Rifampin

Generic and additional names: 5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-[N-(4-methyl-1-piperazinyl)formimidoyl]-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-1,11(2H)-dione 21-acetate; rifampicin; rifaldazine; rifamycin AMP; R/AMPCAS name: 3-{[(4-Methyl-1-piperazinyl)imino]methyl}rifamycinCAS registry #: 13292-46-1Molecular formula: C43H58N4O12Molecular weight: 822.94Intellectual property rights: Generic. Parent compound originally identified as a natural product from Amycolatopsis at Lapetit, Milan, Italy.1 Lapetit collaborated with Ciba-Geigy in the early development of this compound.1Brand names: Rifampin, rifampicin, rifamycin. Abrifam (Abbott); Eremfat (Fatol); Rifa (Grüunenthal); Rifadin(e), Rifaldin (Aventis); Rifapiam (Piam); Rifaprodin (Almirall); Rifoldin (Aventis); Rimactan(e) (Novartis)Derivatives: Rifapentine, rifalazil, rifabutinSolubility: Freely soluble in chloroform and DMSO; soluble in ethyl acetate, methanol, tetrahydrofuran; slightly soluble in acetone, water, carbon tetrachloride [Merck Index]Polarity: Log P 3.719 [DrugBank]Acidity/basicity: pKa 1.7 for the 4-hydroxy and pKa 7.9 for the 3-piperazine nitrogen [Merck Index]Stability: Very stable in DMSO; rather stable in water [Merck Index].Melting point: 183ºC [DrugBank]Formulation and optimal human dosage: 300 mg tablets (Mycobution, Upjohn). Dose 10 mg/kg, in a single daily administration, not to exceed 600 mg/day, oral or i.v.Rifampin is also available as part of fixed-dose combinations with other TB drugs such as isoniazid and pyrazinamide (Rifater® is an example).Figure optionsDownload full-size imageDownload high-quality image (45 K)Download as PowerPoint slide