TRIMETHOPRIM

Search structure
Trade Names:
Synonyms:
Status: Approved (1973)
Entry Type: Small molecule
Molecule Category: Parent
ATC: J01EA01
UNII: AN164J8Y0X

Structure
InChI Key IEDVJHCEMCRBQM-UHFFFAOYSA-N
Smile COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H18N4O3
Molecular Weight 290.32
AlogP 1.26
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 5.0
Polar Surface Area 105.51
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 21.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 0.91 - EXP
pKa Dissociation Constant 7.12 - EXP
Henry's Law Constant 2.39E-14 atm-m3/mole EST
Atmospheric OH Rate Constant 2.03E-10 cm3/molecule-sec EST
Melting Point 199-203 deg C EXP
Water Solubility 400 mg/L EXP
Vapor Pressure 9.88E-09 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Bacterial dihydrofolate reductase inhibitor DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- 7-33100 - 1-1729 22-22
Enzyme
- 7-33100 - 1-1729 22-22
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 19-97
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 50680-56800 - - 58

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Bacterial Infections 4 D001424 ClinicalTrials
Malaria 3 D008288 ClinicalTrials
Abscess 3 D000038 ClinicalTrials
Measles 3 D008457 ClinicalTrials
Pneumonia 3 D011014 ClinicalTrials
Staphylococcal Infections 3 D013203 ClinicalTrials
Toxoplasmosis, Ocular 3 D014126 ClinicalTrials
Pyelonephritis 3 D011704 ClinicalTrials
Tuberculosis 3 D014376 ClinicalTrials
HIV Infections 3 D015658 ClinicalTrials
Sepsis 3 D018805 ClinicalTrials
Idiopathic Pulmonary Fibrosis 3 D054990 ClinicalTrials
Diabetes Mellitus, Type 1 2 D003922 ClinicalTrials
Lymphoma, AIDS-Related 2 D016483 ClinicalTrials
Dermatitis, Atopic 2 D003876 ClinicalTrials
Cystic Fibrosis 2 D003550 ClinicalTrials
Eczema 2 D004485 ClinicalTrials
Epidermolysis Bullosa 2 D004820 ClinicalTrials
Granulomatosis with Polyangiitis 1 D014890 ClinicalTrials
Kidney Diseases 1 D007674 ClinicalTrials
Leukemia, Biphenotypic, Acute 1 D015456 ClinicalTrials
Glioblastoma 1 D005909 ClinicalTrials
Anemia 1 D000740 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Astrocytoma 1 D001254 ClinicalTrials
Brain Neoplasms 1 D001932 ClinicalTrials
Osteomyelitis 0 D010019 ClinicalTrials

Related Entries

MCS

Salt
Mixture
Mixture

Side Effects from Label

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Skin and subcutaneous tissue disorders
13.76
General disorders and administration site conditions
13.19
Gastrointestinal disorders
12.33
Nervous system disorders
12.02
Immune system disorders
6.87
Psychiatric disorders
5.85
Musculoskeletal and connective tissue disorders
4.49
Vascular disorders
4.31
Cardiac disorders
3.65
Respiratory, thoracic and mediastinal disorders
3.53
Investigations
3.04
Renal and urinary disorders
2.87
Metabolism and nutrition disorders
2.73
Injury, poisoning and procedural complications
2.61
Infections and infestations
2.4
Eye disorders
2.26

Cross References

Resources Reference
CAS NUMBER 738-70-5
ChEBI 45924
ChEMBL CHEMBL22
DrugBank DB00440
DrugCentral 2755
EPA CompTox DTXSID3023712
FDA SRS AN164J8Y0X
Human Metabolome Database HMDB0014583
Guide to Pharmacology 10931
KEGG C01965
PDB TOP
PharmGKB PA451788
PubChem 5578
SureChEMBL SCHEMBL24506
ZINC ZINC000006627681
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