CANERTINIB

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H25ClFN5O3
Molecular Weight	485.938
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC1=CC=C(NC2=C3C=C(NC(=O)C=C)C(OCCCN4CCOCC4)=CC3=NC=N2)C=C1Cl

InChI

InChIKey=OMZCMEYTWSXEPZ-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C24H25ClFN5O3
Molecular Weight	485.938
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10753475 | https://www.ncbi.nlm.nih.gov/pubmed/11706399 | https://www.ncbi.nlm.nih.gov/pubmed/14730468 | http://adisinsight.springer.com/drugs/800012072

Canertinib or CI-1033 (N-[4-[N-(3-Chloro-4-fluorophenyl)amino]-7-[3-(4-morpholinyl)propoxy]quinazolin-6-yl]acrylamide) is a pan-erbB tyrosine kinase inhibitor. It selectively inhibits erbB1 (epidermal growth factor receptor), erbB2, erbB3, and erbB4 without inhibiting tyrosine kinase activity of receptors such as platelet-derived growth factor receptor, fibroblast growth factor receptor, and insulin receptor, even at high concentrations. Canertinib was under development by Pfizer Inc as a potential treatment for cancer.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Epidermal growth factor receptor erbB1 62 Target ID: CHEMBL203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10753475	Inhibitor 8504	1.5 nM [IC50]
Receptor protein-tyrosine kinase erbB-2 35 Target ID: CHEMBL1824 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10753475	Inhibitor 8504	9.0 nM [IC50]
Receptor protein-tyrosine kinase erbB-4 12 Target ID: CHEMBL3009 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11706399	Inhibitor 8504	7.0 nM [IC50]
Receptor tyrosine-protein kinase erbB-3 4 Target ID: CHEMBL5838 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11706399	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Non-small cell lung cancer 211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17761977	Primary	Phase II 1147	Unknown Approved Use Unknown
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12138393 https://www.ncbi.nlm.nih.gov/pubmed/19294387	Primary	Phase II 1147	Unknown Approved Use Unknown
Ovarian cancer 160 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16110019	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
1407 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16899614	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CANERTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
175.2 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/15534081	250 mg 1 times / day multiple, oral dose: 250 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CANERTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2233 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16899614	225 mg 3 times / week multiple, intravenous dose: 225 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	CANERTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
265 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16899614	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	CANERTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
1476 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16899614	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CANERTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3518 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16899614	225 mg 3 times / week multiple, intravenous dose: 225 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	CANERTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2385 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16899614	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	CANERTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
3.02 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16899614	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CANERTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.8 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/15534081	250 mg 1 times / day multiple, oral dose: 250 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CANERTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3.2 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16899614	225 mg 3 times / week multiple, intravenous dose: 225 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	CANERTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.4 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16899614	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	CANERTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% REVIEW https://doi.org/10.1124/dmd.116.072983			CANERTINIB plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
337.5 mg 3 times / week multiple, intravenous Highest studied dose Dose: 337.5 mg, 3 times / week Route: intravenous Route: multiple Dose: 337.5 mg, 3 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/16899614	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16899614	DLT: hypersensitivity reaction, diarrhea... Dose limiting toxicities: hypersensitivity reaction (grade 3, 2 patients) diarrhea (grade 3, 2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/16899614
500 mg 3 times / week multiple, intravenous Highest studied dose Dose: 500 mg, 3 times / week Route: intravenous Route: multiple Dose: 500 mg, 3 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/16899614	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16899614	DLT: Myalgia, syncope... Dose limiting toxicities: Myalgia (grade 3, 2 patients) syncope (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/16899614
750 mg 1 times / day multiple, oral Highest studied dose Dose: 750 mg, 1 times / day Route: oral Route: multiple Dose: 750 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17505003	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17505003	DLT: emesis, emesis... Other AEs: Diarrhea... Dose limiting toxicities: emesis (grade 3, 1 pt) emesis (grade 2, 1 pt) rash (grade 2, 1 pt) mouth ulcer (grade 2, 1 pt) Other AEs: Diarrhea (grade 1-2, 2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/17505003
225 mg 3 times / week multiple, intravenous MTD Dose: 225 mg, 3 times / week Route: intravenous Route: multiple Dose: 225 mg, 3 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/16899614	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16899614	Other AEs: Cutaneous toxicities, Nausea... Other AEs: Cutaneous toxicities (7 patients) Nausea (2 patients) Asthenia (2 patients) Pain (2 patients) Vasodilation (2 patients) Stomatitis (2 patients) Myalgia (2 patients) Vomiting (2 patients) Dyspnea (1 pt) Infection (3 patients) Thrombocytopenia (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/16899614
650 mg 1 times / day multiple, oral MTD Dose: 650 mg, 1 times / day Route: oral Route: multiple Dose: 650 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17505003	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17505003	DLT: thrombocytopenia... Other AEs: rash, Nausea... Dose limiting toxicities: thrombocytopenia (grade 4, 1 pt) Other AEs: rash (grade 1-2, 7 patients) Nausea (grade 1-2, 5 patients) Emesis (grade 3, 1 pt) Mucositis (grade 1-2, 6 patients) iarrhea (grade 1-2, 3 patients) Hypersensitivity (grade 1-2, 3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/17505003
200 mg 1 times / day multiple, oral Studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16110019	unhealthy Health Status: unhealthy Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16110019	Disc. AE: Diarrhea... Other AEs: Asthenia, Abdominal pain... AEs leading to discontinuation/dose reduction: Diarrhea (13%) Other AEs: Asthenia (13%) Abdominal pain (13%) Sources: https://pubmed.ncbi.nlm.nih.gov/16110019
50 mg 1 times / day multiple, oral Studied dose Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16110019	unhealthy Health Status: unhealthy Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16110019	Disc. AE: diarrhea, Asthenia... AEs leading to discontinuation/dose reduction: diarrhea (10%) Asthenia (10%) Abdominal pain (10%) Sources: https://pubmed.ncbi.nlm.nih.gov/16110019
50 mg 1 times / day multiple, oral Studied dose Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17505003	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17505003	DLT: Thrombocytopenia... Dose limiting toxicities: Thrombocytopenia (grade 3, 1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/17505003
560 mg 1 times / day multiple, oral Studied dose Dose: 560 mg, 1 times / day Route: oral Route: multiple Dose: 560 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17505003	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17505003	DLT: Hypersensitivity... Dose limiting toxicities: Hypersensitivity (grade 3, 1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/17505003

AEs

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY116239	https://www.001chemical.com/chem/search?q=DY116239
1PlusChem LLC	1P002XN0	https://www.1pchem.com/search?query=1P002XN0
1PlusChem LLC	1P00BD0U	https://www.1pchem.com/search?query=1P00BD0U
A2B Chem	AF29294	http://a2bchem.com/prod/AF29294
AChemBlock	Q70216	http://www.achemblock.com/catalogsearch/result/?q=Q70216
AK Scientific	3516AH	https://aksci.com/item_detail.php?cat=3516AH
AK Scientific	Y0252	https://aksci.com/item_detail.php?cat=Y0252
Ambeed	A239262	http://www.ambeed.com/search/Search.html?keyword=A239262
ApexBio Technology	A1845	https://www.apexbt.com/catalogsearch/result/?q=A1845
ApexBio Technology	A3276	https://www.apexbt.com/catalogsearch/result/?q=A3276
AstaTech	40737	http://astatechinc.com/CPSResult.php?CRNO=40737
AstaTech	41114	http://astatechinc.com/CPSResult.php?CRNO=41114
Axon MedChem	1433	https://www.axonmedchem.com/product/1433
BioSynth	Q-101362	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-101362
BioSynth	Q-200788	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-200788
BLD Pharm	BD119839	http://www.bldpharm.com/search/Search.html?keyword=BD119839
BLD Pharm	BD157893	http://www.bldpharm.com/search/Search.html?keyword=BD157893
BOC Sciences	267243-28-7	http://www.bocsci.com/description.asp?cas=267243-28-7
BOC Sciences	289499-45-2	http://www.bocsci.com/description.asp?cas=289499-45-2
Capot Chemical	22407	https://www.capotchem.com/search.do?q=22407
Cayman Chemical	12076	http://www.caymanchem.com/app/template/Product.vm/catalog/12076
Chem Scene	CS-0121	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0121
Chem Scene	CS-0263	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0263
ChemShuttle	101092	https://www.chemshuttle.com/catalogsearch/result/?q=101092
ChemShuttle	112899	https://www.chemshuttle.com/catalogsearch/result/?q=112899
eMolecules	31430535	https://orderbb.emolecules.com/search/#?query=31430535
eMolecules	46018078	https://orderbb.emolecules.com/search/#?query=46018078
eMolecules	8779390	https://orderbb.emolecules.com/search/#?query=8779390
eNovation Chemicals	D372498	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D372498&searchbtn.x=0&searchbtn.y=0
eNovation Chemicals	D514545	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D514545&searchbtn.x=0&searchbtn.y=0
Excenen	EX-A078	http://www.excenen.com/searchresultlist.php?id=EX-A078
Exclusive Chemistry	2258	http://www.exchemistry.com/chem-catalog/product-2258.html
Hairui	HR113818	http://www.hairuichem.com/en/product/search.do?q=HR113818
Hairui	HR144361	http://www.hairuichem.com/en/product/search.do?q=HR144361
KeyOrganics	AS-56189	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-56189
KeyOrganics	AS-75065	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-75065
Lab Seeker	SC-22834	http://www.labseeker.com/search.php?keywords=SC-22834&category=0
Lab Seeker	SC-23744	http://www.labseeker.com/search.php?keywords=SC-23744&category=0
LabSeeker	SC-22834	http://www.labseeker.com/search.php?keywords=SC-22834&category=0
LabSeeker	SC-23744	http://www.labseeker.com/search.php?keywords=SC-23744&category=0
Matrix Scientific	143588	http://www.matrixscientific.com/143588.html
Matrix Scientific	147556	http://www.matrixscientific.com/147556.html
mcule	MCULE-4299844914	https://mcule.com/MCULE-4299844914/
mcule	MCULE-9046492091	https://mcule.com/MCULE-9046492091/
MedChem Express	HY-10367	https://www.medchemexpress.com/search.html?q=HY-10367A&ft=&fa=&fp=
MedChem Express	HY-10367A	https://www.medchemexpress.com/search.html?q=HY-10367A&ft=&fa=&fp=
Molcore	MC116239	http://www.molcore.com/CatMC116239.html
Molnova	M13886	https://www.molnova.com/en/serch-list.html?keywords=M13886
Molnova	M18334	https://www.molnova.com/en/serch-list.html?keywords=M18334
MolPort	MolPort-006-170-085	https://www.molport.com/shop/molecule-link/MolPort-006-170-085
MolPort	MolPort-008-155-957	https://www.molport.com/shop/molecule-link/MolPort-008-155-957
MuseChem	I002916	https://www.musechem.com/product/I002916.html
MuseChem	I002998	https://www.musechem.com/product/I002998.html
Ryan Scientific	Chidamide	https://ryansci.com/products?q=Chidamide&list_q=&search_type=exact
Selleck Chemicals	S1019	http://www.selleckchem.com/search.html?searchDTO.searchParam=S1019
ShangHai Biochempartner	BCP01790	http://www.biochempartner.com/search_BCP01790
ShangHai Biochempartner	BCP01902	http://www.biochempartner.com/search_BCP01902
TargetMol	T2501	https://www.targetmol.com/search?keyword=T2501
TargetMol	T6136	https://www.targetmol.com/search?keyword=T6136

PubMed

Title	Date	PubMed
Comprehensive analysis of kinase inhibitor selectivity.	2011-10-30	22037378
Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry.	2010-11-24	21095574
Second-generation epidermal growth factor receptor tyrosine kinase inhibitors in non-small cell lung cancer.	2007-03	17405897
Increased bioavailability of intravenous versus oral CI-1033, a pan erbB tyrosine kinase inhibitor: results of a phase I pharmacokinetic study.	2006-08-01	16899614
Potential benefits of the irreversible pan-erbB inhibitor, CI-1033, in the treatment of breast cancer.	2002-06	12138393
Radiosensitization of human breast cancer cells by a novel ErbB family receptor tyrosine kinase inhibitor.	2000-12-01	11121658
Tyrosine kinase inhibitors. 17. Irreversible inhibitors of the epidermal growth factor receptor: 4-(phenylamino)quinazoline- and 4-(phenylamino)pyrido[3,2-d]pyrimidine-6-acrylamides bearing additional solubilizing functions.	2000-04-06	10753475

Patents

Sample Use Guides

In Vivo Use Guide

According to the phase I pharmacokinetic study canertinib (CI-1033) was safely given i.v. up to 225 mg/dose on a thrice-weekly schedule, with evidence of antitumor activity. At equivalent doses, the bioavailability of i.v. CI-1033 is thrice that of the oral formulation.

Route of Administration: Other

In Vitro Use Guide

The effect of canertinib (CI-1033) on esophageal cancer cell proliferation was investigated in the TT, TE2, TE6 and TE10 cell lines. After one day of treatment with CI-1033 (0.1-5.0 nM) significant inhibition of cell growth was observed in all cell lines at all concentrations of CI-1033 examined. The dose of CI-1033 required to inhibit the cell growth was as low as 0.1 nM. The inhibitory effect of CI-1033 on cancer cell growth was dose- and time-dependent.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:52:21 GMT 2025` Edited by `admin` on `Wed Apr 02 08:52:21 GMT 2025`
Record UNII	C78W1K5ASF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CANERTINIB

Official Name

English

PD-183805

Preferred Name

English

CANERTINIB [MI]

Common Name

English

Canertinib [WHO-DD]

Common Name

English

N-(4-(3-CHLORO-4-FLUOROPHENYL)AMINO)-7-(3-MORPHOLIN-4-YL)PROPOXY)QUINAZOLIN-6-YL)PROP-2-ENAMIDE

Common Name

English

2-PROPENAMIDE, N-(4-((3-CHLORO-4-FLUOROPHENYL)AMINO)-7-(3-(4-MORPHOLINYL)PROPOXY)-6-QUINAZOLINYL)-

Systematic Name

English

canertinib [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2167