U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C13H17N5O8S2.C6H14N2O2
Molecular Weight 581.62
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of AZTREONAM LYSINE

SMILES

NCCCC[C@H](N)C(O)=O.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=KPPBAEVZLDHCOK-JHBYREIPSA-N
InChI=1S/C13H17N5O8S2.C6H14N2O2/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;7-4-2-1-3-5(8)6(9)10/h4-5,7H,1-3H3,(H2,14,15)(H,16,19)(H,21,22)(H,23,24,25);5H,1-4,7-8H2,(H,9,10)/b17-8-;/t5-,7-;5-/m00/s1

HIDE SMILES / InChI

Molecular Formula C6H14N2O2
Molecular Weight 146.1876
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C13H17N5O8S2
Molecular Weight 435.433
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050580s040,050632s013lbl.pdf https://www.ncbi.nlm.nih.gov/pubmed/27334663

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.

Originator

Sources: ISBN-13: 978-1461413998

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.03 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
AZACTAM

Approved Use

Aztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms.

Launch Date

5.363712E11
Curative
AZACTAM

Approved Use

Aztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms.

Launch Date

5.363712E11
Curative
AZACTAM

Approved Use

Aztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms.

Launch Date

5.363712E11
Curative
AZACTAM

Approved Use

Aztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms.

Launch Date

5.363712E11
Curative
AZACTAM

Approved Use

Aztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms.

Launch Date

5.363712E11
Curative
AZACTAM

Approved Use

Aztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms.

Launch Date

5.363712E11
Palliative
CAYSTON

Approved Use

CAYSTON® is indicated to improve respiratory symptoms in cystic fibrosis (CF) patients with Pseudomonas aeruginosa.

Launch Date

1.26679686E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
204 μg/mL
2 g single, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AZTREONAM serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
54 μg/mL
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AZTREONAM serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
90 μg/mL
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AZTREONAM serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
208 mg × h/L
1 g 1 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
AZTREONAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.67 h
1 g 1 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
AZTREONAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
44%
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AZTREONAM serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
30 mg/kg single, intravenous
Recommended
Dose: 30 mg/kg
Route: intravenous
Route: single
Dose: 30 mg/kg
Sources:
unhealthy, 10 - 18 years
n = 10
Health Status: unhealthy
Condition: cystic fibrosis
Age Group: 10 - 18 years
Sex: unknown
Population Size: 10
Sources:
1 g single, intramuscular
Recommended
Dose: 1 g
Route: intramuscular
Route: single
Dose: 1 g
Sources:
unhealthy, 18 - 75 years
n = 102
Health Status: unhealthy
Condition: urogenital gonorrhoea
Age Group: 18 - 75 years
Sex: M+F
Population Size: 102
Sources:
1 g 3 times / day steady, intramuscular (median)
Recommended
Dose: 1 g, 3 times / day
Route: intramuscular
Route: steady
Dose: 1 g, 3 times / day
Sources:
unhealthy, children
n = 343
Health Status: unhealthy
Condition: infections
Age Group: children
Sex: unknown
Population Size: 343
Sources:
Other AEs: Pain, Erythema...
Other AEs:
Pain (12%)
Erythema (2.9%)
Induration (0.9%)
Phlebitis (2.1%)
Blood eosinophils increased (6.3%)
Increased platelets (3.6%)
Neutropenia (3.2%)
AST increased (3.8%)
ALT increased (6.5%)
Increased serum creatinine (5.8%)
Sources:
1 g 3 times / day steady, intramuscular (median)
Recommended
Dose: 1 g, 3 times / day
Route: intramuscular
Route: steady
Dose: 1 g, 3 times / day
Sources:
unhealthy, children
n = 612
Health Status: unhealthy
Condition: infections
Age Group: children
Sex: unknown
Population Size: 612
Sources:
Other AEs: Rash, Diarrhea...
Other AEs:
Rash (4.3%)
Diarrhea (1.4%)
Fever (1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Induration 0.9%
1 g 3 times / day steady, intramuscular (median)
Recommended
Dose: 1 g, 3 times / day
Route: intramuscular
Route: steady
Dose: 1 g, 3 times / day
Sources:
unhealthy, children
n = 343
Health Status: unhealthy
Condition: infections
Age Group: children
Sex: unknown
Population Size: 343
Sources:
Pain 12%
1 g 3 times / day steady, intramuscular (median)
Recommended
Dose: 1 g, 3 times / day
Route: intramuscular
Route: steady
Dose: 1 g, 3 times / day
Sources:
unhealthy, children
n = 343
Health Status: unhealthy
Condition: infections
Age Group: children
Sex: unknown
Population Size: 343
Sources:
Phlebitis 2.1%
1 g 3 times / day steady, intramuscular (median)
Recommended
Dose: 1 g, 3 times / day
Route: intramuscular
Route: steady
Dose: 1 g, 3 times / day
Sources:
unhealthy, children
n = 343
Health Status: unhealthy
Condition: infections
Age Group: children
Sex: unknown
Population Size: 343
Sources:
Erythema 2.9%
1 g 3 times / day steady, intramuscular (median)
Recommended
Dose: 1 g, 3 times / day
Route: intramuscular
Route: steady
Dose: 1 g, 3 times / day
Sources:
unhealthy, children
n = 343
Health Status: unhealthy
Condition: infections
Age Group: children
Sex: unknown
Population Size: 343
Sources:
Neutropenia 3.2%
1 g 3 times / day steady, intramuscular (median)
Recommended
Dose: 1 g, 3 times / day
Route: intramuscular
Route: steady
Dose: 1 g, 3 times / day
Sources:
unhealthy, children
n = 343
Health Status: unhealthy
Condition: infections
Age Group: children
Sex: unknown
Population Size: 343
Sources:
Increased platelets 3.6%
1 g 3 times / day steady, intramuscular (median)
Recommended
Dose: 1 g, 3 times / day
Route: intramuscular
Route: steady
Dose: 1 g, 3 times / day
Sources:
unhealthy, children
n = 343
Health Status: unhealthy
Condition: infections
Age Group: children
Sex: unknown
Population Size: 343
Sources:
AST increased 3.8%
1 g 3 times / day steady, intramuscular (median)
Recommended
Dose: 1 g, 3 times / day
Route: intramuscular
Route: steady
Dose: 1 g, 3 times / day
Sources:
unhealthy, children
n = 343
Health Status: unhealthy
Condition: infections
Age Group: children
Sex: unknown
Population Size: 343
Sources:
Increased serum creatinine 5.8%
1 g 3 times / day steady, intramuscular (median)
Recommended
Dose: 1 g, 3 times / day
Route: intramuscular
Route: steady
Dose: 1 g, 3 times / day
Sources:
unhealthy, children
n = 343
Health Status: unhealthy
Condition: infections
Age Group: children
Sex: unknown
Population Size: 343
Sources:
Blood eosinophils increased 6.3%
1 g 3 times / day steady, intramuscular (median)
Recommended
Dose: 1 g, 3 times / day
Route: intramuscular
Route: steady
Dose: 1 g, 3 times / day
Sources:
unhealthy, children
n = 343
Health Status: unhealthy
Condition: infections
Age Group: children
Sex: unknown
Population Size: 343
Sources:
ALT increased 6.5%
1 g 3 times / day steady, intramuscular (median)
Recommended
Dose: 1 g, 3 times / day
Route: intramuscular
Route: steady
Dose: 1 g, 3 times / day
Sources:
unhealthy, children
n = 343
Health Status: unhealthy
Condition: infections
Age Group: children
Sex: unknown
Population Size: 343
Sources:
Fever 1%
1 g 3 times / day steady, intramuscular (median)
Recommended
Dose: 1 g, 3 times / day
Route: intramuscular
Route: steady
Dose: 1 g, 3 times / day
Sources:
unhealthy, children
n = 612
Health Status: unhealthy
Condition: infections
Age Group: children
Sex: unknown
Population Size: 612
Sources:
Diarrhea 1.4%
1 g 3 times / day steady, intramuscular (median)
Recommended
Dose: 1 g, 3 times / day
Route: intramuscular
Route: steady
Dose: 1 g, 3 times / day
Sources:
unhealthy, children
n = 612
Health Status: unhealthy
Condition: infections
Age Group: children
Sex: unknown
Population Size: 612
Sources:
Rash 4.3%
1 g 3 times / day steady, intramuscular (median)
Recommended
Dose: 1 g, 3 times / day
Route: intramuscular
Route: steady
Dose: 1 g, 3 times / day
Sources:
unhealthy, children
n = 612
Health Status: unhealthy
Condition: infections
Age Group: children
Sex: unknown
Population Size: 612
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
PubMed

PubMed

TitleDatePubMed
Broth microdilution testing of susceptibilities to 30 antimicrobial agents of Mycobacterium avium strains from patients with acquired immune deficiency syndrome.
1987 Oct
In-vitro activity of seventeen antimicrobial compounds against seven species of mycobacteria.
1988 Dec
Contribution of beta-lactamases to beta-lactam susceptibilities of susceptible and multidrug-resistant Mycobacterium tuberculosis clinical isolates.
1998 Jun
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050814s007lbl.pdf
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.
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:32:01 UTC 2023
Edited
by admin
on Wed Jul 05 23:32:01 UTC 2023
Record UNII
XNM7LT65NP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZTREONAM LYSINE
EMA EPAR   MART.   USAN   WHO-DD  
USAN  
Official Name English
L-LYSINE, MONO(2-(((Z)-(1-(2-AMINO-4-THIAZOLYL)-2-(((2S,3S)-2-METHYL-4-OXO-1-SULFO-3-AZETIDINYL)AMINO)-2-OXOETHYLIDENE)AMINO)OXY)-2-METHYLPROPANOATE)
Common Name English
L-LYSINE, 2-(((Z)-(1-(2-AMINO-4-THIAZOLYL)-2-(((2S,3S)-2-METHYL-4-OXO-1-SULFO-3-AZETIDINYL)AMINO)-2-OXOETHYLIDENE)AMINO)OXY)-2-METHYLPROPANOATE (1:1)
Common Name English
AZTREONAM L-LYSINE SALT [MI]
Common Name English
AZTREONAM LYSINATE
Common Name English
CORUS1020
Code English
Aztreonam lysine [WHO-DD]
Common Name English
AZTREONAM LYSINE [MART.]
Common Name English
AZTREONAM L-LYSINE SALT
MI  
Common Name English
AZTREONAM LYSINE [USAN]
Common Name English
AZTREONAM LYSINE [EMA EPAR]
Common Name English
CAYSTON
Brand Name English
CORUS-1020
Code English
L-LYSINE, MONO(2-(((Z)-(1-(2-AMINOTHIZOL-4-YL)-2-((2S,3S)-2-METHYL-4-OXO-1-SULFOAZETIDIN-3-YL)AMINO)-2-OXOETHYLIDENE)AMINO)OXY)-2-METHYLPROPANOATE
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/04/204
Created by admin on Wed Jul 05 23:32:01 UTC 2023 , Edited by admin on Wed Jul 05 23:32:01 UTC 2023
EMA ASSESSMENT REPORTS CAYSTON (AUTHORIZED: CYSTIC FIBROSIS)
Created by admin on Wed Jul 05 23:32:01 UTC 2023 , Edited by admin on Wed Jul 05 23:32:01 UTC 2023
NCI_THESAURUS C260
Created by admin on Wed Jul 05 23:32:01 UTC 2023 , Edited by admin on Wed Jul 05 23:32:01 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C76021
Created by admin on Wed Jul 05 23:32:01 UTC 2023 , Edited by admin on Wed Jul 05 23:32:01 UTC 2023
PRIMARY
MERCK INDEX
M2188
Created by admin on Wed Jul 05 23:32:01 UTC 2023 , Edited by admin on Wed Jul 05 23:32:01 UTC 2023
PRIMARY Merck Index
FDA UNII
XNM7LT65NP
Created by admin on Wed Jul 05 23:32:01 UTC 2023 , Edited by admin on Wed Jul 05 23:32:01 UTC 2023
PRIMARY
ChEMBL
CHEMBL3545256
Created by admin on Wed Jul 05 23:32:01 UTC 2023 , Edited by admin on Wed Jul 05 23:32:01 UTC 2023
PRIMARY
PUBCHEM
11204019
Created by admin on Wed Jul 05 23:32:01 UTC 2023 , Edited by admin on Wed Jul 05 23:32:01 UTC 2023
PRIMARY
SMS_ID
100000115887
Created by admin on Wed Jul 05 23:32:01 UTC 2023 , Edited by admin on Wed Jul 05 23:32:01 UTC 2023
PRIMARY
DRUG BANK
DBSALT001061
Created by admin on Wed Jul 05 23:32:01 UTC 2023 , Edited by admin on Wed Jul 05 23:32:01 UTC 2023
PRIMARY
USAN
RR-114
Created by admin on Wed Jul 05 23:32:01 UTC 2023 , Edited by admin on Wed Jul 05 23:32:01 UTC 2023
PRIMARY
EVMPD
SUB30777
Created by admin on Wed Jul 05 23:32:01 UTC 2023 , Edited by admin on Wed Jul 05 23:32:01 UTC 2023
PRIMARY
CAS
827611-49-4
Created by admin on Wed Jul 05 23:32:01 UTC 2023 , Edited by admin on Wed Jul 05 23:32:01 UTC 2023
PRIMARY
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ACTIVE MOIETY