Investigational Drug Details
| Drug ID: | D303 |
| Drug Name: | Sulfamethoxazole |
| Synonyms: | |
| Type: | small molecule |
| DrugBank ID: | DB01015 |
| DrugBank Description: | A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208) |
| PubChem ID: | 5329 |
| CasNo: | 723-46-6 |
| Repositioning for NAFLD: | Yes |
| SMILES: | CC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO1 |
| Structure: |
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| InChiKey: | JLKIGFTWXXRPMT-UHFFFAOYSA-N |
| Molecular Weight: | 253.278 |
| DrugBank Targets: | Dihydropteroate synthase |
| DrugBank MoA: | Sulfonamides inhibit the enzymatic condensation of DHPP and PABA by dihydropteroate synthase, an intermediate step in folate synthesis. Tetrahydrofolate (THF) is required for the synthesis of purines and dTMP and inhibition of its synthesis inhibits bacterial growth. Pyrimethamine and trimethoprim inhibit dihydrofolate reductase, another step in THF synthesis, and therefore act synergistically with the sulfonamides. |
| DrugBank Pharmacology: | Sulfamethoxazole is a sulfonamide drug that inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for binding to dihydropteroate synthase. Sulfamethoxazole is bacteriostatic in nature. Inhibition of dihydrofolic acid synthesis decreases the synthesis of bacterial nucleotides and DNA. Sulfamethoxazole is normally given in combination with Trimethoprim, a dihydrofolate reductase inhibitor, which inhibits the reduction of dihydrofolic acid to tetrahydrofolic acid. Studies have shown that bacterial resistance develops more slowly with the combination of the two drugs than with either Trimethoprim or Sulfamethoxazole alone. Sulfamethoxazole is a sulfonamide that inhibits bacterial dihydrofolic acid synthesis due to its similarity to para-aminobenzoic acid (PABA).[A187343,A187364] Sulfamethoxazole competitively inhibits dihydropteroate synthase, preventing the condensation of 6-hydroxymethyl-7,8-dihydropterin-pyrophosphate (DHPP) and para-aminobenzoic acid (PABA).[A112882] Inhibition of this pathway prevents nucleotide synthesis and the creation of new DNA, resulting in a bacteriostatic effect.[A187340] |
| DrugBank Indication: | For the treatment bacterial infections causing bronchitis, prostatitis and urinary tract infections. |
| Targets: | |
| Therapeutic Category: | |
| Clinical Trial Progress: | |
| Latest Progress: |
| Trial ID | Source ID | Phases | Status | Study Results | Start Date | Last Update Posted | |
|---|---|---|---|---|---|---|---|
| L3300 | NCT00886366 | PHASE1 | TERMINATED | NO | 2009-04 | 2010-12-07 | Details |
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