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Compound Detail

CHEMBL158

AZTREONAM
💊 Approved Drug
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💊 Approved Drug
C[C@H]1[C@H](NC(=O)/C(=N\OC(C)(C)C(=O)O)c2csc(N)n2)C(=O)N1S(=O)(=O)O

Basic Information

ChEMBL ID CHEMBL158
Name AZTREONAM
Phase Approved
Structure Type MOL
InChI Key WZPBZJONDBGPKJ-VEHQQRBSSA-N
Therapeutic ✓ Yes

Known Names

Azactam Azonam Aztreon Aztreonam Nebactam NSC-646279 NSC-758913 Primbactam SO 26776 SQ 26776 SQ-26776
9
Targets
19
Activities
2
Assay Types
30
PK Parameters
20
Publications
11
Known Names
15
Indications
1
Mechanisms

Molecular Properties

435.4
MW (Da)
-1.17
ALogP
10
HBA
4
HBD
201.6
PSA (Ų)
0.17
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1986
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral Topical

Flags

Natural Product
USAN Year 1983

Extended Properties

Molecular Formula C13H17N5O8S2
MW 435.44
Aromatic Rings 1
Heavy Atoms 28
NP-Likeness 0.09

Mechanism of Action

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

Indications

Bacterial Infections Cystic Fibrosis Infections Intraabdominal Infections Pneumonia Pyelonephritis Sepsis Urinary Tract Infections Enterobacteriaceae Infections Skin Diseases Gonorrhea Gram-Negative Bacterial Infections Carcinoma, Non-Small-Cell Lung Renal Insufficiency Osteomyelitis

ATC Classification

J01DF01
aztreonam
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 13 meas. best 8.22
Ki 6 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
Ki 9.0 8.4833 1.0 3
Efflux transporter
CHEMBL1641337
IC50 8.22 8.22 6.0 1
Class C beta-lactamase CMY-36
CHEMBL1641338
IC50 8.22 8.22 6.0 1
Unchecked
CHEMBL612545
IC50 8.22 6.9457 6.0 7
Beta-lactamase ADC-33
CHEMBL1667700
Ki 8.15 8.15 7.0 1
Beta-lactamase ACC-4
CHEMBL5305
IC50 7.5 7.5 32.0 1
AmpC
CHEMBL1255151
IC50 7.22 7.22 60.0 1
PER-2 beta-lactamase
CHEMBL5303
Ki 5.7 5.7 2000.0 1
ADC-11
CHEMBL1667701
Ki 5.52 5.52 3000.0 1
Penicillin-binding protein 1A
CHEMBL3259512
IC50 5.48 5.48 3340.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 336.7 - Homo sapiens
AUC 414.4 - Homo sapiens
AUC 5000.0 ng.hr.mL-1 Mus musculus
AUC 13000.0 ng.hr.mL-1 Rattus norvegicus
AUC 13000.0 ng.hr.mL-1 Canis lupus familiaris
AUC 2410.0 ng.hr.mL-1 Rattus norvegicus
CL 100.1 ml/min Homo sapiens
CL 76.2 ml/min Homo sapiens
CL 4.59 L/hr Homo sapiens
CL 6.052 L/hr Homo sapiens
CL 1.84 mL.min-1.kg-1 Homo sapiens
CL 1.31 mL.min-1.kg-1 Homo sapiens
CL 1.5 mL.min-1.kg-1 Homo sapiens
CL 1.5 mL.min-1.kg-1 Homo sapiens
CL 0.5 mL.min-1.kg-1 Homo sapiens
CL 1.3 mL.min-1.kg-1 Homo sapiens
CL 1.5 mL.min-1.kg-1 Homo sapiens
CL 5.0 mL.min-1.kg-1 Macaca
CL 8.0 mL.min-1.kg-1 Rattus norvegicus
CL 11.0 mL.min-1.kg-1 Canis lupus familiaris
CL 21.0 mL.min-1.kg-1 Rattus norvegicus
CL 16.0 mL.min-1.kg-1 Mus musculus
CL 13.0 mL.min-1.kg-1 Rattus norvegicus
CL 4.0 mL.min-1.kg-1 Canis lupus familiaris
CL 15.2 mL.min-1.kg-1 Rattus norvegicus
F 1.0 % Homo sapiens
F 1.0 % Homo sapiens
F 1.0 % Homo sapiens
F 100.0 % Homo sapiens
Fu 0.72 - Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 1.0 nM 9.0 Activity of Enterobacter cloacae P99 beta-lactamase 19995920
Unchecked Ki = 2.1 nM 8.68 Inhibition of Escherichia coli MC4100 Beta-Lactamase CMY-2 using cephalothin as ... 19470510
Class C beta-lactamase CMY-36 IC50 = 6.0 nM 8.22 Inhibition of Klebsiella pneumoniae HP205 cephalosporinase CMY-36 by UV spectrop... 19104021
Unchecked IC50 = 6.0 nM 8.22 Inhibition of CMY-2 by UV spectrophotometer in presence of 100 uM of cephalothin 19104021
Efflux transporter IC50 = 6.0 nM 8.22 Inhibition of Salmonella enterica serotype Newport AM17274 cephalosporinase CMY-... 19104021
Beta-lactamase ADC-33 Ki = 7.0 nM 8.15 Activity of Acinetobacter baumannii ADC-33 beta-lactamase 20547808
Unchecked IC50 = 8.0 nM 8.1 Inhibition of PBP3 in Pseudomonas aeruginosa ATCC 27853 after 20 mins by fluores... 23755848
Unchecked IC50 = 8.0 nM 8.1 Displacement of fluorescent Bocillin FL from Pseudomonas aeruginosa PBP3 24694215
Unchecked Ki = 17.0 nM 7.77 Inhibition of Escherichia coli MC4100 Beta-Lactamase CMY-30 using cephalothin as... 19470510
Unchecked IC50 = 23.0 nM 7.64 Inhibition of Escherichia coli Penicillin-binding protein 3 20308379
Beta-lactamase ACC-4 IC50 = 32.0 nM 7.5 Inhibition of Escherichia coli beta-lactamase ACC4 17664321
AmpC IC50 = 60.0 nM 7.22 Inhibition of Escherichia coli ATCC 25922 AmpC 20308379
PER-2 beta-lactamase Ki = 2000.0 nM 5.7 Inhibition of Citrobacter freundii PER2 beta lactamase 17438050
Unchecked IC50 = 2870.0 nM 5.54 Displacement of fluorescent Bocillin FL from Pseudomonas aeruginosa PBP1b 24694215
Unchecked IC50 = 2870.0 nM 5.54 Inhibition of PBP1b in Pseudomonas aeruginosa ATCC 27853 after 20 mins by fluore... 23755848
ADC-11 Ki = 3000.0 nM 5.52 Activity of Acinetobacter baumannii ADC-11 beta-lactamase 20547808
Penicillin-binding protein 1A IC50 = 3340.0 nM 5.48 Displacement of fluorescent Bocillin FL from N-terminal His tagged Pseudomonas a... 24694215
Unchecked IC50 = 3340.0 nM 5.48 Inhibition of PBP1a in Pseudomonas aeruginosa ATCC 27853 after 20 mins by fluore... 23755848

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 152
19738025 10.1128/aac.00574-09 Pseudomonas aeruginosa 64
19805554 10.1128/aac.00248-09 Pseudomonas aeruginosa 62
29336873 10.1016/j.bmcl.2018.01.006 Escherichia coli 45
18591275 10.1128/aac.01684-07 Acinetobacter baumannii 40
19188376 10.1128/aac.01264-08 Pseudomonas aeruginosa 33
20194693 10.1128/aac.00816-09 Pseudomonas aeruginosa 32
37672933 10.1016/j.ejmech.2023.115778 Pseudomonas aeruginosa 31
19258280 10.1128/aac.01024-08 Pseudomonas aeruginosa 31
19273679 10.1128/aac.01617-08 Pseudomonas aeruginosa 30
18809945 10.1128/aac.00707-08 Pseudomonas aeruginosa 29
17261619 10.1128/aac.01278-06 Pseudomonas aeruginosa 29
20660683 10.1128/aac.01301-09 Klebsiella pneumoniae 26
17576827 10.1128/aac.01522-06 Homo sapiens 24
21078949 10.1128/aac.00098-10 Unchecked 24
17724156 10.1128/aac.01512-06 Acinetobacter baumannii 24
20566764 10.1128/aac.00385-10 Pseudomonas aeruginosa 24
20308379 10.1128/aac.01525-09 Unchecked 23
20086157 10.1128/aac.01312-09 Escherichia coli 21
17682106 10.1128/aac.00503-07 Pseudomonas aeruginosa 21

Data from ChEMBL 36 via Core Engine