Pyrimethamine

Basic Info

Common NamePyrimethamine(F05786)
2D Structure
FRCD IDF05786
CAS Number58-14-0
PubChem CID4993
FormulaC12H13ClN4
IUPAC Name

5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine

InChI Key

WKSAUQYGYAYLPV-UHFFFAOYSA-N

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)

Canonical SMILES

CCC1=C(C(=NC(=N1)N)N)C2=CC=C(C=C2)Cl

Isomeric SMILES

CCC1=C(C(=NC(=N1)N)N)C2=CC=C(C=C2)Cl

Synonyms
        
            Chloridine
        
            5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine
        
            pyrimethamine
        
            58-14-0
        
            Daraprim
        
            Chloridin
        
            Diaminopyritamin
        
            Ethylpyrimidine
        
            Pirimetamina
        
            Chloridyn
Classifies
                

                  
                    Predicted: Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassDiazines
SubclassPyrimidines and pyrimidine derivatives
Intermediate Tree NodesNot available
Direct ParentAminopyrimidines and derivatives
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsAminopyrimidine - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Hydropyrimidine - Benzenoid - Heteroaromatic compound - Azacycle - Organochloride - Organohalogen compound - Amine - Hydrocarbon derivative - Organopnictogen compound - Organonitrogen compound - Primary amine - Organic nitrogen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as aminopyrimidines and derivatives. These are organic compounds containing an amino group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Properties

Property NameProperty Value
Molecular Weight248.714
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Complexity243
Monoisotopic Mass248.083
Exact Mass248.083
XLogP2.7
Formal Charge0
Heavy Atom Count17
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9383
Human Intestinal AbsorptionHIA+0.9973
Caco-2 PermeabilityCaco2+0.6217
P-glycoprotein SubstrateNon-substrate0.5822
P-glycoprotein InhibitorNon-inhibitor0.8643
Non-inhibitor0.9045
Renal Organic Cation TransporterNon-inhibitor0.7451
Distribution
Subcellular localizationLysosome0.4174
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8103
CYP450 2D6 SubstrateNon-substrate0.9116
CYP450 3A4 SubstrateNon-substrate0.6582
CYP450 1A2 InhibitorInhibitor0.9107
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorInhibitor0.8932
CYP450 2C19 InhibitorNon-inhibitor0.9026
CYP450 3A4 InhibitorNon-inhibitor0.7586
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.6667
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9337
Non-inhibitor0.8586
AMES ToxicityNon AMES toxic0.9133
CarcinogensNon-carcinogens0.8016
Fish ToxicityHigh FHMT0.5263
Tetrahymena Pyriformis ToxicityHigh TPT0.9692
Honey Bee ToxicityLow HBT0.8989
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityII0.7350
Carcinogenicity (Three-class)Non-required0.7004
Model Value Unit
Absorption
Aqueous solubility-3.5909LogS
Caco-2 Permeability1.2598LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.7833LD50, mol/kg
Fish Toxicity1.4471pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6437pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Chicken,Edible OffalJapan0.05ppm
Chicken,KidneyJapan0.05ppm
Chicken,LiverJapan0.05ppm
Chicken,FatJapan0.05ppm
Chicken,MuscleJapan0.05ppm
Pig,Edible OffalJapan0.05ppm
Pig,KidneyJapan0.05ppm
Pig,LiverJapan0.05ppm
Pig,FatJapan0.05ppm
Pig,MuscleJapan0.05ppm

References

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Heavy metal-induced stress in rice crops detected using multi-temporal Sentinel-2satellite images.Sci Total Environ2018 Oct 129738893
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Risk assessment for potentially toxic metal(loid)s in potatoes in the indigenous zinc smelting area of northwestern Guizhou Province, China.Food Chem Toxicol2018 Oct30016697
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Metal(loid)-resistant bacteria reduce wheat Cd and As uptake inmetal(loid)-contaminated soil.Environ Pollut2018 Oct29883954
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A review of soil heavy metal pollution from industrial and agricultural regionsin China: Pollution and risk assessment.Sci Total Environ2018 Nov 1529909337