8214. Rifalazil

Nomenclature

CAS number: 129791-92-0
1′,4-Didehydro-1-deoxy-1,4-dihydro-3′-hydroxy-5′-[4-(2-methylpropyl)-1-piperazinyl]-1-oxorifamycin VIII; (2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-5,12,21,23,25-pentahydroxy-10-(4-isobutyl-1-piperazinyl)-27-methoxy-2,4,16,20,22,24,26-heptamethyl-2,7-(epoxypentadeca[1,11,13]trienimino)-6H-benzofuro[4,5-a]phenoxazine-1(2H),6,15-trione 25-acetate; 3′-hydroxy-5′-(4-isobutyl-1-piperazinyl)benzoxazinorifamycin; KRM-1648.
C51H64N4O13; mol wt 941.07.
C 65.09%, H 6.85%, N 5.95%, O 22.10%.

Description and references

Semisynthetic derivative of rifamycin S, q.v. Prepn: T. Yamane et al., EP 366914; eidem, US 4983602 (1990, 1991 both to Kanegafuchi); eidem, Chem. Pharm. Bull. 41, 148 (1993). Antimycobacterial efficacy in comparison with rifampin, q.v.: T. Yamamoto et al., Antimicrob. Agents Chemother. 40, 426 (1996). Pharmacokinetics: K. Hosoe et al., ibid. 2749. HPLC determn in biological fluids: eidem, J. Chromatogr. B 653, 177 (1994). Review of pharmacology and clinical studies: D. M. Rothstein et al., Expert Opin. Invest. Drugs 12, 255-271 (2003).

Chemical structure

Properties

Crystals from chloroform-hexane, mp 195-200° (dec).

Therapeutic Category

Antibacterial (tuberculostatic).

Keywords

Antibacterial (Tuberculostatic)