trimethoprim   Click here for help

GtoPdb Ligand ID: 10931

Synonyms: BW-56-72 | BW-5672 | NSC-106568 | Primsol® | Proloprim® | Trimpex®
Approved drug PDB Ligand
trimethoprim is an approved drug (FDA (1980))
Compound class: Synthetic organic
Comment: Trimethoprim is a synthetic diaminopyrimidine molecule with antibacterial and antiprotozoal activities. Mechanistically, it inhibits bacterial dihydrofolate reductase and disrupts the conversion of dihydrofolic acid to tetrahydrofolic acid which ultimately inhibits bacterial DNA synthesis. Sulfonamide drugs potentiate trimethoprim's activity.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 105.51
Molecular weight 290.14
XLogP 0.78
No. Lipinski's rules broken 0
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Canonical SMILES COc1cc(Cc2cnc(nc2N)N)cc(c1OC)OC
Isomeric SMILES COc1cc(Cc2cnc(nc2N)N)cc(c1OC)OC
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)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1980))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
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IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
1047 trimethoprim
Synonyms Click here for help
BW-56-72 | BW-5672 | NSC-106568 | Primsol® | Proloprim® | Trimpex®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Trimethoprim
Other databases
BindingDB Ligand 18069
CAS Registry No. 738-70-5 (source: PubChem)
DrugBank Ligand DB00440
DrugCentral Ligand 2755
GtoPdb PubChem SID 405560372
PubChem CID 5578
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UniChem Compound Search for chemical match using the InChIKey IEDVJHCEMCRBQM-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey IEDVJHCEMCRBQM-UHFFFAOYSA-N