AMPICILLIN

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Synonyms
Status
Molecule Category Free-form
ATC J01CA01 S01AA19
UNII 7C782967RD
EPA CompTox DTXSID4022602

Structure

InChI Key AVKUERGKIZMTKX-NJBDSQKTSA-N
Smiles CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H19N3O4S
Molecular Weight 349.41
AlogP 0.32
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 4.0
Polar Surface Area 112.73
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 24.0

Bioactivity

Mechanism of Action Action Reference
Bacterial penicillin-binding protein inhibitor INHIBITOR PubMed Wikipedia
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Tie family
- - 82000 - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 20
Assay Description Organism Bioactivity Reference
inhibition of Bacillus cereus was measured by zone diameter Bacillus cereus 13.0 mm
inhibition of Escherichia coli was measured by zone diameter Escherichia coli 15.0 mm
inhibition of Bacillus subtilis was measured by zone diameter Bacillus subtilis 10.0 mm
inhibition of Pseudomonas aeruginosa was measured by zone diameter Pseudomonas aeruginosa 12.0 mm
Antibacterial activity against Staphylococcus aureus by broth microdilution technique Staphylococcus aureus 0.74 ug.mL-1
Antibacterial activity against Streptococcus faecalis by broth microdilution technique Enterococcus faecalis 0.01 ug.mL-1
Antibacterial activity against Klebsiella pneumoniae by broth microdilution technique Klebsiella pneumoniae 0.08 ug.mL-1
Antibacterial activity against Escherichia coli by broth microdilution technique Escherichia coli 0.01 ug.mL-1
Antibacterial activity against Pseudomonas aeruginosa by broth microdilution technique Pseudomonas aeruginosa 48.74 ug.mL-1
Antibacterial activity against Staphylococcus aureus ATCC 25923 at 200 mg/mL after 24 hrs by disc diffusion method Staphylococcus aureus 16.0 mm
Antibacterial activity against Staphylococcus epidermidis at 200 mg/mL after 24 hrs by disc diffusion method Staphylococcus epidermidis 10.0 mm
Antibacterial activity against Streptococcus pyogenes at 200 mg/mL after 24 hrs by disc diffusion method Streptococcus pyogenes 16.0 mm
Antibacterial activity against Escherichia coli ATCC 25922 at 200 mg/mL after 24 hrs by disc diffusion method Escherichia coli 16.0 mm
Antimicrobial activity against Escherichia coli NCIM2574 by broth microdilution method Escherichia coli 1.0 ug.mL-1
Antimicrobial activity against Staphylococcus aureus NCIM2122 by broth microdilution method Staphylococcus aureus 4.0 ug.mL-1
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 20.3 %
Antibacterial activity against Staphylococcus aureus Staphylococcus aureus 0.1 ug.mL-1
Antibacterial activity against Escherichia coli TP1 harboring pBR322 carrying TEM-1 assessed as inhibition of bacterial growth at 4096 ug/ml after 18 hrs Escherichia coli 25.0 %
Antibacterial activity against Escherichia coli TP1 harboring pBR322 carrying TEM-10 assessed as inhibition of bacterial growth at 4096 ug/ml after 18 hrs Escherichia coli 78.0 %
Antibacterial activity against Escherichia coli TP1 harboring pBR322 carrying TEM-12 assessed as inhibition of bacterial growth at 4096 ug/ml after 18 hrs Escherichia coli 36.0 %
Bactericidal activity against Escherichia coli ATCC 25922 assessed as eradication of pre-formed biofilm at 50 times MIC after 24 hrs Escherichia coli 10.0 %
Bactericidal activity against Pseudomonas aeruginosa ATCC 27853 assessed as eradication of pre-formed biofilm at 50 times MIC after 24 hrs Pseudomonas aeruginosa 10.0 %
Antibacterial activity against Staphylococcus aureus CGMCC 1.24465 after 24 hrs Staphylococcus aureus 60.0 nM
Antimicrobial activity against Branhamella catarrhalis assessed as growth inhibition at 10 ug/ml by agar dilution method Moraxella catarrhalis 100.0 %
Antimicrobial activity against Staphylococcus aureus ATCC 25923 assessed as growth inhibition at 10 ug/ml by agar dilution method Staphylococcus aureus 100.0 %
Antimicrobial activity against Bacillus subtilis ATCC 6633 assessed as growth inhibition at 10 ug/ml by agar dilution method Bacillus subtilis 100.0 %
Antimicrobial activity against Staphylococcus epidermidis ATCC 12228 assessed as growth inhibition at 10 ug/ml by agar dilution method Staphylococcus epidermidis ATCC 12228 100.0 %
Antimicrobial activity against Streptococcus pyogenes assessed as growth inhibition at 10 ug/ml by agar dilution method Streptococcus pyogenes 100.0 %
Antimicrobial activity against Neisseria mucosa assessed as growth inhibition at 10 ug/ml by agar dilution method Neisseria mucosa 100.0 %
Antimicrobial activity against Edwardsiella tarda assessed as growth inhibition at 10 ug/ml by agar dilution method Edwardsiella tarda 100.0 %
Antibacterial activity against Staphylococcus aureus Col CGMCC 1.2465 after 24 hrs by NCCLS M27-A2 method Staphylococcus aureus subsp. aureus COL 0.09 ug.mL-1
Antibacterial activity against Salmonella typhimurium after 18 hrs Salmonella enterica subsp. enterica serovar Typhimurium 39.0 ug.mL-1
TP_TRANSPORTER: inhibition of VACV uptake (VAVC: 20 uM, Ampicillin: 10000 uM) in PEPT1-expressing CHO cells None 50.0 %
Antibacterial activity against Staphylococcus aureus Staphylococcus aureus 0.04 ug.mL-1
Antimicrobial activity against Streptococcus pneumoniae by microplate reader analysis Streptococcus pneumoniae 0.38 ug.mL-1
Antibacterial activity against Enterococcus faecalis ATCC 29212 at 10 ug/ml after 16 hrs Enterococcus faecalis ATCC 29212 66.0 %
Antibacterial activity against Escherichia coli NCIM 2688 after 8 hrs Escherichia coli 0.086 ug.mL-1
Antibacterial activity against Pseudomonas fluorescens NCIM 2036 after 8 hrs Pseudomonas fluorescens 1.87 ug.mL-1
Antibacterial activity against Staphylococcus aureus NCIM 2010 after 12 hrs Staphylococcus aureus 0.42 ug.mL-1
Antibacterial activity against Bacillus subtilis NCIM 2079 after 12 hrs Bacillus subtilis 3.15 ug.mL-1
Antibacterial activity against Escherichia coli after 18 hrs by broth dilution method Escherichia coli 1.46 ug.mL-1
Antibacterial activity against Pseudomonas after 18 hrs by broth dilution method Pseudomonas 4.36 ug.mL-1
Antibacterial activity against Staphylococcus aureus after 18 hrs by broth dilution method Staphylococcus aureus 1.0 ug.mL-1
Antibacterial activity against Bacillus subtilis after 18 hrs by broth dilution method Bacillus subtilis 10.32 ug.mL-1
Antibacterial activity against multidrug resistant Enterococcus faecium NCTC 7171 (ATCC 19434) assessed as reduction in bacterial growth incubated for 6 to 8 hrs Enterococcus faecium 630.0 nM
Antibacterial activity against multidrug resistant Staphylococcus aureus subsp. aureus Seattle 1945 (ATCC 25923) assessed as reduction in bacterial growth incubated for 6 to 8 hrs Staphylococcus aureus subsp. aureus 59.0 nM
Antibacterial activity against Escherichia coli NCIM 2688 after 8 hrs by serial dilution method Escherichia coli 146.0 nM
Antibacterial activity against Pseudomonas aeruginosa NCIM 2036 after 8 hrs by serial dilution method Pseudomonas aeruginosa 436.0 nM
Antibacterial activity against Staphylococcus aureus NCIM 2010 after 12 hrs by serial dilution method Staphylococcus aureus 100.0 nM
Antibacterial activity against Bacillus subtilis MTCC 441 by broth microdilution method Bacillus subtilis 250.0 ug.mL-1
Antibacterial activity against Staphylococcus aureus ATCC 25923 after 6 to 8 hrs by bacterial proliferation assay Staphylococcus aureus 190.0 nM
Antibiofilm activity against Pseudomonas aeruginosa PAO1 assessed as inhibition of biofilm formation at 0.5 times MIC incubated for 24 hrs by crystal violet staining based ELISA method Pseudomonas aeruginosa 65.3 %
Antibiofilm activity against Pseudomonas aeruginosa PAO1 assessed as inhibition of biofilm formation at 0.25 times MIC incubated for 24 hrs by crystal violet staining based ELISA method Pseudomonas aeruginosa 58.9 %
Antibiofilm activity against Pseudomonas aeruginosa PAO1 assessed as inhibition of biofilm formation at 0.125 times MIC incubated for 24 hrs by crystal violet staining based ELISA method Pseudomonas aeruginosa 85.2 %
Antibacterial activity against Bacillus subtilis ATCC 6633 assessed as reduction in microbial growth after incubated for 48 hrs by resazurin dye based assay Bacillus subtilis 900.0 nM
Antibacterial activity against Staphylococcus aureus measured by broth microdilution method Staphylococcus aureus 20.0 nM
Antibacterial activity against Bacillus subtilis measured by broth microdilution method Bacillus subtilis 300.0 nM

Related Entries

Environmental Exposure

Environmental Exposure Map
Countries
India
Vietnam

Cross References

Resources Reference
ChEBI 28971
ChEMBL CHEMBL174
DrugBank DB00415
DrugCentral 198
FDA SRS 7C782967RD
Human Metabolome Database HMDB0014559
Guide to Pharmacology 10896
KEGG C06574
PDB AIC
PharmGKB PA448419
PubChem 6249
SureChEMBL SCHEMBL3526
ZINC ZINC000003830218
CONTENTS