Ampicillin

Basic Info

Common NameAmpicillin(F05834)
2D Structure
FRCD IDF05834
CAS Number69-53-4
PubChem CID6249
FormulaC16H19N3O4S
IUPAC Name

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

InChI Key

AVKUERGKIZMTKX-NJBDSQKTSA-N

InChI

InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1

Canonical SMILES

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

Isomeric SMILES

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

Synonyms
        
            ampicillin
        
            Aminobenzylpenicillin
        
            Ampicillin acid
        
            Amcill
        
            69-53-4
        
            Ampicilline
        
            Polycillin
        
            Principen
        
            Omnipen
        
            Ampicillinum
Classifies
                

                  
                    Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassLactams
SubclassBeta lactams
Intermediate Tree NodesPenams
Direct ParentPenicillins
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsPenicillin - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Alpha-amino acid or derivatives - Phenylacetamide - Aralkylamine - Monocyclic benzene moiety - Benzenoid - Thiazolidine - Tertiary carboxylic acid amide - Amino acid or derivatives - Azetidine - Amino acid - Carboxamide group - Secondary carboxylic acid amide - Azacycle - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Dialkylthioether - Hemithioaminal - Thioether - Primary aliphatic amine - Amine - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Organopnictogen compound - Organonitrogen compound - Organooxygen compound - Organic oxide - Primary amine - Hydrocarbon derivative - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].

Properties

Property NameProperty Value
Molecular Weight349.405
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Complexity562
Monoisotopic Mass349.11
Exact Mass349.11
XLogP-1.1
Formal Charge0
Heavy Atom Count24
Defined Atom Stereocenter Count4
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-0.9961
Human Intestinal AbsorptionHIA-0.9270
Caco-2 PermeabilityCaco2-0.8956
P-glycoprotein SubstrateSubstrate0.5603
P-glycoprotein InhibitorNon-inhibitor0.9626
Non-inhibitor0.9971
Renal Organic Cation TransporterNon-inhibitor0.9689
Distribution
Subcellular localizationLysosome0.5707
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8297
CYP450 2D6 SubstrateNon-substrate0.8447
CYP450 3A4 SubstrateNon-substrate0.5825
CYP450 1A2 InhibitorNon-inhibitor0.9253
CYP450 2C9 InhibitorNon-inhibitor0.9402
CYP450 2D6 InhibitorNon-inhibitor0.9401
CYP450 2C19 InhibitorNon-inhibitor0.9399
CYP450 3A4 InhibitorNon-inhibitor0.8309
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9884
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9998
Non-inhibitor0.9031
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.5363
Fish ToxicityHigh FHMT0.9722
Tetrahymena Pyriformis ToxicityHigh TPT0.7152
Honey Bee ToxicityLow HBT0.7369
BiodegradationNot ready biodegradable0.9844
Acute Oral ToxicityIV0.6698
Carcinogenicity (Three-class)Non-required0.6941
Model Value Unit
Absorption
Aqueous solubility-2.8487LogS
Caco-2 Permeability0.0398LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.5620LD50, mol/kg
Fish Toxicity1.7369pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.2178pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
MilkUnited States0.01ppm
Edible Tissues Of CattleUnited States0.01ppm
Edible Tissues Of SwineUnited States0.01ppm
HoneyJapan0.009ppm
Other Aquatic AnimalJapan0.05ppm
CrustaceansJapan0.05ppm
Shelled MolluscasJapan0.05ppm
Other FishJapan0.05ppm
PerciformesJapan0.06ppm
AnguilliformesJapan0.05ppm
SalmoniformesJapan0.05ppm
Chicken,EggsJapan0.01ppm
Other Poultry Animals,Edible OffalJapan0.05ppm
Chicken,Edible OffalJapan0.02ppm
Other Poultry Animals,KidneyJapan0.05ppm
Chicken,KidneyJapan0.02ppm
Other Poultry Animals,LiverJapan0.05ppm
Chicken,LiverJapan0.03ppm
Other Poultry Animals,FatJapan0.05ppm
Chicken,FatJapan0.02ppm

References

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Environmental superbugs: The case study of Pedobacter spp.Environ Pollut2018 Oct30029312
Comparative Study on Antibiotic Resistance and DNA Profiles of Salmonellaenterica Serovar Typhimurium Isolated from Humans, Retail Foods, and theEnvironment in Shanghai, China.Foodborne Pathog Dis2018 May 929741928
Proactive udder health management in South Africa and monitoring of antibioticresistance of Staphylococcus aureus; in dairy herds from 2001 to 2010.J S Afr Vet Assoc2018 May 729781674
Effect of electron beam and gamma radiation on drug-susceptible anddrug-resistant Listeria monocytogenes strains in salmon under differenttemperature.J Appl Microbiol2018 May 429727511
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Susceptibility to antibiotics in isolates of Lactobacillus plantarum RAPD-typeLp299v, harvested from antibiotic treated, critically ill patients afteradministration of probiotics.Microbiologyopen2018 May 24:e0064229797784
Trans-Cinnamaldehyde and Eugenol Increase Acinetobacter baumannii Sensitivity to Beta-Lactam Antibiotics.Front Microbiol2018 May 2329875743
Validation of the BetaStar® Advanced for Beta-lactams Test Kit for the Screening of Bulk Tank and Tanker Truck Milks for the Presence of Beta-lactam DrugResidues.J AOAC Int2018 May 1829776460
Cloning and Expression of the Organophosphate Pesticide-Degrading α-β HydrolaseGene in Plasmid pMK-07 to Confer Cross-Resistance to Antibiotics.Biomed Res Int2018 May 1629862253
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Effect of the luxS gene on biofilm formation and antibiotic resistance bySalmonella serovar Dublin.Food Res Int2018 May29580499
In Vitro and in Vivo Selection of Potentially Probiotic Lactobacilli FromNocellara del Belice Table Olives.Front Microbiol2018 Mar 2829643848
Chemical, antimicrobial, and molecular characterization of mortiño (Vacciniumfloribundum Kunth) fruits and leaves.Food Sci Nutr2018 Mar 2629983956
Most commensally bacterial strains in human milk of healthy mothers displaymultiple antibiotic resistance.Microbiologyopen2018 Mar 25:e0061829577668
Phenotypic and Genotypic Characterization of Klebsiella pneumoniae Isolated From Retail Foods in China.Front Microbiol2018 Mar 129545778
In vitro activity of Nigella sativa against antibiotic resistant Salmonellaenterica.Environ Toxicol Pharmacol2018 Mar29289818