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| 化学名: | アルテスナート | | 英語化学名: | Artesunate | | 别名: | Artesunate
(3R,5aS,6R,8aS,9R,10S,12R,12aR)-Decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10-ol hydrogen succinate;ARTESUNATE;ArtesunateC19H28O8;Butanedioic Acid Mono(3R,5aS,6R,8aS,9R,10R,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] Ester;Arteannuinum;Arteannuinum succinate;vARTESUNATE;(3R,5aα,8aα,12aR)-Decahydro-10α-(3-carboxypropionyloxy)-3,6α,9β-trimethyl-3β,12α-epoxypyrano[4,3-j]-1,2-benzodioxepin | | CAS番号: | 88495-63-0 | | 分子式: | C19H28O8 | | 分子量: | 384.42 | | EINECS: | 618-170-5 | | カテゴリ情報: | natural product;Antimalarial;Inhibitors;Herb extract;plant extract;Natural Plant Extract;Intermediates & Fine Chemicals;Pharmaceuticals;Active Pharmaceutical Ingredients;88495-63-0 | | Mol File: | 88495-63-0.mol |  |
| 融点 | 132-1350C | | 沸点 | 431.1°C (rough estimate) | | 比重(密度) | 1.2076 (rough estimate) | | 屈折率 | 1.4430 (estimate) | | 貯蔵温度 | 2-8°C | | 溶解性 | acetone: soluble33.4mg/mL | | 外見 | crystalline powder | | 酸解離定数(Pka) | 4.28±0.17(Predicted) | | 色 | white to off-white | | Merck | 14,818 | | BCS Class | 3/1 | | 安定性： | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. | | InChIKey | FIHJKUPKCHIPAT-AHIGJZGOSA-N | | SMILES | C(O[C@@H]1O[C@]2([H])O[C@@]3(C)CC[C@@]4([H])[C@H](C)CC[C@@]([H])([C@H]1C)[C@]42OO3)(=O)CCC(O)=O | | LogP | 3.291 (est) |
| | アルテスナート Usage And Synthesis |
| 外観 | 白色～ほとんど白色粉末～結晶 | | 効能 | 抗マラリア薬 | | 化学的特性 | Artesunate is an odorless bitter-tasting crystalline powder. soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide, which should be purged with an inert gas. The solubility of artesunate in these solvents is approximately 20, 14, and 11 mg/ml, respectively. Artesunate is sparingly soluble in aqueous buffers. | | 使用 | Artesunate, a semi-synthetic artemisinin derivative, has been shown to be effective against parasites, such as liver flukes, and has also shown cytotoxic effects on different types of tumor cell lines. artesunate belong to Antimalarial which is clinically useful for treatment of malaria and other parasitic diseases. | | 定義 | ChEBI: Artesunate is an artemisinin derivative that is the hemisuccinate ester of the lactol resulting from the reduction of the lactone carbonyl group of artemisinin. It is used, generally as the sodium salt, for the treatment of malaria. It has a role as an antimalarial, a ferroptosis inducer and an antineoplastic agent. It is an artemisinin derivative, a sesquiterpenoid, a dicarboxylic acid monoester, a cyclic acetal, a semisynthetic derivative and a hemisuccinate. | | 製造方法 | Artemisinin was discovered in the 1970s as a result of an extensive screening of Chinese herbal extracts in the search of new antimalarial agents. Currently, the primary method for the production of artemisinin is the isolation from dried leaves of the plant Artemisia annua. Furthermore, the global supply of this life-saving drug exclusively from natural sources remains highly limited. As a result, a novel approaches for large-scale production of artemisinin have been developed. Artesunate is prepared from dihydroartemisinin (DHA) by reacting it with succinic acid anhydride in a basic medium.
A simplified and scalable synthesis of artesunate | | brand name | Arsumax
(Knoll, Switzerland). | | 一般的な説明 | Artesunate is a semisynthetic derivative of artemisinin used to treat malaria. It has also been shown to effective against other parasites such as liver flukes. Artesunate also demonstrates cytotoxic action against cancer cell lines of different tumor types. | | Biochem/physiol Actions | Artesunate acts on the electron transport chain, generates local reactive oxygen species, and causes the depolarization of the mitochondrial membrane. It inhibits TNFα-induced production of proinflammatory cytokines via inhibition of NF-κB and PI3 kinase/Akt signal pathway in human rheumatoid arthritis fibroblast-like synoviocytes. | | target | NF-kB | p38MAPK | IFN-γ | IL Receptor | PGE | COX | TNF-α | IkB | TGF-β/Smad | gp120/CD4 | Antifection | IKK | | 貯蔵 | Store at -20°C | | Mode of action | Artesunate is a water-soluble, semi-synthetic derivative of the sesquiterpine lactone artemisinin with anti-malarial, anti-schistosomiasis, antiviral, and potential anti-neoplastic activities. It acts on the electron transport chain to generate local reactive oxygen species and cause depolarization of the mitochondrial membrane. It inhibits TNF-induced proinflammatory cytokine production by inhibiting NF-κB and PI3 kinase/Akt signaling pathways in human rheumatoid arthritis fibroblast-like synoviocytes. Artesunate has also been shown to stimulate cell differentiation, arrest the cell cycle in the G1 and G2/M phases, inhibit cell proliferation, and induce apoptosis through mitochondrial and caspase signaling pathways. Artemisinin is isolated from the plant Artemisia annua. |
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