| Synonyms |
Succinyl dihydroartemisinin; Dihydroartemisinine-12-alpha-succinate; Artesunate (superseded RN); Artesunate; Armax 200; SM-804; WR-256283; HSDB-7458; SM804; WR256283; HSDB7458; SM 804; WR 256283; HSDB 7458 |
| IUPAC Name |
4-oxo-4-[[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxy]butanoic acid |
| Molecular Weight |
384.42 |
| Molecular Formula |
C19H28O8 |
| Canonical SMILES |
CC1CCC2C(C(OC3C24C1CCC(O3)(OO4)C)OC(=O)CCC(=O)O)C |
| InChI |
InChI=1S/C19H28O8/c1-10-4-5-13-11(2)16(23-15(22)7-6-14(20)21)24-17-19(13)12(10)8-9-18(3,25-17)26-27-19/h10-13,16-17H,4-9H2,1-3H3,(H,20,21)/t10-,11-,12+,13+,16+,17-,18?,19-/m1/s1 |
| InChIKey |
FIHJKUPKCHIPAT-JQXDXKTESA-N |
| Boiling Point |
507.1±50.0 °C at 760 mmHg |
| Melting Point |
131-135 °C |
| Flash Point |
175.6±23.6 °C |
| Purity |
>99% |
| Density |
1.3±0.1 g/cm3 |
| Solubility |
Soluble in DMSO (25 mg/ml), and ethanol (25 mg/ml) |
| Appearance |
White Powder |
| 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. |
| Storage |
Store at +4 °C, in dark place. |
| Complexity |
623 |
| Exact Mass |
384.178406 |
| Index Of Refraction |
1.544 |
| In Vitro |
One of the cytotoxic effects of artesunate on cancer cells is mediated by induction of oxidative stress and DNA double-strand breaks (DSBs). In addition to inducing oxidative stress and DSBs, artesunate can also downregulate RAD51 and impair DSB repair in ovarian cancer cells. It was observed that the formation of RAD51 foci and homologous recombination repair (HRR) were significantly reduced in artesunate-treated cells. As a consequence, artesunate and cisplatin synergistically induced DSBs and inhibited the clonogenic formation of ovarian cancer cells. Ectopic expression of RAD51 was able to rescue the increased chemosensitivity conferred by artesunate, confirming that the chemosensitizing effect of artesuante is at least partially mediated by the downregulation of RAD51. |
| In Vivo |
During the actual trial period of 4 ± 1 weeks, three patients experienced six ose-limiting adverse events (DL-AEs) altogether (leucopenia, neutropenia, asthenia, anemia) possibly related to artesunate (ART) (not exceeding 33% in any dose level). Up to 200 mg/d (2.2-3.9 mg/kg/d) oral ART were safe and well tolerated; therefore, 200 mg/d are recommended for phase II/III trials. Safety monitoring should include reticulocytes, NTproBNP, as well as audiological and neurological exploration. |
| PSA |
100.52000 |
| Target |
STAT; Ferroptosis; Parasite; Virus Protease |
| Vapor Pressure |
3.2X10-9 mm Hg at 25 °C (est) |
| XLogP3-AA |
2.5 |
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