PYRIMETHAMINE

Search structure
Trade Names:
Synonyms:
Status: Approved (1953)
Entry Type: Small molecule
Molecule Category: Parent
ATC: P01BD01
UNII: Z3614QOX8W

Structure
InChI Key WKSAUQYGYAYLPV-UHFFFAOYSA-N
Smile CCc1nc(N)nc(N)c1-c1ccc(Cl)cc1
InChI
InChI=1S/C12H13ClN4/c1-2-9-10(11(14)17-12(15)16-9)7-3-5-8(13)6-4-7/h3-6H,2H2,1H3,(H4,14,15,16,17)

Physicochemical Descriptors

Property Name Value
Molecular Formula C12H13ClN4
Molecular Weight 248.72
AlogP 2.52
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 2.0
Polar Surface Area 77.82
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 17.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Dihydrofolate reductase inhibitor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- - - 51500 -
Enzyme Hydrolase
- 3100-17000 - -
Enzyme Kinase
3992 - - - -
Enzyme Oxidoreductase
- 400-6700 1.4-16 0.19-860 40-52.3
Enzyme Transferase
- - - - 15.45-15.51
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -2.33-3.84
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC02 family of hexose and sugar alcohol transporters
- - - - 2.26
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 107.42
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 13570 - 3600 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters
- - - 145 -
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 200100 - - -
Transporter
- 13570 - 145 107.42
Unclassified protein
- 2480 - 0.85 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Schizophrenia 3 D012559 ClinicalTrials
Pregnancy 3 D011247 ClinicalTrials
Anemia 3 D000740 ClinicalTrials
Toxoplasmosis, Congenital 3 D014125 ClinicalTrials
Malaria, Falciparum 3 D016778 ClinicalTrials
Malaria, Vivax 3 D016780 ClinicalTrials
Chorioretinitis 3 D002825 ClinicalTrials
Depressive Disorder 3 D003866 ClinicalTrials
Premature Birth 3 D047928 ClinicalTrials
Schistosomiasis 3 D012552 ClinicalTrials
HIV Infections 3 D015658 ClinicalTrials
HIV Infections 3 D015658 ClinicalTrials
Pneumonia, Pneumocystis 3 D011020 ClinicalTrials
Toxoplasmosis, Cerebral 2 D016781 ClinicalTrials
Gangliosidoses, GM2 1 D020143 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 1 D015451 ClinicalTrials
Myelodysplastic Syndromes 1 D009190 ClinicalTrials
Sandhoff Disease 1 D012497 ClinicalTrials
Tay-Sachs Disease 1 D013661 ClinicalTrials
Head and Neck Neoplasms 1 D006258 ClinicalTrials
Amyotrophic Lateral Sclerosis 1 D000690 ClinicalTrials

Related Entries

Mixture

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Gastrointestinal disorders
13.75
Nervous system disorders
11.47
General disorders and administration site conditions
10.25
Vascular disorders
6.04
Skin and subcutaneous tissue disorders
5.87
Cardiac disorders
4.73
Infections and infestations
4.73
Injury, poisoning and procedural complications
4.73
Investigations
4.73
Blood and lymphatic system disorders
4.64
Respiratory, thoracic and mediastinal disorders
4.64
Psychiatric disorders
4.03
Metabolism and nutrition disorders
3.06
Immune system disorders
2.89
Renal and urinary disorders
2.71
Surgical and medical procedures
2.28

Cross References

Resources Reference
CAS NUMBER 58-14-0
ChEBI 8673
ChEMBL CHEMBL36
DrugBank DB00205
DrugCentral 2332
EPA CompTox DTXSID9021217
FDA SRS Z3614QOX8W
Human Metabolome Database HMDB14350
Guide to Pharmacology 4800
KEGG C07391
PDB CP6
PharmGKB PA451193
PubChem 4993
SureChEMBL SCHEMBL25129
ZINC ZINC000000057464
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