Product Name:    Rifampicin

Synonyms:    ,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,1///;2,7-(epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2-h)-dione,5,6;3-(((4-methyl-1-piperazinyl)imino)methyl)-rifamyci;3-((4-methyl-1-piperazinyl)iminomethyl)rifamycinsv;8-(((4-methyl-1-piperazinyl)imino)methyl)rifamycinsv;8-(4-Methylpiperazinyliminomethyl)rifamycinSV;8-(n-(4-methyl-1-piperazinyl)formidoyl)-rifomycins;RIFAMPIN ''LEPETIT''

CAS:    13292-46-1

MF:    C43H58N4O12

MW:    822.94

EINECS:    236-312-0

Product Categories:    RIFADIN;antibiotic;Antibiotics;Organics;Antibiotics for Research and Experimental Use;Peptide Synthesis/Antibiotics;Antitubercular;Biochemistry;Others (Antibiotics for Research and Experimental Use);Antibiotic Explorer;Intermediates & Fine Chemicals;Pharmaceuticals;Isotope Labeled Compounds;Chiral Reagents;Isotope Labelled Compounds;13292-46-1;APIs

Rifampicin is a semisynthetic derivative of rifamicin B, a macrolactam antibiotic and one of more than five antibiotics from a mixture of rifamicins A, B, C, D, and E, which is called a rifamicin complex, which is produced by actinomycetes Streptomyces mediteranei (Nocardia mediteranei). It was introduced into medical practice in 1968. Synthesis of rifampicin begins with an aqueous solution of rifamicin, which under the reaction conditions is oxidized to a new derivative of rifamicin S (32.7.4), with the intermediate formation of rifamicin O (32.7.3). Reducing the quinone structure of this product with hydrogen using a palladium on carbon catalyst gives rifamicin SV (32.7.5). The resulting product undergoes aminomethylation by a mixture of formaldehyde and pyrrolidine, giving 3-pyrrolidinomethylrifamicin SV (32.7.6). Oxidizing the resulting product with lead tetracetate to an enamine and subsequent hydrolysis with an aqueous solution of ascorbic acid gives 3-formylrifamicin SV (32.7.7). Reacting this with 1-amino-4-methylpiperazine gives the desired rifampicin