Pazopanib Hydrochloride CAS 635702-64-6
Introduction：Basic information about Pazopanib Hydrochloride CAS 635702-64-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Pazopanib Hydrochloride Basic information
| Product Name: | Pazopanib Hydrochloride |
| Synonyms: | Pazopanib HCl;Pazopanib hydrochloride;Unii-33Y9anm545;BenzenesulfonaMide, 5-[[4-[(2,3-diMethyl-2H-indazol-6-yl)MethylaMino]-2-pyriMidinyl]aMino]-2-Methyl-, hydrochloride;786034;ArMala;Pazopanib Hydrochloride (GW786034);5-(4-((2,3-diMethyl-2H-indazol-6-yl)(Methyl)aMino)pyriMidin-2-ylaMino)-2-MethylbenzenesulfonaMide hydrochloride |
| CAS: | 635702-64-6 |
| MF: | C21H24ClN7O2S |
| MW: | 473.98 |
| EINECS: | 619-728-0 |
| Product Categories: | HFC80011;API |
| Mol File: | 635702-64-6.mol |
Pazopanib Hydrochloride Chemical Properties
| Melting point | >290°C (dec.) |
| storage temp. | Hygroscopic, Refrigerator, under inert atmosphere |
| solubility | Acetonitrile (Slightly), DMSO (Slightly) |
| form | Yellow powder. |
| color | White to Off-White |
| Stability: | Hygroscopic |
| InChI | InChI=1S/C21H23N7O2S.ClH/c1-13-5-6-15(11-19(13)31(22,29)30)24-21-23-10-9-20(25-21)27(3)16-7-8-17-14(2)28(4)26-18(17)12-16;/h5-12H,1-4H3,(H2,22,29,30)(H,23,24,25);1H |
| InChIKey | MQHIQUBXFFAOMK-UHFFFAOYSA-N |
| SMILES | CC1N(N=C2C=C(N(C3C=CN=C(NC4C=CC(C)=C(S(=O)(=O)N)C=4)N=3)C)C=CC=12)C.Cl |
Safety Information
| Description | Pazopanib Hydrochloride is the hydrochloride salt of a small molecule inhibitor of multiple protein tyrosine kinases with potential antineoplastic activity. It is an oral second-generation multitarget TKI developed by GSK and approved for marketing by the FDA in 2009 and the EMA in 2010. It targets the VEGFR, platelet-derived growth factor receptor, and c-kit, key proteins responsible for tumor growth and survival. It is used to treat patients with advanced RCC and advanced soft tissue sarcoma who have experienced chemotherapy. Pazopanib Hydrochloride has a role as an antineoplastic agent, a vascular endothelial growth factor receptor antagonist, a tyrosine kinase inhibitor, and an angiogenesis-modulating agent. |
| Originator | GlaxoSmithKline (US) |
| Uses | Pazopanib Hydrochloride (GW786034) is a novel multi-target inhibitor of VEGFR1, VEGFR2, VEGFR3, PDGFR, FGFR, c-Kit and c-Fms with IC50 of 10 nM, 30 nM, 47 nM, 84 nM, 74 nM, 140 nM and 146 nM, respectively - See more at: http://www.selleckchem.com/products/Pazopanib-Hyd |
| Definition | Pazopanib Hydrochloride is used for treatment of kidney cancer. Pazopanib is the latest VEGFR kinase inhibitor to reach the market. It is indicated for the oral treatment of advanced RCC. The biological functions of the VEGF family are mediated by activation of three structurally homologous tyrosine kinase receptors, VEGFR-1, VEGFR-2, and VEGFR3. |
| Brand name | Votrient |
| Clinical Use | Pazopanib is a potent and selective multi-targeted receptortyrosine kinase inhibitor of VEGFR-1, VEGFR-2, VEGFR-3,PDGFR-a/b, and c-kit that blocks tumor growth and inhibits angiogenesis.It was approved for renal cell carcinoma by the U.S. Foodand Drug Administration in 2009 and is marketed under the tradename Votrient by the drug’s manufacturer, GlaxoSmithKline. |
| Side effects | Pazopanib is synthesized in five chemical stepsstarting from 3-methyl-6-nitroindazole, which is converted to the corresponding2,3-dimethylindazole analog via N-methylation with trimethyloxoniumtetrafluoroborate. Subsequent reduction of the nitro group tothe amino group using tin chloride followed by condensation with 2,4dichloropyrimidineyields a chloropyrimidinylaminoindazole intermediate.The final two steps leading up to pazopanib consist of an N-methylationreaction using iodomethane and cesium carbonate followed bycondensation with 5-amino-2-methylbenzenesulfonamide. |
| Synthesis | Thesynthesis of pazopanib begins with methylation of 3-methyl-6-nitroindazole (82) with trimethyl orthoformate in the presence of BF3?¤OEt to give indazole 83 in 65% yield. Reductionof the nitro group was achieved via transfer hydrogenation to give84 in 97% yield, and this was followed by coupling the aniline with2,4-dichloropyrimidine in a THF-ethanol mixture at elevatedtemperature to provide diarylamine 85 in 90% yield. The anilinenitrogen was then methylated using methyl iodide to give 86 in83% yield prior to coupling with 5-amino-2-methylbenzenesulfonamide(87) and salt formation using an alcoholic solution ofHCl to furnish pazopanib hydrochloride (XIV) in 81% yield. |
| target | VEGFR1 |
| References | [1] Sodeifian, G. et al. “Solubility of pazopanib hydrochloride (PZH, anticancer drug) in supercritical CO2: Experimental and thermodynamic modeling.” The Journal of Supercritical Fluids 55 1 (2022): 0. [2] “Stability Indicating HPTLC Method Development and Validation for the Estimation of Pazopanib Hydrochloride in Bulk and its Dosage Form.” International Journal of Pharmaceutical Research 18 1 (2020). [3] K. Kawasaki . “Retrospective Safety Analysis in Advanced Soft Tissue Sarcoma Patients of Pazopanib Hydrochloride.” Annals of Oncology 24 (2013): Page ix38. [4] Gupta, Amit and Rashmi Dahima. “Application of Simplex Lattice Mixture design and desirability function in the development and Optimization of SEDDS for protein kinase inhibitor-Pazopanib Hydrochloride.” Research Journal of Pharmacy and Technology 83 1 (2023): 0. |
Pazopanib Hydrochloride Preparation Products And Raw materials
| Raw materials | 3-Methyl-6-nitroindazole-->5-Amino-2-methylbenzenesulfonamide |
