Artesunate
Artesunic Acid · ARTENSUNATE · WR-256283 · Artemisinin monosuccinate · (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 · 4-Oxo-4-(((3R,5aS,6R,8aS,9R,10R,12R,12aR)-3,6,9-trimethyldecahydro-3H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)butanoic acid · Butanedioic acid, 1-[(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-yl] ester · AsuMax
Identifikatoren & physikalische Daten
| CAS No. | 88495-63-0 |
|---|---|
| Summenformel | C19H28O8 |
| Durchschnittliche Molmasse | 384,4 g/mol |
| Monoisotopische Masse | 384,17841785 g/mol |
| SMILES | C[C@H]1[C@H](OC(=O)CCC(=O)O)O[C@@H]2O[C@@]3(C)CC[C@H]4[C@H](C)CC[C@@H]1[C@@]24OO3 |
| InChIKey | FIHJKUPKCHIPAT-AHIGJZGOSA-N |
| PubChem CID | 6917864 |
| ChEMBL | CHEMBL361497 |
| ChEBI | CHEBI:63918 |
| EC No. | 605-980-9 |
| DTXSID | DTXSID3042681 |
Chemische & physikalische Eigenschaften
| XLogP | 2,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 101 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 8 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 27 |
| Formalladung | 0 |
| Komplexität | 623 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Color/Form | Fine white crystalline powder |
| Human Drugs | Breast FeedingLactationMilk, HumanAnti-infective AgentsAntiparasitic AgentsAntimalarialsAntiprotozoal AgentsFDA approved drugs -> Active ingredientEMA approved medicines: Human medicine (Orphan designations)Antimalarial medicines > Medicines for curative treatment |
| Schmelzpunkt | 131-135132-1350C |
| Stability/Shelf Life | Artesunate is the sodium salt of the hemisuccinate ester of artemisinin. It is soluble in water but has poor stability in aqueous solutions at neutral or acid pH. In the injectable form, artesunic acid is drawn up in sodium bicarbonate to form sodium artesunate immediately before injection. |
| Other Experimental Properties | Poor stability in aqueous solutions /Artesunate sodium salt/ |
| Siedepunkt | 431.1°C (rough estimate) |
| Dichte | 1.2076 (rough estimate) |
| Brechungsindex | 1.4430 (estimate) |
| Flammpunkt | 173.5° |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | acetone: soluble33.4mg/mL |
| Aggregatzustand | crystalline powder |
| pKa (Säurekonstante) | 4.28±0.17(Predicted) |
| Farbe | white to off-white |
| Biologische Quelle | Artemisia annua |
| Merck | 14,818 |
| BCS Class | 3/1 |
| Stabilität | 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. |
| Hauptanwendungen | pharmaceutical small molecule |
| 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 (Verteilungskoeffizient) | 3.291 (est) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (95.7%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 46 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.DangerH251 (100%): Self-heatingmay catch fire [Danger Self-heating substances and mixtures] |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (95.7%)Self-heat. 1 (100%) |
| Wechselwirkungen | The activity of artemisinin in combination with other antimalarial drugs against P. falciparum was measured in vitro and against P. berghei in vivo. A combination of artemisinin with mefloquine was synergistic whereas that with pyrimethamine was antagonistic in vitro and in vivo. A combination of artemisinin with other antimalarials (sulfadiazine, sulfadoxine, sulfadoxine-pyrimethamine, cycloguanil, and dapsone) was also shown to be antagonistic in vivo.There has been some concern that antipyretics might attenuate the host defense against malaria, as their use is associated with delayed parasite clearance. However, this appears to result from delaying cytoadherence, which is likely to be beneficial. There is no reason to withhold antipyretics in malaria. ...Paracetamol (acetaminophen) and ibuprofen are the preferred options for reducing fever. |
| Hepatotoxicity | In an open label study of severe malaria in 104 patients in the United States, elevations in ALT occurred in 27% of subjects, AST in 49%, and bilirubin in 17%. These abnormalities, however, were attributable to the hemolysis and liver involvement that are common in patients with acute, severe malaria. None of the elevations were attributed to drug induced liver injury. Since licensure of artesunate for injection and its more widescale clinical use in the United States, there have been no reports of acute liver injury attributed to its use. |
| Expositionspfade | A 2025 systematic review states that Artesunate's routes of administration include oral, intramuscular, rectal, and intravenous. |
| Toxizitätsübersicht | A 2025 systematic review discusses how treatment with Artesunate can produce liver and kidney damage in specific scenarios, i.e., when patients receive doses that are too high or receive extended periods of therapy. This hepatic and renal damage involves free-radical damage, cellular respiration failure, and inflammatory reaction pathways. The authors note that a combination of antioxidants, natural compounds, and optimized doses is an effective strategy to help protect the liver and kidneys. |
Anwendungen & Verwendung
Verwenden
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.
Herstellung & Synthese
synthetische
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