CLOXACILLIN

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
ATC J01CF02
UNII O6X5QGC2VB
EPA CompTox DTXSID5022853

Structure

InChI Key LQOLIRLGBULYKD-JKIFEVAISA-N
Smiles Cc1onc(-c2ccccc2Cl)c1C(=O)N[C@@H]1C(=O)N2[C@@H]1SC(C)(C)[C@@H]2C(=O)O
InChI
InChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C19H18ClN3O5S
Molecular Weight 435.89
AlogP 2.55
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 4.0
Polar Surface Area 112.74
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 29.0
Assay Description Organism Bioactivity Reference
Antimicrobial activity against methicillin-susceptible Staphylococcus aureus ATCC 25923 after phagocytosis by human THP1 macrophages assessed as reduction in bacterial count after 24 hrs Staphylococcus aureus 0.27 ug.mL-1
Antimicrobial activity against methicillin-resistant Staphylococcus aureus ATCC 25923 after phagocytosis by human THP1 macrophages assessed as reduction in bacterial count after 24 hrs Staphylococcus aureus 0.23 ug.mL-1
Antimicrobial activity against methicillin-susceptible Staphylococcus aureus ATCC 25923 after phagocytosis by human THP1 macrophages assessed as reduction in bacterial count at pH 7.4 after 24 hrs Staphylococcus aureus 0.35 ug.mL-1
Antimicrobial activity against methicillin-resistant Staphylococcus aureus ATCC 25923 after phagocytosis by human THP1 macrophages assessed as reduction in bacterial count at pH 7.4 after 24 hrs Staphylococcus aureus 16.9 ug.mL-1
Antimicrobial activity against methicillin-susceptible Staphylococcus aureus ATCC 25923 after phagocytosis by human THP1 macrophages assessed as reduction in bacterial count at pH 5.5 after 24 hrs Staphylococcus aureus 0.22 ug.mL-1
Antimicrobial activity against methicillin-susceptible Staphylococcus aureus ATCC 25923 after phagocytosis by human THP1 macrophages assessed as reduction in bacterial count at pH 5.5 after 24 hrs Staphylococcus aureus 0.07 ug.mL-1
Inhibition of Escherichia coli beta-lactamase ACC4 Escherichia coli 26.0 nM
Antibacterial activity against methicillin-resistant Staphylococcus aureus by NCCLS method Staphylococcus aureus 8.9 ug.mL-1
Inhibition of Salmonella enterica serotype Newport AM17274 cephalosporinase CMY-31 by UV spectrophotometer in presence of 100 uM of cephalothin Salmonella enterica subsp. enterica serovar Newport 4.0 nM
Inhibition of Klebsiella pneumoniae HP205 cephalosporinase CMY-36 by UV spectrophotometer in presence of 100 uM of cephalothin Klebsiella pneumoniae 4.0 nM
Inhibition of CMY-2 by UV spectrophotometer in presence of 100 uM of cephalothin None 4.0 nM
Antimicrobial activity against intracellular beta-lactamase negative methicillin-susceptible Staphylococcus aureus ATCC 25923 infected in activated human THP-1 cells assessed as decrease in bacterial growth after 24 hrs at pH 7.4 Staphylococcus aureus 0.43 ug.mL-1
Antimicrobial activity against intracellular hospital acquired methicillin-resistant Staphylococcus aureus ATCC 33591 activated infected in human THP-1 cells assessed as decrease in bacterial growth after 24 hrs at pH 7.4 Staphylococcus aureus 0.32 ug.mL-1
Antimicrobial activity against intracellular beta-lactamase negative methicillin-susceptible Staphylococcus aureus ATCC 25923 infected in human keratinocytes assessed as decrease in bacterial growth after 24 hrs at pH 7.4 Staphylococcus aureus 0.42 ug.mL-1
Antimicrobial activity against intracellular hospital acquired methicillin-resistant Staphylococcus aureus ATCC 33591 infected in human keratinocytes assessed as decrease in bacterial growth after 24 hrs at pH 7.4 Staphylococcus aureus 0.39 ug.mL-1
Antimicrobial activity against intracellular beta-lactamase negative methicillin-susceptible Staphylococcus aureus ATCC 25923 infected in human Calu3 cells assessed as decrease in bacterial growth after 24 hrs at pH 7.4 Staphylococcus aureus 0.52 ug.mL-1
Antimicrobial activity against intracellular hospital acquired methicillin-resistant Staphylococcus aureus ATCC 33591 infected in human Calu3 cells assessed as decrease in bacterial growth after 24 hrs at pH 7.4 Staphylococcus aureus 0.39 ug.mL-1
Antimicrobial activity against beta-lactamase negative methicillin-susceptible Staphylococcus aureus ATCC 25923 infected in human THP-1 cells assessed as decrease in bacterial growth after 24 hrs at pH 7.4 Staphylococcus aureus 0.27 ug.mL-1
Antimicrobial activity against hospital acquired methicillin-resistant Staphylococcus aureus ATCC 33591 infected in human THP-1 cells assessed as decrease in bacterial growth after 24 hrs at pH 7.4 Staphylococcus aureus 0.26 ug.mL-1
Antimicrobial activity against beta-lactamase negative methicillin-susceptible Staphylococcus aureus ATCC 25923 infected in human THP-1 cells assessed as decrease in bacterial growth after 24 hrs at pH 5.5 Staphylococcus aureus 4.44 ug.mL-1
Antimicrobial activity against hospital acquired methicillin-resistant Staphylococcus aureus ATCC 33591 infected in human THP-1 cells assessed as decrease in bacterial growth after 24 hrs at pH 5.5 Staphylococcus aureus 4.25 ug.mL-1
Antimicrobial activity against constitutive beta-lactamase negative methicillin-resistant Staphylococcus aureus COL NRS100 infected in human THP-1 cells assessed as decrease in bacterial growth after 24 hrs at pH 5.5 Staphylococcus aureus subsp. aureus COL 2.74 ug.mL-1
Antimicrobial activity against hospital acquired methicillin-resistant Staphylococcus aureus N4120032 obtained from wound infection opf patient infected in human THP-1 cells assessed as decrease in bacterial growth after 24 hrs at pH 5.5 Staphylococcus aureus 9.26 ug.mL-1
Antimicrobial activity against hospital acquired methicillin-resistant Staphylococcus aureus N4120210 obtained from urinary tract infection of patient infected in human THP-1 cells assessed as decrease in bacterial growth after 24 hrs at pH 5.5 Staphylococcus aureus 8.51 ug.mL-1
Antimicrobial activity against hospital acquired methicillin-resistant Staphylococcus aureus HMC546 infected in human THP-1 cells assessed as decrease in bacterial growth after 24 hrs at pH 5.5 Staphylococcus aureus 5.67 ug.mL-1
Antimicrobial activity against Panton-valentine leukocidin positive community acquired methicillin-resistant Staphylococcus aureus N4090440 obtained from wound infection of patient infected in human THP-1 cells assessed as decrease in bacterial growth after 24 hrs at pH 5.5 Staphylococcus aureus 3.14 ug.mL-1
Antimicrobial activity against Panton-valentine leukocidin positive community acquired methicillin-resistant Staphylococcus aureus N4042228 infected in human THP-1 cells assessed as decrease in bacterial growth after 24 hrs at pH 5.5 Staphylococcus aureus 10.8 ug.mL-1
Antimicrobial activity against Panton-valentine leukocidin positive community acquired methicillin-resistant Staphylococcus aureus NRS192 obtained from patient with pneumonia and septic arthritis infected in human THP-1 cells assessed as decrease in bacterial growth after 24 hrs at pH 5.5 Staphylococcus aureus 6.07 ug.mL-1
Antimicrobial activity against hospital acquired methicillin-resistant and vancomycin-intermediate Staphylococcus aureus NRS18 obtained from wound, skin and soft tissue infection of patient infected in human THP-1 cells assessed as decrease in bacterial growth after 24 hrs at pH 5.5 Staphylococcus aureus 3.96 ug.mL-1
Antimicrobial activity against hospital acquired methicillin-resistant and vancomycin-intermediate Staphylococcus aureus NRS126 obtained from bloodstream infection of patient infected in human THP-1 cells assessed as decrease in bacterial growth after 24 hrs at pH 5.5 Staphylococcus aureus 5.33 ug.mL-1
Antimicrobial activity against hospital acquired methicillin-resistant and vancomycin-intermediate Staphylococcus aureus VRS2 obtained from wound, skin and soft tissue infection of patient infected in human THP-1 cells assessed as decrease in bacterial growth after 24 hrs at pH 5.5 Staphylococcus aureus VRS2 3.63 ug.mL-1
Antimicrobial activity against animal acquired methicillin-resistant Staphylococcus aureus N7112046 infected in human THP-1 cells assessed as decrease in bacterial growth after 24 hrs at pH 5.5 Staphylococcus aureus 6.99 ug.mL-1
Inhibition of Escherichia coli MC4100 Beta-Lactamase CMY-30 using cephalothin as reporter substrate Escherichia coli 2.3 nM
Inhibition of Escherichia coli MC4100 Beta-Lactamase CMY-2 using cephalothin as reporter substrate Escherichia coli 0.2 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 7.15 %
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

Cross References

Resources Reference
ChEBI 49566
ChEMBL CHEMBL891
DrugBank DB01147
DrugCentral 720
FDA SRS O6X5QGC2VB
Human Metabolome Database HMDB0015278
Guide to Pharmacology 11126
KEGG C06923
PDB CXN
PharmGKB PA449059
PubChem 6098
SureChEMBL SCHEMBL2953
ZINC ZINC000003875417
CONTENTS