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Dihydropteroate

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Dihydropteroate
Names
IUPAC name 4-{amino}benzoic acid
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1226443
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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)Key: WBFYVDCHGVNRBH-UHFFFAOYSA-N
  • 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
SMILES
  • 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
Chemical formula C14H14N6O3
Molar mass 314.3 g/mol
Hazards
GHS labelling:
Pictograms GHS06: Toxic
Signal word 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 , 100 kPa). ☒N verify (what is  ?) 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.

Tetrahydrofolate synthesis pathway

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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