Phenoxymethylpenicillin

Basic Info

Common NamePhenoxymethylpenicillin(F06184)
2D Structure
FRCD IDF06184
CAS Number
PubChem CID6869
FormulaC16H18N2O5S
IUPAC Name

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

InChI Key

BPLBGHOLXOTWMN-MBNYWOFBSA-N

InChI

InChI=1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1

Canonical SMILES

CC1(C(N2C(S1)C(C2=O)NC(=O)COC3=CC=CC=C3)C(=O)O)C

Isomeric SMILES

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)COC3=CC=CC=C3)C(=O)O)C

Synonyms
        
            penicillin v
        
            Phenoxymethylpenicillin
        
            Penicillin phenoxymethyl
        
            Oracillin
        
            Phenomycilline
        
            Phenopenicillin
        
            Beromycin
        
            Fenospen
        
            Phenoxymethyl penicillin
        
            V-Cillin
Classifies
                

                  
                    Predicted: Veterinary Drug
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 - Phenoxy compound - Phenol ether - Penam - Alkyl aryl ether - Monocyclic benzene moiety - Benzenoid - Beta-lactam - Tertiary carboxylic acid amide - Thiazolidine - Lactam - Carboxamide group - Secondary carboxylic acid amide - Azetidine - Azacycle - Carboxylic acid - Ether - 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 Weight350.389
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Complexity547
Monoisotopic Mass350.094
Exact Mass350.094
XLogP2.1
Formal Charge0
Heavy Atom Count24
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-1.0000
Human Intestinal AbsorptionHIA-0.9071
Caco-2 PermeabilityCaco2-0.8957
P-glycoprotein SubstrateSubstrate0.6858
P-glycoprotein InhibitorNon-inhibitor0.9131
Non-inhibitor0.9726
Renal Organic Cation TransporterNon-inhibitor0.9219
Distribution
Subcellular localizationMitochondria0.4391
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8176
CYP450 2D6 SubstrateNon-substrate0.8470
CYP450 3A4 SubstrateSubstrate0.5576
CYP450 1A2 InhibitorNon-inhibitor0.8802
CYP450 2C9 InhibitorNon-inhibitor0.8501
CYP450 2D6 InhibitorNon-inhibitor0.8725
CYP450 2C19 InhibitorNon-inhibitor0.8361
CYP450 3A4 InhibitorNon-inhibitor0.8257
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8785
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9995
Non-inhibitor0.8344
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.7079
Fish ToxicityHigh FHMT0.9198
Tetrahymena Pyriformis ToxicityHigh TPT0.9379
Honey Bee ToxicityLow HBT0.6800
BiodegradationNot ready biodegradable0.9747
Acute Oral ToxicityIII0.4535
Carcinogenicity (Three-class)Non-required0.6952
Model Value Unit
Absorption
Aqueous solubility-2.9656LogS
Caco-2 Permeability-0.1919LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.8953LD50, mol/kg
Fish Toxicity1.3195pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3758pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Pig,Edible OffalJapan0.03ppm
Pig,KidneyJapan0.03ppm
Pig,LiverJapan0.03ppm
Pig,FatJapan0.03ppm
Pig,MuscleJapan0.03ppm

References

TitleJournalDatePubmed ID
Quantitative analysis of veterinary drugs in bovine muscle and milk by liquidchromatography quadrupole time-of-flight mass spectrometry.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2017Jul28524783
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
Determination of selected veterinary antimicrobials in poultry excreta byUHPLC-MS/MS, for application in Salmonella control programs.Anal Bioanal Chem2015 Jun25633214
Research on degradation of penicillins in milk by β-lactamase usingultra-performance liquid chromatography coupled with time-of-flight massspectrometry.J Dairy Sci2014 Jul24792795
Development and validation of an HPLC method for the determination of sixpenicillin and three amphenicol antibiotics in gilthead seabream (Sparus Aurata) tissue according to the European Union Decision 2002/657/EC.Food Chem2013 Feb 1523194530
Synthesis of novel hapten and production of generic monoclonal antibody forimmunoassay of penicillins residues in milk.J Environ Sci Health B201323452214
Voltammetric determination of penicillin V in pharmaceutical formulations andhuman urine using a boron-doped diamond electrode.Bioelectrochemistry2012 Dec22763423
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
β-lactam antibiotics residues analysis in bovine milk by LC-ESI-MS/MS: a simpleand fast liquid-liquid extraction method.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201221988179
On-line concentration sample stacking coupled with water-in-oil microemulsionelectrokinetic chromatography.J Chromatogr A2011 Oct 2121689819
Rapid and simultaneous determination of amoxicillin, penicillin G, and theirmajor metabolites in bovine milk by ultra-high-performance liquidchromatography-tandem mass spectrometry.J Chromatogr B Analyt Technol Biomed Life Sci2011 Mar 121300578
Trace determination of 10 beta-lactam antibiotics in environmental and foodsamples by capillary liquid chromatography.J Chromatogr A2009 Nov 2019836022
Quantitative determination of penicillin V and amoxicillin in feed samples bypressurised liquid extraction and liquid chromatography with ultravioletdetection.J Pharm Biomed Anal2009 Feb 2019121911
[Simultaneous determination of four beta-lactam antibiotics in milk bysolid-phase extraction-micellar electrokinetic chromatography].Se Pu2008 Nov19253544
Simultaneous determination of different classes of antibiotics in fish andlivestock by CE-MS.Electrophoresis2007 Nov17932875
The evidence base for cephalosporin superiority over penicillin in streptococcal pharyngitis.Diagn Microbiol Infect Dis2007 Mar17292576
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
Development of a novel and automated fluorescent immunoassay for the analysis of beta-lactam antibiotics.J Agric Food Chem2005 Aug 2416104778
Simple and rapid liquid chromatography-tandem mass spectrometry confirmatoryassay for determining amoxicillin and ampicillin in bovine tissues and milk.J Agric Food Chem2004 Jun 215161184
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