Nafcillin

Basic Info

Common NameNafcillin(F06229)
2D Structure
FRCD IDF06229
CAS Number
PubChem CID8982
FormulaC21H22N2O5S
IUPAC Name

(2S,5R,6R)-6-[(2-ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

InChI Key

GPXLMGHLHQJAGZ-JTDSTZFVSA-N

InChI

InChI=1S/C21H22N2O5S/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27)/t15-,16+,19-/m1/s1

Canonical SMILES

CCOC1=C(C2=CC=CC=C2C=C1)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O

Isomeric SMILES

CCOC1=C(C2=CC=CC=C2C=C1)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O

Synonyms
        
            Nafcilina [INN-Spanish]
        
            nafcillin
        
            Naphcillin
        
            Nafcilina
        
            Nafcilline
        
            Nafcillinum
        
            Nallpen
        
            Unipen
        
            Nafcilin-1
        
            Nafcilline [INN-French]
Classifies
                

                  
                    Predicted: Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassAmino acids, peptides, and analogues
Intermediate Tree NodesPeptides
Direct ParentDipeptides
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsAlpha-dipeptide - Penicillin - 1-naphthalenecarboxylic acid or derivatives - N-acyl-alpha amino acid or derivatives - 1-naphthalenecarboxamide - Alpha-amino acid or derivatives - Naphthalene - Penam - Alkyl aryl ether - Benzenoid - Beta-lactam - Tertiary carboxylic acid amide - Thiazolidine - Azetidine - Secondary carboxylic acid amide - Carboxamide group - Lactam - Carboxylic acid - Ether - Azacycle - Monocarboxylic acid or derivatives - Organoheterocyclic compound - Dialkylthioether - Hemithioaminal - Thioether - Organic oxygen compound - Organopnictogen compound - Organic oxide - Carbonyl group - Hydrocarbon derivative - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Properties

Property NameProperty Value
Molecular Weight414.476
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Complexity699
Monoisotopic Mass414.125
Exact Mass414.125
XLogP2.9
Formal Charge0
Heavy Atom Count29
Defined Atom Stereocenter Count3
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-0.9938
Human Intestinal AbsorptionHIA-0.5328
Caco-2 PermeabilityCaco2-0.6248
P-glycoprotein SubstrateSubstrate0.7080
P-glycoprotein InhibitorNon-inhibitor0.8782
Non-inhibitor0.8807
Renal Organic Cation TransporterNon-inhibitor0.9230
Distribution
Subcellular localizationMitochondria0.5262
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7898
CYP450 2D6 SubstrateNon-substrate0.9116
CYP450 3A4 SubstrateNon-substrate0.5000
CYP450 1A2 InhibitorNon-inhibitor0.8164
CYP450 2C9 InhibitorNon-inhibitor0.7263
CYP450 2D6 InhibitorNon-inhibitor0.8869
CYP450 2C19 InhibitorNon-inhibitor0.8082
CYP450 3A4 InhibitorInhibitor0.5653
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7437
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9994
Non-inhibitor0.6449
AMES ToxicityNon AMES toxic0.7960
CarcinogensNon-carcinogens0.6679
Fish ToxicityHigh FHMT0.9957
Tetrahymena Pyriformis ToxicityHigh TPT0.9776
Honey Bee ToxicityLow HBT0.5903
BiodegradationNot ready biodegradable0.9972
Acute Oral ToxicityIII0.5592
Carcinogenicity (Three-class)Non-required0.6523
Model Value Unit
Absorption
Aqueous solubility-4.0826LogS
Caco-2 Permeability0.5981LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.1208LD50, mol/kg
Fish Toxicity0.9405pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6758pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
HoneyJapan0.005ppm
Other Aquatic AnimalJapan0.005ppm
CrustaceansJapan0.005ppm
Shelled MolluscasJapan0.005ppm
Other FishJapan0.005ppm
PerciformesJapan0.005ppm
AnguilliformesJapan0.005ppm
SalmoniformesJapan0.005ppm
Other Poultry,EggsJapan0.005ppm
Chicken,EggsJapan0.005ppm
Other Poultry Animals,Edible OffalJapan0.005ppm
Chicken,Edible OffalJapan0.005ppm
Other Poultry Animals,KidneyJapan0.005ppm
Chicken,KidneyJapan0.005ppm
Other Poultry Animals,LiverJapan0.005ppm
Chicken,LiverJapan0.005ppm
Other Poultry Animals,FatJapan0.005ppm
Chicken,FatJapan0.005ppm
Other Poultry Animals,MuscleJapan0.005ppm
Chicken,MuscleJapan0.005ppm

References

TitleJournalDatePubmed ID
Tacrolimus interaction with nafcillin resulting in significant decreases intacrolimus concentrations: A case report.Transpl Infect Dis2017 Apr28067989
In vitro activity of ceftaroline: A novel antibiotic againstmethicillin-resistant Staphylococcus aureus.Indian J Pathol Microbiol2016 Oct-Dec27721280
Aluminum based metal-organic framework-polymer monolith in solid-phasemicroextraction of penicillins in river water and milk samples.J Chromatogr A2016 Jan 826065570
Wildlife contamination with fluoroquinolones from livestock: Widespreadoccurrence of enrofloxacin and marbofloxacin in vultures.Chemosphere2016 Feb26498102
A gold immunochromatographic assay for the rapid and simultaneous detection offifteen β-lactams.Nanoscale2015 Oct 2126394361
Development of a direct ELISA based on carboxy-terminal of penicillin-bindingprotein BlaR for the detection of β-lactam antibiotics in foods.Anal Bioanal Chem2013 Nov24013636
Evaluation of the Charm maximum residue limit β-lactam and tetracycline test for the detection of antibiotics in ewe and goat milk.J Dairy Sci2013 May23453521
Development of a rapid multi-residue assay for detecting β-lactams usingpenicillin binding protein 2x*.Biomed Environ Sci2013 Feb23336133
Synthesis of novel hapten and production of generic monoclonal antibody forimmunoassay of penicillins residues in milk.J Environ Sci Health B201323452214
Optimisation and validation of a quantitative and confirmatory LC-MS method formulti-residue analyses of β-lactam and tetracycline antibiotics in bovine muscle.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201222070766
On-line concentration sample stacking coupled with water-in-oil microemulsionelectrokinetic chromatography.J Chromatogr A2011 Oct 2121689819
Determination of eight penicillin antibiotics in pharmaceuticals, milk andporcine tissues by nano-liquid chromatography.J Chromatogr A2009 Oct 2319523644
Stable competitive enzyme-linked immunosorbent assay kit for rapid measurement of11 active beta-lactams in milk, tissue, urine, and serum.J AOAC Int2007 Jan-Feb17373465
Application of ion-exchange cartridge clean-up in food analysis. VI.Determination of six penicillins in bovine tissues by liquidchromatography-electrospray ionization tandem mass spectrometry.J Chromatogr A2004 Jul 915296394
Application of ion-exchange cartridge clean-up in food analysis IV. Confirmatory assay of benzylpenicillin, phenoxymethylpenicillin, oxacillin, cloxacillin,nafcillin and dicloxacillin, in bovine tissues by liquidchromatography-electrospray ionization tandem mass spectrometry.J Chromatogr A2001 Mar 1611293583
Solid-phase extraction followed by liquid chromatography-mass spectrometry fortrace determination of beta-lactam antibiotics in bovine milk.J Agric Food Chem2001 Jul11453792
Application of ion-exchange cartridge clean-up in food analysis III.Determination of benzylpenicillin, phenoxymethyl-penicillin, oxacillin,cloxacillin, nafcillin and dicloxacillin in bovine liver and kidney by liquidchromatography with ultraviolet detection.J Chromatogr A2000 Jun 210890512
Application of ion-exchange cartridge clean-up in food analysis. II.Determination of benzylpenicillin, phenoxymethylpenicillin, oxacillin,cloxacillin, nafcillin and dicloxacillin in meat using liquid chromatography withultraviolet detection.J Chromatogr A1999 Sep 310514989
Simultaneous determination of nafcillin and methicillin by different fluorimetrictechniques using partial least-squares calibration.Analyst1998 May9709491
Simultaneous determination of beta-lactam antibiotics in milk by ion-pair liquid chromatography.J Chromatogr A1998 Jul 39691319