Oxacillin

Basic Info

Common NameOxacillin(F05851)
2D Structure
FRCD IDF05851
CAS Number
PubChem CID6196
FormulaC19H19N3O5S
IUPAC Name

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

InChI Key

UWYHMGVUTGAWSP-JKIFEVAISA-N

InChI

InChI=1S/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1

Canonical SMILES

CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O

Isomeric SMILES

CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O

Synonyms
        
            oxacillin
        
            Oxazocillin
        
            MPI-penicillin
        
            Oxacilline
        
            Oxacillinum
        
            Oxazocilline
        
            Oxacilina
        
            Ossacillina
        
            Prostaphlin
        
            Prostaphlyn
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 - N-acyl-alpha amino acid or derivatives - Alpha-amino acid or derivatives - Penam - Benzenoid - Monocyclic benzene moiety - Isoxazole - Tertiary carboxylic acid amide - Azole - Thiazolidine - Heteroaromatic compound - Beta-lactam - Carboxamide group - Lactam - Secondary carboxylic acid amide - Azetidine - Oxacycle - Carboxylic acid - Azacycle - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Dialkylthioether - Hemithioaminal - Thioether - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Carbonyl group - Organic nitrogen 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 Weight401.437
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Complexity681
Monoisotopic Mass401.105
Exact Mass401.105
XLogP2.4
Formal Charge0
Heavy Atom Count28
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-0.9923
Human Intestinal AbsorptionHIA+0.8002
Caco-2 PermeabilityCaco2+0.7059
P-glycoprotein SubstrateNon-substrate0.6161
P-glycoprotein InhibitorNon-inhibitor0.8670
Non-inhibitor0.9220
Renal Organic Cation TransporterNon-inhibitor0.9669
Distribution
Subcellular localizationMitochondria0.4730
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8181
CYP450 2D6 SubstrateNon-substrate0.8807
CYP450 3A4 SubstrateSubstrate0.5347
CYP450 1A2 InhibitorInhibitor0.5746
CYP450 2C9 InhibitorNon-inhibitor0.8725
CYP450 2D6 InhibitorNon-inhibitor0.9111
CYP450 2C19 InhibitorNon-inhibitor0.8665
CYP450 3A4 InhibitorNon-inhibitor0.6650
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9564
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9997
Non-inhibitor0.8773
AMES ToxicityNon AMES toxic0.7304
CarcinogensNon-carcinogens0.5273
Fish ToxicityHigh FHMT0.9790
Tetrahymena Pyriformis ToxicityHigh TPT0.8442
Honey Bee ToxicityLow HBT0.7277
BiodegradationNot ready biodegradable0.9759
Acute Oral ToxicityIV0.6126
Carcinogenicity (Three-class)Non-required0.6170
Model Value Unit
Absorption
Aqueous solubility-3.1826LogS
Caco-2 Permeability0.7564LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.6583LD50, mol/kg
Fish Toxicity1.3642pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5206pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Aquatic AnimalJapan0.3ppm
CrustaceansJapan0.3ppm
Shelled MolluscasJapan0.3ppm
Other FishJapan0.3ppm
PerciformesJapan0.3ppm
AnguilliformesJapan0.3ppm
SalmoniformesJapan0.3ppm
Other Poultry Animals,Edible OffalJapan0.3ppm
Chicken,Edible OffalJapan0.3ppm
Other Poultry Animals,KidneyJapan0.3ppm
Chicken,KidneyJapan0.3ppm
Other Poultry Animals,LiverJapan0.3ppm
Chicken,LiverJapan0.3ppm
Other Poultry Animals,FatJapan0.3ppm
Chicken,FatJapan0.3ppm
Other Poultry Animals,MuscleJapan0.3ppm
Chicken,MuscleJapan0.3ppm
MilkJapan0.03ppm
Other Terrestrial Mammals,Edible OffalJapan0.3ppm
Pig,Edible OffalJapan0.3ppm

References

TitleJournalDatePubmed ID
Prevalence and Characterization of Staphylococcus aureus Strains in the PorkChain Supply in Chile.Foodborne Pathog Dis2018 May29364698
Diversity and Antibiotic Susceptibility of Acinetobacter Strains From Milk PowderProduced in Germany.Front Microbiol2018 Mar 2729636733
Most commensally bacterial strains in human milk of healthy mothers displaymultiple antibiotic resistance.Microbiologyopen2018 Mar 25:e0061829577668
Safety hazards in bacteriocinogenic Staphylococcus strains isolated from goat and sheep milk.Microb Pathog2018 Mar29355699
Prevalence, Potential Virulence, and Genetic Diversity of Listeria monocytogenes Isolates From Edible Mushrooms in Chinese Markets.Front Microbiol2018 Jul 2730100901
Seasonal Distribution and Genotyping of Antibiotic Resistant Strains ofListeriaInnocua Isolated from A River Basin Categorized by ERIC-PCR.Int J Environ Res Public Health2018 Jul 2330041470
In Vitro Antistaphylococcal Synergistic Effect of Isoflavone MetaboliteDemethyltexasin with Amoxicillin and Oxacillin.Microb Drug Resist2018 Jan/Feb28570834
Resensitization of methicillin-resistant Staphylococcus aureus by amoxapine, anFDA-approved antidepressant.Heliyon2018 Jan 1229349359
Characterization of the Lytic Capability of a LysK-Like Endolysin, Lys-phiSA012, Derived from a Polyvalent Staphylococcus aureus Bacteriophage.Pharmaceuticals (Basel)2018 Feb 2429495305
Pathogenic Characteristics and Antibiotic Resistance of Bacterial Isolates from Farmstead Cheeses.Korean J Food Sci Anim Resour2018 Feb29725238
High prevalence and antimicrobial resistance of mecA Staphylococcus aureus indairy cattle, sheep, and goat bulk tank milk in Jordan.Trop Anim Health Prod2018 Feb29063353
Antimicrobial resistance in bacteria isolated from mastitis in dairy cattle inFrance, 2006-2016.J Dairy Sci2018 Aug 930100506
[Molecular typing characterization of food-borne methicillin-resistantStaphylococcus aureus in China].Zhonghua Yu Fang Yi Xue Za Zhi2018 Apr 629614602
Naphtho[1,2-b]furan-4,5-dione is a potent anti-MRSA agent against planktonic,biofilm and intracellular bacteria.Future Microbiol2017 Sep28799789
Phenotypic and genotypic characterization of antibiotic resistance ofmethicillin-resistant Staphylococcus aureus isolated from hospital food.Antimicrob Resist Infect Control2017 Oct 429034091
First report on MRSA CC398 recovered from wild boars in the north of Portugal.Are we facing a problem?Sci Total Environ2017 Oct 1528412568
Prevalence and characterization of methicillin-resistant Staphylococcus aureus carrying mecA or mecC and methicillin-susceptible Staphylococcus aureus in dairy sheep farms in central Italy.J Dairy Sci2017 Oct28780098
Prevalence, virulence factor genes and antibiotic resistance of Bacillus cereus sensu lato isolated from dairy farms and traditional dairy products.BMC Microbiol2017 Mar 1428288581
Antimicrobial peptide isolated from Bacillus amyloliquefaciens K14 revitalizesits use in combinatorial drug therapy.Folia Microbiol (Praha)2017 Mar27787755
Development and validation of a quantitative confirmatory method for 30 β-lactam antibiotics in bovine muscle using liquid chromatography coupled to tandem massspectrometry.J Chromatogr A2017 Jun 228449875