OSI-420 (DesMethyl Erlotinib, CP-473420) is an active metabolite of Erlotinib (an EGFR inhibitor with an IC50 of 2 nM).

 

Brand: BCM

 

Target: Drug Metabolite; EGFR

 

Signaling Pathways: Angiogenesis; JAK/STAT signaling; Metabolism; Tyrosine Kinase/Adaptors

 

In Vitro: OSI-420 is the main metabolite of Erlotinib in human plasma. After a short intravenous infusion, Erlotinib disappeared from the plasma in a double exponential form with a mean terminal half-life of 5.2 hours and a mean clearance of 128 ml/min/m2. The area under the drug curve of OSI-420 in plasma is 30% of that of erlotinib (range 12-59%), and the clearance of OSI-420 is more than five times higher than that of erlotinib. Erlotinib and OSI-420 are equivalent, and the binding concentration of erlotinib + OSI-420 in CSF can exceed the IC50 (7.9 ng/ml or 20 nM) for EGFR tyrosine kinase inhibition in intact tumor cells. In intact cells, including HNS human head and neck tumor cells (IC50 20nM), DiFi human colon cancer cells, and MDA MB-468 human breast cancer cells, Erlotinib effectively inhibited EGFR activation. Erlotinib (1 μM) induces apoptosis in DiFi human colon cancer cells. Erlotinib inhibits the growth of a group of NSCLC cell lines, including A549, H322, H3255, H358, H661, H1650, H1975, H1299, H596, The IC50 range was 29 nM to >20 μM. Erlotinib(2 μM) significantly inhibited the growth of AsPC-1 and BxPC-3 pancreatic cancer cells. Erlotinib HCl combined with gemcitabine has a superposition effect in KRAS mutant pancreatic cancer cells. 10 μM Erlotinib inhibits EGFR phosphorylation at Y845 (SRc-dependent phosphorylation) and Y1068 (autophosphorylation) sites. OSI-420 in combination with Erlotinib down-regulates Akt activity stimulated by rapamycin and has a coordinated effect on cell growth inhibition.

 

Solubility: Soluble in DMSO. Insoluble in Water; insoluble in Ethanol.

 

Isomeric SMILES: COCCOC1=C(C=C2C(=C1)N=CN=C2NC3=CC=CC(=C3)C#C)OCCO.Cl  

 

InChIKey: BUOXOWNQZVIETJ-UHFFFAOYSA-N  

 

InChI: InChI=1S/C21H21N3O4.ClH/c1-3-15-5-4-6-16(11-15)24-21-17-12-19(27-8-7-25)20(28-10-9-26-2)13-18(17)22-14-23-21;/h1,4-6,11-14,25H,7-10H2,2H3,(H,22,23,24);1H

 

Attribute
[Chem Name]	2-[4-(3-ethynylanilino)-7-(2-methoxyethoxy)quinazolin-6-yl]oxyethanol;hydrochloride
[Synonym]	OSI-420; DesMethyl Erlotinib
[CAS No.]	183320-51-6
[EINECS]	200-258-5
[MDL No.]	MFCD22420811
[Formula]	C21H22ClN3O4
[Molecular]	415.87
[Form]	Solid Powder
[Storage]	Inert atmosphere. Store in freezer, under -20°C

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