Dihydropteroate
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Names | |
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IUPAC name 4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoic acid | |
Identifiers | |
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3D model (JSmol) |
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Beilstein Reference | 1226443 |
ChEBI |
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KEGG |
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PubChem CID |
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CompTox Dashboard (EPA) |
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InChI
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Properties | |
Chemical formula | C14H14N6O3 |
Molar mass | 314.3 g/mol |
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Pictograms | ![]() |
Danger | |
Hazard statements | H300 |
Precautionary statements | P264, P301+P310 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ![]() ![]() ![]() Infobox references |
Chemical compound
Dihydropteroate is an important intermediate in folate biosynthesis. It is a pterin created from para-aminobenzoic acid (PABA) by the enzyme dihydropteroate synthase.[2]
![](http://upload.wikimedia.org/wikipedia/commons/e/e9/THFsynthesispathway.png)
Bacteriostatic agents such as sulfonamides target dihydropteroate synthetase. The effect of dihydropteroate synthetase inhibition is comparable to that of dihydrofolate reductase inhibition by trimethoprim, another bacteriostatic agent. Combinations of these two drug types, such as the combination trimethoprim/sulfamethoxazole (TMP-SMX]), are commonly used to treat recurrent urinary tract, Shigella, Salmonella, and Pneumocystis jivoreci infections.
See also
References
- ^ GHS: GESTIS 492946
- ^ Hevener, Kirk E; Yun, Mi-Kyung; Qi, Jianjun; Kerr, Iain D; Babaoglu, Kerim; Hurdle, Julian G; Balakrishna, Kanya; White, Stephen W; Lee, Richard E (2010). "Structural Studies of Pterin-Based Inhibitors of Dihydropteroate Synthase". Journal of Medicinal Chemistry. 53 (1): 166–177. doi:10.1021/jm900861d. PMC 2804029. PMID 19899766.