Ormetoprim

Basic Info

Common NameOrmetoprim(F05997)
2D Structure
FRCD IDF05997
CAS Number6981-18-6
PubChem CID23418
FormulaC14H18N4O2
IUPAC Name

5-[(4,5-dimethoxy-2-methylphenyl)methyl]pyrimidine-2,4-diamine

InChI Key

KEEYRKYKLYARHO-UHFFFAOYSA-N

InChI

InChI=1S/C14H18N4O2/c1-8-4-11(19-2)12(20-3)6-9(8)5-10-7-17-14(16)18-13(10)15/h4,6-7H,5H2,1-3H3,(H4,15,16,17,18)

Canonical SMILES

CC1=CC(=C(C=C1CC2=CN=C(N=C2N)N)OC)OC

Isomeric SMILES

CC1=CC(=C(C=C1CC2=CN=C(N=C2N)N)OC)OC

Synonyms
        
            5-[(4,5-dimethoxy-2-methylphenyl)methyl]pyrimidine-2,4-diamine
        
            ORMETOPRIM
        
            6981-18-6
        
            Ormethoprim
        
            Ormetorprim
        
            component of Rofenaid
        
            2,4-Diamino-5-(6-methylveratryl)pyrimidine
        
            Ro 5-9754
        
            UNII-M3EFS94984
        
            NSC 95072
Classifies
                

                  
                    Predicted: Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassMethoxybenzenes
Intermediate Tree NodesNot available
Direct ParentDimethoxybenzenes
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsO-dimethoxybenzene - Dimethoxybenzene - Phenoxy compound - Anisole - Phenol ether - Alkyl aryl ether - Aminopyrimidine - Toluene - Pyrimidine - Imidolactam - Heteroaromatic compound - Ether - Azacycle - Organoheterocyclic compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Organopnictogen compound - Primary amine - Amine - Organic oxygen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.

Properties

Property NameProperty Value
Molecular Weight274.324
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Complexity305
Monoisotopic Mass274.143
Exact Mass274.143
XLogP1.2
Formal Charge0
Heavy Atom Count20
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+0.9406
Human Intestinal AbsorptionHIA+0.9932
Caco-2 PermeabilityCaco2+0.8224
P-glycoprotein SubstrateNon-substrate0.5525
P-glycoprotein InhibitorNon-inhibitor0.8014
Non-inhibitor0.8103
Renal Organic Cation TransporterNon-inhibitor0.8120
Distribution
Subcellular localizationNucleus0.4694
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8587
CYP450 2D6 SubstrateNon-substrate0.8605
CYP450 3A4 SubstrateNon-substrate0.5428
CYP450 1A2 InhibitorNon-inhibitor0.8766
CYP450 2C9 InhibitorNon-inhibitor0.8771
CYP450 2D6 InhibitorNon-inhibitor0.8564
CYP450 2C19 InhibitorNon-inhibitor0.8847
CYP450 3A4 InhibitorNon-inhibitor0.7179
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.5505
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9322
Non-inhibitor0.7814
AMES ToxicityAMES toxic0.5514
CarcinogensNon-carcinogens0.9493
Fish ToxicityLow FHMT0.9006
Tetrahymena Pyriformis ToxicityHigh TPT0.8439
Honey Bee ToxicityLow HBT0.6572
BiodegradationNot ready biodegradable0.9931
Acute Oral ToxicityIII0.7228
Carcinogenicity (Three-class)Non-required0.3810
Model Value Unit
Absorption
Aqueous solubility-3.0739LogS
Caco-2 Permeability1.7315LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0214LD50, mol/kg
Fish Toxicity1.7483pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5634pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Edible Tissues Of Chukar PartridgesUnited States0.1ppm
Edible Tissues Of CatfishUnited States0.1ppm
Edible Tissues Of SalmonidsUnited States0.1ppm
Edible Tissues Of DucksUnited States0.1ppm
Edible Tissues Of TurkeysUnited States0.1ppm
Edible Tissues Of ChickensUnited States0.1ppm
Other FishJapan0.1ppm
AnguilliformesJapan0.1ppm
SalmoniformesJapan0.1ppm
Other Poultry Animals,Edible OffalJapan0.1ppm
Chicken,Edible OffalJapan0.1ppm
Other Poultry Animals,KidneyJapan0.1ppm
Chicken,KidneyJapan0.1ppm
Other Poultry Animals,LiverJapan0.1ppm
Chicken,LiverJapan0.1ppm
Other Poultry Animals,FatJapan0.1ppm
Chicken,FatJapan0.1ppm
Other Poultry Animals,MuscleJapan0.1ppm
Chicken,MuscleJapan0.1ppm
Pig,Edible OffalJapan0.05ppm

References

TitleJournalDatePubmed ID
Antibiotic Application and Emergence of Multiple Antibiotic Resistance (MAR) inGlobal Catfish Aquaculture.Curr Environ Health Rep2016 Jun27038482
Reconnaissance of 47 antibiotics and associated microbial risks in seafood soldin the United States.J Hazard Mater2015 Jan 2325449970
Quality control ranges for testing broth microdilution susceptibility ofFlavobacterium columnare and F. psychrophilum to nine antimicrobials.Dis Aquat Organ2012 Nov 1923324417
Sulfadimethoxine and ormetoprim residues in three species of fish after oraldosing in feed.J Aquat Anim Health2007 Jun18201051
Standardization of a broth microdilution susceptibility testing method todetermine minimum inhibitory concentrations of aquatic bacteria.Dis Aquat Organ2005 May 2015997819
Antimicrobial residue detection in chicken yolk samples following administration to egg-producing chickens and effects of residue detection on competitiveexclusion culture (PREEMPT) establishment.J Agric Food Chem2000 Dec11141299
Prevention of coccidiosis in the chukar partridge (Alectoris chukar) bymedication with sulfadimethoxine and ormetoprim (Rofenaid).Poult Sci1990 Oct2263542