TAZOBACTAM

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
ATC J01CG02
UNII SE10G96M8W
EPA CompTox DTXSID8023634

Structure

InChI Key LPQZKKCYTLCDGQ-WEDXCCLWSA-N
Smiles C[C@]1(Cn2ccnn2)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O
InChI
InChI=1S/C10H12N4O5S/c1-10(5-13-3-2-11-12-13)8(9(16)17)14-6(15)4-7(14)20(10,18)19/h2-3,7-8H,4-5H2,1H3,(H,16,17)/t7-,8+,10+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C10H12N4O5S
Molecular Weight 300.3
AlogP -1.52
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 122.46
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 20.0
Assay Description Organism Bioactivity Reference
Inhibitory activity against Branhamella catarrhalis 89001 Class-III BRO-1 type beta-lactamase enzyme b.catarr 0.01 ug.mL-1
Compound was tested for inhibition of Beta-lactamase from Bacillus licheniformis 749/C Bacillus licheniformis 510.0 nM
Inhibitory activity against Bacteroides fragilis 88854 Class-I beta-lactamase enzyme Bacteroides fragilis 0.8 ug.mL-1
Compound was tested for inhibition of Beta-lactamase from Citrobacter freundii 1982 Citrobacter freundii 930.0 nM
Inhibitory activity against Citrobacter freundii 87470 Class-I beta-lactamase enzyme Citrobacter freundii 0.05 ug.mL-1
Inhibitory activity against beta-Lactamase enzyme derived from Enterobacter cloacae P99 Enterobacter cloacae 943.0 nM
Inhibitory activity against Enterobacter cloacae HC8 Class-I beta-lactamase enzyme type P99 Enterobacter cloacae 0.1 ug.mL-1
Inhibitory activity against Escherichia coli HA208 Class-III SHV-1 type beta-lactamase enzyme Escherichia coli 0.04 ug.mL-1
Inhibitory activity against Escherichia coli HA209 Class-V OXA-1 type beta-lactamase enzyme Escherichia coli 0.13 ug.mL-1
Inhibitory activity against Escherichia coli HA58R Class-III TEM-1 type beta-lactamase enzyme Escherichia coli 0.006 ug.mL-1
Inhibitory activity against Klebsiella oxytoca HC7 Class-IV K1 type beta-lactamase enzyme Klebsiella oxytoca 0.032 ug.mL-1
Compound was tested for inhibition of beta-Lactamases from Morganell morgani U1627 Morganella morganii 190.0 nM
Inhibitory activity against Proteus vulgaris HJ33C Class-I beta-lactamase enzyme Proteus vulgaris 0.006 ug.mL-1
Compound was tested for inhibition of Beta-lactamase from Pseudomonas aeruginosa 18SH Pseudomonas aeruginosa 820.0 nM
Compound was tested for inhibition of Beta-lactamase from Staphylococcus aureus PCI Staphylococcus aureus 500.0 nM
Inhibitory activity against Staphylococcus aureus CJ8 beta-lactamase enzyme Staphylococcus aureus 0.05 ug.mL-1
In vitro inhibitory activity against Class A (Imi-1) beta-Lactamases None 30.0 nM
In vitro inhibitory activity against Class A (TEM-1) beta-Lactamases None 100.0 nM
Compound was tested for inhibition of Beta-lactamase from OXA-1 None 240.0 nM
Compound was tested for inhibition of Beta-lactamase from PSE-1 None 560.0 nM
Compound was tested for inhibition of Beta-lactamase from RTEM-1 None 420.0 nM
Compound was tested for inhibition of Beta-lactamase from RTEM-2 None 560.0 nM
Compound was tested for inhibition of Beta-lactamase from RTEM-3 None 150.0 nM
Compound was tested for inhibition of Beta-lactamase from SHV-2 None 930.0 nM
Compound was tested for inhibition of Beta-lactamase fromOXA-2 None 830.0 nM
In vitro inhibitory activity against Beta-lactamase TEM-1 of class A enzyme None 100.0 nM
Inhibitory activity against class A Beta-lactamase TEM isolated from Enterobacter coli Enterobacter cloacae 60.0 nM
Inhibitory activity against beta-Lactamase enzyme derived from Escherichia coli WC3310 TEM-2 Escherichia coli 25.0 nM
Inhibitory activity against class A TEM-1 beta-lactamase None 250.0 nM
In vitro inhibitory concentration against TEM-1 enzyme Escherichia coli 60.0 nM
Inhibition of Escherichia coli TEM1 Escherichia coli 100.0 nM
Inhibition of Escherichia coli BL21(DE3) beta-lactamase TEM151 Escherichia coli 270.0 nM
Inhibition of Escherichia coli BL21(DE3) beta-lactamase TEM152 Escherichia coli 400.0 nM
Inhibition of Escherichia coli BL21(DE3) beta-lactamase TEM28 Escherichia coli 20.0 nM
Inhibition of Escherichia coli BL21(DE3) beta-lactamase TEM36 Escherichia coli 130.0 nM
Inhibition of Escherichia coli BL21(DE3) beta-lactamase TEM1 Escherichia coli 30.0 nM
Inhibition of Citrobacter gillenii CIP 106783 Beta-lactamase GIL1 expressed in Escherichia coli DH10B Citrobacter gillenii 40.0 nM
Inhibition of Escherichia coli TEM1 Escherichia coli 17.0 nM
Inhibition of Escherichia coli SHV1 Escherichia coli 222.0 nM
Inhibition of Escherichia coli beta-lactamase SCO1 Escherichia coli 10.0 nM
Inhibition of Escherichia coli K12 CARB1 Escherichia coli 80.0 nM
Inhibition of Escherichia coli K12 TEM1 Escherichia coli 90.0 nM
Inhibition of Escherichia coli CTX-M-15 Escherichia coli 2.0 nM
Inhibition of Escherichia coli DH5alpha beta-lactamase TEM-158 Escherichia coli 240.0 nM
Inhibition of Escherichia coli DH5alpha beta-lactamase TEM-12 Escherichia coli 130.0 nM
Inhibition of Escherichia coli DH5alpha beta-lactamase TEM-1 Escherichia coli 130.0 nM
Inhibition of Bacillus clausii NR beta-lactamase BCL1 expressed in Escherichia coli BL21 (DE3) Bacillus clausii 4.0 nM
Inhibition of Enterobacter cloacae IMI1 beta lactamase expressed in Escherichia coli DH5alpha by SDS-PAGE Enterobacter cloacae 30.0 nM
Inhibition of Klebsiella pneumoniae KPC-1 beta lactamase expressed in Escherichia coli DH5alpha by SDS-PAGE Klebsiella pneumoniae 374.0 nM
Inhibition of Citrobacter freundii PER2 beta lactamase Citrobacter freundii 96.0 nM
Inhibition of Carnobacterium divergens BM4489 penicillinase Cad-1 Carnobacterium divergens 270.0 nM
Inhibition of Pseudomonas luteola LAM Beta-lactamase LUT-1 Pseudomonas luteola 40.0 nM
Inhibition of carbapenem-resistant Klebsiella pneumoniae carbepenem-hydrolyzing beta-lactamase KPC-1 Klebsiella pneumoniae 370.0 nM
Inhibition of Pseudomonas aeruginosa GES-13 beta lactamase Pseudomonas aeruginosa 60.0 nM
Inhibition of Brachyspira pilosicoli beta-lactamase OXA-63 expressed in Escherichia coli BL21 (DE3) assessed as reduction in nitrocefin hydrolysis by spectrophotometry relative to oxacillin Brachyspira pilosicoli 160.0 nM
Inhibition of Klebsiella pneumoniae Beta-Lactamase SHV-1 Klebsiella pneumoniae 110.0 nM
Inhibition of Klebsiella pneumoniae Beta-Lactamase SHV-72 Klebsiella pneumoniae 80.0 nM
Inhibition of Burkholderia cenocepacia 07-34 beta-lactamase PenB1 Burkholderia cenocepacia 500.0 nM
Inhibition of Salmonella enterica serotype Westhampton beta-lactamase CTX-M-53 Salmonella enterica subsp. enterica serovar Westhampton 2.2 nM
Inhibition of recombinant beta-lactamase RTG4 expressed in Escherichia coli TOP10 by nitrocefin hydrolysis assay None 350.0 nM
Inhibition of recombinant beta-lactamase RTG3 expressed in Escherichia coli TOP10 by nitrocefin hydrolysis assay None 100.0 nM
Inhibition of Escherichia coli MC4100 Beta-Lactamase CMY-2 using cephalothin as reporter substrate Escherichia coli 800.0 nM
Inhibition of Klebsiella pneumoniae Beta-lactamase SHV-1 Klebsiella pneumoniae 206.0 nM
Inhibition of Beta-lactamase TEM-1 None 14.0 nM
Inhibition of beta-lactamase SHV-4 assessed as nitrocefin hydrolysis after 5 mins enzyme-compound preincubation None 55.0 nM
Inhibition of beta-lactamase CTX-M-15 assessed as nitrocefin hydrolysis after 5 mins enzyme-compound preincubation None 6.0 nM
Inhibition of beta-lactamase TEM- 1 assessed as nitrocefin hydrolysis after 5 mins enzyme-compound preincubation None 32.0 nM
Inhibition of beta-lactamase TEM-1 after 5 seconds incubation with nitrocefin substrate by spectrophotometry None 30.0 nM
Inhibition of Beta-lactamase GES-1 E104, G170 mutant preincubated for 5 mins before substrate addition using cephalothin substrate by spectrophotometry None 30.0 nM
Inhibition of Beta-lactamase GES-7 K104, G170 mutant preincubated for 5 mins before substrate addition using cephalothin substrate by spectrophotometry None 60.0 nM
Inhibition of Beta-lactamase GES-2 E104, N170 mutant preincubated for 5 mins before substrate addition using cephalothin substrate by spectrophotometry None 30.0 nM
Inhibition of Beta-lactamase GES-5 E104, S170 mutant preincubated for 5 mins before substrate addition using cephalothin substrate by spectrophotometry None 500.0 nM
Inhibition of Beta-lactamase GES-6 K104, S170 mutant preincubated for 5 mins before substrate addition using cephalothin substrate by spectrophotometry None 500.0 nM
Inhibition of Beta-lactamase GES-13 K104, N170 mutant preincubated for 5 mins before substrate addition using cephalothin substrate by spectrophotometry None 40.0 nM
DRUGMATRIX: beta-Lactamase enzyme inhibition (substrate: Nitrocefin) Bacillus cereus 299.0 nM
Inhibition of Beta-lactamase SHV-1 K234R protein mutant in Escherichia coli DH10B by Henri-Michaelis-Menten steady state equation analysis Escherichia coli 900.0 nM
Inhibition of wild type Beta-lactamase SHV-1 in Escherichia coli DH10B by Henri-Michaelis-Menten steady state equation analysis Escherichia coli 440.0 nM
Inhibition of Klebsiella pneumoniae CTX-M-15 pre-incubated with enzyme for 5 mins before nitrocefin substrate addition by colorimetric assay Klebsiella pneumoniae 7.0 nM
Inhibition of Escherichia coli recombinant CTX-M-15 assessed as substrate nitrocefin degradation preincubated for 10 mins followed by substrate addition measured every 10 secs for 10 mins by spectrophotometric analysis Escherichia coli 1.0 nM
Inhibition of Escherichia coli recombinant SHV-12 assessed as substrate nitrocefin degradation preincubated for 10 mins followed by substrate addition measured every 10 secs for 10 mins by spectrophotometric analysis Escherichia coli 0.4 nM
Inhibition of Escherichia coli recombinant TEM-10 assessed as substrate nitrocefin degradation preincubated for 10 mins followed by substrate addition measured every 10 secs for 10 mins by spectrophotometric analysis Escherichia coli 5.0 nM
Inhibition of Escherichia coli recombinant CMY-2 assessed as substrate nitrocefin degradation preincubated for 10 mins followed by substrate addition measured every 10 secs for 10 mins by spectrophotometric analysis Escherichia coli 710.0 nM
Cell Free Inhibition Assay: The inhibitory concentrations (IC50, [uM]) of the beta -lactamase inhibitors against purified TEM-1, SHV-1 and AmpC beta -lactamases are assessed by determining the concentration of inhibitor at which 50% of the nitrocefin hydrolysis is inhibited by the particular enzyme. Assays are performed with beta -lactamases expressed in the pET system (Novagen, San Diego, Calif.) without signal peptides. They contain an N-terminal hexa-Histidine tag that is used for purification on Ni-NTA (Qiagen, Hilden, Germany). The compounds are prepared as 50 mM stocks in DMSO and diluted into buffer P1 (50 mM phosphate, pH 7) to a final concentration of 10% DMSO. All further dilutions are done in P2 (P1 with 10% DMSO). Enzyme and compound dilutions are pre-incubated for 10 min at 37 C. and the reaction is started with the addition of pre-warmed (37 C.) nitrocefin at a final concentration of 50 mM. The change in absorption at 490 nm is followed at 37 C. for 10 min with 30 s intervals. None 222.0 nM
Cell Free Inhibition Assay: The inhibitory concentrations (IC50, [uM]) of the beta -lactamase inhibitors against purified TEM-1, SHV-1 and AmpC beta -lactamases are assessed by determining the concentration of inhibitor at which 50% of the nitrocefin hydrolysis is inhibited by the particular enzyme. Assays are performed with beta -lactamases expressed in the pET system (Novagen, San Diego, Calif.) without signal peptides. They contain an N-terminal hexa-Histidine tag that is used for purification on Ni-NTA (Qiagen, Hilden, Germany). The compounds are prepared as 50 mM stocks in DMSO and diluted into buffer P1 (50 mM phosphate, pH 7) to a final concentration of 10% DMSO. All further dilutions are done in P2 (P1 with 10% DMSO). Enzyme and compound dilutions are pre-incubated for 10 min at 37 C. and the reaction is started with the addition of pre-warmed (37 C.) nitrocefin at a final concentration of 50 mM. The change in absorption at 490 nm is followed at 37 C. for 10 min with 30 s intervals. None 17.2 nM
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 1.29 %
Inhibition of bacterial AmpC using nitrocefin as substrate preincubated for 15 mins followed by susbtrate addition and measured after 10 mins by spectrophotometric method Bacteria 730.0 nM
Inhibition of bacterial OXA-48 using nitrocefin as substrate preincubated for 15 mins followed by susbtrate addition and measured after 10 mins by spectrophotometric method Bacteria 550.0 nM
Inhibition of bacterial SHV-5 using cefotaxime as substrate preincubated for 15 mins followed by susbtrate addition and measured after 10 mins by spectrophotometric method Bacteria 15.0 nM
Inhibition of bacterial CTX-M-15 using cefotaxime as substrate preincubated for 15 mins followed by susbtrate addition and measured after 10 mins by spectrophotometric method Bacteria 1.0 nM
Inhibition of bacterial CMY-2 using nitrocefin as substrate preincubated for 15 mins followed by susbtrate addition and measured after 10 mins by spectrophotometric method Bacteria 410.0 nM
Inhibition of bacterial OXA-1 using nitrocefin as substrate preincubated for 15 mins followed by susbtrate addition and measured after 10 mins by spectrophotometric method Bacteria 430.0 nM
Inhibition of bacterial N-terminal His-tagged TEV protease site linked KPC-2 (29 to 289 amino acids) expressed in Escherichia coli Transetta (DE3) preincubated for 10 mins followed by FC5 fluorescent substrate addition by fluorescence assay Bacteria 200.0 nM
Inhibition of bacterial N-terminal His-tagged TEV protease site linked TEM-1 (24 to 286 amino acids) expressed in Escherichia coli Transetta (DE3) preincubated for 10 mins followed by FC5 fluorescent substrate addition by fluorescence assay Bacteria 190.0 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 8.33 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 6.566 %
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 -0.06 % 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 0.1 % 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 0.1 % 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 -0.06 %
Inhibition beta lactamase PDC-1 in Pseudomonas aeruginosa PAO1 using nitrocefin as substrate measured by 96 well microtitre plate Pseudomonas aeruginosa PAO1 844.4 nM

Related Entries

Cross References

Resources Reference
ChEBI 9421
ChEMBL CHEMBL404
DrugBank DB01606
DrugCentral 2572
FDA SRS SE10G96M8W
Human Metabolome Database HMDB0015544
Guide to Pharmacology 10789
KEGG C07771
PharmGKB PA164764504
PubChem 123630
SureChEMBL SCHEMBL122302
ZINC ZINC000003787060
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