AQ4

[6,7-BIS(2-METHOXY-ETHOXY)QUINAZOLINE-4-YL]-(3-ETHYNYLPHENYL)AMINE

Created:	2002-06-26
Last modified:	2020-06-05

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3 entries where AQ4 is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	52
Chiral Atom Count	0
Bond Count	54
Aromatic Bond Count	17

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Chemical Component Summary
Name	[6,7-BIS(2-METHOXY-ETHOXY)QUINAZOLINE-4-YL]-(3-ETHYNYLPHENYL)AMINE
Synonyms	ERLOTINIB
Systematic Name (OpenEye OEToolkits)	N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine
Formula	C₂₂ H₂₃ N₃ O₄
Molecular Weight	393.436
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	n2c1c(cc(OCCOC)c(OCCOC)c1)c(nc2)Nc3cc(C#C)ccc3
SMILES	CACTVS	3.370	COCCOc1cc2ncnc(Nc3cccc(c3)C#C)c2cc1OCCOC
SMILES	OpenEye OEToolkits	1.7.6	COCCOc1cc2c(cc1OCCOC)ncnc2Nc3cccc(c3)C#C
Canonical SMILES	CACTVS	3.370	COCCOc1cc2ncnc(Nc3cccc(c3)C#C)c2cc1OCCOC
Canonical SMILES	OpenEye OEToolkits	1.7.6	COCCOc1cc2c(cc1OCCOC)ncnc2Nc3cccc(c3)C#C
InChI	InChI	1.03	InChI=1S/C22H23N3O4/c1-4-16-6-5-7-17(12-16)25-22-18-13-20(28-10-8-26-2)21(29-11-9-27-3)14-19(18)23-15-24-22/h1,5-7,12-15H,8-11H2,2-3H3,(H,23,24,25)
InChIKey	InChI	1.03	AAKJLRGGTJKAMG-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank ID	DB00530
Name	Erlotinib
Groups	approved investigational
Description	Erlotinib is an inhibitor of the epidermal growth factor receptor (EGFR) tyrosine kinase that is used in the treatment of non-small cell lung cancer, pancreatic cancer and several other types of cancer. It is typically marketed under the trade name Tarceva. Erlotinib binds to the epidermal growth factor receptor (EGFR) tyrosine kinase in a reversible fashion at the adenosine triphosphate (ATP) binding site of the receptor. Recent studies demonstrate that erlotinib is also a potent inhibitor of JAK2V617F, which is a mutant form of tyrosine kinase JAK2 found in most patients with polycythemia vera (PV) and a substantial proportion of patients with idiopathic myelofibrosis or essential thrombocythemia. This finding introduces the potential use of erlotinib in the treatment of JAK2V617F-positive PV and other myeloproliferative disorders.
Synonyms	Erlotinib hydrochloride Erlotinib [6,7-Bis-(2-methoxy-ethoxy)-quinazolin-4-yl]-(3-ethynyl-phenyl)-amine
Brand Names	PMS-erlotinib Erlotinib Hydrochloride Erlotinib Teva-erlotinib Tarceva Nat-erlotinib Apo-erlotinib
Indication	Erlotinib is indicated for: - The treatment of metastatic non-small cell lung cancer (NSCLC) with tumors showing epidermal growth factor receptor (EGFR) exon 19 deletions or exon 21 (L858R) substitution mutations [FDA label]. - In combination with first-line treatment for patients diagnosed with locally advanced, unresectable or metastatic pancreatic cancer [FDA label]. The safety and efficacy of erlotinib have not been established for patients with NSCLC whose tumors show other EGFR mutations. Additionally it is not recommended for use in combination with platinum-based chemotherapy. [FDA label]
Categories	Antineoplastic Agents Antineoplastic and Immunomodulating Agents BCRP/ABCG2 Inhibitors Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP1A2 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2C8 Inhibitors Cytochrome P-450 CYP2C8 Inhibitors (strong) Cytochrome P-450 CYP2C8 Substrates Cytochrome P-450 CYP2C8 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 CYP2D6 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 CYP3A5 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 Highest Risk QTc-Prolonging Agents Kinase Inhibitor Narrow Therapeutic Index Drugs Organic Anion Transporting Polypeptide 2B1 Inhibitors P-glycoprotein inhibitors P-glycoprotein substrates P-glycoprotein substrates with a Narrow Therapeutic Index Protein Kinase Inhibitors QTc Prolonging Agents Quinazolines Tyrosine Kinase Inhibitors UGT1A1 Inhibitors
ATC-Code	L01EB02
CAS number	183321-74-6

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Nuclear receptor subfamily 1 group I member 2	MEVRPKESWNHADFVHCEDTESVPGKPSVNADEEVGGPQICRVCGDKATG...	unknown	agonist
Epidermal growth factor receptor	MRPSGTAGAALLALLAALCPASRALEEKKVCQGTSNKLTQLGTFEDHFLS...	unknown	antagonist
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	substrate
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	substrate
Cytochrome P450 1A1	MLFPISMSATEFLLASVIFCLVFWVIRASRPQVPKGLKNPPGPWGWPLIG...	unknown	substrate
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	substrate
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	substrate,inhibitor
Cytochrome P450 1B1	MGTSLSPNDPWPLNPLSIQQTTLLLLLSVLATVHVGQRLLRQRRRQLRSA...	unknown	substrate
UDP-glucuronosyltransferase 1-1	MAVESQGGRPLVLGLLLCVLGPVVSHAGKILLIPVDGSHWLSMLGAIQQL...	unknown	inhibitor
Epidermal growth factor receptor	MRPSGTAGAALLALLAALCPASRALEEKKVCQGTSNKLTQLGTFEDHFLS...	unknown	inhibitor
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	substrate
Alpha-1-acid glycoprotein 1	MALSWVLTVLSLLPLLEAQIPLCANLVPVPITNATLDQITGKWFYIASAF...	unknown	substrate
ATP-binding cassette sub-family G member 2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate,inhibitor
Solute carrier organic anion transporter family member 2B1	MGPRIGPAGEVPQVPDKETKATMGTENTPGGKASPDPQDVRPSVFHNIKL...	unknown	inhibitor
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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