canertinib

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 460016047

| ImageFile = Canertinib.svg

| ImageSize = 200px

| PIN = N-{4-(3-Chloro-4-fluoroanilino)-7-[3-(morpholin-4-yl)propoxy]quinazolin-6-yl}prop-2-enamide

| OtherNames = CI-1033; PD-183805

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 5675

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 267243-28-7

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

| UNII = C78W1K5ASF

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 61399

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 31965

| ChEMBL1_Ref = {{ebicite|changed|EBI}}

| ChEMBL1 = 545315

| PubChem = 156414

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 137741

| SMILES = Fc1ccc(cc1Cl)Nc4ncnc3cc(OCCCN2CCOCC2)c(NC(=O)\C=C)cc34

| 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)

| InChIKey = OMZCMEYTWSXEPZ-UHFFFAOYAG

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OMZCMEYTWSXEPZ-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| C=24 | H=25 | Cl=1 | F=1 | N=5 | O=3

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

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}}

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).{{cite journal | pmid = 10753475 | year = 2000 | last1 = Smaill | first1 = JB | last2 = Rewcastle | first2 = GW | last3 = Loo | first3 = JA | last4 = Greis | first4 = KD | last5 = Chan | first5 = OH | last6 = Reyner | first6 = EL | last7 = Lipka | first7 = E | last8 = Showalter | first8 = HD | last9 = Vincent | first9 = PW | last10 = Elliott | first10 = William L | last11 = Denny | first11 = William A | title = 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 | volume = 43 | issue = 7 | pages = 1380–97 | journal = Journal of Medicinal Chemistry | doi=10.1021/jm990482t| display-authors = 8 }}[http://www.selleckchem.com/products/CI-1033%28Canertinib%29.html CI-1033 (Canertinib)], Selleck Chemicals By 2015, Pfizer had discontinued development of the drug.{{Cite web|url=http://adisinsight.springer.com/drugs/800012072|title = Canertinib - AdisInsight}}

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.{{cite journal |vauthors=Khurana V, Minocha M, Pal D, Mitra AK | title = Role of OATP-1B1 and/or OATP-1B3 in hepatic disposition of tyrosine kinase inhibitors. | journal = Drug Metabol Drug Interact. | volume = 29| issue = 3 | pages = 179–90 |date=March 2014 | pmid = 24643910 | doi = 10.1515/dmdi-2013-0062 | pmc=4407685}} Canertinib is not an inhibitor of the OATP1B1 or OATP1B3 transporters.{{cite journal |vauthors=Khurana V, Minocha M, Pal D, Mitra AK | title = Inhibition of OATP-1B1 and OATP-1B3 by tyrosine kinase inhibitors. | journal = Drug Metabol Drug Interact. | volume = 29| issue = 4 | pages = 249–59 |date=May 2014 | pmid = 24807167 | doi = 10.1515/dmdi-2014-0014 | pmc=4407688}}