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33069-62-4CC(=O)O[C@H]1C(=O)[C@@]2(C)C([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2OWhite Powder
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개요Paclitaxel, a natural product isolated from the bark of the Pacific yew, is effective in treating refractory metastatic ovarian cancer. Unlike any other antineoplastic agents, paclitaxel appears to have several possible mechanisms of action, including an antimicrotubule action through the promotion of tubulin polymerization and stabilization of microtubules, thereby, halting mitosis and promoting cell death. The supply of paclitaxel is limited by its low natural abundance and currently it is being manufactured by a semi-synthetic route from deacetylbaccatin Ⅲ that is isolated from the needles of the yew tree. Recent completion of two total syntheses of taxol conquered the structural complexity of the title compound and may be useful in obtaining certain closely related analogs, some of which have been found to have antitumor activity. Paclitaxel has potential uses in the treatment of metastatic breast cancer, lung cancer, head and neck cancer, and malignant melanoma.
역사Paclitaxel, initially named taxol, is a naturally occurring diterpenoid compound extracted from the Pacific yew tree, Taxus brevifolia. Paclitaxel was discovered by National Cancer Institute (NCI) in 1960s. Scientists were conducting screenings of plant extracts in search of potential anticancer agents when they discovered the distinctive cytotoxic properties of paclitaxel against cancer cells. In October of 1995, China became the second country with formal production of paclitaxel and its injection in the world.Paclitaxel/Taxol is on the World Health Organization’s Model List of Essential Medicines, and was at one point the best-selling cancer drug ever manufactured, with annual sales of $1.6 billion in 2000.
용도Paclitaxel is an antineoplastic that used to treat patients with lung, ovarian, breast cancer, head and neck cancer, and advanc ed forms of Kaposi's sarcoma. Paclitaxel is a mitotic inhibitor used in cancer chemotherapy. It is also used in the study of structure and function of microtubles into tubulin.
일반 설명Paclitaxel (commercial name, Taxol) a complex diterpene alkaloid isnaturally obtained from Taxus species (family Taxaceae). Paclitaxel has been provedas highly effective in the treatment of various types of cancers, since it acts as amicrotubule-stabilizing agent to protect against disassembly. Paclitaxel was developed by the National Cancer Institute, USA, as a drug for cancer therapy andused for the treatment of refractory ovarian cancer, metastatic breast and lung cancer,and Kaposi’s sarcoma (Srivastava et al. 2005). The natural source of paclitaxelis the bark of several Taxus species; however, the cost of extraction is very highsince the concentration of paclitaxel accumulation is very low (0.02% of dry weight)and also entails the destruction of natural resources (Cusido et al. 2014). Eventhough, paclitaxel can be chemically synthesized, but this process is not commerciallyviable. Plant cell cultures have been developed for the production of paclitaxelby Phyton Biotech in 1995, and in 2004 the FDA has approved the use of plantculture supply of paclitaxel/Taxol (Leone and Roberts 2013).
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33069-62-4CHEMBL48The total synthesis of paclitaxel (Taxol) is described. Double Rubottom oxidation of the bis(silyl enol ether) derived from a tricarbocyclic diketone effectively installed a bridgehead olefin and C-5/C-13 hydroxy groups in a one-step operation. The novel Ag-promoted oxetane formation smoothly constructed the tetracyclic framework of paclitaxel.Total Synthesis of PaclitaxelThe biosynthesis of paclitaxel involves the condensation of the three isoprenyl diphosphate (IPP) units with dimethylallyl diphosphate (DMAPP). Plants are unique in producing IPP and DMAPP by both the mevalonic pathway (MVA) in the cytosol or via the methylerythritol phosphate (MEP) pathway in the plastids.Paclitaxel: biosynthesis, production and future prospects