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Chapter 32 : Ansamycins

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Abstract:

Rifampin was obtained by semisynthesis from the 3-formylrifamycin derivative. It is possible to separate two groups of molecules within the ansamycin family according to the aromatic nucleus: ansamycins of the naphthalene type and ansamycins of the benzene type. Chemical modifications of the ansa in general cause a reduction or even complete abolition of antibacterial activity. The chapter discusses the physiochemical properties and production of rifamycin. The activity of the ansamycins decreases in parallel over time in phosphate-buffered saline (PBS) medium or in 7 H10 medium with or without Tween 80. The majority of rifamycins inhibit the transcription of DNA to RNA. The use of rifampin as monotherapy is associated with the rapid appearance of resistant mutants among common pathogens, particularly , , , and . The ansamycins have weak activity against enteric gram-negative bacilli and non-fermenting gram-negative bacteria. Rifampin is one of the pivotal drugs in the treatment of tuberculosis. The ansamycins are extensively concentrated in phagocytic cells. Rifampin is one of the pivotal drugs in the treatment of tuberculosis. The ansamycins are extensively concentrated in phagocytic cells. Rifampin, rifabutin, and rifapentine are primarily antituberculosis and antileprosy agents. Staphylococcal infections are one of the indications of rifampin. The adverse effects of rifampin are dependent on treatment duration and dose.

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
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Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
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Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
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Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
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Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
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Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
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Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
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Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
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Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
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Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
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Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
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Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
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Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
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References

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1. Bergamini N,, Fowst G, 1965, Rifamycin SV, Arzneim Forsch, 15, 9511002.
2. Binda G,, Domenichini E,, Gottardi A,, Orlandi B,, Ortelli E,, Pacini B,, Fowst G, 1971, Rifampicin, a general review, Arzneim Forsch, 21, 19071977.
3. Dhople AM, 1995, In vitro and in vivo activities of T9, a new rifampicin derivative, against Mycobacterium leprae, 35th Intersci Conf Antimicrob Agents Chemother, abstract F-10.
4. Dickinson JM,, Mitchison DA, 1970, In vitro activities against mycobacteria of two long-acting rifamycins, FCE 22807 and CGP 1469 A (SPA-S-565), Tubercle, 71, 109115.
5. Geeta B,, Reddy MV,, Dimova V,, Gangadharam PRJ, 1995, In vitro and intracellular antimycobacterial activity of new rifampicin analogue 3-(4-cinnamyl-piperazimyl-iminomethyl-) rifampicin-SV, 19th Int Congr Chemother, abstract 1152.
6. Gurgoc A,, Bridges S,, Green M, 1982, Rifamycins, p 519555, in Came PE,, Caliguiri LA, ed, Chemotherapy of Viral Infections, Springer-Verlag.
7. Loos U,, Musch E,, Jensen JC,, Mikus G,, Sehwabe HR,, Eichelbaum M, 1985, Pharmacokinetics of oral and intravenous rifampicin during chronic administration, Klin Wochenschr, 63, 12051211.
8. Morris AB,, Brown RB,, Sands M, 1993, Use of rifampin in nonstaphylococcal, nonmycobacterial disease, Antimicrob Agents Chemother, 37, 17.
9. Pallanza R,, Füre’sz S,, Timbal MT,, Carniti G, 1963, In vitro bacteriological studies on rifamycin B diethylamide (rifamide), Arzneim Forsch, 13, 800802.
10. Pascual A,, Tsukayama D,, Kovarik J,, Gekker G,, Peterson P, 1987, Uptake and activity of rifapentine in human peritoneal macrophages and polymorphonuclear leukocytes, Eur J Clin Microbiol, 6, 152157.
11. Shalit I, 1988, Rifampin, p 373403, in Koren G,, Prober CG,, Gold R, ed, Antimicrobial Therapy in Infants and Children, Marcel Dekker.
12. Venkatesan K, 1992, Pharmacokinetic drug interaction with rifampicin, Clin Pharmacokinet, 22, 4765.
13. Williams JD,, Phillips I, 1984, Rifampicin as an anti-staphylococcal agent, J Antimicrob Chemother, 13, suppl C.

Tables

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Table 1

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
Generic image for table
Table 2

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
Generic image for table
Table 3

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
Generic image for table
Table 4

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
Generic image for table
Table 5

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
Generic image for table
Table 6

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
Generic image for table
Table 7

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
Generic image for table
Table 8

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
Generic image for table
Table 9

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
Generic image for table
Table 10

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
Generic image for table
Table 11

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
Generic image for table
Table 12

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
Generic image for table
Table 13

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
Generic image for table
Table 14

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
Generic image for table
Table 15

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
Generic image for table
Table 16

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
Generic image for table
Table 17

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32
Generic image for table
Table 18

Citation: Bryskier A. 2005. Ansamycins, p 906-924. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch32

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