Identification
- Summary
Trimethoprim is an antifolate antibiotic often used in combination with sulfamethoxazole to treat a number of infections, including those of the urinary tract, respiratory tract, and gastrointestinal tract.
- Brand Names
- Bactrim, Polytrim, Primsol, Septra, Sulfatrim
- Generic Name
- Trimethoprim
- DrugBank Accession Number
- DB00440
- Background
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.14 Trimethoprim is often used in combination with sulfamethoxazole due to their complementary and synergistic mechanisms but may be used as a monotherapy in the treatment and/or prophylaxis of urinary tract infections.14,16 It is structurally and chemically related to pyrimethamine, another antifolate antimicrobial used in the treatment of plasmodial infections.11
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Trimethoprim (DB00440)
- Weight
- Average: 290.3177
Monoisotopic: 290.137890462 - Chemical Formula
- C14H18N4O3
- Synonyms
- 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine
- 5-[(3,4,5-trimethoxyphenyl)methyl]-2,4-pyrimidinediamine
- Trimethoprim
- Triméthoprime
- Trimethoprimum
- Trimetoprima
- External IDs
- BW 56-72
- BW-56-72
- NIH-204
- NSC-106568
- Ro 6-2153-12 F
Pharmacology
- Indication
As a monotherapy, trimethoprim is indicated for the treatment of acute episodes of uncomplicated urinary tract infections caused by susceptible bacteria, including E. coli., K. pneumoniae, Enterobacter spp., P. mirabilis, and coagulase-negative Staphylococcus species.14,13 In various formulations in combination with sulfamethoxazole, trimethoprim is indicated for the following infections caused by bacteria with documented susceptibility: urinary tract infections, acute otitis media in pediatric patients (when clinically indicated), acute exacerbations of chronic bronchitis in adults, enteritis caused by susceptible Shigella, prophylaxis and treatment of Pneumocystis jiroveci pneumonia, and travelers' diarrhea caused by enterotoxigenic E. coli.16,19
Trimethoprim is available as an ophthalmic solution in combination with polymyxin B for the treatment of acute bacterial conjunctivitis, blepharitis, and blepharoconjunctivitis caused by susceptible bacteria.12
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Acute exacerbation of chronic bronchitis (aecb) caused by susceptible bacteria Combination Product in combination with: Sulfamethoxazole (DB01015) •••••••••••• ••••• Used in combination to treat Acute otitis media caused by susceptible bacteria Combination Product in combination with: Sulfamethoxazole (DB01015) •••••••••••• ••••••••• Treatment of Acute otitis media caused by susceptible bacteria •••••••••••• ••••••••• •••••••• Used in combination to treat Bacterial conjunctivitis caused by susceptible bacteria Combination Product in combination with: Polymyxin B (DB00781) •••••••••••• •••••••• Used in combination to treat Blepharoconjunctivitis caused by susceptible bacteria Combination Product in combination with: Polymyxin B (DB00781) •••••••••••• •••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Trimethoprim exerts its antimicrobial effects by inhibiting an essential step in the synthesis of bacterial nucleic acids and proteins.14 It has shown activity against several species of gram-negative bacteria, as well as coagulase-negative Staphylococcus species. 14 Resistance to trimethoprim may arise via a variety of mechanisms, including alterations to the bacterial cell wall, overproduction of dihydrofolate reductase, or production of resistant dihydrofolate reductase.14 Rarely, trimethoprim can precipitate the development of blood disorders (e.g. thrombocytopenia, leukopenia, etc.) which may be preceded by symptoms such as sore throat, fever, pallor, and or purpura - patients should be monitored closely for the development of these symptoms throught the course of therapy.14
As antimicrobial susceptibility patterns are geographically distinct, local antibiograms should be consulted to ensure adequate coverage of relevant pathogens prior to use.
- Mechanism of action
Trimethoprim is a reversible inhibitor of dihydrofolate reductase, one of the principal enzymes catalyzing the formation of tetrahydrofolic acid (THF) from dihydrofolic acid (DHF).14 Tetrahydrofolic acid is necessary for the biosynthesis of bacterial nucleic acids and proteins and ultimately for continued bacterial survival - inhibiting its synthesis, then, results in bactericidal activity. Trimethoprim binds with a much stronger affinity to bacterial dihydrofolate reductase as compared to its mammalian counterpart, allowing trimethoprim to selectively interfere with bacterial biosynthetic processes.14
Trimethoprim is often given in combination with sulfamethoxazole, which inhibits the preceding step in bacterial protein synthesis - given together, sulfamethoxazole and trimethoprim inhibit two consecutive steps in the biosynthesis of bacterial nucleic acids and proteins.16 As a monotherapy trimethoprim is considered bacteriostatic, but in combination with sulfamethoxazole is thought to exert bactericidal activity.12,10
Target Actions Organism ADihydrofolate reductase inhibitorEscherichia coli (strain K12) - Absorption
Steady-state concentrations are achieved after approximately 3 days of repeat administration.9 Average peak serum concentrations of approximately 1 µg/mL (Cmax) are achieved within 1 to 4 hours (Tmax) following the administration of a single 100mg dose.14 Trimethoprim appears to follow first-order pharmacokinetics,9 as a single 200mg dose results in serum concentrations approximately double that of a 100mg dose.14 The steady-state AUC of orally administered trimethoprim is approximately 30 mg/L·h.9
- Volume of distribution
Trimethoprim is extensively distributed into various tissues following oral administration. It distributes well into sputum, middle ear fluid, and bronchial secretions.16 Trimethoprim distributes efficiently into vaginal fluids, with observed concentrations approximately 1.6-fold higher than those seen in the serum.14 It may pass the placental barrier and into breast milk.16 Trimethoprim is also sufficiently excreted in the feces to markedly reduce and/or eliminate trimethoprim-susceptible fecal flora.14
- Protein binding
Trimethoprim is 44% bound to plasma proteins, though the specific proteins to which it binds have not been elucidated.13
- Metabolism
Trimethoprim undergoes oxidative metabolism to a number of metabolites, the most abundant of which are the demethylated 3'- and 4'- metabolites, accounting for approximately 65% and 25% of the total metabolite formation, respectively.6 Minor products include N-oxide metabolites (<5%) and benzylic metabolites in even smaller quantities.6 The parent drug is considered to be the therapeutically active form.14
The majority of trimethoprim biotransformation appears to involve CYP2C9 and CYP3A4 enzymes, with CYP1A2 contributing to a lesser extent.6
Hover over products below to view reaction partners
- Route of elimination
Approximately 10-20% of an ingested trimethoprim dose is metabolized, primarily in the liver, while a large portion of the remainder is excreted unchanged in the urine.14 Following oral administration, 50% to 60% of trimethoprim is excreted in the urine within 24 hours, approximately 80% of which is unchanged parent drug.13
- Half-life
Trimethoprim half-life ranges from 8-10 hours, but may be prolonged in patients with renal dysfunction.13
- Clearance
Following oral administration, the renal clearance of trimethoprim has been variably reported between 51.7 - 91.3 mL/min.9
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
The oral LD50 in mice and rats is 2764 mg/kg and >5300 mg/kg, respectively.18
Prescribing information for trimethoprim states that signs of overdose may be evident following ingestion of doses >1 gram, and may include nausea, vomiting, dizziness, headaches, mental depression, confusion, and bone marrow depression.14 Treatment should consist of general supportive measures and gastric lavage, if applicable. Urinary acidification may increase renal elimination of trimethoprim. Hemodialysis is only moderately effective in eliminating trimethoprim and peritoneal dialysis is of no benefit.14
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Glucose-6-phosphate 1-dehydrogenase Villeurbanne Not Available 1000_1002delACC ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Torun Not Available 1006A->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Sunderland Not Available 105_107delCAT ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Iwatsuki Not Available 1081G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Serres Not Available 1082C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Tondela Not Available 1084_1101delCTGAACGAGCGCAAGGCC ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Loma Linda Not Available 1089C->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Aachen Not Available 1089C->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Tenri Not Available 1096A->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Montpellier Not Available 1132G>A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Calvo Mackenna Not Available 1138A->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Riley Not Available 1139T->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Olomouc Not Available 1141T->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Tomah Not Available 1153T->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Lynwood Not Available 1154G->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Madrid Not Available 1155C->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Iowa, Walter Reed, Springfield Not Available 1156A->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Beverly Hills, Genova, Iwate, Niigata, Yamaguchi Not Available 1160G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Hartford Not Available 1162A->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Praha Not Available 1166A->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Krakow Not Available 1175T>C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Wisconsin Not Available 1177C->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Nashville, Anaheim, Portici Not Available 1178G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Alhambra Not Available 1180G->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Bari Not Available 1187C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Puerto Limon Not Available 1192G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Covao do Lobo Not Available 1205C>A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Clinic Not Available 1215G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Utrecht Not Available 1225C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Suwalki Not Available 1226C->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Riverside Not Available 1228G->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Japan, Shinagawa Not Available 1229G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Kawasaki Not Available 1229G->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Munich Not Available 1231A->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Georgia Not Available 1284C->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Sumare Not Available 1292T->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Telti/Kobe Not Available 1318C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Santiago de Cuba, Morioka Not Available 1339G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Harima Not Available 1358T->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Figuera da Foz Not Available 1366G->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Amiens Not Available 1367A>T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Bangkok Noi Not Available 1376G->T, 1502T->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Fukaya Not Available 1462G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Campinas Not Available 1463G->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Buenos Aires Not Available 1465C>T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Arakawa Not Available 1466C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Brighton Not Available 1488_1490delGAA ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Kozukata Not Available 159G->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Amsterdam Not Available 180_182delTCT ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase No name Not Available 202G->A, 376A->G, 1264C>G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Swansea Not Available 224T->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Urayasu Not Available 281_283delAGA ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Vancouver Not Available 317C->G544C->T592C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Mt Sinai Not Available 376A->G, 1159C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Plymouth Not Available 488G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Volendam Not Available 514C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Shinshu Not Available 527A->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Chikugo Not Available 535A->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Tsukui Not Available 561_563delCTC ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Pedoplis-Ckaro Not Available 573C>G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Santiago Not Available 593G->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Minnesota, Marion, Gastonia, LeJeune Not Available 637G->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Cincinnati Not Available 637G->T, 1037A->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Harilaou Not Available 648T->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase North Dallas Not Available 683_685delACA ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Asahikawa Not Available 695G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Durham Not Available 713A->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Stonybrook Not Available 724_729delGGCACT ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Wayne Not Available 769C->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Aveiro Not Available 806G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Cleveland Corum Not Available 820G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Lille Not Available 821A>T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Bangkok Not Available 825G>C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Sugao Not Available 826C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase La Jolla Not Available 832T->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Wexham Not Available 833C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Piotrkow Not Available 851T>C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase West Virginia Not Available 910G->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Omiya Not Available 921G->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Nara Not Available 953_976delCCACCAAAGGGTACCTGGAC GACC ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Manhattan Not Available 962G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Rehevot Not Available 964T->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Honiara Not Available 99A->G / 1360C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Tokyo, Fukushima Not Available 1246G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Chatham Not Available 1003G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Fushan Not Available 1004C->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Partenope Not Available 1052G->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Ierapetra Not Available 1057C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Anadia Not Available 1193A->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Abeno Not Available 1220A->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Surabaya Not Available 1291G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Pawnee Not Available 1316G->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase S. Antioco Not Available 1342A->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Cassano Not Available 1347G->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Hermoupolis Not Available 1347G->C / 1360C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Union,Maewo, Chinese-2, Kalo Not Available 1360C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Andalus Not Available 1361G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Cosenza Not Available 1376G->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Canton, Taiwan- Hakka, Gifu-like, Agrigento-like Not Available 1376G->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Flores Not Available 1387C->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Kaiping, Anant, Dhon, Sapporo-like, Wosera Not Available 1388G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Kamogawa Not Available 169C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Costanzo Not Available 179T>C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Amazonia Not Available 185C->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Songklanagarind Not Available 196T->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Hechi Not Available 202G->A / 871G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Namouru Not Available 208T->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Bao Loc Not Available 352T>C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Crispim Not Available 375G->T, 379G->T383T->C384C>T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Acrokorinthos Not Available 376A->G / 463C->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Santa Maria Not Available 376A->G / 542A->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Ananindeua Not Available 376A->G / 871G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Vanua Lava Not Available 383T->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Valladolid Not Available 406C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Belem Not Available 409C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Liuzhou Not Available 442G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Shenzen Not Available 473G>A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Taipei ‚ÄúChinese- 3‚Äù Not Available 493A->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Toledo Not Available 496C>T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Naone Not Available 497G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Nankang Not Available 517T->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Miaoli Not Available 519C->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Mediterranean, Dallas, Panama‚ Sassari, Cagliari, Birmingham Not Available 563C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Coimbra Shunde Not Available 592C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Nilgiri Not Available 593G>A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Radlowo Not Available 679C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Roubaix Not Available 811G>C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Haikou Not Available 835A->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Chinese-1 Not Available 835A->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Mizushima Not Available 848A>G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Osaka Not Available 853C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Viangchan, Jammu Not Available 871G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Seoul Not Available 916G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Ludhiana Not Available 929G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Farroupilha Not Available 977C->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Chinese-5 Not Available 1024C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Rignano Not Available 130G>A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Orissa Not Available 131C->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase G6PDNice Not Available 1380G>C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Kamiube, Keelung Not Available 1387C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Neapolis Not Available 1400C->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Aures Not Available 143T->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Split Not Available 1442C->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Kambos Not Available 148C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Palestrina Not Available 170G>A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Metaponto Not Available 172G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Musashino Not Available 185C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Asahi Not Available 202G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase A- (202), Ferrara I Not Available 202G->A / 376A->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Murcia Oristano Not Available 209A->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Ube Konan Not Available 241C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Lagosanto Not Available 242G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Guangzhou Not Available 274C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Hammersmith Not Available 323T->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Sinnai Not Available 34G->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase A- (680) Not Available 376A->G / 680G->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase A- (968), Betica,Selma, Guantanamo Not Available 376A->G / 968T->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Salerno Pyrgos Not Available 383T>G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Quing Yan Not Available 392G->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Lages Not Available 40G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Ilesha Not Available 466G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Mahidol Not Available 487G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Malaga Not Available 542A->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Sibari Not Available 634A->G ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Mexico City Not Available 680G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Nanning Not Available 703C->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Seattle, Lodi, Modena, Ferrara II, Athens-like Not Available 844G->C ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Bajo Maumere Not Available 844G->T ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Montalbano Not Available 854G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Kalyan-Kerala, Jamnaga, Rohini Not Available 949G->A ADR Inferred Increased risk of dose-related hemolysis. Details Glucose-6-phosphate 1-dehydrogenase Gaohe Not Available 95A->G ADR Inferred Increased risk of dose-related hemolysis. Details
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Trimethoprim may decrease the excretion rate of Abacavir which could result in a higher serum level. Abametapir The serum concentration of Trimethoprim can be increased when it is combined with Abametapir. Abatacept The metabolism of Trimethoprim can be increased when combined with Abatacept. Abemaciclib The excretion of Abemaciclib can be decreased when combined with Trimethoprim. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Trimethoprim. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Trimethoprim hydrochloride 9XE000OU9B 60834-30-2 YLCCEQZHUHUYPA-UHFFFAOYSA-N Trimethoprim sulfate E377MF8EQ8 56585-33-2 UILMMYFRNCCPLK-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Alprim (Alphapharm) / Catin (Kojar) / Eumi (Hwang's) / Inflamnil (Swiss Pharm) / Lannacher (Root) / Lariago (Ipca Laboratories) / Meprim (Johnson) / Metipine (Kojar) / Monotrim (GlaxoSmithKline) / Motrim (Lannacher) / Trimpex / Triprim (GlaxoSmithKline)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image PrimSol Solution 50 mg/5mL Oral Allegis Holdings, Llc 2017-05-04 Not applicable US 
Primsol Solution 50 mg/5mL Oral Fsc Laboratories, Inc. 2000-01-24 Not applicable US Primsol Solution 50 mg/5mL Oral Aytu BioScience, Inc. 2015-09-15 2018-01-01 US Proloprim Tablet 100 mg/1 Oral Monarch Pharmaceuticals, Inc. 1982-07-14 2007-01-31 US Proloprim Tablet 200 mg/1 Oral Monarch Pharmaceuticals, Inc. 1982-07-14 2007-01-31 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Trimethoprim Tablet 100 mg/1 Oral Carilion Materials Management 2010-04-04 Not applicable US 
Trimethoprim Tablet 100 mg/1 Oral Physicians Total Care, Inc. 2012-05-02 Not applicable US 
Trimethoprim Tablet 100 mg/1 Oral Golden State Medical Supply, Inc. 2022-10-28 Not applicable US Trimethoprim Tablet 100 mg/1 Oral AvPAK 2013-07-31 2019-03-31 US Trimethoprim Tablet 100 mg/1 Oral bryant ranch prepack 2011-06-24 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Apo-sulfatrim Oral Suspension Trimethoprim (8 mg / mL) + Sulfamethoxazole (40 mg / mL) Suspension Oral Apotex Corporation 1989-12-31 Not applicable Canada 
APO-SULFATRIM PEDIATRIC TABLET Trimethoprim (20 mg) + Sulfamethoxazole (100 mg) Tablet Oral PHARMAFORTE SINGAPORE PTE LTD 1988-04-28 Not applicable Singapore 
APO-SULFATRIM TABLET Trimethoprim (80 mg) + Sulfamethoxazole (400 mg) Tablet Oral PHARMAFORTE SINGAPORE PTE LTD 1988-04-27 Not applicable Singapore B.S. SUSPENSION Trimethoprim (40 mg/5ml) + Sulfamethoxazole (200 mg/5ml) Suspension Oral APEX PHARMA MARKETING PTE. LTD. 1988-04-28 Not applicable Singapore B.S. TABLET Trimethoprim (80 mg) + Sulfamethoxazole (400 mg) Tablet Oral APEX PHARMA MARKETING PTE. LTD. 1988-10-05 Not applicable Singapore - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image TRIMOKS FORT TABLET, 20 ADET Trimethoprim (160 mg) + Sulfamethoxazole (800 mg) Tablet Oral ATABAY KİMYA SAN. VE TİC. A.Ş. 2013-01-29 Not applicable Turkey 
TRIMOKS PED. 100 ML SUSPANSIYON Trimethoprim (80 mg) + Sulfamethoxazole (400 mg) Suspension Oral ATABAY KİMYA SAN. VE TİC. A.Ş. 2013-01-29 Not applicable Turkey TRIMOKS TABLET, 30 ADET Trimethoprim (80 mg) + Sulfamethoxazole (400 mg) Tablet Oral ATABAY KİMYA SAN. VE TİC. A.Ş. 2013-01-29 Not applicable Turkey
Categories
- ATC Codes
- J01EE03 — Sulfametrole and trimethoprim
- J01EE — Combinations of sulfonamides and trimethoprim, incl. derivatives
- J01E — SULFONAMIDES AND TRIMETHOPRIM
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J01EA — Trimethoprim and derivatives
- J01E — SULFONAMIDES AND TRIMETHOPRIM
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J04AM — Combinations of drugs for treatment of tuberculosis
- J04A — DRUGS FOR TREATMENT OF TUBERCULOSIS
- J04 — ANTIMYCOBACTERIALS
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J01EE — Combinations of sulfonamides and trimethoprim, incl. derivatives
- J01E — SULFONAMIDES AND TRIMETHOPRIM
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J01EE — Combinations of sulfonamides and trimethoprim, incl. derivatives
- J01E — SULFONAMIDES AND TRIMETHOPRIM
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J01EE — Combinations of sulfonamides and trimethoprim, incl. derivatives
- J01E — SULFONAMIDES AND TRIMETHOPRIM
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J01EE — Combinations of sulfonamides and trimethoprim, incl. derivatives
- J01E — SULFONAMIDES AND TRIMETHOPRIM
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Agents causing hyperkalemia
- Agents Causing Muscle Toxicity
- 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
- OCT2 Inhibitors
- P-glycoprotein inducers
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- Photosensitizing Agents
- Pyrimidines
- Renal Agents
- Sulfonamides and trimethoprim
- Trimethoprim and Derivatives
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenol ethers
- Sub Class
- Anisoles
- Direct Parent
- Anisoles
- Alternative Parents
- Phenoxy compounds / Methoxybenzenes / Aminopyrimidines and derivatives / Alkyl aryl ethers / Imidolactams / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Alkyl aryl ether / Amine / Aminopyrimidine / Anisole / Aromatic heteromonocyclic compound / Azacycle / Ether / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- aminopyrimidine, methoxybenzene (CHEBI:45924) / a small molecule (CPD0-1581)
- Affected organisms
- Staphylococcus saprophyticus
- Escherichia coli
- Proteus mirabilis
- Klebsiella pneumoniae
- Enterobacter spp.
Chemical Identifiers
- UNII
- AN164J8Y0X
- CAS number
- 738-70-5
- InChI Key
- IEDVJHCEMCRBQM-UHFFFAOYSA-N
- InChI
- InChI=1S/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15/h5-7H,4H2,1-3H3,(H4,15,16,17,18)
- IUPAC Name
- 5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
- SMILES
- COC1=CC(CC2=CN=C(N)N=C2N)=CC(OC)=C1OC
References
- Synthesis Reference
Yasushi Takagishi, Kiichiro Ohsuga, Sadao Ohama, "Suppository containing sulfamethoxazole/trimethoprim complex and process for preparing the same." U.S. Patent US4461765, issued December, 1975.
US4461765- General References
- Brumfitt W, Hamilton-Miller JM: Reassessment of the rationale for the combinations of sulphonamides with diaminopyrimidines. J Chemother. 1993 Dec;5(6):465-9. [Article]
- Brumfitt W, Hamilton-Miller JM: Limitations of and indications for the use of co-trimoxazole. J Chemother. 1994 Feb;6(1):3-11. [Article]
- Bean DC, Livermore DM, Papa I, Hall LM: Resistance among Escherichia coli to sulphonamides and other antimicrobials now little used in man. J Antimicrob Chemother. 2005 Nov;56(5):962-4. Epub 2005 Sep 8. [Article]
- Felmingham D, Reinert RR, Hirakata Y, Rodloff A: Increasing prevalence of antimicrobial resistance among isolates of Streptococcus pneumoniae from the PROTEKT surveillance study, and compatative in vitro activity of the ketolide, telithromycin. J Antimicrob Chemother. 2002 Sep;50 Suppl S1:25-37. [Article]
- Johnson JR, Manges AR, O'Bryan TT, Riley LW: A disseminated multidrug-resistant clonal group of uropathogenic Escherichia coli in pyelonephritis. Lancet. 2002 Jun 29;359(9325):2249-51. [Article]
- Goldman JL, Leeder JS, Van Haandel L, Pearce RE: In Vitro Hepatic Oxidative Biotransformation of Trimethoprim. Drug Metab Dispos. 2015 Sep;43(9):1372-80. doi: 10.1124/dmd.115.065193. Epub 2015 Jul 2. [Article]
- Kito T, Ito S, Mizuno T, Maeda K, Kusuhara H: Investigation of non-linear Mate1-mediated efflux of trimethoprim in the mouse kidney as the mechanism underlying drug-drug interactions between trimethoprim and organic cations in the kidney. Drug Metab Pharmacokinet. 2019 Feb;34(1):87-94. doi: 10.1016/j.dmpk.2018.08.005. Epub 2018 Sep 20. [Article]
- Misaka S, Knop J, Singer K, Hoier E, Keiser M, Muller F, Glaeser H, Konig J, Fromm MF: The Nonmetabolized beta-Blocker Nadolol Is a Substrate of OCT1, OCT2, MATE1, MATE2-K, and P-Glycoprotein, but Not of OATP1B1 and OATP1B3. Mol Pharm. 2016 Feb 1;13(2):512-9. doi: 10.1021/acs.molpharmaceut.5b00733. Epub 2016 Jan 19. [Article]
- Bergan T, Ortengren B, Westerlund D: Clinical pharmacokinetics of co-trimazine. Clin Pharmacokinet. 1986 Sep-Oct;11(5):372-86. doi: 10.2165/00003088-198611050-00003. [Article]
- Bushby SR: Synergy of trimethoprim-sulfamethoxazole. Can Med Assoc J. 1975 Jun 14;112(13 Spec No):63-6. [Article]
- Antibacterial Agents That Interfere With Folate Synthesis. (2020). In Rang and Dale's Pharmacology (9th ed.). Edinburgh: Elsevier. [ISBN:9780702080609]
- Health Canada Product Monograph: Polyrimethoprim (polymyxin B/trimethoprim) ophthalmic solution [Link]
- Health Canada Product Monograph: Trimethoprim oral tablets [Link]
- FDA Approved Drug Products: Trimethoprim oral tablets [Link]
- FDA Approved Drug Products: Primsol (trimethoprim) oral solution [Link]
- FDA Approved Drug Products: Bactrim (sulfamethoxazole/trimethoprim) oral tablets [Link]
- Health Canada Product Monograph: Septra (sulfamethoxazole/trimethoprim) for intravenous injection [Link]
- CaymanChem: Trimethoprim MSDS [Link]
- FDA Approved Drug Products: Sulfamethoxazole/Trimethoprim oral suspension [Link]
- External Links
- Human Metabolome Database
- HMDB0014583
- KEGG Drug
- D00145
- KEGG Compound
- C01965
- PubChem Compound
- 5578
- PubChem Substance
- 46507125
- ChemSpider
- 5376
- BindingDB
- 18069
- 10829
- ChEBI
- 45924
- ChEMBL
- CHEMBL22
- ZINC
- ZINC000006627681
- Therapeutic Targets Database
- DAP000927
- PharmGKB
- PA451788
- PDBe Ligand
- TOP
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Trimethoprim
- PDB Entries
- 1dg5 / 1dyr / 2bfm / 2w3a / 2w3v / 2w9g / 2w9h / 2w9s / 3frb / 3fre … show 18 more
- FDA label
- Download (98.5 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Basic Science Thiamine Deficiency / Vitamin B1 deficiency 1 4 Completed Educational/Counseling/Training Diarrhea / Human Immunodeficiency Virus (HIV) Infections / Malaria / Opportunistic Infections / Pneumonia 1 4 Completed Prevention Acquired Immune Deficiency Syndrome (AIDS) / Anemia / Human Immunodeficiency Virus (HIV) Infections / Neutropenia / Newborn Infants 1 4 Completed Prevention Allograft Rejection / Asymptomatic Bacteriuria / Hospitalizations / Microbiologic Resistance / Urinary Tract Infection 1 4 Completed Prevention Anemia in Children / Malaria caused by Plasmodium falciparum 1
Pharmacoeconomics
- Manufacturers
- Monarch pharmaceuticals inc
- Mutual pharmaceutical co inc
- Teva pharmaceuticals usa inc
- Watson laboratories inc
- Hoffmann la roche inc
- Fsc laboratories inc
- Packagers
- Actavis Group
- Advanced Pharmaceutical Services Inc.
- Aidarex Pharmacuticals LLC
- Akorn Inc.
- Alcon Laboratories
- Allergan Inc.
- Amerisource Health Services Corp.
- Amneal Pharmaceuticals
- Apotheca Inc.
- Apothecon
- A-S Medication Solutions LLC
- Ascent Pediatrics Inc.
- Atlantic Biologicals Corporation
- Aurobindo Pharma Ltd.
- Avkare Incorporated
- Bausch & Lomb Inc.
- Baxter International Inc.
- Bryant Ranch Prepack
- Cardinal Health
- Carlisle Laboratories Inc.
- Casa De Amigos Pharmacy
- Central Texas Community Health Centers
- Comprehensive Consultant Services Inc.
- Coupler Enterprises Inc.
- Darby Dental Supply Co. Inc.
- Dept Health Central Pharmacy
- Direct Dispensing Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Eon Labs
- Falcon Pharmaceuticals Ltd.
- FSC Laboratories
- Golden State Medical Supply Inc.
- Greenstone LLC
- Group Health Cooperative
- H.J. Harkins Co. Inc.
- Heartland Repack Services LLC
- Hi Tech Pharmacal Co. Inc.
- Innovative Manufacturing and Distribution Services Inc.
- Innoviant Pharmacy Inc.
- Kaiser Foundation Hospital
- Keltman Pharmaceuticals Inc.
- King Pharmaceuticals Inc.
- Laboratoires Docteur Pierre Ricaud
- Lake Erie Medical and Surgical Supply
- Lark Pharmaceuticals Inc.
- Liberty Pharmaceuticals
- Long Island Pharmacal
- Lyne Laboratories Inc.
- Major Pharmaceuticals
- Mckesson Corp.
- Medisca Inc.
- Medvantx Inc.
- Midland Healthcare LLC
- Midland Pharmaceutical LLC
- Monarch Pharmacy
- Murfreesboro Pharmaceutical Nursing Supply
- Mutual Pharmaceutical Co.
- Novopharm Ltd.
- Nucare Pharmaceuticals Inc.
- Pacific Pharma Lp
- Palmetto Pharmaceuticals Inc.
- Patient First Corp.
- PCA LLC
- PD-Rx Pharmaceuticals Inc.
- Pfizer Animal Health
- Pfizer Inc.
- Pharmaceutical Association
- Pharmaceutical Utilization Management Program VA Inc.
- Pharmacia Inc.
- Pharmedix
- Physicians Total Care Inc.
- Pliva Inc.
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- Prepak Systems Inc.
- Prescript Pharmaceuticals
- Qualitest
- Rebel Distributors Corp.
- Redpharm Drug
- Remedy Repack
- Resource Optimization and Innovation LLC
- Sandhills Packaging Inc.
- Sandoz
- Sicor Pharmaceuticals
- Southwood Pharmaceuticals
- St Mary's Medical Park Pharmacy
- Stat Scripts LLC
- Talbert Medical Management Corp.
- Taro Pharmaceuticals USA
- Taylor Pharmaceuticals
- Teva Pharmaceutical Industries Ltd.
- Tya Pharmaceuticals
- UDL Laboratories
- United Research Laboratories Inc.
- Va Cmop Dallas
- Vangard Labs Inc.
- Vintage Pharmaceuticals Inc.
- Vista Pharmaceuticals Inc.
- Watson Pharmaceuticals
- Women First Healthcare Inc.
- Xactdose Inc.
- Dosage Forms
Form Route Strength Tablet Oral 100 mg Tablet Oral 400 mg Tablet Oral 400 MG Tablet Oral 800 MG Tablet, soluble Oral 800 MG Injection, solution Intravenous Injection, solution, concentrate Intramuscular; Intravenous Liquid Intravenous Suspension Suspension Oral 200 mg/5ml Tablet, film coated Oral Injection, solution Tablet Oral 800 mg Tablet Oral Solution Conjunctival; Ophthalmic Tablet Liquid Ophthalmic Solution Ophthalmic Solution / drops Ophthalmic Capsule, coated Oral Solution Oral 50 mg/5mL Tablet Oral 100 mg/1 Tablet Oral 200 mg/1 Powder, for solution Oral Tablet, soluble Oral Injection Intravenous Injection, solution, concentrate Intravenous Suspension Oral Tablet Oral Suspension Parenteral Solution Oral Solution Parenteral Tablet Oral 400.00 mg Solution Powder Syrup Oral Powder Not applicable 1 g/1g Tablet Oral 100 mg Solution Intravenous Injection, solution Intramuscular; Intravenous Solution Intramuscular Tablet, delayed release Oral 35 mg Powder, for suspension Oral Capsule Tablet, coated Oral Tablet, sugar coated Oral Tablet Oral 200 mg - Prices
Unit description Cost Unit Bactrim ds tablet 5.53USD tablet Bactrim DS 800-160 mg tablet 3.0USD tablet Septra DS 800-160 mg tablet 2.43USD tablet Septra ds tablet 2.33USD tablet Trimethoprim powder 1.79USD g Bactrim 400-80 mg tablet 1.63USD tablet Septra 80-400 tablet 1.49USD tablet Sulfamethoxazole-tmp ds tablet 1.44USD tablet Sulfamethoxazole-tmp vial 0.84USD ml Trimethoprim 100 mg tablet 0.7USD tablet Sulfamethoxazole-Trimethoprim 400-80 mg tablet 0.69USD tablet Apo-Trimethoprim 200 mg Tablet 0.55USD tablet Primsol 50 mg/5 ml oral soln 0.39USD ml Apo-Trimethoprim 100 mg Tablet 0.27USD tablet Sulfamethoxazole-tmp ss tablet 0.17USD tablet Sulfamethoxazole-Trimethoprim 200-40 mg/5ml Suspension 0.13USD ml Sulfatrim 200-40 mg/5ml Suspension 0.13USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5962461 No 1999-10-05 2016-08-07 US US5763449 No 1998-06-09 2016-08-07 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 199-203 °C PhysProp water solubility 400 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 0.91 HANSCH,C ET AL. (1995) logS -2.86 ADME Research, USCD pKa 7.12 (at 20 °C) PERRIN,DD (1972) - Predicted Properties
Property Value Source Water Solubility 0.615 mg/mL ALOGPS logP 1.26 ALOGPS logP 1.28 Chemaxon logS -2.7 ALOGPS pKa (Strongest Acidic) 17.33 Chemaxon pKa (Strongest Basic) 7.16 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 105.51 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 81.51 m3·mol-1 Chemaxon Polarizability 29.71 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.994 Blood Brain Barrier + 0.9381 Caco-2 permeable + 0.8867 P-glycoprotein substrate Non-substrate 0.5845 P-glycoprotein inhibitor I Non-inhibitor 0.8631 P-glycoprotein inhibitor II Non-inhibitor 0.8382 Renal organic cation transporter Non-inhibitor 0.8531 CYP450 2C9 substrate Non-substrate 0.8799 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.5732 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8467 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5 Ames test Non AMES toxic 0.8227 Carcinogenicity Non-carcinogens 0.9369 Biodegradation Not ready biodegradable 0.9949 Rat acute toxicity 1.7701 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9394 hERG inhibition (predictor II) Non-inhibitor 0.8734
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 183.016087 predictedDarkChem Lite v0.1.0 [M-H]- 183.992287 predictedDarkChem Lite v0.1.0 [M-H]- 164.57677 predictedDeepCCS 1.0 (2019) [M+H]+ 183.619187 predictedDarkChem Lite v0.1.0 [M+H]+ 184.881187 predictedDarkChem Lite v0.1.0 [M+H]+ 166.93477 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.613087 predictedDarkChem Lite v0.1.0 [M+Na]+ 184.213787 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.02791 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- Curator comments
- Note: The above was chosen as a representative target protein in a representative bacterium, and does not encompass all proteins/bacteria affected by this agent.
- General Function
- Nadp binding
- Specific Function
- Key enzyme in folate metabolism. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis.
- Gene Name
- folA
- Uniprot ID
- P0ABQ4
- Uniprot Name
- Dihydrofolate reductase
- Molecular Weight
- 17999.21 Da
References
- Laskowska E, Kuczynska-Wisnik D, Bak M, Lipinska B: Trimethoprim induces heat shock proteins and protein aggregation in E. coli cells. Curr Microbiol. 2003 Oct;47(4):286-9. [Article]
- Rosowsky A, Fu H, Chan DC, Queener SF: Synthesis of 2,4-diamino-6-[2'-O-(omega-carboxyalkyl)oxydibenz[b,f]azepin-5-yl]methylpteridine s as potent and selective inhibitors of Pneumocystis carinii, Toxoplasma gondii, and Mycobacterium avium dihydrofolate reductase. J Med Chem. 2004 May 6;47(10):2475-85. [Article]
- Nahimana A, Rabodonirina M, Bille J, Francioli P, Hauser PM: Mutations of Pneumocystis jirovecii dihydrofolate reductase associated with failure of prophylaxis. Antimicrob Agents Chemother. 2004 Nov;48(11):4301-5. [Article]
- Barrow EW, Bourne PC, Barrow WW: Functional cloning of Bacillus anthracis dihydrofolate reductase and confirmation of natural resistance to trimethoprim. Antimicrob Agents Chemother. 2004 Dec;48(12):4643-9. [Article]
- FDA Approved Drug Products: Bactrim (sulfamethoxazole and trimethoprim) [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Wen X, Wang JS, Backman JT, Laitila J, Neuvonen PJ: Trimethoprim and sulfamethoxazole are selective inhibitors of CYP2C8 and CYP2C9, respectively. Drug Metab Dispos. 2002 Jun;30(6):631-5. doi: 10.1124/dmd.30.6.631. [Article]
- Goldman JL, Leeder JS, Van Haandel L, Pearce RE: In Vitro Hepatic Oxidative Biotransformation of Trimethoprim. Drug Metab Dispos. 2015 Sep;43(9):1372-80. doi: 10.1124/dmd.115.065193. Epub 2015 Jul 2. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Goldman JL, Leeder JS, Van Haandel L, Pearce RE: In Vitro Hepatic Oxidative Biotransformation of Trimethoprim. Drug Metab Dispos. 2015 Sep;43(9):1372-80. doi: 10.1124/dmd.115.065193. Epub 2015 Jul 2. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Goldman JL, Leeder JS, Van Haandel L, Pearce RE: In Vitro Hepatic Oxidative Biotransformation of Trimethoprim. Drug Metab Dispos. 2015 Sep;43(9):1372-80. doi: 10.1124/dmd.115.065193. Epub 2015 Jul 2. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Wen X, Wang JS, Backman JT, Laitila J, Neuvonen PJ: Trimethoprim and sulfamethoxazole are selective inhibitors of CYP2C8 and CYP2C9, respectively. Drug Metab Dispos. 2002 Jun;30(6):631-5. doi: 10.1124/dmd.30.6.631. [Article]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Trimethoprim FDA label [File]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Susanto M, Benet LZ: Can the enhanced renal clearance of antibiotics in cystic fibrosis patients be explained by P-glycoprotein transport? Pharm Res. 2002 Apr;19(4):457-62. doi: 10.1023/a:1015191511817. [Article]
- Park MS, Okochi H, Benet LZ: Is Ciprofloxacin a Substrate of P-glycoprotein? Arch Drug Inf. 2011 Mar;4(1):1-9. doi: 10.1111/j.1753-5174.2010.00032.x. [Article]
- FDA Approved Drug Products: Bactrim (sulfamethoxazole/trimethoprim) oral tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Monovalent cation:proton antiporter activity
- Specific Function
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
- Gene Name
- SLC47A1
- Uniprot ID
- Q96FL8
- Uniprot Name
- Multidrug and toxin extrusion protein 1
- Molecular Weight
- 61921.585 Da
References
- Kito T, Ito S, Mizuno T, Maeda K, Kusuhara H: Investigation of non-linear Mate1-mediated efflux of trimethoprim in the mouse kidney as the mechanism underlying drug-drug interactions between trimethoprim and organic cations in the kidney. Drug Metab Pharmacokinet. 2019 Feb;34(1):87-94. doi: 10.1016/j.dmpk.2018.08.005. Epub 2018 Sep 20. [Article]
- Elsby R, Chidlaw S, Outteridge S, Pickering S, Radcliffe A, Sullivan R, Jones H, Butler P: Mechanistic in vitro studies confirm that inhibition of the renal apical efflux transporter multidrug and toxin extrusion (MATE) 1, and not altered absorption, underlies the increased metformin exposure observed in clinical interactions with cimetidine, trimethoprim or pyrimethamine. Pharmacol Res Perspect. 2017 Oct;5(5). doi: 10.1002/prp2.357. [Article]
- Misaka S, Knop J, Singer K, Hoier E, Keiser M, Muller F, Glaeser H, Konig J, Fromm MF: The Nonmetabolized beta-Blocker Nadolol Is a Substrate of OCT1, OCT2, MATE1, MATE2-K, and P-Glycoprotein, but Not of OATP1B1 and OATP1B3. Mol Pharm. 2016 Feb 1;13(2):512-9. doi: 10.1021/acs.molpharmaceut.5b00733. Epub 2016 Jan 19. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Drug transmembrane transporter activity
- Specific Function
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide, metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acy...
- Gene Name
- SLC47A2
- Uniprot ID
- Q86VL8
- Uniprot Name
- Multidrug and toxin extrusion protein 2
- Molecular Weight
- 65083.915 Da
References
- Kito T, Ito S, Mizuno T, Maeda K, Kusuhara H: Investigation of non-linear Mate1-mediated efflux of trimethoprim in the mouse kidney as the mechanism underlying drug-drug interactions between trimethoprim and organic cations in the kidney. Drug Metab Pharmacokinet. 2019 Feb;34(1):87-94. doi: 10.1016/j.dmpk.2018.08.005. Epub 2018 Sep 20. [Article]
- Misaka S, Knop J, Singer K, Hoier E, Keiser M, Muller F, Glaeser H, Konig J, Fromm MF: The Nonmetabolized beta-Blocker Nadolol Is a Substrate of OCT1, OCT2, MATE1, MATE2-K, and P-Glycoprotein, but Not of OATP1B1 and OATP1B3. Mol Pharm. 2016 Feb 1;13(2):512-9. doi: 10.1021/acs.molpharmaceut.5b00733. Epub 2016 Jan 19. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54