Artemisinin
Title: Artemisinin
CAS Registry Number: 63968-64-9
CAS Name: (3R,5aS,6R,8aS,9R,12S,12aR)-Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one
Additional Names: artemisine; arteannuin; huanghuahaosu; QHS; qinghaosu; qing hau sau
Molecular Formula: C15H22O5
Molecular Weight: 282.33
Percent Composition: C 63.81%, H 7.85%, O 28.33%
Literature References: Active antimalarial constituent of the traditional Chinese medicinal herb Artemisia annua L., Compositae, which has been known for almost 2000 years as Qinghao. Isolated in 1972 and shown to be a sesquiterpene lactone with a peroxide moiety: K'o Hsueh T'ung Pao 22, 142 (1977), C.A. 87, 98788g (1977); L. Jing-Ming et al., Acta Chim. Sin. 37, 129 (1979), C.A. 92, 94594w (1980). Total synthesis and absolute configuration: G. Schmid, W. Hofheinz, J. Am. Chem. Soc. 105, 624 (1983). NMR spectral study: F. S. El-Feraly et al., Spectrosc. Lett. 18, 843 (1985). Antimalarial activity: Qinghaosu Antimalaria Coordinating Research Group, Chin. Med. J. 92, 811 (1979); L. J. Bruce-Chwatt, Br. Med. J. 284, 767 (1982). Clinical trials: J.-B. Jiang et al., Lancet 2, 285 (1982); W. Tongyin, X. Ruchang, J. Tradit. Chin. Med. 5, 240 (1985). Toxicity data: China Cooperative Research Group on Qinghaosu, ibid. 2, 31 (1982). Series of articles on chemistry, pharmacology, and antimalarial efficacy: ibid. 3-50. Brief reviews: H. Koch, Pharm. Int. 2, 184-185 (1981); D. L. Klayman, Science 228, 1049-1055 (1985). Review: R. N. Price, Expert Opin. Invest. Drugs 9, 1815-1827 (2000). Review of chemistry, pharmacology and clinical applications: X. D. Luo, C. C. Shen, Med. Res. Rev. 7, 29-52 (1987). Review of mechanism of action: S. R. Meshnick, Int. J. Parasitol. 32, 1655-1660 (2002).
Properties: Needles, mp 156-157°. [a]D17 +66.3°. (c = 1.64 in CHCl3). Sol in most aprotic solvents. Slightly sol in oil. LD50 in mice (mg/kg): 5105 orally; 2800 i.m.; 1558 i.p. (Koch). LD50 in mice, rats (mg/kg): 4228, 5576 orally; 3840, 2571 i.m. (China Cooperative Research Group on Qinghaosu).
Melting point: mp 156-157°
Optical Rotation: [a]D17 +66.3°
Toxicity data: LD50 in mice (mg/kg): 5105 orally; 2800 i.m.; 1558 i.p. (Koch); LD50 in mice, rats (mg/kg): 4228, 5576 orally; 3840, 2571 i.m. (China Cooperative Research Group on Qinghaosu)
 
Derivative Type: Dihydroartemisinin
CAS Registry Number: 71939-50-9
Additional Names: Dihydroqinghaosu
Molecular Formula: C15H24O5
Molecular Weight: 284.35
Percent Composition: C 63.36%, H 8.51%, O 28.13%
Literature References: Main metabolite of artemisinin, arteether, artemether, artesunate, qqv. HPLC determn: X.-D. Luo et al., Chromatographia 23, 112 (1987); in plasma: H. Naik et al., J. Chromatogr. B 816, 233 (2005).
 
Therap-Cat: Antimalarial.
Keywords: Antimalarial.

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