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Compound Detail

CHEMBL127

MEROPENEM
💊 Approved Drug
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💊 Approved Drug
C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O)=C(S[C@@H]3CN[C@H](C(=O)N(C)C)C3)[C@H](C)[C@H]12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL127
Name MEROPENEM
Phase Approved
Structure Type MOL
InChI Key DMJNNHOOLUXYBV-PQTSNVLCSA-N
Therapeutic ✓ Yes

Known Names

ICI 194,660 ICI-194660 Meronem Meropenem Meropenem (as trihydrate) Meropenem anhydrous Meropenem component of vabomere Meropenem hydrate Meropenem trihydrate Meropenem, anhydrous Merrem Merrem i.v. +2 more
10
Targets
10
Activities
3
Assay Types
30
PK Parameters
20
Publications
14
Known Names
20
Indications
1
Mechanisms

Molecular Properties

383.5
MW (Da)
-0.31
ALogP
6
HBA
3
HBD
110.2
PSA (Ų)
0.56
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1996
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -penem
USAN Year 1992

Extended Properties

Molecular Formula C17H25N3O5S
MW 383.47
Aromatic Rings 0
Heavy Atoms 26
NP-Likeness 0.78

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bacterial penicillin-binding protein inhibitor INHIBITOR Bacterial penicillin-binding protein ✓ ✓

Indications

Bacteremia Bacterial Infections Infections Intraabdominal Infections Meningitis Meningitis Meningitis, Bacterial Urinary Tract Infections Enterobacteriaceae Infections Lung Diseases Mental Disorders Neonatal Sepsis Pneumonia Pneumonia, Bacterial Pneumonia, Ventilator-Associated Pyelonephritis Sepsis Shock, Septic Urinary Bladder Neoplasms Appendicitis

ATC Classification

J01DH02
meropenem
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

Kd 4 meas. best 6.07
EC50 3 meas. best 6.9
IC50 3 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Staphylococcus aureus
CHEMBL352
 IC50 8.0 8.0 10.0 1
Escherichia coli
CHEMBL354
 IC50 8.0 8.0 10.0 1
Pseudomonas aeruginosa
CHEMBL348
 IC50 7.7 7.7 20.0 1
Streptokinase A
CHEMBL1293228
 EC50 6.9 6.9 127.0 1
Streptococcus sp. 'group A'
CHEMBL612389
 EC50 6.82 6.82 153.0 1
OXA-48
CHEMBL1287604
 Kd 6.07 6.07 850.0 1
Streptococcus
CHEMBL612313
 EC50 5.94 5.94 1154.0 1
Metallo-beta-lactamase type 2
CHEMBL1667695
 Kd 4.96 4.96 11000.0 1
Beta-lactamase VIM-2
CHEMBL5798
 Kd 4.92 4.92 12000.0 1
Unchecked
CHEMBL612545
 Kd 4.12 4.12 75000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 6383.33 ng.hr.mL-1 Rattus norvegicus
AUC 6860.0 ng.hr.mL-1 Mus musculus
AUC - hr Mus musculus
AUC 3.29 ug ml-1 -
AUC 2.0 hr -
AUC 6383.33 ng.hr.mL-1 Rattus norvegicus
AUC 6383.33 ng.hr.mL-1 Rattus norvegicus
AUC 3.29 ug ml-1 Mus musculus
AUC 6383.33 ng.hr.mL-1 Rattus norvegicus
AUC 11583.33 ng.hr.mL-1 Canis lupus familiaris
AUC 166500.0 ng.hr.mL-1 Homo sapiens
AUC 129500.0 ng.hr.mL-1 Homo sapiens
AUC 6383.33 ng.hr.mL-1 Rattus norvegicus
CL 54.2 mL.min-1.kg-1 Rattus norvegicus
CL 54.16 mL.min-1.kg-1 Rattus norvegicus
CL 54.16 mL.min-1.kg-1 Rattus norvegicus
CL 52.0 mL.min-1.kg-1 Rattus norvegicus
CL 7.0 mL.min-1.kg-1 Canis lupus familiaris
CL 3.9 mL.min-1.kg-1 Homo sapiens
CL 6.0 L/hr Homo sapiens
CL 2.4 L/hr Homo sapiens
CL 3.5 L/hr Homo sapiens
CL 47.0 mL.min-1.kg-1 Rattus norvegicus
CL 3.9 mL.min-1.kg-1 Homo sapiens
CL 4.0 mL.min-1.kg-1 Canis lupus familiaris
CL 4.0 mL.min-1.kg-1 Homo sapiens
CL 7.0 mL.min-1.kg-1 Macaca
CL 51.16 mL.min-1.kg-1 Rattus norvegicus
Cmax 40602.92 nM Mus musculus
Cmax 19819.02 nM -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Staphylococcus aureus IC50 = 10.0 nM 8.0 Antimicrobial activity against methicillin-resistant Staphylococcus aureus ATCC ... 31287681
Escherichia coli IC50 = 10.0 nM 8.0 Antimicrobial activity against Escherichia coli ATCC 35218 assessed as inhibitio... 31287681
Pseudomonas aeruginosa IC50 = 20.0 nM 7.7 Antimicrobial activity against Pseudomonas aeruginosa ATCC 27853 assessed as inh... 31287681
Streptokinase A EC50 = 127.0 nM 6.9 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Streptococcus sp. 'group A' EC50 = 153.0 nM 6.82 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
OXA-48 Kd = 850.0 nM 6.07 Binding affinity to native signal deficient and TEV cleavage site containing His... 27165692
Streptococcus EC50 = 1154.0 nM 5.94 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify... -
Metallo-beta-lactamase type 2 Kd = 11000.0 nM 4.96 Binding affinity to His-tagged Klebsiella pneumoniae NDM-1 expressed in Escheric... 26976213
Beta-lactamase VIM-2 Kd = 12000.0 nM 4.92 Reversible binding affinity to Pseudomonas aeruginosa 301-5473 metallo-beta-lact... 26477515
Unchecked Kd = 75000.0 nM 4.12 Binding affinity to recombinant bacteria NDM-1 (I31 to K268 residues)expressed i... 32229085

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 228
19029333 10.1128/aac.00485-08 Acinetobacter pittii 92
20679510 10.1128/aac.00257-10 Pseudomonas aeruginosa 79
20308376 10.1128/aac.00033-10 Acinetobacter baumannii 75
20308376 10.1128/aac.00033-10 Pseudomonas aeruginosa 75
20308376 10.1128/aac.00033-10 Escherichia coli 75
20308376 10.1128/aac.00033-10 Klebsiella pneumoniae 75
19995927 10.1128/aac.01190-09 Klebsiella pneumoniae 66
19738025 10.1128/aac.00574-09 Pseudomonas aeruginosa 64
19307366 10.1128/aac.01531-08 Streptococcus pneumoniae 55
17967915 10.1128/aac.00689-07 Acinetobacter baumannii 52
17967915 10.1128/aac.00689-07 Pseudomonas aeruginosa 51
- 10.1039/C1MD00095K Pseudomonas aeruginosa 51
29336873 10.1016/j.bmcl.2018.01.006 Escherichia coli 45
18779357 10.1128/aac.00381-08 Pseudomonas aeruginosa 42
20308379 10.1128/aac.01525-09 Pseudomonas aeruginosa 41
19805565 10.1128/aac.01099-09 Klebsiella pneumoniae 40
18591275 10.1128/aac.01684-07 Acinetobacter baumannii 40
17283197 10.1128/aac.00752-06 Klebsiella pneumoniae 39
19188398 10.1128/aac.01172-08 Pseudomonas aeruginosa 38

Data from ChEMBL 36 via Core Engine