U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C13H17N5O8S2
Molecular Weight 435.433
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of AZTREONAM

SMILES

C[C@H]1[C@H](NC(=O)C(=N/OC(C)(C)C(O)=O)\C2=CSC(N)=N2)C(=O)N1S(O)(=O)=O

InChI

InChIKey=WZPBZJONDBGPKJ-VEHQQRBSSA-N
InChI=1S/C13H17N5O8S2/c1-5-7(10(20)18(5)28(23,24)25)16-9(19)8(6-4-27-12(14)15-6)17-26-13(2,3)11(21)22/h4-5,7H,1-3H3,(H2,14,15)(H,16,19)(H,21,22)(H,23,24,25)/b17-8-/t5-,7-/m0/s1

HIDE SMILES / InChI

Description

Aztreonam is the first monocyclic beta-lactam antibiotic (monobactam) originally isolated from Chromobacterium violaceum. Aztreonam has a high affinity for the protein-binding protein 3 (PBP-3) of aerobic gram-negative bacteria. Most of these organisms are inhibited and killed at low concentrations of the drug. Aztreonam must be administered as an intravenous or intramuscular injection (AZACTAM®), or inhaled (CAYSTON®). Aztreonam for injection is indicated for the treatment of the following infections caused by susceptible gram-negative microorganisms: urinary tract, lower respiratory tract, skin and skin-structure, intra-abdominal and gynecologic infections as well as for septicemia. Aztreonam for inhalation solution is indicated to improve respiratory symptoms in cystic fibrosis patients with Pseudomonas aeruginosa.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.03 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
AZACTAM
Curative
AZACTAM
Curative
AZACTAM
Curative
AZACTAM
Curative
AZACTAM
Curative
AZACTAM
Palliative
CAYSTON

Cmax

ValueDoseCo-administeredAnalytePopulation
54 μg/mL
500 mg single, intravenous
AZTREONAM serum
Homo sapiens
90 μg/mL
1 g single, intravenous
AZTREONAM serum
Homo sapiens
204 μg/mL
2 g single, intravenous
AZTREONAM serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
208 mg × h/L
1 g 1 times / day steady-state, intravenous
AZTREONAM plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.67 h
1 g 1 times / day steady-state, intravenous
AZTREONAM plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
44%
500 mg single, intravenous
AZTREONAM serum
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Urinary tract infections (adults): 0.5-1 g 2-3 times/day. Moderately severe systemic infections (adults): 1-2 g 2-3 times/day. Severe systemic or life-threatening infections (adults): 2 g 3-4 times/day. Maximum recommended dose for adults is 8 g per day. Mild to moderate infections (pediatric patients): 30 mg/kg 3 times/day Moderate to severe infections (pediatric patients): 30 mg/kg 3-4 times/day. Maximum recommended dose for pediatric patients is 120 mg/kg/day. Inhalation solution: one dose (one single use vial and one ampule of diluent) 3 times a day for 28 days.
Route of Administration: Other
In Vitro Use Guide
In vitro, minimum inhibition concentration (MIC) values against almost all of the Enterobacteriaceae, Neisseria and Haemophilus strains were below 1 microgram per milliliter. MIC values against Pseudomonas aeruginosa were about 8 ug/ml.