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Compound Detail

CHEMBL702

PIPERACILLIN
💊 Approved Drug
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💊 Approved Drug
CCN1CCN(C(=O)N[C@@H](C(=O)N[C@@H]2C(=O)N3[C@@H]2SC(C)(C)[C@@H]3C(=O)O)c2ccccc2)C(=O)C1=O

Basic Information

ChEMBL ID CHEMBL702
Name PIPERACILLIN
Phase Approved
Structure Type MOL
InChI Key IVBHGBMCVLDMKU-GXNBUGAJSA-N
Therapeutic ✓ Yes

Known Names

Peracin Piperacilina Piperacillin Piperacillin anhydrous Piperacillin hydrate Piperacillin monohydrate Piperacillin, anhydrous Piperacilline
2
Targets
7
Activities
2
Assay Types
13
PK Parameters
20
Publications
8
Known Names
20
Indications

Molecular Properties

517.6
MW (Da)
-0.24
ALogP
7
HBA
3
HBD
156.4
PSA (Ų)
0.34
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1981
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -cillin
USAN Year 1977

Extended Properties

Molecular Formula C23H27N5O7S
MW 517.56
Aromatic Rings 1
Heavy Atoms 36
NP-Likeness 0.03

Indications

Bacterial Infections Abscess Cholecystitis, Acute Diabetic Foot Enterobacteriaceae Infections Hematologic Neoplasms Infections Influenza, Human Pneumonia Pneumonia, Bacterial Pneumonia, Ventilator-Associated Pseudomonas Infections Sepsis Severe Acute Respiratory Syndrome Shock, Septic Urinary Tract Infections Appendicitis Communicable Diseases Graft vs Host Disease Otitis Media

ATC Classification

J01CA12
piperacillin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

Ki 4 meas. best 6.7
IC50 3 meas. best 6.78

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
IC50 6.78 6.78 166.0 1
PER-2 beta-lactamase
CHEMBL5303
Ki 6.7 6.7 200.0 1
Unchecked
CHEMBL612545
Ki 6.7 5.8333 200.0 3

Pharmacokinetic Data

Parameter Value Units Species
CL 8.78 L/hr Homo sapiens
CL 11.7 L/hr Homo sapiens
CL 11.3 L/hr Homo sapiens
CL 11.3 L/hr Homo sapiens
CL 4.0 mL.min-1.kg-1 Homo sapiens
CL 4.0 mL.min-1.kg-1 Homo sapiens
Fu 0.5 - Homo sapiens
MRT 0.85 hr Homo sapiens
MRT 1.02 hr Homo sapiens
MRT 1.1 hr Homo sapiens
T1/2 0.69 hr Homo sapiens
T1/2 1.05 hr Homo sapiens
T1/2 0.96 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
18809945 10.1128/aac.00707-08 Pseudomonas aeruginosa 57
20421396 10.1128/aac.00197-10 Escherichia coli 46
29336873 10.1016/j.bmcl.2018.01.006 Escherichia coli 45
17261619 10.1128/aac.01278-06 Pseudomonas aeruginosa 40
19188398 10.1128/aac.01172-08 Pseudomonas aeruginosa 38
19001109 10.1128/aac.01047-08 Escherichia coli 36
18779357 10.1128/aac.00381-08 Pseudomonas aeruginosa 36
19001109 10.1128/aac.01047-08 Klebsiella pneumoniae 36
20498315 10.1128/aac.00080-10 Pseudomonas aeruginosa 32
18519713 10.1128/aac.01341-07 Enterobacter cloacae 32
20585132 10.1128/aac.00481-10 NON-PROTEIN TARGET 32
19188386 10.1128/aac.01549-08 Escherichia coli 30
18490501 10.1128/aac.00679-07 Pseudomonas aeruginosa 28
19001109 10.1128/aac.01047-08 Streptococcus pneumoniae 27
20660683 10.1128/aac.01301-09 Klebsiella pneumoniae 26
20921306 10.1128/aac.00598-10 Acinetobacter lwoffii 26
18981261 10.1128/aac.00642-08 Escherichia coli 24
20566764 10.1128/aac.00385-10 Pseudomonas aeruginosa 24
19651910 10.1128/aac.00192-09 Haemophilus influenzae 24
19506058 10.1128/aac.01655-08 Campylobacter jejuni 24

Data from ChEMBL 36 via Core Engine