8213. Rifabutin

Nomenclature

CAS number: 72559-06-9
1′,4-Didehydro-1-deoxy-1,4-dihydro-5′-(2-methylpropyl)-1-oxorifamycin XIV; (9S,12E,14S,15R,16S,17R,18R,19R,20S,21S,22E,24Z)-6,16,18,20-tetrahydroxy-1′-isobutyl-14-methoxy-7,9,15,17,19,21,25-heptamethylspiro[9,4-(epoxypentadeca[1,11,13]trienimino)-2H-furo[2′,3′:7,8]naphth[1,2-d]imidazole-2,4′-piperidine]-5,10,26-(3H,9H)-trione-16-acetate; 4-deoxo-3,4-[2-spiro-(N-isobutyl-4-piperidyl)]-(1H)-imidazo-(2,5-dihydro)rifamycin S; 4-N-isobutylspiropiperidylrifamycin S; LM-427; Ansatipine (Farmitalia); Mycobutin (Farmitalia).
C46H62N4O11; mol wt 847.00.
C 65.23%, H 7.38%, N 6.61%, O 20.78%.

Description and references

Semisynthetic derivative of rifamycin S that inhibits nucleic acid synthesis. Prepn: L. Marsili et al., DE 2825445 (1979 to Farmitalia); eidem, US 4219478 (1980 to Archifar Labs). In vitro and in vivo antibacterial activity: A. Sanfilippo et al., J. Antibiot. 33, 1193 (1980); C. Della Bruna et al., ibid. 36, 1502 (1983). Mechanism of action: D. Ungheri et al., Drugs Exp. Clin. Res. 10, 681 (1984). Comparative in vitro antimycobacterial spectrum: J. M. Dickinson, D. A. Mitchison, Tubercle 68, 177 (1987). In vitro inhibition of HIV-1 replication: R. Anand et al., Antimicrob. Agents Chemother. 32, 684 (1988). Clinical pharmacokinetics: M. H. Skinner et al., ibid. 33, 1237 (1989). Pharmacology and clinical efficacy in mycobacterial infections: R. J. O'Brien et al., Rev. Infect. Dis. 9, 519 (1987).

Chemical structure

Properties

Violet-red crystalline powder. Highly sol in chloroform, sol in methanol, slightly sol in ethanol, minimally sol in water. uv max (methanol): 493, 315, 274, 238 nm.

Therapeutic Category

Antibacterial (tuberculostatic).

Keywords

Antibacterial (Tuberculostatic)