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Chapter 4 : Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone

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Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, Page 1 of 2

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Abstract:

This chapter talks about the antimicrobials and antimalarials like Prontosil, pyrimethamine, proguanil, and atovaquone for the treatment of infectious diseases. The development of Prontosil began with the synthesis of a group of red azo dyes. The discovery of Prontosil opened up undreamed prospects for the treatment of infectious diseases. Prontosil treatment saved many people from the death sentence imposed by . Almost at the same time that sulfanilamide was identified as the active principle of Prontosil, it was found to be an effective antimalarial in monkeys infected with . The success of sulfa drugs encouraged the discovery of newer drugs, established research methods needed to find them, and created a business model for their development. The highest antimalarial activity was found in pyrimethamine, which resembled the antimalarial cycloguanil. Pyrimethamine inhibits the action of dihydrofolate reductase (DHFR) as it mimics DHF. The binding of pyrimethamine to DHFR relies on the structural differences between the host enzyme and that of the malaria parasite, and this is the basis for its selectivity and potency. Proguanil was inactive against the preblood (exoerythrocytic) stages of . Although proguanil on its own was inactive, antimalarial activity resulted from host metabolism to form the active molecule, when the serum from proguanil-treated monkeys inhibited the test tube growth of the preblood stages of . Proguanil emerged as the most promising partner for atovaquone. Atovaquone is also effective as a monotherapy against infections in AIDS patients.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4

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Electron Transport System
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Antibacterial Agents
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Figures

Image of Figure 1
Figure 1

The core of an azo dye.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 2
Figure 2

Structure of phenazopyridine.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 3
Figure 3

Structure of chrysoidine.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 4
Figure 4

Structure of the first antibacterial sulfonamide.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 5
Figure 5

Structures of Streptozon and Prontosil.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 6
Figure 6

Structure of sulfapyridine.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 7
Figure 7

Structures of sulfanilamide and pABA.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 8
Figure 8

(A) Structure of DHF. The pterin component is 2-amino-4-hydroxy-7,8-dihydropteridine; the pAB moiety derives from pABA. (B) Formation of THF and inhibitors of the pathway.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 9
Figure 9

Structures of thymine and 2,4-diaminopyrimidine.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 10
Figure 10

Structures of cycloguanil and pyrimethamine.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 11
Figure 11

The thymidylate cycle.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 12
Figure 12

Structures of Atabrine and compound 2666.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 13
Figure 13

Structures of biguanide, proguanil, compound 4430, and cycloguanil.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 14
Figure 14

Conversion of dihydroorotate to orotate, the electron transport chain, and the inhibitor atovaquone.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 15
Figure 15

Structure of a naphthoquinone.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 16
Figure 16

Structures of coenzymes Q and Q.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 17
Figure 17

Structures of lapinone, menoctone, and parvaquone.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 18
Figure 18

Structure of BW58C.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 19
Figure 19

Structures of 1,4-naphthoquinone and atovaquone.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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Image of Figure 20
Figure 20

The interrelationship of the de novo pyrimidine pathway and the folate pathway.

Citation: Sherman I. 2011. Antimicrobials to Antimalarials: Prontosil, Pyrimethamine, Proguanil, and Atovaquone, p 81-119. In Magic Bullets to Conquer Malaria. ASM Press, Washington, DC. doi: 10.1128/9781555816889.ch4
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References

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