Trimethoprim

Basic Info

Common NameTrimethoprim(F06053)
2D Structure
FRCD IDF06053
CAS Number738-70-5
PubChem CID5578
FormulaC14H18N4O3
IUPAC Name

5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine

InChI Key

IEDVJHCEMCRBQM-UHFFFAOYSA-N

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)

Canonical SMILES

COC1=CC(=CC(=C1OC)OC)CC2=CN=C(N=C2N)N

Isomeric SMILES

COC1=CC(=CC(=C1OC)OC)CC2=CN=C(N=C2N)N

Synonyms
        
            Monotrim
        
            trimethoprim
        
            738-70-5
        
            Proloprim
        
            Trimpex
        
            Bactramin
        
            Monotrimin
        
            Trimetoprim
        
            Trimopan
        
            Monoprim
Classifies
                

                  
                    Predicted: Pollutant
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassPhenol ethers
SubclassAnisoles
Intermediate Tree NodesNot available
Direct ParentAnisoles
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsPhenoxy compound - Anisole - Methoxybenzene - Alkyl aryl ether - Aminopyrimidine - Monocyclic benzene moiety - Pyrimidine - Imidolactam - Heteroaromatic compound - Organoheterocyclic compound - Ether - Azacycle - Organic oxygen compound - Amine - Primary amine - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Properties

Property NameProperty Value
Molecular Weight290.323
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count5
Complexity307
Monoisotopic Mass290.138
Exact Mass290.138
XLogP0.9
Formal Charge0
Heavy Atom Count21
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+0.9381
Human Intestinal AbsorptionHIA+0.9940
Caco-2 PermeabilityCaco2+0.8867
P-glycoprotein SubstrateNon-substrate0.5845
P-glycoprotein InhibitorNon-inhibitor0.8631
Non-inhibitor0.8382
Renal Organic Cation TransporterNon-inhibitor0.8531
Distribution
Subcellular localizationNucleus0.5359
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8799
CYP450 2D6 SubstrateNon-substrate0.9116
CYP450 3A4 SubstrateNon-substrate0.5732
CYP450 1A2 InhibitorNon-inhibitor0.9046
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorNon-inhibitor0.9231
CYP450 2C19 InhibitorNon-inhibitor0.9025
CYP450 3A4 InhibitorNon-inhibitor0.8467
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.5000
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9394
Non-inhibitor0.8734
AMES ToxicityNon AMES toxic0.8227
CarcinogensNon-carcinogens0.9369
Fish ToxicityLow FHMT0.9448
Tetrahymena Pyriformis ToxicityHigh TPT0.8918
Honey Bee ToxicityLow HBT0.6616
BiodegradationNot ready biodegradable0.9949
Acute Oral ToxicityIV0.6235
Carcinogenicity (Three-class)Non-required0.3953
Model Value Unit
Absorption
Aqueous solubility-2.9022LogS
Caco-2 Permeability1.7411LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.7701LD50, mol/kg
Fish Toxicity1.7535pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5919pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Aquatic AnimalJapan0.05ppm
Cattle,Edible OffalJapan0.05ppm
Cattle,KidneyJapan0.05ppm
Other Terrestrial Mammals,LiverJapan0.08ppm
Pig,LiverJapan0.1ppm
Cattle,LiverJapan0.05ppm
Other Terrestrial Mammals,FatJapan0.1ppm
Pig,FatJapan0.1ppm
Cattle,FatJapan0.05ppm
Other Terrestrial Mammals,MuscleJapan0.08ppm
CrustaceansJapan0.05ppm
Shelled MolluscasJapan0.05ppm
Other FishJapan0.05ppm
PerciformesJapan0.05ppm
AnguilliformesJapan0.05ppm
SalmoniformesJapan0.08ppm
Other Poultry,EggsJapan0.02ppm
Chicken,EggsJapan0.02ppm
Other Poultry Animals,Edible OffalJapan0.05ppm
Chicken,Edible OffalJapan0.05ppm

References

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Kinetic and thermodynamic parameters, and partial characterization of the crudeextract of tannase produced by Saccharomyces cerevisiae CCMB 520.Nat Prod Res2018 May28931328
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Consumption of antibacterial molecules in broiler production in Morocco.Vet Med Sci2018 May29851315
Safety hazards in bacteriocinogenic Staphylococcus strains isolated from goat and sheep milk.Microb Pathog2018 Mar29355699
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