CEFTOBIPROLE

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
UNII 5T97333YZK
EPA CompTox DTXSID40870229

Structure

InChI Key VOAZJEPQLGBXGO-SDAWRPRTSA-N
Smiles Nc1nc(/C(=N/O)C(=O)N[C@@H]2C(=O)N3C(C(=O)O)=C(/C=C4\CCN([C@@H]5CCNC5)C4=O)CS[C@H]23)ns1
InChI
InChI=1S/C20H22N8O6S2/c21-20-24-14(26-36-20)11(25-34)15(29)23-12-17(31)28-13(19(32)33)9(7-35-18(12)28)5-8-2-4-27(16(8)30)10-1-3-22-6-10/h5,10,12,18,22,34H,1-4,6-7H2,(H,23,29)(H,32,33)(H2,21,24,26)/b8-5+,25-11-/t10-,12-,18-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H22N8O6S2
Molecular Weight 534.58
AlogP -1.44
Hydrogen Bond Acceptor 12.0
Hydrogen Bond Donor 5.0
Number of Rotational Bond 6.0
Polar Surface Area 203.44
Molecular species ZWITTERION
Aromatic Rings 1.0
Heavy Atoms 36.0

Bioactivity

Mechanism of Action Action Reference
Bacterial penicillin-binding protein inhibitor INHIBITOR BNF EMA
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Transferase
- 1900-7400 - - 66
Assay Description Organism Bioactivity Reference
Inhibition of bocillin FL binding to Pseudomonas aeruginosa PAO1 penicillin-binding protein 1b Pseudomonas aeruginosa PAO1 0.5 ug.mL-1
Inhibition of bocillin FL binding to Pseudomonas aeruginosa PAO1 penicillin-binding protein 1a Pseudomonas aeruginosa PAO1 0.1 ug.mL-1
Inhibition of bocillin FL binding to Escherichia coli MC4100 penicillin-binding protein 6 Escherichia coli 3.0 ug.mL-1
Inhibition of bocillin FL binding to Escherichia coli MC4100 penicillin-binding protein 5 Escherichia coli 8.0 ug.mL-1
Inhibition of bocillin FL binding to Escherichia coli MC4100 penicillin-binding protein 4 Escherichia coli 0.5 ug.mL-1
Inhibition of bocillin FL binding to Escherichia coli MC4100 penicillin-binding protein 3 Escherichia coli 0.2 ug.mL-1
Inhibition of bocillin FL binding to Escherichia coli MC4100 penicillin-binding protein 2 Escherichia coli 0.2 ug.mL-1
Inhibition of bocillin FL binding to Escherichia coli MC4100 penicillin-binding protein 1b Escherichia coli 8.0 ug.mL-1
Inhibition of bocillin FL binding to Escherichia coli MC4100 penicillin-binding protein 1a Escherichia coli 0.3 ug.mL-1
Inhibition of bocillin FL binding to Pseudomonas aeruginosa PAO1 penicillin-binding protein 2 Pseudomonas aeruginosa PAO1 3.0 ug.mL-1
Inhibition of bocillin FL binding to Pseudomonas aeruginosa PAO1 penicillin-binding protein 3 Pseudomonas aeruginosa PAO1 0.1 ug.mL-1
Inhibition of bocillin FL binding to Pseudomonas aeruginosa PAO1 penicillin-binding protein 4 Pseudomonas aeruginosa PAO1 0.2 ug.mL-1
Inhibition of bocillin FL binding to Pseudomonas aeruginosa PAO1 penicillin-binding protein 5/6 Pseudomonas aeruginosa PAO1 32.0 ug.mL-1
Inhibition of bocillin FL binding to methicillin-susceptible Staphylococcus aureus ATCC 29213 penicillin-binding protein 1 Staphylococcus aureus 0.1 ug.mL-1
Inhibition of bocillin FL binding to methicillin-susceptible Staphylococcus aureus ATCC 29213 penicillin-binding protein 2 Staphylococcus aureus 0.5 ug.mL-1
Inhibition of bocillin FL binding to methicillin-susceptible Staphylococcus aureus ATCC 29213 penicillin-binding protein 3 Staphylococcus aureus 0.05 ug.mL-1
Inhibition of bocillin FL binding to methicillin-susceptible Staphylococcus aureus ATCC 29213 penicillin-binding protein 4 Staphylococcus aureus 1.0 ug.mL-1
Inhibition of bocillin FL binding to methicillin-resistant Staphylococcus aureus OC 3726 penicillin-binding protein 2a Staphylococcus aureus 0.9 ug.mL-1
Inhibition of bocillin FL binding to penicillin-susceptible Streptococcus pneumoniae OC 8865 penicillin-binding protein 1a Streptococcus pneumoniae 0.03 ug.mL-1
Inhibition of bocillin FL binding to penicillin-susceptible Streptococcus pneumoniae OC 8865 penicillin-binding protein 1b Streptococcus pneumoniae 0.05 ug.mL-1
Inhibition of bocillin FL binding to penicillin-susceptible Streptococcus pneumoniae OC 8865 penicillin-binding protein 2x Streptococcus pneumoniae 0.01 ug.mL-1
Inhibition of bocillin FL binding to penicillin-susceptible Streptococcus pneumoniae OC 8865 penicillin-binding protein 2a Streptococcus pneumoniae 0.03 ug.mL-1
Inhibition of bocillin FL binding to penicillin-susceptible Streptococcus pneumoniae OC 8865 penicillin-binding protein 2b Streptococcus pneumoniae 0.06 ug.mL-1
Inhibition of bocillin FL binding to penicillin-susceptible Streptococcus pneumoniae OC 8865 penicillin-binding protein 3 Streptococcus pneumoniae 0.02 ug.mL-1
Inhibition of bocillin FL binding to penicillin-resistant Streptococcus pneumoniae OC 8819 penicillin-binding protein 1a Streptococcus pneumoniae 0.1 ug.mL-1
Inhibition of bocillin FL binding to penicillin-resistant Streptococcus pneumoniae OC 8819 penicillin-binding protein 1b Streptococcus pneumoniae 8.0 ug.mL-1
Inhibition of bocillin FL binding to penicillin-resistant Streptococcus pneumoniae OC 8819 penicillin-binding protein 2x Streptococcus pneumoniae 1.0 ug.mL-1
Inhibition of bocillin FL binding to penicillin-resistant Streptococcus pneumoniae OC 8819 penicillin-binding protein 2a Streptococcus pneumoniae 0.1 ug.mL-1
Inhibition of bocillin FL binding to penicillin-resistant Streptococcus pneumoniae OC 8819 penicillin-binding protein 2b Streptococcus pneumoniae 8.0 ug.mL-1
Inhibition of bocillin FL binding to penicillin-resistant Streptococcus pneumoniae OC 8819 penicillin-binding protein 3 Streptococcus pneumoniae 0.01 ug.mL-1
Inhibition of PBP1 in penicillin-resistant Enterococcus faecium D63r membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 0.7 ug.mL-1
Inhibition of PBP2 in penicillin-resistant Enterococcus faecium D63r membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 0.2 ug.mL-1
Inhibition of PBP3 in penicillin-resistant Enterococcus faecium D63r membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 0.5 ug.mL-1
Inhibition of PBP4 in penicillin-resistant Enterococcus faecium D63r membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 1.8 ug.mL-1
Inhibition of PBP5 in penicillin-resistant Enterococcus faecium D63r membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 1.0 ug.mL-1
Inhibition of low-affinity PBP5fm in penicillin-resistant Enterococcus faecium D63r membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 1.4 ug.mL-1
Inhibition of PBP6 in penicillin-resistant Enterococcus faecium D63r membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 16.0 ug.mL-1
Inhibition of PBP1 in wild type Enterococcus faecium D63 membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 0.6 ug.mL-1
Inhibition of PBP2 in wild type Enterococcus faecium D63 membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 0.2 ug.mL-1
Inhibition of PBP3 in wild type Enterococcus faecium D63 membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 0.6 ug.mL-1
Inhibition of PBP4 in wild type Enterococcus faecium D63 membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 1.5 ug.mL-1
Inhibition of PBP5 in wild type Enterococcus faecium D63 membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 0.7 ug.mL-1
Inhibition of low-affinity PBP5fm in wild type Enterococcus faecium D63 membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 1.0 ug.mL-1
Inhibition of PBP6 in wild type Enterococcus faecium D63 membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 16.0 ug.mL-1
Inhibition of methicillin-resistant Staphylococcus aureus COL PBP2a at 10 uM by competitive assay Staphylococcus aureus subsp. aureus COL 66.0 %
Antimicrobial activity against hospital-acquired vancomycin-intermediate Staphylococcus aureus NRS126 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 5.5 Staphylococcus aureus 0.77 ug.mL-1
Antimicrobial activity against hospital-acquired vancomycin-resistant Staphylococcus aureus VRS1 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 5.5 Staphylococcus aureus VRS1 0.77 ug.mL-1
Antimicrobial activity against Panton-valentine leucocidin-positive community-acquired methicillin-resistant Staphylococcus aureus NRS192 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 5.5 Staphylococcus aureus 0.54 ug.mL-1
Antimicrobial activity against Panton-valentine leucocidin-positive community-acquired methicillin-resistant Staphylococcus aureus N4090440 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 5.5 Staphylococcus aureus 0.54 ug.mL-1
Antimicrobial activity against Panton-valentine leucocidin-positive community-acquired methicillin-resistant Staphylococcus aureus N4042228 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 5.5 Staphylococcus aureus 0.54 ug.mL-1
Antimicrobial activity against Panton-valentine leucocidin-positive community-acquired methicillin-resistant Staphylococcus aureus STA 44 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 5.5 Staphylococcus aureus 0.54 ug.mL-1
Antimicrobial activity against Panton-valentine leucocidin-positive community-acquired methicillin-resistant Staphylococcus aureus STA 228 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 5.5 Staphylococcus aureus 0.54 ug.mL-1
Antimicrobial activity against Panton-valentine leucocidin-positive community-acquired methicillin-resistant Staphylococcus aureus isolate MEH2225605 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 5.5 Staphylococcus aureus 0.54 ug.mL-1
Antimicrobial activity against methicillin-susceptible Staphylococcus aureus ATCC 25293 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 7.4 Staphylococcus aureus 0.2 ug.mL-1
Antimicrobial activity against methicillin-susceptible Staphylococcus aureus ATCC 11632 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 7.4 Staphylococcus aureus 0.2 ug.mL-1
Antimicrobial activity against methicillin-susceptible Staphylococcus aureus NRS52 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 7.4 Staphylococcus aureus 0.2 ug.mL-1
Antimicrobial activity against hospital-acquired methicillin-resistant Staphylococcus aureus ATCC 33591 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 7.4 Staphylococcus aureus 0.28 ug.mL-1
Antimicrobial activity against hospital-acquired methicillin-resistant Staphylococcus aureus ATCC 33592 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 7.4 Staphylococcus aureus 0.28 ug.mL-1
Antimicrobial activity against hospital-acquired methicillin-resistant Staphylococcus aureus ATCC 433000 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 7.4 Staphylococcus aureus 0.28 ug.mL-1
Antimicrobial activity against hospital-acquired vancomycin-intermediate Staphylococcus aureus NRS18 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 7.4 Staphylococcus aureus 0.28 ug.mL-1
Antimicrobial activity against hospital-acquired vancomycin-intermediate Staphylococcus aureus NRS126 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 7.4 Staphylococcus aureus 0.28 ug.mL-1
Antimicrobial activity against hospital-acquired vancomycin-resistant Staphylococcus aureus VRS1 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 7.4 Staphylococcus aureus VRS1 0.28 ug.mL-1
Antimicrobial activity against Panton-valentine leucocidin-positive community-acquired methicillin-resistant Staphylococcus aureus NRS192 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 7.4 Staphylococcus aureus 0.33 ug.mL-1
Antimicrobial activity against Panton-valentine leucocidin-positive community-acquired methicillin-resistant Staphylococcus aureus N4090440 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 7.4 Staphylococcus aureus 0.33 ug.mL-1
Antimicrobial activity against Panton-valentine leucocidin-positive community-acquired methicillin-resistant Staphylococcus aureus N4042228 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 7.4 Staphylococcus aureus 0.33 ug.mL-1
Antimicrobial activity against methicillin-susceptible Staphylococcus aureus ATCC 25293 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 5.5 Staphylococcus aureus 0.41 ug.mL-1
Antimicrobial activity against methicillin-susceptible Staphylococcus aureus ATCC 11632 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 5.5 Staphylococcus aureus 0.41 ug.mL-1
Antimicrobial activity against methicillin-susceptible Staphylococcus aureus NRS52 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 5.5 Staphylococcus aureus 0.41 ug.mL-1
Antimicrobial activity against hospital-acquired methicillin-resistant Staphylococcus aureus ATCC 33591 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 5.5 Staphylococcus aureus 0.77 ug.mL-1
Antimicrobial activity against hospital-acquired methicillin-resistant Staphylococcus aureus ATCC 33592 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 5.5 Staphylococcus aureus 0.77 ug.mL-1
Antimicrobial activity against hospital-acquired methicillin-resistant Staphylococcus aureus ATCC 433000 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 5.5 Staphylococcus aureus 0.77 ug.mL-1
Antimicrobial activity against hospital-acquired vancomycin-intermediate Staphylococcus aureus NRS18 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 5.5 Staphylococcus aureus 0.77 ug.mL-1
Antimicrobial activity against Panton-valentine leucocidin-positive community-acquired methicillin-resistant Staphylococcus aureus STA 44 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 7.4 Staphylococcus aureus 0.33 ug.mL-1
Antimicrobial activity against Panton-valentine leucocidin-positive community-acquired methicillin-resistant Staphylococcus aureus STA 228 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 7.4 Staphylococcus aureus 0.33 ug.mL-1
Antimicrobial activity against Panton-valentine leucocidin-positive community-acquired methicillin-resistant Staphylococcus aureus isolate MEH2225605 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs at pH 7.4 Staphylococcus aureus 0.33 ug.mL-1
Antimicrobial activity against methicillin-susceptible Staphylococcus aureus ATCC 25923 infected in human keratinocytes assessed as change in bacterial count after 24 hrs Staphylococcus aureus 0.35 ug.mL-1
Antimicrobial activity against methicillin-resistant Staphylococcus aureus ATCC 33591 infected in human keratinocytes assessed as change in bacterial count after 24 hrs Staphylococcus aureus 1.08 ug.mL-1
Antimicrobial activity against methicillin-susceptible Staphylococcus aureus ATCC 25293 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs Staphylococcus aureus 0.07 ug.mL-1
Antimicrobial activity against methicillin-susceptible Staphylococcus aureus ATCC 11632 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs Staphylococcus aureus 0.205 ug.mL-1
Antimicrobial activity against methicillin-susceptible Staphylococcus aureus NRS52 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs Staphylococcus aureus 0.19 ug.mL-1
Antimicrobial activity against hospital-acquired methicillin-resistant Staphylococcus aureus ATCC 33591 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs Staphylococcus aureus 0.28 ug.mL-1
Antimicrobial activity against hospital-acquired methicillin-resistant Staphylococcus aureus ATCC 33592 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs Staphylococcus aureus 1.23 ug.mL-1
Antimicrobial activity against hospital-acquired methicillin-resistant Staphylococcus aureus ATCC 433000 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs Staphylococcus aureus 0.73 ug.mL-1
Antimicrobial activity against hospital-acquired vancomycin-intermediate Staphylococcus aureus NRS18 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs Staphylococcus aureus 0.26 ug.mL-1
Antimicrobial activity against hospital-acquired vancomycin-intermediate Staphylococcus aureus NRS126 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs Staphylococcus aureus 0.23 ug.mL-1
Antimicrobial activity against hospital-acquired vancomycin-resistant Staphylococcus aureus VRS1 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs Staphylococcus aureus VRS1 0.25 ug.mL-1
Antimicrobial activity against Panton-valentine leucocidin-positive community-acquired methicillin-resistant Staphylococcus aureus NRS192 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs Staphylococcus aureus 0.7 ug.mL-1
Antimicrobial activity against Panton-valentine leucocidin-positive community-acquired methicillin-resistant Staphylococcus aureus N4090440 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs Staphylococcus aureus 0.08 ug.mL-1
Antimicrobial activity against Panton-valentine leucocidin-positive community-acquired methicillin-resistant Staphylococcus aureus N4042228 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs Staphylococcus aureus 0.07 ug.mL-1
Antimicrobial activity against Panton-valentine leucocidin-positive community-acquired methicillin-resistant Staphylococcus aureus STA 44 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs Staphylococcus aureus 0.94 ug.mL-1
Antimicrobial activity against Panton-valentine leucocidin-positive community-acquired methicillin-resistant Staphylococcus aureus STA 228 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs Staphylococcus aureus 0.88 ug.mL-1
Antimicrobial activity against Panton-valentine leucocidin-positive community-acquired methicillin-resistant Staphylococcus aureus isolate MEH2225605 infected in human THP-1 cells assessed as change in bacterial count after 24 hrs Staphylococcus aureus 0.82 ug.mL-1
Inhibition of Bocillin FL binding to Streptococcus pneumoniae isolate 8865 PBP2b Streptococcus pneumoniae 0.06 ug.mL-1
Inhibition of Streptococcus pneumoniae isolate 8882 Bocillin FL binding to PBP2b 443SSNA mutant Streptococcus pneumoniae 1.2 ug.mL-1
Inhibition of Bocillin FL binding to PBP2b PBP2b 443SSNA mutant in Streptococcus pneumoniae isolate 8009 harboring E333G, N470K, E476G, T489S, E506D, and N538D mutant genes Streptococcus pneumoniae 0.9 ug.mL-1
Inhibition of Bocillin FL binding to PBP2b in Streptococcus pneumoniae isolate 8819 harboring E333G, I361L, E369D, S412P, N422Y, T426K, Q427L, Q438E, L455I, S473T, E476G, S480A, T489A, N538D, D561E, Q564K, and D625G mutant genes Streptococcus pneumoniae 8.0 ug.mL-1
Inhibition of Bocillin FL binding to PBP2b in laboratory-derived Streptococcus pneumoniae isolate R6 Streptococcus pneumoniae 0.06 ug.mL-1
Inhibition of Bocillin FL binding to PBP2b Thr446Ala mutant in laboratory-derived Streptococcus pneumoniae isolate R6 Streptococcus pneumoniae 0.7 ug.mL-1
Inhibition of Bocillin FL binding to PBP2b Thr446Ala/Ala-619-Gly mutant in laboratory-derived Streptococcus pneumoniae isolate R6 Streptococcus pneumoniae 1.7 ug.mL-1

Related Entries

Cross References

Resources Reference
ChEBI 140407
ChEMBL CHEMBL520642
DrugBank DB04918
FDA SRS 5T97333YZK
Guide to Pharmacology 10787
PubChem 135413542
SureChEMBL SCHEMBL2671901
ZINC ZINC000004424091
CONTENTS