AMOXICILLIN

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category Free-form
ATC J01CA04
UNII 9EM05410Q9
EPA CompTox DTXSID3037044

Structure

InChI Key LSQZJLSUYDQPKJ-NJBDSQKTSA-N
Smiles CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccc(O)cc3)C(=O)N2[C@H]1C(=O)O
InChI
InChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-,10-,11+,14-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H19N3O5S
Molecular Weight 365.41
AlogP 0.02
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 4.0
Polar Surface Area 132.96
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 25.0

Bioactivity

Mechanism of Action Action Reference
Bacterial penicillin-binding protein inhibitor INHIBITOR ISBN
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 75
Assay Description Organism Bioactivity Reference
Antimicrobial activity against Staphylococcus aureus after 24 hrs by broth microdilution method Staphylococcus aureus 1.82 ug.mL-1
Antimicrobial activity against Streptococcus pyogenes after 24 hrs by broth microdilution method Streptococcus pyogenes 1.8 ug.mL-1
Antimicrobial activity against Salmonella Typhimurium after 24 hrs by broth microdilution method Salmonella enterica subsp. enterica serovar Typhimurium 1.85 ug.mL-1
Antimicrobial activity against Escherichia coli after 24 hrs by broth microdilution method Escherichia coli 1.9 ug.mL-1
Inhibition of Helicobacter pylori invasion into human AGS cells at 2.5 uM after 6 hrs Helicobacter pylori 90.0 %
Inhibition of Helicobacter pylori-induced inflammation in human AGS cells assessed as reduction of IL-8 production at 10 uM by ELISA Helicobacter pylori 81.9 %
Displacement of Biocillin FL from Streptococcus pneumoniae 24 PBP1A Streptococcus pneumoniae 0.004 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3413 PBP1A Streptococcus pneumoniae 0.124 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 2527 PBP1A Streptococcus pneumoniae 0.049 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3676 PBP1A Streptococcus pneumoniae 0.422 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3243 PBP1A Streptococcus pneumoniae 0.059 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3665 PBP1A Streptococcus pneumoniae 0.067 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3009 PBP1A Streptococcus pneumoniae 0.09 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1076 PBP1A Streptococcus pneumoniae 0.044 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1077 PBP1A Streptococcus pneumoniae 0.017 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 24 PBP1B Streptococcus pneumoniae 1.103 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3413 PBP1B Streptococcus pneumoniae 0.035 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 2527 PBP1B Streptococcus pneumoniae 0.029 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3676 PBP1B Streptococcus pneumoniae 0.116 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3243 PBP1B Streptococcus pneumoniae 0.165 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3665 PBP1B Streptococcus pneumoniae 0.079 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3009 PBP1B Streptococcus pneumoniae 0.059 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1076 PBP1B Streptococcus pneumoniae 0.068 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1077 PBP1B Streptococcus pneumoniae 0.006 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 24 PBP2X Streptococcus pneumoniae 0.117 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3413 PBP2X Streptococcus pneumoniae 0.062 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 2527 PBP2X Streptococcus pneumoniae 0.004 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3676 PBP2X Streptococcus pneumoniae 0.043 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3243 PBP2X Streptococcus pneumoniae 0.018 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3665 PBP2X Streptococcus pneumoniae 0.094 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3009 PBP2X Streptococcus pneumoniae 0.008 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1076 PBP2X Streptococcus pneumoniae 0.037 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1077 PBP2X Streptococcus pneumoniae 0.022 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 24 PBP2A Streptococcus pneumoniae 0.077 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3413 PBP2A Streptococcus pneumoniae 0.034 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 2527 PBP2A Streptococcus pneumoniae 0.051 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3676 PBP2A Streptococcus pneumoniae 0.066 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3665 PBP2A Streptococcus pneumoniae 0.05 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3009 PBP2A Streptococcus pneumoniae 0.08 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1076 PBP2A Streptococcus pneumoniae 0.08 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 24 PBP2B Streptococcus pneumoniae 0.176 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3413 PBP2B Streptococcus pneumoniae 0.165 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 2527 PBP2B Streptococcus pneumoniae 0.033 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3676 PBP2B Streptococcus pneumoniae 0.144 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3243 PBP2B Streptococcus pneumoniae 0.029 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3665 PBP2B Streptococcus pneumoniae 0.22 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3009 PBP2B Streptococcus pneumoniae 0.05 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1076 PBP2B Streptococcus pneumoniae 0.055 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1077 PBP2B Streptococcus pneumoniae 0.03 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 24 PBP3 Streptococcus pneumoniae 0.049 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3413 PBP3 Streptococcus pneumoniae 0.029 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 2527 PBP3 Streptococcus pneumoniae 0.022 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3676 PBP3 Streptococcus pneumoniae 0.019 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3243 PBP3 Streptococcus pneumoniae 0.006 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3665 PBP3 Streptococcus pneumoniae 0.019 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3009 PBP3 Streptococcus pneumoniae 0.047 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1076 PBP3 Streptococcus pneumoniae 0.051 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1077 PBP3 Streptococcus pneumoniae 0.022 ug.mL-1
Antibacterial activity against Staphylococcus aureus Staphylococcus aureus 2.84 ug.mL-1
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 75.16 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 87.94 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 15.09 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 7.14 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 10.29 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 10.8 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 22.8 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 9.25 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -2.09 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 1.48 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.63 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.02 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.02 %

Related Entries

Environmental Exposure

Environmental Exposure Map
Countries
Croatia
Romania

Cross References

Resources Reference
ChEBI 2676
ChEMBL CHEMBL1082
DrugBank DB01060
DrugCentral 192
FDA SRS 9EM05410Q9
Human Metabolome Database HMDB0015193
Guide to Pharmacology 10895
KEGG C06827
PharmGKB PA448406
PubChem 62883
SureChEMBL SCHEMBL3427
ZINC ZINC000003830215
CONTENTS