Erlotinib

Base Information

• Chemical Name: Erlotinib
• CAS No.: 183321-74-6
• Molecular Formula: C22H23N3O4
• Molecular Weight: 393.442
• Hs Code.: 29335990
• European Community (EC) Number: 689-196-2
• UNII: J4T82NDH7E
• DSSTox Substance ID: DTXSID8046454
• Nikkaji Number: J910.423B
• Wikipedia: Erlotinib
• Wikidata: Q418369
• NCI Thesaurus Code: C65530
• RXCUI: 337525
• Pharos Ligand ID: NUXHNF3XHDN6
• Metabolomics Workbench ID: 42869
• ChEMBL ID: CHEMBL553
• Mol file: 183321-74-6.mol

Synonyms:11C erlotinib;11C-erlotinib;358,774, CP;358774, CP;CP 358,774;CP 358774;CP-358,774;CP-358774;CP358,774;CP358774;erlotinib;erlotinib HCl;erlotinib hydrochloride;HCl, Erlotinib;Hydrochloride, Erlotinib;N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine;OSI 774;OSI-774;OSI774;Tarceva

Chemical Property of Erlotinib

Chemical Property:

• Appearance/Colour: white to off-white powder
• Melting Point: 223 - 228oC
• Boiling Point: 553.6 °C at 760 mmHg
• PKA: 5.32±0.30(Predicted)
• Flash Point: 288.6 °C
• PSA: 74.73000
• Density: 1.247 g/cm³
• LogP: 3.47810
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 393.16885622
• Heavy Atom Count: 29
• Complexity: 525

Purity/Quality:

99% ^*data from raw suppliers

Erlotinibfreebase 99% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antineoplastic Agents
• Canonical SMILES: COCCOC1=C(C=C2C(=C1)C(=NC=N2)NC3=CC=CC(=C3)C#C)OCCOC
• Recent ClinicalTrials: Genetic Testing in Screening Patients With Stage IB-IIIA Non-small Cell Lung Cancer That Has Been or Will Be Removed by Surgery (The ALCHEMIST Screening Trial)
• Recent EU Clinical Trials: The ROME trial from histology to target: the road to personalize target therapy and immunotherapy
• Recent NIPH Clinical Trials: Phase II study of ramucirumab in combination with erlotinib for untreated EGFR mutation-positive non-squamous non-small cell lung cancer patients with pleural effusion: RELAY-Effusion
• Description: Erlotinib is a tyrosine kinase inhibitor which acts on the epidermal growth factor receptor (EGFR), inhibiting EGFR-associated kinase activity (IC50 = 2.5 μM). This inhibits tumor growth in human head and neck carcinoma HN5 tumor xenografts in mice with an ED50 value of 9 mg/kg. Erlotinib also suppresses cyclin-dependent kinase 2 (Cdk2) activity in breast cancer cells (IC50 = 4.6 μM) and JAK2 mutant JAK2V617F positive hematopoietic progenitor cells (IC50 = 5 μM), which is associated with polycythemia vera, idiopathic myelofibrosis, and essential thrombocythemia. Formulations containing erlotinib have been used to treat certain forms of cancer, including non-small cell lung cancer.
• Uses: antineoplastic;tyrosine kinase inhibitor A tyrosine kinase inhibitor
• Clinical Use: ErlotinibTreatment of locally advanced or metastatic nonsmall cell lung cancer after failure of at least 1 other regimePancreatic cancer
• Drug interactions: Potentially hazardous interactions with other drugs Analgesics: increased risk of bleeding with NSAIDs.Antacids: concentration possibly reduced by antacids, give at least 4 hours before or 2 hours after erlotinib. Anticoagulants: increased risk of bleeding with coumarinsAntipsychotics: avoid concomitant use with clozapine, increased risk of agranulocytosis.Antivirals: avoid with boceprevir.Ulcer-healing drugs: avoid with cimetidine, esomeprazole, famotidine, lansoprazole, nizatidine, pantoprazole and rabeprazole; concentration reduced by ranitidine, give at least 2 hours before or 10 hours after ranitidine; concentration reduced by omeprazole - avoid.

Technology Process of Erlotinib

There total 55 articles about Erlotinib which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.6%

3-acetylenephenylamine (54060-30-9) + 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline (183322-18-1) → erlotinib (183321-74-6)

Guidance literature:

In isopropyl alcohol; Concentration; Reflux;

Reference yield: 96.3%

erlotinib hydrochloride (183319-69-9) → erlotinib (183321-74-6)

Guidance literature:

With sodium hydroxide; In water; pH=5 - 12; Product distribution / selectivity;

Reference yield: 91.5%

N′-[2-cyano-4,5-{bis(2-methoxyethoxy)phenyl}]-N,N-dimethylformamidine (950596-59-5) + 3-acetylenephenylamine (54060-30-9) → erlotinib (183321-74-6)

Guidance literature:

With acetic acid; In N,N-dimethyl-formamide; at 125 ℃; for 1h;

upstream raw materials:

N'-(3-ethynylphenyl) N,N-dimethyl formamidine

2-amino-4,5-bis-(2-methoxyethoxy)-benzonitrile

N′-[2-cyano-4,5-{bis(2-methoxyethoxy)phenyl}]-N,N-dimethylformamidine

3-acetylenephenylamine

Downstream raw materials:

erlotinib hydrochloride

Refernces

Synthesis, biological evaluation and molecular docking studies of amide-coupled benzoic nitrogen mustard derivatives as potential antitumor agents

10.1016/j.bmc.2009.11.037

The study reports the synthesis, biological evaluation, and molecular docking studies of a series of amide-coupled benzoic nitrogen mustard derivatives as potential antitumor agents targeting EGFR and HER-2 kinases. The researchers synthesized these derivatives, which were evaluated for their ability to inhibit the autophosphorylation of EGFR and HER-2 kinases using a solid-phase ELISA assay. Compounds 5b and 5t exhibited the most potent inhibitory activity, comparable to the positive control erlotinib. Molecular docking simulations were performed to explore the binding modes of these compounds at the EGFR active site. The antiproliferative activity of the synthesized compounds was also evaluated on the MCF-7 human tumor cell line, with compounds 5b and 5t showing significant inhibitory activity in tumor growth inhibition. Overall, the study suggests that these benzoic nitrogen mustard derivatives, particularly compounds 5b and 5t, have potential as antitumor agents due to their potent inhibitory activity against EGFR and HER-2 kinases.