CEFUROXIME

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category Free-form
ATC J01DC02 S01AA27
UNII O1R9FJ93ED

Structure

InChI Key JFPVXVDWJQMJEE-IZRZKJBUSA-N
Smiles CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(COC(N)=O)CS[C@H]12)c1ccco1
InChI
InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9-/t10-,14-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H16N4O8S
Molecular Weight 424.39
AlogP -0.54
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 7.0
Polar Surface Area 173.76
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 29.0
Assay Description Organism Bioactivity Reference
Antimicrobial activity against methicillin-susceptible Staphylococcus aureus ATCC 25923 infected in human keratinocytes assessed as change in bacterial count after 24 hrs Staphylococcus aureus 0.27 ug.mL-1
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 0.001 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 2527 PBP1A Streptococcus pneumoniae 0.006 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3676 PBP1A Streptococcus pneumoniae 0.008 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3243 PBP1A Streptococcus pneumoniae 0.006 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3665 PBP1A Streptococcus pneumoniae 0.002 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3009 PBP1A Streptococcus pneumoniae 0.01 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1076 PBP1A Streptococcus pneumoniae 0.004 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1077 PBP1A Streptococcus pneumoniae 0.164 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 24 PBP1B Streptococcus pneumoniae 0.923 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3413 PBP1B Streptococcus pneumoniae 0.032 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 2527 PBP1B Streptococcus pneumoniae 0.028 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3676 PBP1B Streptococcus pneumoniae 0.038 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3243 PBP1B Streptococcus pneumoniae 0.075 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3665 PBP1B Streptococcus pneumoniae 0.016 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3009 PBP1B Streptococcus pneumoniae 0.024 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1076 PBP1B Streptococcus pneumoniae 0.008 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1077 PBP1B Streptococcus pneumoniae 0.008 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 24 PBP2X Streptococcus pneumoniae 0.198 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3413 PBP2X Streptococcus pneumoniae 0.004 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 2527 PBP2X Streptococcus pneumoniae 0.003 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3676 PBP2X Streptococcus pneumoniae 0.02 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3243 PBP2X Streptococcus pneumoniae 0.014 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3665 PBP2X Streptococcus pneumoniae 0.014 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3009 PBP2X Streptococcus pneumoniae 4e-05 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1076 PBP2X Streptococcus pneumoniae 0.002 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1077 PBP2X Streptococcus pneumoniae 0.006 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 24 PBP2A Streptococcus pneumoniae 0.016 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3413 PBP2A Streptococcus pneumoniae 0.002 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 2527 PBP2A Streptococcus pneumoniae 0.01 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3676 PBP2A Streptococcus pneumoniae 0.011 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3665 PBP2A Streptococcus pneumoniae 0.009 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3009 PBP2A Streptococcus pneumoniae 0.008 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1076 PBP2A Streptococcus pneumoniae 0.004 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 24 PBP2B Streptococcus pneumoniae 0.038 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3413 PBP2B Streptococcus pneumoniae 0.0005 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 2527 PBP2B Streptococcus pneumoniae 2.646 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3676 PBP2B Streptococcus pneumoniae 0.472 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3243 PBP2B Streptococcus pneumoniae 0.023 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3665 PBP2B Streptococcus pneumoniae 14.74 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3009 PBP2B Streptococcus pneumoniae 1.656 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1076 PBP2B Streptococcus pneumoniae 0.171 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1077 PBP2B Streptococcus pneumoniae 1.164 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 24 PBP3 Streptococcus pneumoniae 0.002 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3413 PBP3 Streptococcus pneumoniae 0.004 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 2527 PBP3 Streptococcus pneumoniae 0.038 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3676 PBP3 Streptococcus pneumoniae 0.048 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3243 PBP3 Streptococcus pneumoniae 0.023 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3665 PBP3 Streptococcus pneumoniae 0.047 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3009 PBP3 Streptococcus pneumoniae 0.024 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1076 PBP3 Streptococcus pneumoniae 0.021 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1077 PBP3 Streptococcus pneumoniae 0.071 ug.mL-1
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 3.14 %
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 0.18 % 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 0.18 %

Related Entries

Cross References

Resources Reference
ChEBI 3515
ChEMBL CHEMBL1436
DrugBank DB01112
DrugCentral 565
FDA SRS O1R9FJ93ED
Human Metabolome Database HMDB0015244
Guide to Pharmacology 10900
KEGG C06894
PDB KOV
PubChem 5479529
SureChEMBL SCHEMBL1821942
ZINC ZINC000003871978
CONTENTS