Dihydropteroate

Dihydropteroate is an important intermediate in folate synthesis. It is a pterin created from para-aminobenzoic acid (PABA) by the enzyme dihydropteroate synthase.[2]

Tetrahydrofolate synthesis pathway
Dihydropteroate
Names
IUPAC name
4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoic acid
Identifiers
3D model (JSmol)
1226443
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C14H14N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,16H,5-6H2,(H,22,23)(H4,15,17,19,20,21) checkY
    Key: WBFYVDCHGVNRBH-UHFFFAOYSA-N checkY
  • InChI=1/C14H14N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,16H,5-6H2,(H,22,23)(H4,15,17,19,20,21)
    Key: WBFYVDCHGVNRBH-UHFFFAOYAH
  • O=C(O)c1ccc(cc1)NCC/2=N/C=3C(=O)\N=C(/NC=3NC\2)N
  • C1C(=NC2=C(N1)NC(=NC2=O)N)CNC3=CC=C(C=C3)C(=O)O
Properties
C14H14N6O3
Molar mass 314.3 g/mol
Hazards
GHS labelling:[1]
GHS06: Toxic
Danger
H300
P264, P301+P310
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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
  1. GHS: GESTIS 492946
  2. 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.
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