1B3 by tyrosine kinase inhibitors". Drug Metabol Drug Interact. 29 (4): 249–59. doi:10.1515/dmdi-2014-0014. PMC 4407688. PMID 24807167.

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[1] Smaill, JB; Rewcastle, GW; Loo, JA; Greis, KD; Chan, OH; Reyner, EL; Lipka, E; Showalter, HD; et al. (2000). "Tyrosine kinase inhibitors. 17. Irreversible inhibitors of the epidermal growth factor receptor: 4-(phenylamino)quinazoline- and 4-(phenylamino)pyrido3,2-dpyrimidine-6-acrylamides bearing additional solubilizing functions". Journal of Medicinal Chemistry. 43 (7): 1380–97. doi:10.1021/jm990482t. PMID 10753475.

[2] CI-1033 (Canertinib), Selleck Chemicals

[3] "Canertinib - AdisInsight".

[pmid24643910-4] Khurana V, Minocha M, Pal D, Mitra AK (March 2014). "Role of OATP-1B1 and/or OATP-1B3 in hepatic disposition of tyrosine kinase inhibitors". Drug Metabol Drug Interact. 29 (3): 179–90. doi:10.1515/dmdi-2013-0062. PMC 4407685. PMID 24643910.

[Khurana_V_2014-5] Khurana V, Minocha M, Pal D, Mitra AK (May 2014). "Inhibition of OATP-1B1 and OATP-1B3 by tyrosine kinase inhibitors". Drug Metabol Drug Interact. 29 (4): 249–59. doi:10.1515/dmdi-2014-0014. PMC 4407688. PMID 24807167.

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