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Chapter 35 : Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines

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Abstract:

This chapter talks about dihydrofolate reductase inhibitors (DHFR), nitroheterocycles (furans), and 8-hydroxyquinolines. Trimethoprim and brodimoprim contain two nitrogen atoms on the pyrimidine ring which are easily protonable according to the pH of environment. Co-trimoxazole is one of the main antibacterial agents for the treatment of uncomplicated cystitis. Pharmacology studies show that the combination of compounds does not modify their behavior and that if co-trimoxazole is compared with the other combinations an advantage may be found for trimethoprim-sulfadiazine in urinary tract infections and renal insufficiency. Many 6-6 fused rings have been prepared with the aim of increasing the selectivity for and DHFR. A series of hybrids was synthesized. Within this series one analog was 500-fold more potent than trimethoprim against and and displayed an excellent selectivity. The combination of epiroprim and dapsone is highly effective against pneumonia in rats and infection in mice. In vitro, the sulfones are active against , particularly dapsone. In murine pneumocystosis, dapsone is effective in treatment and prevention. In humans, the combination trimethoprim-dapsone in curative treatment and dapsone alone in preventive treatment are effective. Like the sulfonamides, the sulfones interfere with folate synthesis. They also have a potent antioxidant action. Lastly, dapsone inhibits the transport of adenosine through the erythrocyte wall and prevents its incorporation in the nucleic acid of plasmodia and probably toxoplasmas and .

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
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References

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17. Wolff M, 1990, Posologie des médicaments antiparasitaires chez l’adulte en insuffisance rénale, p 153161, in Journees de reanimation de l’hopital Claude Bernard, Arnette, Paris.
18. Biggs JT,, Uher AK,, Levy L,, Gordon GR,, Peters JH, 1975, Renal and biliary dispositions of dapsone in the dog, Antimicrob Agents Chemother, 7, 816824.
19. Bryskier A,, Labro MT, 1989, Les antifolates—classification, relation structure-activité, propriétés biologiques, p 69100, in Paludisme et Medicaments, Arnette, Paris.
20. Medina L,, Mills J,, Leoung G,, Hopewell PC,, Lee B,, Modin G,, Benowitz N,, Wofsy CB, 1990, Oral therapy for Pneumocystis carinii pneumonia in the acquired immunodeficiency syndrome: a controlled trial of trimethoprim-sulfamethoxazole versus trimethoprim-dapsone, N Engl J Med, 323, 776782.
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Tables

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Table 1

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 2

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 3

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 4

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 5

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 6

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 7

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 8

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 9

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 10

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 11

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 12

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 13

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 14

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 15

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 16

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 17

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 18

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 19

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 20

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 21

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 22

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 23

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 24

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 25

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 26

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 27

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 28

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 29

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 30

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35
Generic image for table
Table 31

Citation: Veyssier P, Bryskier A. 2005. Dihydrofolate Reductase Inhibitors, Nitroheterocycles (Furans), and 8-Hydroxyquinolines, p 941-963. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch35

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