Rifampicin (rifampin)

Alan C. Street, Tony M. Korman

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Abstract

In 1957, a new class of antibiotics called rifamycins was recognized at Lepetit Laboratories in Italy. These antibiotics were isolated from Amycolatopsis (previously Streptomyces and Nocardia) mediterranei. The name “rifamycin” was derived from the 1955 French movie Rififi (Sensi, 1983). Chemical modifications to one of the original compounds, designated rifamycin B, resulted in others with increased antibacterial activity. Two of these were introduced for clinical use in some countries, rifamycin SV in 1963 and rifamycin B diethylamide, or rifamide, in 1965; both were active against Mycobacterium tuberculosis and various other bacteria, but they were rapidly excreted by the liver and required parenteral administration. Further chemical modifications of rifamycin were made with the aim of producing a drug which was absorbed after oral administration, had a more prolonged antibacterial level in the blood, and had greater activity against mycobacteria and other bacteria. Rifampicin (also called rifampin) was synthesized in 1965 and introduced for clinical use in 1968. The name rifampin is used in the United States, while the drug is called rifampicin in Europe and Australia. Rifampicin has the chemical formula of 3-4 (4-methylpiperazinyl-iminomethylidene)-rifamycin SV (Sensi et al., 1966). The chemical structure of rifampicin is C43H58N4O12 and its molecular weight is 822.95; its molecular structure is shown in Figure 126.1. Additional semisynthetic rifamycins in clinical use include rifabutin (see Chapter 127, Rifabutin), rifapentine (see Chapter 129, Rifapentine), and rifaximin (see Chapter 128, Rifaximin).

Original languageEnglish
Title of host publicationKucers the Use of Antibiotics
Subtitle of host publicationA Clinical Review of Antibacterial, Antifungal, Antiparasitic, and Antiviral Drugs
EditorsM. Lindsay Grayson
Place of PublicationBoca Raton FL USA
PublisherCRC Press
Chapter126
Pages2369-2433
Number of pages65
Edition7th
ISBN (Electronic)9781498747967
ISBN (Print)9781498747950
Publication statusPublished - 2 Oct 2017

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