9-Aminocamptothecin
Structural Formula Vector Image
Title: 9-Aminocamptothecin
CAS Registry Number: 91421-43-1
CAS Name: (4S)-10-Amino-4-ethyl-4-hydroxy-1H-pyrano[3¢,4¢:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
Additional Names: 9-Amino-20(S)-camptothecin; 9-AC
Molecular Formula: C20H17N3O4
Molecular Weight: 363.37
Percent Composition: C 66.11%, H 4.72%, N 11.56%, O 17.61%
Literature References: Semisynthetic camptothecin which inhibits DNA topoisomerase I. Prepn: T. Miyasaka et al., JP Kokai 59 51289 (1984 to Yakult Honsha); M. C. Wani et al., J. Med. Chem. 29, 2358 (1986); and activity: S. Sawada et al., Chem. Pharm. Bull. 39, 3183 (1991). Synthesis: W. Cabri et al., Tetrahedron Lett. 36, 9197 (1995). HPLC determn in plasma: W. J. Loos et al., J. Chromatogr. B 694, 435 (1997). Structure/activity study: M.-L. Li et al., Clin. Cancer Res. 7, 168 (2001). Clinical pharmacodynamics and pharmacokinetics: C. H. Takimoto et al., J. Clin. Oncol. 15, 1492 (1997). Clinical evaluation in colorectal cancer: H. C. Pitot et al., Cancer 89, 1699 (2000). Review of clinical developments: C. H. Takimoto, R. Thomas, Ann. N.Y. Acad. Sci. 922, 224-236 (2000).
Properties: Orange-yellow solid from CH3OH/CHCl3 (13:87), mp 300° (dec). [a]D23 +16° (c = 0.05 in CH3OH/CHCl3 1:4). Insol in water.
Melting point: Orange-yellow solid from CH3OH/CHCl3 (13:87), mp 300° (dec)
Optical Rotation: [a]D23 +16° (c = 0.05 in CH3OH/CHCl3 1:4)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Alkaloids/Natural Products; Camptothecin Derivatives; Topoisomerase I Inhibitor.

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