8219. Rifapentine

Nomenclature

CAS number: 61379-65-5
3-[[(4-Cyclopentyl-1-piperazinyl)imino]methyl]rifamycin; MDL-473; DL-473; R-773; Priftin (Aventis).
C47H64N4O12; mol wt 877.03.
C 64.37%, H 7.36%, N 6.39%, O 21.89%.

Description and references

Semi-synthetic rifamycin. Prepn: R. Cricchio, V. Arioli, DE 2608218; eidem, US 4002752 (1976, 1977 both to Lepetit). Antibacterial activity: V. Arioli et al., J. Antibiot. 34, 1026 (1981); H. C. Neu, Antimicrob. Agents Chemother. 24, 457 (1983). Pharmacokinetics: A. Assandri et al., J. Antibiot. 37, 1066 (1984). HPLC determn in plasma: E. Riva et al., J. Chromatogr. 553, 35 (1991). Clinical trial in tuberculosis: Natl. Co-op Group Clin. Study Rifapentine, Chin. J. Antibiot. 17, 313 (1992), B.A. 95, 70840 (1993). Review of pharmacology and clinical efficacy: B. Jarvis, H. M. Lamb, Drugs 56, 607-616 (1998).

Chemical structure

Properties

Crystals from ethyl acetate, mp 179-180°. uv max: 475, 334 nm (ε 15200, 26700). LD50 in mice (mg/kg): >2000 orally; 750 i.p. (Cricchio). Also reported as LD50 in mice (mg/kg): 3300 orally; 710 i.p. (Aroli).

Therapeutic Category

Antibacterial (tuberculostatic).

Keywords

Antibacterial (Antibiotics); Ansamycins; Antibacterial (Tuberculostatic)