Dihydropteroate

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| ImageFile = Dihydropteroic acid.svg

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| IUPACName = 4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoic acid

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|Section1={{Chembox Identifiers

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| 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)

| InChIKey = WBFYVDCHGVNRBH-UHFFFAOYAH

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = WBFYVDCHGVNRBH-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 2134-76-1

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = Y3GL4V652E

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| PubChem = 170

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 165

| SMILES1 = O=C(O)c1ccc(cc1)NCC/2=N/C=3C(=O)\N=C(/NC=3NC\2)N

| SMILES2 = C1C(=NC2=C(N1)NC(=NC2=O)N)CNC3=CC=C(C=C3)C(=O)O

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| ChEBI = 4581

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| KEGG = C00921

| Beilstein = 1226443

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|Section2={{Chembox Properties

| Formula = C14H14N6O3

| MolarMass = 314.3 g/mol

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|Section4={{Chembox Thermochemistry

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|Section5={{Chembox Pharmacology

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|Section7={{Chembox Hazards

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| GHSPictograms = {{GHS06}}

| GHSSignalWord = danger

| HPhrases = {{HPhrases|H300}}

| PPhrases = {{PPhrases|P264|P301+P310}}

| GHS_ref = GHS: [https://gestis.dguv.de/data?name=492946 GESTIS 492946]

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|Section8={{Chembox Related

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Dihydropteroate is an important intermediate in folate biosynthesis. It is a pterin created from para-aminobenzoic acid (PABA) by the enzyme dihydropteroate synthase.{{cite journal|title=Structural Studies of Pterin-Based Inhibitors of Dihydropteroate Synthase|journal=Journal of Medicinal Chemistry|volume=53|issue=1|pages=166–177|doi=10.1021/jm900861d|pmid=19899766|pmc=2804029|year=2010|last1=Hevener|first1=Kirk E|last2=Yun|first2=Mi-Kyung|last3=Qi|first3=Jianjun|last4=Kerr|first4=Iain D|last5=Babaoglu|first5=Kerim|last6=Hurdle|first6=Julian G|last7=Balakrishna|first7=Kanya|last8=White|first8=Stephen W|last9=Lee|first9=Richard E}}

Image:THFsynthesispathway.png synthesis pathway]]{{clear-left}}

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.{{cite journal|last1=Libecco|first1=Julia A.|last2=Powell|first2=Keith R.|title=Trimethoprim/Sulfamethoxazole: Clinical Update|journal=Pediatrics in Review|volume=25|issue=11|pages=375–380|year=2004|doi=10.1542/pir.25-11-375|pmid=15520082}}

See also

References