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Compound Detail

CHEMBL1359

ERTAPENEM
💊 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)Nc4cccc(C(=O)O)c4)C3)[C@H](C)[C@H]12

Basic Information

ChEMBL ID CHEMBL1359
Name ERTAPENEM
Phase Approved
Structure Type MOL
InChI Key JUZNIMUFDBIJCM-ANEDZVCMSA-N
Therapeutic ✓ Yes

Known Names

Ertapenem
0
Targets
0
Activities
0
Assay Types
20
PK Parameters
20
Publications
1
Known Names
13
Indications
3
Mechanisms

Molecular Properties

475.5
MW (Da)
0.94
ALogP
7
HBA
5
HBD
156.3
PSA (Ų)
0.36
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2001
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -penem
USAN Year 2000

Extended Properties

Molecular Formula C22H25N3O7S
MW 475.52
Aromatic Rings 1
Heavy Atoms 33
NP-Likeness 0.16

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bacterial penicillin-binding protein inhibitor INHIBITOR Bacterial penicillin-binding protein
Peptidoglycan D,D-transpeptidase FtsI inhibitor INHIBITOR Peptidoglycan D,D-transpeptidase FtsI
Cell shape peptidoglycan synthetase penicillin-binding protein 2 inhibitor INHIBITOR Cell shape peptidoglycan synthetase penicillin-binding protein 2

Indications

Bacterial Infections Diabetic Foot Gonorrhea Infections Osteomyelitis Pneumonia Urinary Tract Infections Appendicitis Pyelonephritis Renal Insufficiency, Chronic Tuberculosis Tuberculosis, Pulmonary Endometritis

ATC Classification

J01DH03
ertapenem
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Pharmacokinetic Data

Parameter Value Units Species
AUC 4232.13 ng.hr.mL-1 Canis lupus familiaris
AUC 3728.08 ng.hr.mL-1 Rattus norvegicus
AUC 228.25 ng.hr.mL-1 Rattus norvegicus
AUC 185.45 ng.hr.mL-1 Rattus norvegicus
CL 3.8 L/hr Homo sapiens
CL 0.45 mL.min-1.kg-1 Homo sapiens
Cmax 241840.51 nM Homo sapiens
Cmax 90427.32 nM Homo sapiens
F 0.65 % Rattus norvegicus
F 0.53 % Rattus norvegicus
Fu 0.1 - Homo sapiens
MRT 4.4 hr Homo sapiens
T1/2 3.9 hr Homo sapiens
T1/2 5.4 hr Homo sapiens
T1/2 5.0 hr Homo sapiens
T1/2 5.0 hr Macaca mulatta
T1/2 3.8 hr Homo sapiens
T1/2 4.0 hr Homo sapiens
Tmax 0.5 hr Homo sapiens
Tmax 2.7 hr Homo sapiens

Literature References

PubMed DOI Target Context # Activities
20308376 10.1128/aac.00033-10 Escherichia coli 75
20308376 10.1128/aac.00033-10 Pseudomonas aeruginosa 75
20308376 10.1128/aac.00033-10 Klebsiella pneumoniae 75
20308376 10.1128/aac.00033-10 Acinetobacter baumannii 75
19805565 10.1128/aac.01099-09 Klebsiella pneumoniae 40
17283197 10.1128/aac.00752-06 Klebsiella pneumoniae 40
17283197 10.1128/aac.00752-06 Escherichia coli 28
20660684 10.1128/aac.00008-10 Klebsiella pneumoniae 27
20660683 10.1128/aac.01301-09 Klebsiella pneumoniae 26
20421396 10.1128/aac.00197-10 Escherichia coli 23
20086157 10.1128/aac.01312-09 Escherichia coli 21
20350950 10.1128/aac.01818-09 Klebsiella pneumoniae 20
18347108 10.1128/aac.01440-07 Klebsiella pneumoniae 20
20231393 10.1128/aac.01359-09 Escherichia coli 19
19029330 10.1128/aac.01007-08 Klebsiella pneumoniae 18
20679507 10.1128/aac.01607-09 Klebsiella pneumoniae 17
19029330 10.1128/aac.01007-08 Escherichia coli 16
18519713 10.1128/aac.01341-07 Enterobacter cloacae 16
19805565 10.1128/aac.01099-09 Escherichia coli 15
18227185 10.1128/aac.01451-07 Escherichia coli 14

Data from ChEMBL 36 via Core Engine