Menogaril
Title: Menogaril
CAS Registry Number: 71628-96-1
CAS Name: (2R,3S,4R,5R,6R,11R,13R)-4-(Dimethylamino)-3,4,5,6,11,12,13,14-octahydro-3,5,8,10,13-pentahydroxy-11-methoxy-6,13-dimethyl-2,6-epoxy-2H-naphthaceno[1,2-b]oxocin-9,16-dione
Additional Names: 7-con-O-methylnogarol; 7-OMEN; 7(R)-O-methylnogarol; menogarol; TUT-7
Manufacturers' Codes: NSC-269148; U-52047
Molecular Formula: C28H31NO10
Molecular Weight: 541.55
Percent Composition: C 62.10%, H 5.77%, N 2.59%, O 29.54%
Literature References: Antitumor antibiotic; semi-synthetic derivative of nogalamycin. Prepn: P. F. Wiley, D. J. Houser, US 4086245 (1978 to Upjohn). Total synthesis: M. Kawasaki et al., Tetrahedron 44, 5727 (1988). Antitumor activity: G. L. Neil et al., Cancer Treat. Rep. 63, 1971 (1979). HPLC determn in plasma: J. E. Brown et al., J. Chromatogr. 226, 521 (1981); J. P. McGovren et al., Anal. Chem. 56, 1587 (1984). Pharmacokinetics and metabolism: M. J. Egorin et al., Cancer Res. 46, 1513 (1986). Mechanism of action: K. Wierzba et al., Jpn. J. Cancer Res. 81, 842 (1990). Clinical studies in non-small cell lung cancer: R. B. Vance et al., Invest. New Drugs 9, 73 (1991); in non-Hodgkin's lymphoma: J. Skillings et al., ibid., 79. Brief review of antitumor, biochemical, and toxicological studies: J. P. McGovren et al., ibid. 2, 359-367 (1984).
Properties: Orange crystals, mp 247-249° (dec). [a]D20 +857° (c = 0.112 in CHCl3). Also reported as mp 250-254° (dec). [a]D20 +867° (c = 0.045 in CHCl3); [a]D +958° (c = 0.163 in CHCl3). uv max (ethanol): 235, 251, 257, 290, 479 nm (e 41200, 25500, 24150, 10500, 15530).
Melting point: mp 247-249° (dec); mp 250-254° (dec)
Optical Rotation: [a]D20 +857° (c = 0.112 in CHCl3); [a]D20 +867° (c = 0.045 in CHCl3); [a]D +958° (c = 0.163 in CHCl3)
Absorption maximum: uv max (ethanol): 235, 251, 257, 290, 479 nm (e 41200, 25500, 24150, 10500, 15530)
 
 
Status: This monograph has been retired and is no longer subject to revision or update.

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