Erlotinib HydrochlorideSelective EGFR inhibitor CAS# 183319-69-9 |
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Quality Control & MSDS
3D structure
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| Cas No. | 183319-69-9 | SDF | Download SDF |
| PubChem ID | 176871 | Appearance | Powder |
| Formula | C22H24ClN3O4 | M.Wt | 429.91 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | CP-358774; OSI-774; NSC 718781 | ||
| Solubility | DMSO : 6.2 mg/mL (14.42 mM; Need ultrasonic and warming) | ||
| Chemical Name | N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine;hydrochloride | ||
| SMILES | COCCOC1=C(C=C2C(=C1)C(=NC=N2)NC3=CC=CC(=C3)C#C)OCCOC.Cl | ||
| Standard InChIKey | GTTBEUCJPZQMDZ-UHFFFAOYSA-N | ||
| Standard 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 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Erlotinib HCl (OSI-744) is an inhibitor of EGFR with IC50 of 2 nM, >1000-fold more sensitive for EGFR than human c-Src or v-Abl. | |||||
| Targets | HER1/EGFR | |||||
| IC50 | 2 nM | |||||
| Cell experiment: [1] | |
| Cell lines | Calu1 cells |
| Preparation method | The solubility of this compound in DMSO is <10 mm. general tips for obtaining a higher concentration: please warm the tube at 37 °c 10 minutes and> |
| Reacting condition | 1 µM, 24 hours |
| Applications | Cells were treated with single dose of erlotinib (1 µM, 24 hours), docetaxel (50 nM, 18 hours) or the combination of erlotinib and docetaxel. The greatest cell death was observed in the Txt->OSI-774->media sequence, while the cells treated with the OSI-774->Txt->media sequence resumed proliferation by 72hrs post-treatment. Cleaved PARP and Caspase-3 were detected in the sequence of Txt->OSI-774, and with simultaneous treatment, but not in the sequence of OSI-774->Txt. Further, cleaved PARP and Caspase-3 persisted to 72hrs after the Txt->OSI-774 treatment. These data support the previous results on sub-G1 cells, and molecularly demonstrate an apoptotic response. |
| Animal experiment: [2] | |
| Animal models | Female, athymic, nu/nu-nuBR nude mice injected with H460a cells |
| Dosage form | Oral administration, 100mg/kg, daily for 3 weeks |
| Application | Erlotinib had significant dose-dependent efficacy. In the 100mg/kg group there was growth inhibition of 61%. The other groups had the following growth inhibition: 25mg/kg: 46%; 12.5mg/kg: 36%; 6.25mg/kg: 28%. There were no partial or complete regressions. |
| Other notes | Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
| References: [1] Kimura T, Mahaffey C M, Pryde B J, et al. Apoptotic effects of the docetaxel→ OSI-774 combination in non-small cell lung carcinoma (NSCLC) cells//Proc Am Soc Clin Oncol. 2004, 22: 7143. [2] Higgins B, Kolinsky K, Smith M, et al. Antitumor activity of erlotinib (OSI-774, Tarceva) alone or in combination in human non-small cell lung cancer tumor xenograft models. Anti-cancer drugs, 2004, 15(5): 503-512. | |
Erlotinib Hydrochloride Dilution Calculator
Erlotinib Hydrochloride Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.3261 mL | 11.6303 mL | 23.2607 mL | 46.5214 mL | 58.1517 mL |
| 5 mM | 0.4652 mL | 2.3261 mL | 4.6521 mL | 9.3043 mL | 11.6303 mL |
| 10 mM | 0.2326 mL | 1.163 mL | 2.3261 mL | 4.6521 mL | 5.8152 mL |
| 50 mM | 0.0465 mL | 0.2326 mL | 0.4652 mL | 0.9304 mL | 1.163 mL |
| 100 mM | 0.0233 mL | 0.1163 mL | 0.2326 mL | 0.4652 mL | 0.5815 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Erlotinib hydrochloride (the trade name Tarceva?) is a directly acting inhibitor of epidermal growth factor receptor (EGFR/HER-1) tyrosine kinase with an IC50 of 2 nM.
Epidermal growth factor receptor (EGFR) is one member of the ErbB family which includes EGFR (ErbB1), ErbB2, ErbB3 and ErbB4. The activation of EGFR is dependent on the binding of peptide growth factors to the receptor. In many carcinomas, the presence of EGFR mutation leads to the activation of EGFP, which causes cell proliferation and other cancer processes [1].
Selective inhibition of EGFR tyrosine kinase by erlotinib hydrochloride leads to the disruption of cancer growth and development which include cell migration, proliferation, angiogenesis, and apoptosis. For instance, erlotinib hydrochloride was shown to induce cell apoptosis and G0/G1 cell cycle arrest in hepatocellular cancer cells, Bxpc-3 and PANC-1 cells, thereby enhancing chemosensitivity towards cytostatics [2, 3].
In addition, this product is widely researched and used for the treatment of human advanced non-small cell lung cancer (NSCLC) [4]. In pancreatic cancer, erlotinib hydrochloride was also reported to exhibit an anti-tumour effect [5].
References:
1. Melosky B. Review of EGFR TKIs in Metastatic NSCLC, Including Ongoing Trials. Front Oncol 2014,4:244.
2. Zheng YT, Yang HY, Li T, Zhao B, Shao TF, Xiang XQ, et al. Amiloride sensitizes human pancreatic cancer cells to erlotinib in vitro through inhibition of the PI3K/AKT signaling pathway. Acta Pharmacol Sin 2015,36:614-626.
3. Huether A, Hopfner M, Sutter AP, Schuppan D, Scherubl H. Erlotinib induces cell cycle arrest and apoptosis in hepatocellular cancer cells and enhances chemosensitivity towards cytostatics. J Hepatol 2005,43:661-669.
4. Singh N, Jindal A, Behera D. Erlotinib usage after prior treatment with gefitinib in advanced non-small cell lung cancer: A clinical perspective and review of published literature. World J Clin Oncol 2014,5:858-864.
5. Renouf DJ, Tang PA, Hedley D, Chen E, Kamel-Reid S, Tsao MS, et al. A phase II study of erlotinib in gemcitabine refractory advanced pancreatic cancer. Eur J Cancer 2014,50:1909-1915.
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Design, optimization and in vitro evaluation of reverse micelle-loaded lipid nanocarriers containing erlotinib hydrochloride.[Pubmed:22721853]
Int J Pharm. 2012 Oct 15;436(1-2):194-200.
Erlotinib Hydrochloride (ERLO) belongs to the tyrosine kinase inhibitor family and is used for the treatment of pancreatic cancers. In the present study, ERLO was entrapped in lipid nanocarriers by means of reverse micellar incorporation. This study aims to optimize the formulation of ERLO-loaded nanoparticles. Surfactants forming reverse micelles in Labrafac((R)) were filled with ERLO under various conditions. Both the initial amount of drug incubated with reverse micelles and the surfactant composing the reverse micelles are crucial parameters for reverse micelle capacity to load ERLO. The optimal loading system for reverse micelles was obtained with a mix of sorbitan trioleate (Span((R)) 85) and Labrafac((R)) oil at a 1:1 (w/w) ratio. Reverse micelle composition influenced the nanocarrier's hydrodynamic diameter, polydispersity index, and zeta potential. In lipid nanoparticles formulated by using the phase inversion temperature (PIT) method, ERLO entrapment efficiency was around 56%. In vitro, the efficacy of ERLO-loaded nanocarriers on BxPC-3 pancreatic adenocarcinoma cells was comparable to free ERLO, and led to a cell death rate of around 40%.
[A response to erlotinib hydrochloride in the case of post-operative recurrent thymoma].[Pubmed:22202329]
Gan To Kagaku Ryoho. 2011 Nov;38(12):2200-1.
A 43-year-old female was diagnosed with a recurrence of thymoma 6 years after the operation. Eight kinds of systemic chemotherapy were undergone for over 6 years. As the 9th chemotherapy, Erlotinib Hydrochloride was prescribed and the tumor decreased in size about 8 weeks later.
Investigation on the site-selective binding of bovine serum albumin by erlotinib hydrochloride.[Pubmed:23072300]
J Biomol Struct Dyn. 2013 Oct;31(10):1160-74.
The purpose of this study was to investigate the site-selective binding of Erlotinib Hydrochloride (ET), a targeted anticancer drug, to bovine serum albumin (BSA) through 1H NMR, spectroscopic, thermodynamic, and molecular modeling methods. The fluorescence quenching of BSA by ET was a result of the formation of BSA-ET complex with high binding affinity. The site marker competition study combined with isothermal titration calorimetry experiment revealed that ET binds to site II of BSA mainly through hydrogen bond and van der Waals force. Molecular docking was further applied to define the specific binding site of ET to BSA. The conformation of BSA was changed in the presence of ET, revealed by synchronous fluorescence, circular dichroism, and three-dimensional fluorescence spectroscopy results. Further, NMR analysis of the complex revealed that the binding capacity contributed by the aromatic protons in the binding site of BSA might be greater than the aliphatic protons. An animated interactive 3D complement (I3DC) is available in Proteopedia at http://proteopedia.org/w/Journal:JBSD:26.
Modified synthesis of erlotinib hydrochloride.[Pubmed:24312780]
Adv Pharm Bull. 2012;2(1):119-22.
PURPOSE: An improved and economical method has been described for the synthesis of Erlotinib Hydrochloride, as a useful drug in treatment of non-small-cell lung cancer. METHOD: Erlotinib Hydrochloride was synthesized in seven steps starting from 3, 4-dihydroxy benzoic acid. In this study, we were able to modify one of the key steps which involved the reduction of the 6-nitrobenzoic acid derivative to 6-aminobenzoic acid derivative. An inexpensive reagent such as ammonium formate was used as an in situ hydrogen donor in the presence of palladium/charcoal (Pd/C) instead of hydrogen gas at high pressure. RESULT: This proposed method proceeded with 92% yield at room temperature. Synthesis of erlotinib was completed in 7 steps with overall yield of 44%. CONCLUSION: From the results obtained it can be concluded that the modified method eliminated the potential danger associated with the use of hydrogen gas in the presence of flammable catalysts. It should be mentioned that the catalyst was recovered after the reaction and could be used again.
