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Compound Detail

CHEMBL44354

CEFTAZIDIME
💊 Approved Drug
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💊 Approved Drug
CC(C)(O/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[n+]3ccccc3)CS[C@H]12)c1csc(N)n1)C(=O)O

Basic Information

ChEMBL ID CHEMBL44354
Name CEFTAZIDIME
Phase Approved
Structure Type MOL
InChI Key ORFOPKXBNMVMKC-DWVKKRMSSA-N
Therapeutic ✓ Yes

Known Names

Ceftazidima Ceftazidime Ceftazidime (arginine formulation) Ceftazidime anhydrous Ceftazidime component of avycaz Ceftazidime component of zavicefta Ceftazidime hydrate Ceftazidime pentahydrate Ceptaz Fortam Fortaz Fortum +10 more
1
Targets
3
Activities
2
Assay Types
30
PK Parameters
20
Publications
22
Known Names
15
Indications
1
Mechanisms

Molecular Properties

546.6
MW (Da)
-1.30
ALogP
11
HBA
3
HBD
191.2
PSA (Ų)
0.15
QED
2
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1985
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Black Box Warning Natural Product
USAN Stem cef-
USAN Year 1980

Extended Properties

Molecular Formula C22H22N6O7S2
MW 546.59
Aromatic Rings 2
Heavy Atoms 37
NP-Likeness 0.12

Mechanism of Action

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

Indications

Bacterial Infections Infections Intraabdominal Infections Parametritis Peritonitis Pneumonia Pyelonephritis Urinary Tract Infections Enterobacteriaceae Infections Skin Diseases Staphylococcal Skin Infections Esophageal Achalasia Meningitis, Bacterial Cystic Fibrosis Osteomyelitis

ATC Classification

J01DD02
ceftazidime
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

Ki 2 meas. best 7.7
Kd 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
Ki 7.7 7.275 20.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 14000.0 ng.hr.mL-1 Canis lupus familiaris
AUC 14000.0 ng.hr.mL-1 -
AUC 14000.0 ng.hr.mL-1 marmosets
CL 2.4 mL.min-1.kg-1 Homo sapiens
CL 5.37 L/hr Homo sapiens
CL 6.59 L/hr Homo sapiens
CL 8.5 L/hr Homo sapiens
CL 7.6 L/hr Homo sapiens
CL 8.0 L/hr Homo sapiens
CL 101.0 ml/min Homo sapiens
CL 2.4 mL.min-1.kg-1 Homo sapiens
Cmax 317971.42 nM -
Cmax 814138.57 nM Homo sapiens
Cmax 384200.22 nM Homo sapiens
F - % Homo sapiens
Fu 0.79 - Homo sapiens
MRT 1.54 hr Homo sapiens
MRT 2.1 hr Homo sapiens
MRT 2.2 hr Homo sapiens
T1/2 0.3833 hr Rattus norvegicus
T1/2 0.8167 hr Simiiformes
T1/2 1.8 hr Homo sapiens
T1/2 0.3817 hr Rattus norvegicus
T1/2 0.9333 hr Macaca mulatta
T1/2 0.7 hr Callithrix
T1/2 0.7 hr -
T1/2 0.4 hr Mus musculus
T1/2 1.96 hr -
T1/2 1.48 hr Homo sapiens
T1/2 1.94 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
33705899 10.1016/j.bmcl.2021.127928 Klebsiella pneumoniae 112
17261619 10.1128/aac.01278-06 Pseudomonas aeruginosa 104
33705899 10.1016/j.bmcl.2021.127928 Escherichia coli 85
20679510 10.1128/aac.00257-10 Pseudomonas aeruginosa 80
19738025 10.1128/aac.00574-09 Pseudomonas aeruginosa 64
33705899 10.1016/j.bmcl.2021.127928 Pseudomonas aeruginosa 63
17591851 10.1128/aac.00218-07 Beta-lactamase 57
20498315 10.1128/aac.00080-10 Pseudomonas aeruginosa 51
33705899 10.1016/j.bmcl.2021.127928 Acinetobacter baumannii 46
29336873 10.1016/j.bmcl.2018.01.006 Escherichia coli 45
19258272 10.1128/aac.01410-08 Pseudomonas aeruginosa 43
18347108 10.1128/aac.01440-07 Klebsiella pneumoniae 40
18663030 10.1128/aac.00877-08 Escherichia coli 40
18591275 10.1128/aac.01684-07 Acinetobacter baumannii 40
19805565 10.1128/aac.01099-09 Klebsiella pneumoniae 40
33705899 10.1016/j.bmcl.2021.127928 Enterobacter cloacae 40
33705899 10.1016/j.bmcl.2021.127928 Klebsiella aerogenes 39
19188398 10.1128/aac.01172-08 Pseudomonas aeruginosa 38
21041503 10.1128/aac.01198-10 Klebsiella pneumoniae 38
18779357 10.1128/aac.00381-08 Pseudomonas aeruginosa 36

Data from ChEMBL 36 via Core Engine