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Compound Detail

CHEMBL2107817

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

Basic Information

ChEMBL ID CHEMBL2107817
Name AVIBACTAM SODIUM
Phase Approved
Structure Type MOL
InChI Key RTCIKUMODPANKX-JBUOLDKXSA-M
Therapeutic ✓ Yes
Parent Compound CHEMBL1689063
Active Moiety CHEMBL1689063

Known Names

Avibactam sodium Avibactam sodium component of avycaz Avibactam sodium salt Nxl 104 Nxl-104 NXL104
3
Targets
15
Activities
3
Assay Types
7
PK Parameters
20
Publications
6
Known Names
4
Indications
1
Mechanisms

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
USAN Stem -bactam
USAN Year 2012

Extended Properties

Molecular Formula C7H10N3NaO6S
MW 287.23
Aromatic Rings 0
Heavy Atoms 17
NP-Likeness -0.25

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bacterial beta-lactamase TEM inhibitor INHIBITOR Beta-lactamase TEM ✓ ✓

Indications

Intraabdominal Infections Pyelonephritis Urinary Tract Infections Infections

Activity Summary

Kd 6 meas. best 8.05
Ki 5 meas. best 6.05
IC50 4 meas. best 7.29

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Kd 8.05 7.5183 9.0 6
Unchecked
CHEMBL612545
 IC50 7.29 5.745 51.0 2
Peptidoglycan D,D-transpeptidase MrdA
CHEMBL1840
 IC50 6.23 6.23 590.0 1
Beta-lactamase
CHEMBL5031
 IC50 6.19 6.19 650.0 1
Unchecked
CHEMBL612545
 Ki 6.05 5.378 900.0 5

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.4667 hr Pseudomonas aeruginosa PAO1
T1/2 1.367 hr Bacteria
T1/2 0.55 hr Bacteria
T1/2 0.24 hr Bacteria
T1/2 23.93 hr Bacteria
T1/2 30.38 hr Bacteria
T1/2 16.67 hr Bacteria

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Kd = 9.0 nM 8.05 Binding affinity to bacteria OXA-48 assessed as dissociation constant 29627985
Unchecked Kd = 11.0 nM 7.96 Binding affinity to bacteria KPC-2 assessed as dissociation constant 29627985
Unchecked Kd = 27.0 nM 7.57 Binding affinity to bacteria Oxa-23 assessed as dissociation constant 29627985
Unchecked Kd = 27.6 nM 7.56 Binding affinity to bacteria PDC-3 assessed as dissociation constant 29627985
Unchecked IC50 = 51.0 nM 7.29 Inhibition beta lactamase PDC-1 in Pseudomonas aeruginosa PAO1 using nitrocefin ... 33913328
Unchecked Kd = 90.0 nM 7.05 Binding affinity to bacteria ADC-7 assessed as dissociation constant 29627985
Unchecked Kd = 121.0 nM 6.92 Binding affinity to bacteria OXA-23/40 assessed as dissociation constant 29627985
Peptidoglycan D,D-transpeptidase MrdA IC50 = 590.0 nM 6.23 Inhibition of bocillin-FL binding to Escherichia coli K12 NusA-fused/His6-tagged... 30995398
Beta-lactamase IC50 = 650.0 nM 6.19 Beta-Lactamase Enzyme Inhibition Assay: For the measurement of β-lactamase inhib... -
Unchecked Ki = 900.0 nM 6.05 Inhibition of bacteria KPC-2 assessed as apparent inhibition constant using nitr... 29627985
Unchecked Ki = 990.0 nM 6.0 Inhibition beta lactamase PDC-1 in Pseudomonas aeruginosa PAO1 assessed as appar... 33913328
Unchecked Ki = 2500.0 nM 5.6 Inhibition of bacteria PDC-3 assessed as apparent inhibition constant using nitr... 29627985
Unchecked Ki = 19000.0 nM 4.72 Inhibition of bacteria ADC-7 assessed as apparent inhibition constant using nitr... 29627985
Unchecked Ki = 30000.0 nM 4.52 Inhibition of bacteria OXA-48 assessed as apparent inhibition constant using nit... 29627985
Unchecked IC50 = 63000.0 nM 4.2 Inhibition of Escherichia coli PBP2 28594170

Literature References

PubMed DOI Target Context # Activities
29627985 10.1021/acs.jmedchem.8b00091 Klebsiella pneumoniae 60
29627985 10.1021/acs.jmedchem.8b00091 Acinetobacter baumannii 42
33913328 10.1021/acs.jmedchem.1c00369 Unchecked 41
29627985 10.1021/acs.jmedchem.8b00091 Unchecked 36
29627985 10.1021/acs.jmedchem.8b00091 Escherichia coli 18
29627985 10.1021/acs.jmedchem.8b00091 Pseudomonas aeruginosa 15
32242415 10.1021/acs.jmedchem.9b02125 Escherichia coli 10
30288219 10.1039/C8MD00342D Unchecked 7
32242415 10.1021/acs.jmedchem.9b02125 Unchecked 7
30995398 10.1021/acs.jmedchem.9b00338 Escherichia coli 3
30995398 10.1021/acs.jmedchem.9b00338 Pseudomonas aeruginosa 3
31663735 10.1021/acs.jmedchem.9b01279 Unchecked 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
32196336 10.1021/acs.jmedchem.0c00127 Beta-lactamase OXA-23 1
32196336 10.1021/acs.jmedchem.0c00127 Klebsiella pneumoniae 1
32196336 10.1021/acs.jmedchem.0c00127 Acinetobacter baumannii 1
32196336 10.1021/acs.jmedchem.0c00127 Unchecked 1
28594170 10.1021/acs.jmedchem.7b00215 Unchecked 1
- 10.1101/2020.04.21.054387 SARS-CoV-2 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1

Data from ChEMBL 36 via Core Engine