◎ Sugi Atlas

Atlas / Drug / Trimethoprim

Trimethoprim

drug
On this page

Also known as InfectotrimetIpralLedatrimMonotrimNIH-204NSC-106568ProloprimProloprinSyraprimTCMDC-125538TiempeTrimethoprim component of bactrimTrimethoprim component of bactrim dsTrimethoprim component of co-trimoxazoleTrimethoprim component of cotrimTrimethoprim component of cotrim d.s.Trimethoprim component of septraTrimethoprim component of sulfamethoprimTrimethoprim component of sulfatrim

Summary

Trimethoprim (CHEMBL22) is an approved small-molecule EC 1.5.1.3 (dihydrofolate reductase) inhibitor (ATC J01EA01); indicated across 36 conditions including urinary tract infection and pneumocystosis.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: J01EA01
  • Indications: 36 conditions
  • Clinical trials: 56
  • Chemistry: 290.32 Da · C14H18N4O3

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL22
NameTrimethoprim
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID5578
ChEBICHEBI:45924
ATCJ01EA01
Molecular formulaC14H18N4O3
Molecular weight290.32
InChIKeyIEDVJHCEMCRBQM-UHFFFAOYSA-N

SMILES: COC1=CC(=CC(=C1OC)OC)CC2=CN=C(N=C2N)N

IUPAC name: 5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine

ChEBI definition: An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.

Pharmacological roles (ChEBI): EC 1.5.1.3 (dihydrofolate reductase) inhibitor, drug allergen, antibacterial drug, diuretic.

Other ChEBI roles (chemical / environmental): xenobiotic, environmental contaminant.

Also known as: Infectotrimet, Ipral, Ledatrim, Monotrim, NIH-204, NSC-106568, Proloprim, Proloprin, Syraprim, TCMDC-125538, Tiempe, Trimethoprim

Parent form; salt/anhydrous children: CHEMBL1201080, CHEMBL1430611, CHEMBL2110367, CHEMBL2237501, CHEMBL2237502

Patent coverage: 16,908 distinct patent families (56,015 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 56,007 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 31 (assay-derived). Sample: RecQ-like DNA helicase BLM, Endonuclease 4, Dihydrofolate reductase, Dihydrofolate reductase, Dihydrofolate reductase, Bifunctional dihydrofolate reductase-thymidylate synthase, Thyrotropin receptor, Dihydrofolate reductase, Menin/Histone-lysine N-methyltransferase MLL, Dihydrofolate reductase.

Bioactivity

ChEMBL activities: 148 potent at pChembl ≥ 5 of 219 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
P0ABQ49.66Ki0.22nMCHEMBL_ACT_16653423
P139229.23Ki0.59nMCHEMBL_ACT_25596749
P0A0178.92Ki1.2nMCHEMBL_ACT_13939400
P0A0178.91Ki1.24nMCHEMBL_ACT_6329027
P0ABQ48.89Ki1.3nMCHEMBL_ACT_1149305
P0ABQ48.89Ki1.3nMCHEMBL_ACT_216327
P0ABQ48.89Ki1.3nMCHEMBL_ACT_300561
P0ABQ48.89Ki1.3nMCHEMBL_ACT_379368
P0ABQ48.87Ki1.35nMCHEMBL_ACT_1158566
P229068.66IC502.2nMCHEMBL_ACT_529963
BLM8.49Potency3.2nMCHEMBL_ACT_4746034
BLM8.49Potency3.2nMCHEMBL_ACT_4929780
P0A0178.46Ki3.43nMCHEMBL_ACT_16653414
P0A0178.46Ki3.43nMCHEMBL_ACT_19471512
P0ABQ48.42Ki3.8nMCHEMBL_ACT_962279
P0A0178.36Ki4.4nMCHEMBL_ACT_5225713
P0ABQ48.3IC505nMCHEMBL_ACT_1123353
P0ABQ48.3IC505nMCHEMBL_ACT_1208515
P0ABQ48.3IC505nMCHEMBL_ACT_300557
P0ABQ48.3IC505nMCHEMBL_ACT_637379
P0ABQ48.3IC505nMCHEMBL_ACT_800295
P0ABQ48.3IC505nMCHEMBL_ACT_890108
P0ABQ48.3IC505nMCHEMBL_ACT_980988
P0A0178.29Ki5.1nMCHEMBL_ACT_300560
P0ABQ48.23IC505.89nMCHEMBL_ACT_619503
P0ABQ48.22IC506nMCHEMBL_ACT_300564
HSD17B108.2Potency6.3nMCHEMBL_ACT_4881163
P0A0178.16Ki6.89nMCHEMBL_ACT_19471519
P0ABQ48.15IC507nMCHEMBL_ACT_1126168
P0A0178.15IC507nMCHEMBL_ACT_1126169

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

36 indications (5 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
urinary tract infection4MONDO:0100338EFO:0003103
pneumocystosis4MONDO:0019121EFO:0007448
bacterial infectious disease4MONDO:0005113EFO:0000771
otitis media4MONDO:0005441EFO:0004992
idiopathic pulmonary fibrosis3MONDO:0800504EFO:0000768
malaria3MONDO:0005136EFO:0001068
abscess3MONDO:0005227EFO:0003030
pneumonia3MONDO:0005249EFO:0003106
staphylococcus aureus infection3MONDO:0005545EFO:0005681
ocular toxoplasmosis3MONDO:0005879EFO:0007399
pyelonephritis3MONDO:0006939EFO:1001141
HIV infectious disease3MONDO:0005109EFO:0000764
measles3MONDO:0004619EFO:1002025
tuberculosis3MONDO:0018076MONDO:0018076
epidermolysis bullosa2MONDO:0006541EFO:1000690
type 1 diabetes mellitus2MONDO:0005147MONDO:0005147
cystic fibrosis2MONDO:0009061MONDO:0009061
skin disorder2MONDO:0005093EFO:0000701
dermatitis2MONDO:0002406MONDO:0002406
neoplasm1MONDO:0005070EFO:0000616
kidney disorder1MONDO:0005240EFO:0003086
anemia1MONDO:0002280EFO:0004272
granulomatosis with polyangiitis1MONDO:0012105EFO:0005297
glioblastoma1MONDO:0018177EFO:0000519
anaplastic astrocytoma1MONDO:0016684EFO:0002499
B-cell acute lymphoblastic leukemia1MONDO:0004947EFO:0000094
brain neoplasm1MONDO:0021211EFO:0003833
chronic obstructive pulmonary disease1MONDO:0005002EFO:0000341
T-cell acute lymphoblastic leukemia1MONDO:0004963EFO:0000209
leukemia1MONDO:0005059EFO:0000565
age-related macular degeneration1MONDO:0005150EFO:0001365
osteomyelitis0MONDO:0005246EFO:0003102

4 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 56.

Phase distribution

PhaseTrials
Not specified13
PHASE411
PHASE211
PHASE37
PHASE2/PHASE35
PHASE1/PHASE25
PHASE14

Top trials by phase / activity

NCTPhaseStatusTitle
NCT06499233PHASE4RECRUITINGEfficacy and Safety of Prophylactic Treatment for Pneumocystis Jirovecii Pneumonia in Patients With Autoimmune Inflammatory Rheumatic Disease
NCT06709196PHASE4RECRUITINGClinical Trial Testing Whether Targeted Antibiotic Prophylaxis Can Reduce Infections After Cystectomy Compared to Empiric Prophylaxis
NCT06982105PHASE4RECRUITINGTrimethoprim-sulfamethoxazole vs. Clindamycin for the Treatment of Children With Invasive MRSA Infections
NCT00382343PHASE4COMPLETEDA Randomized Controlled Trial on Antibiotic Prophylaxis in Children With Vesico-Ureteral Reflux
NCT01167452PHASE4COMPLETEDEffect of Weight and/or Obesity on Sulfamethoxazole and Trimethoprim Concentrations
NCT01723150PHASE4COMPLETEDAntibiotics for Klebsiella Liver Abscess Study
NCT01820897PHASE4COMPLETEDEfficacy of Fosfomycin-Trometamol in Urinary Tract Infection Prophylaxis After Kidney Transplantation
NCT03077711PHASE4COMPLETEDMethenamine Hippurate Versus Trimethoprim in the Prevention of Recurrent UTIs
NCT03228108PHASE4COMPLETEDCulture-guided Antimicrobial Prophylaxis in Men Undergoing Prostate Biopsy.
NCT03235947PHASE4COMPLETEDPerioperative Fosfomycin in the Prophylaxis of Urinary Tract Infection in Kidney Transplant Recipients
NCT03746106PHASE4COMPLETEDThe Effect of SLC19A3 Inhibition on the Pharmacokinetics of Thiamine
NCT06737016PHASE3RECRUITINGEfficacy and Safety of Tamsulosin for Children with Posterior Urethral Valve.
NCT07202052PHASE2/PHASE3RECRUITINGRole of Antibiotic Therapy or Immunoglobulin On iNfections in hAematoLogy Platform Trial (RATIONAL-PT)
NCT07202078PHASE2/PHASE3RECRUITINGRole of Antibiotic Therapy or Immunoglobulin On iNfections in hAematoLogy: Starting Immunoglobulin (Start Ig)
NCT07202091PHASE2/PHASE3RECRUITINGRole of Antibiotic Therapy or Immunoglobulin On iNfections in hAematoLogy Immunoglobulin Stopping or Extension (Stop Ig)
NCT00000727PHASE3COMPLETEDA Controlled Comparative Trial of Sulfamethoxazole-Trimethoprim Versus Aerosolized Pentamidine for Secondary Prophylaxis of Pneumocystis Carinii Pneumonia in AIDS Patients Receiving Azidothymidine (AZT)
NCT00002850PHASE3COMPLETEDAntibiotic Therapy in Preventing Early Infection in Patients With Multiple Myeloma Who Are Receiving Chemotherapy
NCT00080119PHASE2/PHASE3TERMINATEDDaily Isoniazid to Prevent Tuberculosis in Infants Born to Mothers With HIV
NCT00691600PHASE3COMPLETEDManagement of Skin and Soft Tissue Abscesses in Pediatric Patients After Incision and Drainage
NCT00752375PHASE3WITHDRAWNAntibiotic Prophylaxis in Children With Pyelonephritis
NCT01747278PHASE2/PHASE3UNKNOWNStudy of Trimethoprim/Sulfamethoxazole as PCP Prophylaxis in CTD Patients
NCT01808755PHASE3COMPLETEDD Mannose in Recurrent Urinary Tract Infections
NCT02021006PHASE3UNKNOWNAntibiotic Prophylaxis and Renal Damage In Congenital Abnormalities of the Kidney and Urinary Tract
NCT01631617PHASE2RECRUITINGEffects of Treatments on Atopic Dermatitis
NCT03919435PHASE1/PHASE2ACTIVE_NOT_RECRUITINGTEMPO Study: Trimethoprim-Sulfamethoxazole in Granulomatosis With Polyangiitis
NCT03920007PHASE1/PHASE2ACTIVE_NOT_RECRUITINGStudy of Subretinally Injected ATSN-101 Administered in Patients With Leber Congenital Amaurosis Caused by Biallelic Mutations in GUCY2D
NCT06536374PHASE2NOT_YET_RECRUITINGFolate Study in Men With Advanced Prostate Cancer
NCT07485010PHASE2NOT_YET_RECRUITINGTesting a Novel Combination Treatment (Arm D) Versus Standard of Care for Intensive Phase Treatment for Mycobacterium Abscessus Pulmonary Disease in People With or Without Cystic Fibrosis in the Finding the Optimal Regimen for Mycobacterium Abscessus Treatment (FORMaT) Adaptive Platform Trial
NCT00014911PHASE2COMPLETEDIslet Transplantation for Type 1 Diabetes
NCT00141037PHASE1/PHASE2COMPLETEDSteroid-Free Versus Steroid-Based Immunosuppression in Pediatric Renal (Kidney) Transplantation
NCT00380640PHASE2COMPLETEDThe Efficacy of Trimethoprim in Wound Healing of Patients With Epidermolysis Bullosa
NCT00789464PHASE2WITHDRAWNProbiotics for Girls With Recurring Urinary Tract Infections
NCT01349192PHASE2TERMINATEDEarly Methicillin-resistant Staphylococcus Aureus (MRSA) Therapy in Cystic Fibrosis (CF)
NCT01594827PHASE2COMPLETEDPersistent Methicillin Resistant Staphylococcus Aureus Eradication Protocol (PMEP)
NCT01595529PHASE2COMPLETEDThe SCOUT Study: Short Course Therapy for Urinary Tract Infections in Children
NCT01632891PHASE1/PHASE2COMPLETEDComparing PI-Based to a nNRTI-based ART for Clearance of Plasmodium Falciparum Parasitemia in HIV-Infected
NCT02624440PHASE2UNKNOWNClarithromycin, Sulfamethoxazole/Trimethoprim or Observation in Newly Diagnosed Multiple Myeloma
NCT02734732PHASE2UNKNOWNAntibiotic Prophylaxis for Transrectal Prostate Biopsy-Ciprofloxacin vs. Trimethoprim/Sulfamethoxazole
NCT05418777PHASE1/PHASE2TERMINATEDTreatment of Pneumocystis in COPD (the TOPIC Study)
NCT05302531PHASE1RECRUITINGAbsorption of Antibiotics With High Oral Bioavailability in Short-bowel Syndrome

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 0 clinical and 5 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 17

This page pulls from 17 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclinical_trialsefogtopdb_interactiongtopdb_ligandhgncmeshmondopatent_compoundpharmgkbpharmgkb_guidelinepubchemuniprot