Erlotinib hydrochloride

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Erlotinib hydrochloride
Category Antineoplastic
Catalog number BBF-04613
CAS 183319-69-9
Molecular Weight 429.90
Molecular Formula C22H23N3O4.HCl
Purity >98%

Ordering Information

Catalog Number Size Price Stock Quantity
BBF-04613 25 g $199 In stock

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Description

Erlotinib HCl potently inhibits EGFR activation in intact cells including HNS human head and neck tumor cells (IC50 = 20 nM), DiFi humancolon cancer cells and MDA MB-468 human breast cancer cells.

Specification

Related CAS 183321-74-6 (free base)
Synonyms OSI-744; OSI744; OSI 744; Tarceva; 4-(m-Ethynylanilino)-6,7-bis(2-methoxyethoxy)quinazoline monohydrochloride; 6,7-bis(2-methoxyethoxy)-4-(3-ethynylanilino)quinazoline hydrochloride
Storage Store at 2-8°C
IUPAC Name N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine;hydrochloride
Canonical SMILES COCCOC1=C(C=C2C(=C1)C(=NC=N2)NC3=CC=CC(=C3)C#C)OCCOC.Cl
InChI InChI=1S/C22H23N3O4.ClH/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);1H
InChI Key GTTBEUCJPZQMDZ-UHFFFAOYSA-N
Source Synthetic

Properties

Appearance Off-white Solid
Application Antineoplastic Agents
Boiling Point 553.6°C at 760 mmHg
Melting Point 223-225°C
Solubility Soluble in Acetic Acid, Dimethylformamide, Dimethyl Sulfoxide, Methanol

Reference Reading

1.Effect of Sulindac and Erlotinib vs Placebo on Duodenal Neoplasia in Familial Adenomatous Polyposis: A Randomized Clinical Trial.
Samadder NJ1, Neklason DW2, Boucher KM3, Byrne KR4, Kanth P4, Samowitz W5, Jones D6, Tavtigian SV6, Done MW7, Berry T7, Jasperson K7, Pappas L7, Smith L7, Sample D7, Davis R7, Topham MK8, Lynch P9, Strait E10, McKinnon W11, Burt RW12, Kuwada SK13. JAMA. 2016 Mar 22-29;315(12):1266-75. doi: 10.1001/jama.2016.2522.
IMPORTANCE: Patients with familial adenomatous polyposis (FAP) are at markedly increased risk for duodenal polyps and cancer. Surgical and endoscopic management of duodenal neoplasia is difficult and chemoprevention has not been successful.
2.Potential of erlotinib cyclodextrin nanosponge complex to enhance solubility, dissolution rate, in vitro cytotoxicity and oral bioavailability.
Dora CP1, Trotta F2, Kushwah V3, Devasari N4, Singh C4, Suresh S5, Jain S6. Carbohydr Polym. 2016 Feb 10;137:339-49. doi: 10.1016/j.carbpol.2015.10.080. Epub 2015 Oct 28.
The present study was envisaged to evaluate the effect of erlotinib β-cyclodextrin nanosponge (ERL-NS) on the solubility, dissolution, in vitro cytotoxicity and oral bioavailability of erlotinib (ERL). Preliminary studies were conducted to select the optimized stoichiometry concentration of ERL and NS. The drug nanosponge complex comprising of 1:4 proportions of ERL and NS was prepared by freeze drying. ERL-NS formed nanoparticles of 372 ± 31 nm size with narrow size distribution (0.21 ± 0.07 PDI) and high zeta potential (-32.07 ± 4.58 mV). The complexation phenomenon was confirmed by DSC, SEM, PXRD, FTIR, and TEM studies. In vitro dissolution studies revealed an increased dissolution rate (2-folds) with an enhanced dissolution efficiency of the nanosponge complex in comparison to pure drug. In vitro cytotoxicity study and apoptosis assay in pancreatic cell lines (MIA PaCa-2 and PANC-1) indicates the increased toxicity of ERL-NS. Both, quantitative and qualitative cell uptake studies unveiled the higher uptake efficiency of ERL-NS than free drug.

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