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Compound Detail

CHEMBL1689063

AVIBACTAM
💊 Approved Drug
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💊 Approved Drug
NC(=O)[C@@H]1CC[C@@H]2CN1C(=O)N2OS(=O)(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1689063
Name AVIBACTAM
Phase Approved
Structure Type MOL
InChI Key NDCUAPJVLWFHHB-UHNVWZDZSA-N
Therapeutic ✓ Yes

Known Names

Avibactam Avibactam component of zavicefta Nxl-104 Nxl-104 free acid
11
Targets
55
Activities
2
Assay Types
7
PK Parameters
20
Publications
4
Known Names
8
Indications

Molecular Properties

265.2
MW (Da)
-1.53
ALogP
5
HBA
2
HBD
130.2
PSA (Ų)
0.60
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2015
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -bactam
USAN Year 2012

Extended Properties

Molecular Formula C7H11N3O6S
MW 265.25
Aromatic Rings 0
Heavy Atoms 17
NP-Likeness -0.25

Indications

Bacterial Infections Infections Pneumonia Pyelonephritis Gram-Negative Bacterial Infections Urinary Tract Infections Renal Insufficiency Systemic Inflammatory Response Syndrome

Activity Summary

IC50 45 meas. best 9.0
Ki 10 meas. best 9.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 9.57 8.2186 0.3 7
Unchecked
CHEMBL612545
 IC50 9.0 7.4454 1.0 35
Beta-lactamase TEM
CHEMBL2364670
 IC50 8.72 8.72 1.9 1
Beta-lactamase CTX-M-14
CHEMBL1287630
 IC50 8.52 8.52 3.0 1
Beta-lactamase TEM-1
CHEMBL1287599
 IC50 8.15 8.15 7.0 1
Class A carbapenemase KPC-2
CHEMBL5437
 Ki 7.96 7.96 11.0 1
Beta-lactamase
CHEMBL2725
 IC50 7.0 6.52 100.0 2
Beta-lactamase OXA-1
CHEMBL4951
 IC50 6.89 6.89 130.0 1
Beta-lactamase
CHEMBL5031
 IC50 6.89 6.89 128.0 1
Metallo-beta-lactamase type 2
CHEMBL1744488
 IC50 6.85 6.85 141.1 1
Carbapenem-hydrolyzing beta-lactamase KPC
CHEMBL6132
 IC50 6.73 6.73 186.0 1
Beta-lactamase OXA-23
CHEMBL3885669
 Ki 5.77 5.77 1700.0 1
Beta-lactamase OXA-23
CHEMBL3885669
 IC50 5.63 5.63 2320.0 1
Beta-lactamase
CHEMBL2725
 Ki 5.11 5.11 7700.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 8075.0 ng.hr.mL-1 Mus musculus
AUC 279.0 ng.hr.mL-1 Rattus norvegicus
CL 20.63 mL.min-1.kg-1 Mus musculus
CL 59.0 mL.min-1.kg-1 Rattus norvegicus
T1/2 0.1 hr Mus musculus
T1/2 0.37 hr Rattus norvegicus
Vd 1.9 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.27 nM 9.57 Inhibition of recombinant Escherichia coli SHV-12 using nitrocefin as substrate ... 32150407
Unchecked Ki = 0.41 nM 9.39 Inhibition of recombinant Escherichia coli CTX-M-14 using nitrocefin as substrat... 32150407
Unchecked IC50 = 1.0 nM 9.0 Inhibition of beta lactamase CTXM-15 in Enterobacter cloacae assessed as decreas... 33306385
Unchecked IC50 = 1.0 nM 9.0 Inhibition of Escherichia coli beta-lactamase CTX-M-15 35988449
Unchecked Ki = 1.4 nM 8.85 Inhibition of recombinant Escherichia coli TEM-10 using nitrocefin as substrate ... 32150407
Beta-lactamase TEM IC50 = 1.9 nM 8.72 Inhibition of bacterial Beta-lactamase TEM-1 (24 - 286) (unknown origin) express... 33744439
Beta-lactamase CTX-M-14 IC50 = 3.0 nM 8.52 Inhibition of Escherichia coli beta-lactamase CTX-M-14 35988449
Unchecked IC50 = 3.0 nM 8.52 Inhibition of beta-lactamase SHV-4 assessed as nitrocefin hydrolysis after 5 min... 20921316
Unchecked IC50 = 3.0 nM 8.52 Inhibition of bacterial CTX-M-15 using cefotaxime as substrate preincubated for ... 31765155
Unchecked IC50 = 3.7 nM 8.43 Inhibition of bacterial Beta-lactamase KPC-2 (29 - 289) (unknown origin) express... 33744439
Unchecked IC50 = 4.0 nM 8.4 Inhibition of Escherichia coli beta-lactamase CTX-M-44 35988449
Unchecked IC50 = 5.0 nM 8.3 Inhibition of beta-lactamase CTX-M-15 assessed as nitrocefin hydrolysis after 5 ... 20921316
Unchecked IC50 = 5.0 nM 8.3 Inhibition of beta lactamase TEM-1 in Enterobacter cloacae assessed as decrease ... 33306385
Unchecked IC50 = 7.0 nM 8.15 Inhibition of bacterial CMY-2 using nitrocefin as substrate preincubated for 15 ... 31765155
Beta-lactamase TEM-1 IC50 = 7.0 nM 8.15 Inhibition of Escherichia coli beta-lactamase TEM-1 35988449
Unchecked IC50 = 8.0 nM 8.1 Inhibition of beta lactamase AmpC in Enterobacter cloacae assessed as decrease i... 33306385
Unchecked IC50 = 8.0 nM 8.1 Inhibition of beta-lactamase TEM- 1 assessed as nitrocefin hydrolysis after 5 mi... 20921316
Unchecked IC50 = 8.0 nM 8.1 Inhibition of beta lactamase KPC-2 in Enterobacter cloacae assessed as decrease ... 33306385
Unchecked Ki = 10.0 nM 8.0 Inhibition of recombinant Escherichia coli AmpC using nitrocefin as substrate pr... 32150407
Class A carbapenemase KPC-2 Ki = 11.0 nM 7.96 Inhibition of recombinant Escherichia coli KPC-2 using nitrocefin as substrate p... 32150407

Literature References

PubMed DOI Target Context # Activities
31765155 10.1021/acs.jmedchem.9b01518 Unchecked 49
32658473 10.1021/acs.jmedchem.0c00579 Unchecked 20
34143627 10.1021/acs.jmedchem.1c00799 Klebsiella pneumoniae 16
32150407 10.1021/acs.jmedchem.9b01976 Unchecked 11
32980511 10.1016/j.bmcl.2020.127575 Pseudomonas aeruginosa 10
20921316 10.1128/aac.00568-10 Unchecked 8
20921316 10.1128/aac.00568-10 Beta-lactamase 6
33306385 10.1021/acs.jmedchem.0c01535 Unchecked 6
33306385 10.1021/acs.jmedchem.0c01535 Klebsiella pneumoniae 6
33744439 10.1016/j.bmcl.2021.127956 Unchecked 6
34143627 10.1021/acs.jmedchem.1c00799 Enterobacter cloacae 6
31063379 10.1021/acs.jmedchem.8b01781 Unchecked 5
35988449 10.1016/j.ejmech.2022.114677 Unchecked 5
37127102 10.1016/j.bmcl.2023.129308 Klebsiella pneumoniae 4
37127102 10.1016/j.bmcl.2023.129308 Escherichia coli 4
31765155 10.1021/acs.jmedchem.9b01518 ADMET 4
34143627 10.1021/acs.jmedchem.1c00799 Unchecked 4
34143627 10.1021/acs.jmedchem.1c00799 Escherichia coli 4
33306385 10.1021/acs.jmedchem.0c01535 ADMET 4
31483651 10.1021/acs.jmedchem.9b00728 Unchecked 3

Data from ChEMBL 36 via Core Engine