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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL22
CHEMBL22
Compound Name TRIMETHOPRIM
ChEMBL Synonyms BW 56-72 | Trimethoprim hydrochloride | TIEMPE | MONOTRIM | TRIMETHOPRIM SULFATE | Primsol | IPRAL | TRIMETHOPRIM | SYRAPRIM | PROLOPRIM | TRIPRIMIX 200 | TRIMOGAL | Proloprin | PRIMSOL | TRIMPEX 200 | TRIMPEX | TRIMOPAN | Polytrim | LEDATRIM | BW-56-72 | BW 72U
Max Phase 4 (Approved)
Trade Names IPRAL | MONOTRIM | TIEMPE | TRIMOGAL | TRIPRIMIX 200 | PROLOPRIM | SYRAPRIM | TRIMETHOPRIM | LEDATRIM | TRIMOPAN | TRIMPEX | TRIMPEX 200 | PRIMSOL | Proloprin
Molecular Formula C14H18N4O3

Additional synonyms for CHEMBL22 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC
Standard InChI InChI=1S/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7- ...
Download InChI
Standard InChI Key IEDVJHCEMCRBQM-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • GSK Malaria Screening
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL22

Molecule Features

CHEMBL22 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:Y Topical:Y Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Bacterial dihydrofolate reductase inhibitor Bacterial dihydrofolate reductase DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Dermatitis, AtopicD003876EFO:0000274atopic eczema2ClinicalTrials
AnemiaD000740EFO:0004272anemia1ClinicalTrials
Diabetes Mellitus, Type 1D003922EFO:0001359type I diabetes mellitus2ClinicalTrials
PyelonephritisD011704EFO:1001141pyelonephritis3ClinicalTrials
Staphylococcal InfectionsD013203EFO:0005681Staphylococcus aureus infection3ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm1ClinicalTrials
Kidney DiseasesD007674EFO:0003086kidney disease1ClinicalTrials
Urinary Tract InfectionsD014552EFO:0003103urinary tract infection4ClinicalTrials
FDA
Cystic FibrosisD003550Orphanet:586Cystic fibrosis2ClinicalTrials
AbscessD000038EFO:0003030abscess3ClinicalTrials
Idiopathic Pulmonary FibrosisD054990EFO:0000768idiopathic pulmonary fibrosis3ClinicalTrials
LeukemiaD007938EFO:0000565leukemia1ClinicalTrials
Lymphoma, AIDS-RelatedD016483EFO:1001365Lymphoma, AIDS-Related2ClinicalTrials
MalariaD008288EFO:0001068malaria3ClinicalTrials
PneumoniaD011014EFO:0003106pneumonia3ClinicalTrials
Toxoplasmosis, OcularD014126EFO:0007399ocular toxoplasmosis3ClinicalTrials
InfectionD007239EFO:0000544infection2ClinicalTrials
TuberculosisD014376Orphanet:3389Tuberculosis3ClinicalTrials
Epidermolysis BullosaD004820EFO:1000690epidermolysis bullosa2ClinicalTrials
OsteomyelitisD010019EFO:0003102osteomyelitis2ClinicalTrials
ClinicalTrials
Pneumonia, PneumocystisD011020EFO:0007448pneumocystosis2ClinicalTrials

Clinical Data

ClinicalTrials.gov TRIMETHOPRIM
The Cochrane Collaboration TRIMETHOPRIM

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL22. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL202 Dihydrofolate reductase Homo sapiens 1.000
CHEMBL1939 Dihydrofolate reductase Plasmodium falciparum K1 1.000
CHEMBL2902 Dihydrofolate reductase Lactobacillus casei 1.000
CHEMBL2363 Dihydrofolate reductase Rattus norvegicus 1.000
CHEMBL1681620 Dihydrofolate reductase Staphylococcus aureus 1.000
CHEMBL5441 Dihydrofolate reductase Escherichia coli 1.000
CHEMBL2329 Dihydrofolate reductase Candida albicans 1.000
CHEMBL3963 Dihydrofolate reductase Plasmodium berghei str. ANKA 1.000
CHEMBL2425 Dihydrofolate reductase Toxoplasma gondii 1.000
CHEMBL3565 Dihydrofolate reductase Neisseria gonorrhoeae 1.000
CHEMBL1926 Dihydrofolate reductase Pneumocystis carinii 1.000
CHEMBL2627 Dihydrofolate reductase type 1 Escherichia coli 1.000
CHEMBL5457 Dihydrofolate reductase Mycobacterium avium 1.000
CHEMBL4564 Dihydrofolate reductase Mus musculus 0.905
CHEMBL2304402 Phosphodiesterase 5A Canis lupus famiaris 0.841
CHEMBL1075051 Dihydrofolate reductase Bos taurus 0.442
CHEMBL4898 Neurotrophic tyrosine kinase receptor type 2 Homo sapiens 0.385
CHEMBL5508 Dual specificity tyrosine-phosphorylation-regulated kinase 1A Rattus norvegicus 0.330



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL202 Dihydrofolate reductase Homo sapiens 1.000
CHEMBL1939 Dihydrofolate reductase Plasmodium falciparum K1 1.000
CHEMBL2902 Dihydrofolate reductase Lactobacillus casei 1.000
CHEMBL2363 Dihydrofolate reductase Rattus norvegicus 1.000
CHEMBL1681620 Dihydrofolate reductase Staphylococcus aureus 1.000
CHEMBL2329 Dihydrofolate reductase Candida albicans 1.000
CHEMBL3963 Dihydrofolate reductase Plasmodium berghei str. ANKA 1.000
CHEMBL2425 Dihydrofolate reductase Toxoplasma gondii 1.000
CHEMBL3565 Dihydrofolate reductase Neisseria gonorrhoeae 1.000
CHEMBL1926 Dihydrofolate reductase Pneumocystis carinii 1.000
CHEMBL2627 Dihydrofolate reductase type 1 Escherichia coli 1.000
CHEMBL5457 Dihydrofolate reductase Mycobacterium avium 1.000
CHEMBL5441 Dihydrofolate reductase Escherichia coli 1.000
CHEMBL1809 Dihydrofolate reductase Escherichia coli K-12 1.000
CHEMBL2304402 Phosphodiesterase 5A Canis lupus famiaris 0.934
CHEMBL4564 Dihydrofolate reductase Mus musculus 0.893
CHEMBL3835 Serine/threonine-protein kinase NEK2 Homo sapiens 0.256

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
290.3 290.1379 1.26 5 105.51 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
7 2 0 7 4 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 6.9 .59 .47 2 21 0.85

Structural Alerts

There are 1 structural alerts for CHEMBL22. To view alerts please click here.

Compound Cross References

ATC J - ANTIINFECTIVES FOR SYSTEMIC USE
J01 - ANTIBACTERIALS FOR SYSTEMIC USE
J01E - SULFONAMIDES AND TRIMETHOPRIM
J01EA - Trimethoprim and derivatives
J01EA01 - trimethoprim

ChemSpider ChemSpider:IEDVJHCEMCRBQM-UHFFFAOYSA-N
DailyMed trimethoprim trimethoprim hydrochloride trimethoprim sulfate
PubChem SID: 104171255 SID: 11111923 SID: 11111924 SID: 11113621 SID: 124881732 SID: 144203842 SID: 144207355 SID: 170464633 SID: 17389524 SID: 174316130 SID: 26747124 SID: 26747125 SID: 26751820 SID: 50085866 SID: 50104512 SID: 50104513 SID: 85231275 SID: 85747719 SID: 857743 SID: 90340764
Wikipedia Trimethoprim

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL22



ACToR 8064-90-2 738-70-5
BindingDB 18069
Brenda 503 55818 155221 95248
ChEBI 45924
ChemicalBook CB2745185
DrugBank DB00440
DrugCentral 2755
eMolecules 511466 27524526
EPA CompTox Dashboard DTXSID3023712
FDA SRS AN164J8Y0X
Human Metabolome Database HMDB0014583
IBM Patent System CC4E9AB1276ED07F9C272CBF1385561C
KEGG Ligand C01965
LINCS LSM-5246
Mcule MCULE-6670904388
MolPort MolPort-001-826-685
NIH Clinical Collection SAM002264649
Nikkaji J9.454D
PDBe TOP
PharmGKB PA451788
PubChem 5578
PubChem: Thomson Pharma 14824824
Selleck trimethoprim
SureChEMBL SCHEMBL24506
ZINC ZINC000006627681

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/IEDVJHCEMCRBQM-UHFFFAOYSA-N spacer
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