Molecule Details
| InChIKey | IEDVJHCEMCRBQM-UHFFFAOYSA-N |
|---|---|
| Compound Name | Trimethoprim |
| Canonical SMILES | COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC |
| Clinical Status | Data-mined Candidate |
| Targets (Human+Pathogen) | 7 |
| Pfam Stratification | Homologous |
| Avg pChEMBL | 7.41 |
| Source | BindingDB;ChEMBL |
2D Structure
Activity Profile
DrugBank Annotations
| DrugBank ID | DB00440 |
|---|---|
| Drug Name | Trimethoprim |
| CAS Number | 738-70-5 |
| Groups | approved investigational vet_approved |
| ATC Codes | J04AM08 J01EE03 J01EA01 J01EE01 J01EE04 J01EE02 J01EE05 J01EE07 |
| Description | Trimethoprim is an antifolate antibacterial agent that inhibits bacterial dihydrofolate reductase (DHFR), a critical enzyme that catalyzes the formation of tetrahydrofolic acid (THF) - in doing so, it prevents the synthesis of bacterial DNA and ultimately continued bacterial survival.[L11893] Trimet... |
Categories: Agents Causing Muscle Toxicity Agents causing hyperkalemia Anti-Infective Agents Anti-Infective Agents, Urinary Antibacterials for Systemic Use Antibiotics for Pneumocystis Pneumonia Antiinfectives for Systemic Use Antimycobacterials Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP2C8 Inhibitors Cytochrome P-450 CYP2C8 Inhibitors (moderate) Cytochrome P-450 CYP2C8 Substrates Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Drugs causing inadvertant photosensitivity Drugs that are Mainly Renally Excreted Enzyme Inhibitors Folic Acid Antagonists MATE 1 Inhibitors MATE 1 Substrates MATE 2 Inhibitors MATE 2 Substrates MATE inhibitors MATE substrates P-glycoprotein inducers P-glycoprotein inhibitors P-glycoprotein substrates Photosensitizing Agents Pyrimidines Renal Agents Sulfonamides and trimethoprim Trimethoprim and Derivatives
Cross-references: BindingDB: 18069 ChEBI: 45924 CHEMBL22 ChemSpider: 5376 Drugs Product Database (DPD): 8452 C01965 D00145 PDB: TOP PharmGKB: PA451788 PubChem:5578 PubChem:46507125 RxCUI: 10829 Therapeutic Targets Database: DAP000927 Wikipedia: Trimethoprim ZINC: ZINC000006627681
Target Activities (7)
| Target | Gene | Organism | Category | Pfam | pChEMBL | Type | Source |
|---|---|---|---|---|---|---|---|
| P00374 | DHFR | Homo sapiens | Human | PF00186 | 6.9 | IC50 | ChEMBL;BindingDB |
| B0BL08 | dfrA17 | Escherichia coli | Pathogen | PF00186 | 8.4 | Ki | BindingDB |
| P0ABQ4 | folA | Escherichia coli (strain K12) | Pathogen | PF00186 | 8.2 | IC50 | ChEMBL;BindingDB |
| Q07422 | Toxoplasma gondii | Pathogen | PF00186 PF00303 | 8.1 | IC50 | ChEMBL;BindingDB | |
| P22906 | DFR1 | Candida albicans | Pathogen | PF00186 | 7.6 | IC50 | ChEMBL |
| Q81R22 | dfrA | Bacillus anthracis | Pathogen | PF00186 | 6.3 | Ki | ChEMBL |
| P00382 | dhfrI | Escherichia coli | Pathogen | PF00186 | 6.3 | IC50 | ChEMBL |
DrugBank Target Actions (12)
| Target | Gene | Target Name | Action | Type |
|---|---|---|---|---|
| P10632 | CYP2C8 | Cytochrome P450 2C8 | inhibitor | enzymes |
| P05177 | CYP1A2 | Cytochrome P450 1A2 | substrate | enzymes |
| P08684 | CYP3A4 | Cytochrome P450 3A4 | substrate | enzymes |
| P10632 | CYP2C8 | Cytochrome P450 2C8 | substrate | enzymes |
| P11712 | CYP2C9 | Cytochrome P450 2C9 | substrate | enzymes |
| P0ABQ4 | folA | Dihydrofolate reductase | inhibitor | targets |
| P00374 | DHFR | Dihydrofolate reductase | modulator | targets |
| Q86VL8 | SLC47A2 | Multidrug and toxin extrusion protein 2 | inhibitor | transporters |
| Q96FL8 | SLC47A1 | Multidrug and toxin extrusion protein 1 | inhibitor | transporters |
| P08183 | ABCB1 | ATP-dependent translocase ABCB1 | substrate | transporters |
| Q86VL8 | SLC47A2 | Multidrug and toxin extrusion protein 2 | substrate | transporters |
| Q96FL8 | SLC47A1 | Multidrug and toxin extrusion protein 1 | substrate | transporters |