1C9

(2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}-4-(piperidin-1-yl)but-2-enamide

Created:	2012-12-03
Last modified:	2024-09-27

Find Related PDB Entry
1 entries where 1C9 is found as a standalone ligand1 entries where 1C9 is covalently linked to polymer or other heterogen groups

Help Find related ligands:
Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Help

Find related ligands:

Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Chemical Details
Formal Charge	0
Atom Count	58
Chiral Atom Count	0
Bond Count	61
Aromatic Bond Count	17

Toggle Hydrogen Toggle Labels

Chemical Component Summary
Name	(2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}-4-(piperidin-1-yl)but-2-enamide
Synonyms	Dacomitinib
Systematic Name (OpenEye OEToolkits)	(E)-N-[4-[(3-chloranyl-4-fluoranyl-phenyl)amino]-7-methoxy-quinazolin-6-yl]-4-piperidin-1-yl-but-2-enamide
Formula	C₂₄ H₂₅ Cl F N₅ O₂
Molecular Weight	469.939
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	Fc1ccc(cc1Cl)Nc4ncnc2c4cc(c(OC)c2)NC(=O)/C=C/CN3CCCCC3
SMILES	CACTVS	3.370	COc1cc2ncnc(Nc3ccc(F)c(Cl)c3)c2cc1NC(=O)C=CCN4CCCCC4
SMILES	OpenEye OEToolkits	1.7.6	COc1cc2c(cc1NC(=O)C=CCN3CCCCC3)c(ncn2)Nc4ccc(c(c4)Cl)F
Canonical SMILES	CACTVS	3.370	COc1cc2ncnc(Nc3ccc(F)c(Cl)c3)c2cc1NC(=O)\C=C\CN4CCCCC4
Canonical SMILES	OpenEye OEToolkits	1.7.6	COc1cc2c(cc1NC(=O)/C=C/CN3CCCCC3)c(ncn2)Nc4ccc(c(c4)Cl)F
InChI	InChI	1.03	InChI=1S/C24H25ClFN5O2/c1-33-22-14-20-17(24(28-15-27-20)29-16-7-8-19(26)18(25)12-16)13-21(22)30-23(32)6-5-11-31-9-3-2-4-10-31/h5-8,12-15H,2-4,9-11H2,1H3,(H,30,32)(H,27,28,29)/b6-5+
InChIKey	InChI	1.03	LVXJQMNHJWSHET-AATRIKPKSA-N

Drug Info: DrugBank

DrugBank ID	DB11963
Name	Dacomitinib
Groups	approved investigational
Description	Dacomitinib, designed as (2E)-N-16-4-(piperidin-1-yl) but-2-enamide, is an oral highly selective quinazalone part of the second-generation tyrosine kinase inhibitors which are characterized by the irreversible binding at the ATP domain of the epidermal growth factor receptor family kinase domains.[A40009] Dacomitinib was developed by Pfizer Inc and approved by the FDA on September 27, 2018.[L4810] Some evidence in the literature suggests the therapeutic potential of dacomitinib in the epithelial ovarian cancer model[A39624], although further investigations are needed.
Synonyms	Dacomitinib Dacomitinib anhydrous Dacomitinib monohydrate Dacomitinibum
Brand Names	Vizimpro
Indication	Dacomitinib is indicated as the first-line treatment of patients with metastatic non-small cell lung cancer (NSCLC) with epidermal growth factor receptor (EGFR) exon 19 deletion or exon 21 L858R substitution mutations as verified by an FDA-approved test.[L4812] Lung cancer is the leading cause of cancer death and NSCLC accounts for 85% of lung cancer cases. From the cases of NSCLC, approximately 75% of the patients present a late diagnosis with metastatic and advanced disease which produces a survival rate of 5%. The presence of a mutation in EGFR accounts for more than the 60% of the NSCLC cases and the overexpression of EGFR is associated with frequent lymph node metastasis and poor chemosensitivity.[A40018, A19201]
Categories	Antineoplastic Agents Antineoplastic and Immunomodulating Agents BCRP/ABCG2 Inhibitors BCRP/ABCG2 Substrates Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP2C9 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (strong) Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 CYP2D6 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates (strength unknown) Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Enzyme Inhibitors Epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors Heterocyclic Compounds, Fused-Ring Kinase Inhibitor Narrow Therapeutic Index Drugs OCT1 inhibitors P-glycoprotein inhibitors P-glycoprotein substrates P-glycoprotein substrates with a Narrow Therapeutic Index Protein Kinase Inhibitors Quinazolines Tyrosine Kinase Inhibitors UGT1A1 Inhibitors
ATC-Code	L01EB07
CAS number	1110813-31-4

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Epidermal growth factor receptor	MRPSGTAGAALLALLAALCPASRALEEKKVCQGTSNKLTQLGTFEDHFLS...	unknown	inhibitor
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	substrate,inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate
UDP-glucuronosyltransferase 1-1	MAVESQGGRPLVLGLLLCVLGPVVSHAGKILLIPVDGSHWLSMLGAIQQL...	unknown	inhibitor
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	binder
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate,inhibitor
ATP-binding cassette sub-family G member 2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	substrate,inhibitor
Solute carrier family 22 member 1	MPTVDDILEQVGESGWFQKQAFLILCLLSAAFAPICVGIVFLGFTPDHHC...	unknown	inhibitor
View More

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682