Isepamicin
Title: Isepamicin
CAS Registry Number: 58152-03-7
CAS Name: O-6-Amino-6-deoxy-a-D-glucopyranosyl-(1®4)-O-[3-deoxy-4-C-methyl-3-(methylamino)-b-L-arabinopyranosyl-(1®6)]-N1-[(2S)-3-amino-2-hydroxy-1-oxopropyl]-2-deoxy-D-streptamine
Additional Names: 1-N-[(S)-3-amino-2-hydroxypropionyl]gentamicin B; HAPA-B
Manufacturers' Codes: Sch-21420
Molecular Formula: C22H43N5O12
Molecular Weight: 569.60
Percent Composition: C 46.39%, H 7.61%, N 12.30%, O 33.71%
Literature References: Aminoglycoside antibiotic; semisynthetic derivative of gentamicin B. Prepn: M. J. Weinstein et al., BE 818431; J. J. Wright, P. J. L. Daniels, BE 824657 (both 1975 to Sherico); J. J. Wright et al., US 4002742 (1977 to Schering Corp.); T. L. Nagabhushan et al., J. Antibiot. 31, 681 (1978). Antibacterial spectrum in vitro and in vivo: G. H. Miller et al., ibid. 688. Comparison with amikacin of nephrotoxic potential: L. I. Rankin et al., Antimicrob. Agents Chemother. 16, 491 (1979). Series of articles on antibacterial activity, toxicology and clinical efficacy: Chemotherapy (Tokyo) 35, Suppl 5, 1-610 (1985); on toxicology: Jpn. J. Antibiot. 39, 3164-3328 (1986), C.A. 107, 32666r-32673r (1987). Acute toxicity: T. Morino et al., ibid. 3164, C.A. 107, 32667s (1987).
 
Derivative Type: Sulfate
CAS Registry Number: 67814-76-0
Trademarks: Exacin (Schering); Isepacin (Toyo Jozo); Isépalline (Schering)
Properties: [a]D26 +110.9° (c = 1 in water as the disulfate hydrate). LD50 in male, female mice, rats (mg/kg): 234, 236, 489, 476 i.v.; 3312, 3320, 3451, 3392 s.c.; >5000 orally both species (Morino).
Optical Rotation: [a]D26 +110.9° (c = 1 in water as the disulfate hydrate)
Toxicity data: LD50 in male, female mice, rats (mg/kg): 234, 236, 489, 476 i.v.; 3312, 3320, 3451, 3392 s.c.; >5000 orally both species (Morino)
 
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Aminoglycosides.

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