Dihydropteroate

Dihydropteroate

Names
IUPAC name 4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoic acid
Identifiers
CAS Number	2134-76-1  N
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	1226443
ChEBI	CHEBI:4581  Y
ChemSpider	165  Y
KEGG	C00921  N
PubChem CID	170
UNII	Y3GL4V652E  Y
CompTox Dashboard (EPA)	DTXSID40175605
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) Y Key: WBFYVDCHGVNRBH-UHFFFAOYSA-N Y 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: [1]
Pictograms
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 [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

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

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 or TMP-SMX), are commonly used to treat recurrent urinary tract, Shigella , Salmonella , and Pneumocystis jirovecii infections, though resistance is known. ^[3]

See also

• Dihydrofolic acid

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.
3. Libecco, Julia A.; Powell, Keith R. (2004). "Trimethoprim/Sulfamethoxazole: Clinical Update". Pediatrics in Review. 25 (11): 375–380. doi:10.1542/pir.25-11-375. PMID   15520082.