AZTREONAM

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2244291
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 234 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2244291	Inhibitor 8504		0.03 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 207 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/2010/065439Orig1s000.pdf	Curative	Approved 8583	AZACTAM Approved Use Aztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms. Launch Date 1986
Lower respiratory tract infections 52 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/2010/065439Orig1s000.pdf	Curative	Approved 8583	AZACTAM Approved Use Aztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms. Launch Date 1986
Sepsis 74 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/2010/065439Orig1s000.pdf	Curative	Approved 8583	AZACTAM Approved Use Aztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms. Launch Date 1986
Skin and skin structure infections 81 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050580s040,050632s013lbl.pdf	Curative	Approved 8583	AZACTAM Approved Use Aztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms. Launch Date 1986
Intra-abdominal infections 50 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/2010/065439Orig1s000.pdf	Curative	Approved 8583	AZACTAM Approved Use Aztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms. Launch Date 1986
Gynecologic infections 19 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/2010/065439Orig1s000.pdf	Curative	Approved 8583	AZACTAM Approved Use Aztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms. Launch Date 1986
Respiratory symptoms in cystic fibrosis (CF) patients with Pseudomonas aeruginosa 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050814s007lbl.pdf	Palliative	Approved 8583	CAYSTON Approved Use CAYSTON® is indicated to improve respiratory symptoms in cystic fibrosis (CF) patients with Pseudomonas aeruginosa. Launch Date 2010

C_max

Value	Dose	Analyte	Population
54 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050580s040,050632s013lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050580s040,050632s013lbl.pdf	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
204 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050580s040,050632s013lbl.pdf	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

AUC

Value	Dose	Co-administered	Analyte	Population
208 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3710959	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.67 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3710959	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
44% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050580s040,050632s013lbl.pdf	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

Dose	Population	Adverse events
30 mg/kg single, intravenous Recommended Dose: 30 mg/kg Route: intravenous Route: single Dose: 30 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/3774385/	unhealthy, 10 - 18 years Health Status: unhealthy Age Group: 10 - 18 years Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/3774385/	Sources: https://pubmed.ncbi.nlm.nih.gov/3774385/
1 g single, intramuscular Recommended Dose: 1 g Route: intramuscular Route: single Dose: 1 g Sources: https://pubmed.ncbi.nlm.nih.gov/3102347/	unhealthy, 18 - 75 years Health Status: unhealthy Age Group: 18 - 75 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/3102347/	Sources: https://pubmed.ncbi.nlm.nih.gov/3102347/
1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf	unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf	Other AEs: Rash, Diarrhea... Other AEs: Rash (4.3%) Diarrhea (1.4%) Fever (1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf
1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf	unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf

AEs

AE	Significance	Dose	Population
Fever	1%	1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf	unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf
Diarrhea	1.4%	1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf	unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf
Rash	4.3%	1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf	unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf
Induration	0.9%	1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf	unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf
Pain	12%	1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf	unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf
Phlebitis	2.1%	1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf	unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf
Erythema	2.9%	1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf	unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf
Neutropenia	3.2%	1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf	unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf
Increased platelets	3.6%	1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf	unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf
AST increased	3.8%	1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf	unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf
Increased serum creatinine	5.8%	1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf	unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf
Blood eosinophils increased	6.3%	1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf	unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf
ALT increased	6.5%	1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf	unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050580s042lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP 450 20	CYP 450 32	CYP 450 12

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 450 22	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/050814Orig1s000PharmR.pdf#page=3 Page: 3.0	unlikely
CYP 450 22	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/050814Orig1s000PharmR.pdf#page=3 Page: 3.0	unlikely

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 450 32	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/050814Orig1s000PharmR.pdf#page=3 Page: 3.0	no

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:161680	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:161680
ChemicalBook	CB0386184	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0386184
eMolecules	17497503	https://www.emolecules.com/cgi-bin/more?vid=17497503
MolPort	MolPort-003-886-345	https://www.molport.com/shop/molecule-link/MolPort-003-886-345
Selleck Chemicals	Aztreonam(Azactam)	http://www.selleckchem.com/products/Aztreonam(Azactam).html
ZINC	ZINC000003830264	http://zinc15.docking.org/substances/ZINC000003830264

PubMed

Title	Date	PubMed
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
Contribution of beta-lactamases to beta-lactam susceptibilities of susceptible and multidrug-resistant Mycobacterium tuberculosis clinical isolates.	1998-06	9624510
In-vitro activity of seventeen antimicrobial compounds against seven species of mycobacteria.	1988-12	3243734
Broth microdilution testing of susceptibilities to 30 antimicrobial agents of Mycobacterium avium strains from patients with acquired immune deficiency syndrome.	1987-10	3501698

Patents

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.

Name

Type

Language

AZACTAM

Preferred Name

English

AZTREONAM

Official Name

English

AZTREONAM [JAN]

Common Name

English

EMBLAVEO COMPONENT AZTREONAM

Brand Name

English

AZTREON

Brand Name

English

AZTREONAM [USP-RS]

Common Name

English

SQ 26776

Code

English

AZTREONAM [MI]

Common Name

English

AZONAM

Brand Name

English

AZTREONAM [USP MONOGRAPH]

Common Name

English

AZTREONAM [VANDF]

Common Name

English

AZTREONAM [USAN]

Common Name

English

NEBACTAM

Brand Name

English

Aztreonam [WHO-DD]

Common Name

English

NSC-646279

Code

English

PRIMBACTAM

Brand Name

English

(Z)-2-[[[(2-Amino-4-thiazolyl)[[(2S,3S)-2-methyl-4-oxo-1-sulfo-3-azetidinyl]carbamoyl]methylene]amino]oxy]-2-methylpropionic acid

Systematic Name

English

PROPANOIC ACID, 2-(((1-(2-AMINO-4-THIAZOLYL)-2-((2-METHYL-4-OXO-1-SULFO-3-AZETIDINYL)AMINO)-2-OXOETHYLIDENE)AMINO)OXY)-2-METHYL-, (2S-(2.ALPHA.,3.BETA.(Z)))-

Common Name

English

AZTREONAM [MART.]

Common Name

English

aztreonam [INN]

Common Name

English

NSC-758913

Code

English

SQ-26776

Code

English

AZTREONAM [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000011311