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Compound Detail

CHEMBL3301605

RELEBACTAM
💊 Approved Drug
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💊 Approved Drug
O.O=C(NC1CCNCC1)[C@@H]1CC[C@@H]2CN1C(=O)N2OS(=O)(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3301605
Name RELEBACTAM
Phase Approved
Structure Type MOL
InChI Key TWFRCSHLWKJBQH-UXQCFNEQSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL3112741
Active Moiety CHEMBL3112741

Known Names

(-)-relebactam monohydrate MK-7655 MONOHYDRATE Relebactam Relebactam component of mk-7655a Relebactam component of recarbrio Relebactam component of recarbrio monohydrate Relebactam hydrate Relebactam monohydrate
3
Targets
12
Activities
3
Assay Types
6
PK Parameters
17
Publications
8
Known Names
8
Indications
6
Mechanisms

Molecular Properties

348.4
MW (Da)
-1.14
ALogP
6
HBA
3
HBD
128.3
PSA (Ų)
0.55
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2019
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral
USAN Stem -bactam
USAN Year 2014

Extended Properties

Molecular Formula C12H22N4O7S
MW 366.40
Aromatic Rings 0
Heavy Atoms 23
NP-Likeness -0.47

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Beta-lactamase SHV-1 inhibitor INHIBITOR Beta-lactamase SHV-1 ✓ ✓
Bacterial beta-lactamase TEM inhibitor INHIBITOR Beta-lactamase TEM ✓ ✓
Beta-lactamase inhibitor INHIBITOR Beta-lactamase ✓ ✓
Beta-lactamase inhibitor INHIBITOR Beta-lactamase ✓ ✓
Carbapenem-hydrolyzing beta-lactamase KPC inhibitor INHIBITOR Carbapenem-hydrolyzing beta-lactamase KPC ✓ ✓
Beta-lactamase CTX-M inhibitor INHIBITOR Beta-lactamase CTX-M ✓ ✓

Indications

Intraabdominal Infections Pyelonephritis Urinary Tract Infections Bacterial Infections Pneumonia, Bacterial Hematologic Neoplasms Communicable Diseases Sepsis

Activity Summary

IC50 5 meas. best 6.68
Ki 4 meas. best 5.92
Kd 3 meas. best 8.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Kd 8.05 7.72 9.0 3
Beta-lactamase
CHEMBL1641358
 IC50 6.68 6.68 210.0 1
Unchecked
CHEMBL612545
 IC50 6.68 6.1333 210.0 3
Beta-lactamase
CHEMBL1641350
 IC50 6.33 6.33 465.0 1
Unchecked
CHEMBL612545
 Ki 5.92 5.495 1200.0 4

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.7667 hr Bacteria
T1/2 0.65 hr Bacteria
T1/2 0.2133 hr Bacteria
t1/2 - - Bacteria
t1/2 - - Bacteria
t1/2 - - 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 KPC-2 assessed as dissociation constant 29627985
Unchecked Kd = 20.0 nM 7.7 Binding affinity to bacteria PDC-3 assessed as dissociation constant 29627985
Unchecked Kd = 39.0 nM 7.41 Binding affinity to bacteria ADC-7 assessed as dissociation constant 29627985
Unchecked IC50 = 210.0 nM 6.68 Inhibition of beta-lactamase KPC-2 in Klebsiella pneumoniae assessed as inhibiti... 24433862
Beta-lactamase IC50 = 210.0 nM 6.68 Spectrophotometric Assay: Enzyme activities were measured in the presence of the... -
Unchecked IC50 = 465.0 nM 6.33 Inhibition of beta-lactamase AmpC in Pseudomonas aeruginosa assessed as inhibiti... 24433862
Beta-lactamase IC50 = 465.0 nM 6.33 Spectrophotometric Assay: Enzyme activities were measured in the presence of the... -
Unchecked Ki = 1200.0 nM 5.92 Inhibition of beta lactamase KPC-2 in Klebsiella pneumoniae assessed as apparent... 33479650
Unchecked Ki = 2200.0 nM 5.66 Inhibition of bacteria KPC-2 assessed as apparent inhibition constant using nitr... 29627985
Unchecked Ki = 3200.0 nM 5.5 Inhibition of bacteria PDC-3 assessed as apparent inhibition constant using nitr... 29627985
Unchecked IC50 = 4100.0 nM 5.39 Inhibition of beta-lactamase AmpC in Acinetobacter baumannii assessed as inhibit... 24433862
Unchecked Ki = 12600.0 nM 4.9 Inhibition of bacteria ADC-7 assessed as apparent inhibition constant using nitr... 29627985

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
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
30288219 10.1039/C8MD00342D Unchecked 12
32196336 10.1021/acs.jmedchem.0c00127 Unchecked 6
24433862 10.1016/j.bmcl.2013.12.101 Unchecked 6
32980511 10.1016/j.bmcl.2020.127575 Pseudomonas aeruginosa 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
33479650 10.1039/c9md00557a Unchecked 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
32196336 10.1021/acs.jmedchem.0c00127 Beta-lactamase TEM-1 1
32196336 10.1021/acs.jmedchem.0c00127 Beta-lactamase OXA-23 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
24433862 10.1016/j.bmcl.2013.12.101 Beta-lactamase 1

Data from ChEMBL 36 via Core Engine