Explore a selection of our essential drug information below, or:
Identification
- Summary
Aztreonam is a beta-lactam antibiotic used to treat select aztreonam sensitive gram negative bacteria.
- Brand Names
- Azactam, Cayston
- Generic Name
- Aztreonam
- DrugBank Accession Number
- DB00355
- Background
A monocyclic beta-lactam antibiotic originally isolated from Chromobacterium violaceum. It is resistant to beta-lactamases and is used in gram-negative infections, especially of the meninges, bladder, and kidneys. It may cause a superinfection with gram-positive organisms.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Aztreonam (DB00355)
- Weight
- Average: 435.433
Monoisotopic: 435.051853925 - Chemical Formula
- C13H17N5O8S2
- Synonyms
- (Z,)-2-((((2-Amino-4-thiazolyl)(((2S,3S,)-2-methyl-4-oxo-1-sulfo-3-azetidinyl)carbamoyl)methylene)amino)oxy)-2-methylpropionic acid
- 2-({[(1Z)-1-(2-amino-1,3-thiazol-4-yl) -2- {[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]amino} -2- oxoethylidene]amino}oxy)-2-methylpropanoic acid
- Aztreonam
- Aztréonam
- Aztreonamum
- External IDs
- Corus 1020
- SQ 26776
- SQ-26776
Pharmacology
- Indication
For the treatment of the following infections caused by susceptible gram-negative microorganisms: urinary tract infections, lower respiratory tract infections, septicemia, skin and skin-structure infections, intra-abdominal infections, and gynecologic infections.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Bone and joint infections ••• ••••• Management of Cystic fibrosis (cf) •••••••••••• ••••••••••• •••••••••• ••••••••• Treatment of Febrile neutropenia ••• ••••• Treatment of Intra-abdominal infections •••••••••••• Treatment of Lower respiratory tract infections •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Aztreonam is a monocyclic beta-lactam antibiotic (a monobactam) originally isolated from Chromobacterium violaceum. Aztreonam exhibits potent and specific activity in vitro against a wide spectrum of gram-negative aerobic pathogens including Pseudomonas aeruginosa. It has no useful activity against gram-positive bacteria or anaerobes, but has very broad spectrum against gram-negative aerobes, including Pseudomonas aeruginosa. This has given it the nickname "the magic bullet for aerobic gram-negative bacteria". Aztreonam, unlike the majority of beta-lactam antibiotics, does not induce beta-lactamase activity and its molecular structure confers a high degree of resistance to hydrolysis by beta-lactamases (such as penicillinases and cephalosporinases) produced by most gram-negative and gram-positive pathogens; it is, therefore, usually active against gram-negative aerobic microorganisms that are resistant to antibiotics hydrolyzed by beta-lactamases. It is active against many strains that are multiply-resistant to other antibiotics, such as certain cephalosporins, penicillin, and aminoglycosides. Aztreonam maintains its antimicrobial activity over a pH range of 6 to 8 in vitro, as well as in the presence of human serum and under anaerobic conditions.
- Mechanism of action
The bactericidal action of aztreonam results from the inhibition of bacterial cell wall synthesis due to a high affinity of aztreonam for penicillin binding protein 3 (PBP3). By binding to PBP3, aztreonam inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins. It is possible that aztreonam interferes with an autolysin inhibitor.
Target Actions Organism APenicillin-binding protein 3 inhibitorBacillus subtilis (strain 168) APeptidoglycan synthase FtsI binderEscherichia coli (strain K12) ABeta-lactamase potentiatorCitrobacter freundii UBeta-lactamase Toho-1 substrateEscherichia coli - Absorption
Less than 1% absorbed from the gastrointestinal tract following oral administration. Completely absorbed following intramuscular administration.
- Volume of distribution
- 12.6 L
- Protein binding
Serum protein binding averaged 56% and is independent of dose. Impaired renal function, 36 to 43%.
- Metabolism
Approximately 6 to 16% metabolized to inactive metabolites by hydrolysis of the beta-lactam bond, resulting in an open-ring compound.
- Route of elimination
In healthy subjects, aztreonam is excreted in the urine about equally by active tubular secretion and glomerular filtration. Urinary excretion of a single parenteral dose was essentially complete by 12 hours after injection.
- Half-life
The serum half-life of aztreonam averaged 1.7 hours (1.5 to 2.0) in subjects with normal renal function, independent of the dose. In elderly patients and in patients with impaired renal function, the mean serum half-life of aztreonam increased (4.7 to 6 hours and 2.1 hours, respectively).
- Clearance
- 91 mL/min [healthy]
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Aztreonam may decrease the excretion rate of Abacavir which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Aztreonam which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Aztreonam which could result in a higher serum level. Acenocoumarol The risk or severity of bleeding can be increased when Aztreonam is combined with Acenocoumarol. Acetaminophen Acetaminophen may decrease the excretion rate of Aztreonam which could result in a higher serum level. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Aztreonam lysine XNM7LT65NP 827611-49-4 KPPBAEVZLDHCOK-JHBYREIPSA-N - International/Other Brands
- Azenam (Aristo) / Aztram (Shanxi C & Y) / Aztreo (Zydus Cadila) / Bencipen (AC Farma) / Primbactam (Menarini) / Trezam (Glenmark) / Vebac (Fahrenheit)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Azactam Injection, powder, for solution 1 g/1 Intramuscular; Intravenous Cardinal Health 2009-06-01 2011-11-30 US 
Azactam Injection, solution 1 g/50mL Intravenous Elan Pharmaceuticals 2009-06-01 2012-02-04 US Azactam Injection, powder, for solution 1 g/1 Intramuscular; Intravenous Elan Pharmaceuticals 2009-06-01 2013-03-14 US Azactam Injection, powder, for solution 1 g/1 Intramuscular; Intravenous E.R. Squibb & Sons, L.L.C. 2010-04-01 Not applicable US Azactam Injection, powder, for solution 2 g/1 Intramuscular; Intravenous Elan Pharmaceuticals 2009-06-01 2013-03-14 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Aztreonam Injection, powder, lyophilized, for solution 2 g/1 Intramuscular; Intravenous Hospira, Inc. 2022-01-24 Not applicable US Aztreonam Injection, powder, lyophilized, for solution 500 mg/1 Intramuscular; Intravenous APP Pharmaceuticals, LLC 2009-11-05 2010-06-25 US Aztreonam Injection, powder, lyophilized, for solution 2 g/1 Intramuscular; Intravenous Fresenius Kabi USA, LLC 2009-11-05 Not applicable US Aztreonam Injection, powder, lyophilized, for solution 1 g/1 Intramuscular; Intravenous Hospira, Inc. 2022-01-24 Not applicable US Aztreonam Injection, powder, lyophilized, for solution 1 g/1 Intramuscular; Intravenous Fresenius Kabi USA, LLC 2009-11-05 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Emblaveo Aztreonam (1.5 g) + Avibactam sodium (0.5 g) Injection, powder, for solution Intravenous Pfizer Europe Ma Eeig 2024-07-10 Not applicable EU 
Categories
- ATC Codes
- J01DF01 — Aztreonam
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as monobactams. These are compounds comprising beta-lactam ring is alone and not fused to another ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactams
- Sub Class
- Beta lactams
- Direct Parent
- Monobactams
- Alternative Parents
- N-acyl-alpha amino acids and derivatives / 2,4-disubstituted thiazoles / 2-amino-1,3-thiazoles / Heteroaromatic compounds / Organic sulfuric acids and derivatives / Secondary carboxylic acid amides / Amino acids / Azetidines / Carboxylic acids / Azacyclic compounds show 7 more
- Substituents
- 1,3-thiazol-2-amine / 2,4-disubstituted 1,3-thiazole / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aromatic heteromonocyclic compound / Azacycle / Azetidine / Azole show 20 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- monobactam (CHEBI:161680) / Monobactams (C06840)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- G2B4VE5GH8
- CAS number
- 78110-38-0
- InChI Key
- WZPBZJONDBGPKJ-VEHQQRBSSA-N
- InChI
- 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
- IUPAC Name
- (2S,3S)-3-[(2Z)-2-(2-azaniumyl-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-methyl-4-oxoazetidine-1-sulfonate
- SMILES
- C[C@H]1[C@H](NC(=O)C(=N/OC(C)(C)C(=O)O)\C2=CSC([NH3+])=N2)C(=O)N1S([O-])(=O)=O
References
- Synthesis Reference
Neal G. Anderson, Carl F. Anderson, "Delta form of aztreonam and preparation thereof." U.S. Patent US4826973, issued January, 1983.
US4826973- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014499
- KEGG Drug
- D00240
- KEGG Compound
- C06840
- PubChem Compound
- 9568617
- PubChem Substance
- 46505419
- ChemSpider
- 4674940
- BindingDB
- 50240480
- 1272
- ChEBI
- 161680
- ChEMBL
- CHEMBL158
- ZINC
- ZINC000003830264
- Therapeutic Targets Database
- DAP000117
- PharmGKB
- PA448523
- PDBe Ligand
- AZR
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Aztreonam
- FDA label
- Download (1.57 MB)
- MSDS
- Download (42 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Approved for Marketing Not Available Cystic Fibrosis (CF) / Pseudomonas Aeruginosa 1 somestatus stop reason just information to hide Not Available Approved for Marketing Not Available Cystic Fibrosis (CF) / Pseudomonas aeruginosa respiratory tract infection 1 somestatus stop reason just information to hide Not Available Completed Not Available Cystic Fibrosis (CF) 1 somestatus stop reason just information to hide Not Available Completed Not Available Pseudomonas Aeruginosa in Cystic Fibrosis 1 somestatus stop reason just information to hide Not Available Recruiting Treatment Carbapenem Resistant Enterobacteriaceae Infection 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Gilead sciences inc
- Bristol myers squibb
- Bristol myers squibb co
- App pharmaceuticals llc
- Packagers
- APP Pharmaceuticals
- Baxter International Inc.
- Ben Venue Laboratories Inc.
- Bristol-Myers Squibb Co.
- Cardinal Health
- E.R. Squibb and Sons LLC
- Elan Pharmaceuticals Inc.
- Gilead Sciences Inc.
- Dosage Forms
Form Route Strength Injection, powder, for solution Intramuscular; Intravenous 1 g/1 Injection, powder, for solution Intramuscular; Intravenous 2 g/1 Injection, solution Intravenous 1 g/50mL Injection, solution Intravenous 2 g/50mL Injection, powder, for solution Parenteral Injection, powder, for solution Intramuscular; Intravenous 1 g Injection, powder, lyophilized, for solution Intramuscular; Intravenous 1 g/1 Injection, powder, lyophilized, for solution Intramuscular; Intravenous 2 g/1 Injection, powder, lyophilized, for solution Intramuscular; Intravenous 500 mg/1 Injection, powder, lyophilized, for solution Intramuscular; Intravenous 1 g Injection, powder, lyophilized, for solution Intramuscular; Intravenous 100000 g Powder, for solution Respiratory (inhalation) 75 mg / vial Powder, for solution Respiratory (inhalation) 75 mg/1mL Powder, for suspension Respiratory (inhalation) 75 mg Solution Respiratory (inhalation) Injection, powder, for solution Intravenous Injection, powder, for solution Powder, for solution Respiratory (inhalation) Injection, powder, for solution 1 g - Prices
Unit description Cost Unit Azactam 2 gm vial 81.4USD vial Cayston 75 mg inhal solution 63.24USD ml Azactam 1 gm vial 40.78USD vial Azactam-iso-osmot 2 gm/50 ml 1.6USD ml Azactam-iso-osmot 1 gm/50 ml 0.8USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region CA1340253 No 1998-12-15 2015-12-15 Canada 
CA1338670 No 1996-10-22 2013-10-22 Canada US7208141 No 2007-04-24 2021-12-20 US US7427633 No 2008-09-23 2021-12-20 US US8399496 No 2013-03-19 2021-12-20 US US7214364 No 2007-05-08 2021-12-20 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Insoluble Not Available - Predicted Properties
Property Value Source Water Solubility 0.0429 mg/mL ALOGPS logP 0.04 ALOGPS logP -3.1 Chemaxon logS -4.1 ALOGPS pKa (Strongest Acidic) -1.5 Chemaxon pKa (Strongest Basic) 3.91 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 206.03 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 102.09 m3·mol-1 Chemaxon Polarizability 39.95 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9601 Blood Brain Barrier - 0.9657 Caco-2 permeable - 0.5885 P-glycoprotein substrate Non-substrate 0.6472 P-glycoprotein inhibitor I Non-inhibitor 0.8047 P-glycoprotein inhibitor II Non-inhibitor 0.6293 Renal organic cation transporter Non-inhibitor 0.9324 CYP450 2C9 substrate Non-substrate 0.7736 CYP450 2D6 substrate Non-substrate 0.8142 CYP450 3A4 substrate Non-substrate 0.5784 CYP450 1A2 substrate Non-inhibitor 0.8562 CYP450 2C9 inhibitor Non-inhibitor 0.8404 CYP450 2D6 inhibitor Non-inhibitor 0.9023 CYP450 2C19 inhibitor Non-inhibitor 0.8306 CYP450 3A4 inhibitor Non-inhibitor 0.8763 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9005 Ames test Non AMES toxic 0.6319 Carcinogenicity Carcinogens 0.5839 Biodegradation Not ready biodegradable 0.8146 Rat acute toxicity 1.9822 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9967 hERG inhibition (predictor II) Non-inhibitor 0.8329
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-007c-9425200000-e19e767dba01d637f0c9 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0004900000-193aec4acaec20b1b3ea Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0029000000-b52fb91b198d02849ff0 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0udr-1359200000-77bf77471c7945280de0 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0hi2-1569000000-57ea30183f0699d41ad6 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-053v-9514000000-44dae1d878b1869a4c56 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-06to-8479000000-852130896906a3311d36 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 199.4459472 predictedDarkChem Lite v0.1.0 [M-H]- 191.16994 predictedDeepCCS 1.0 (2019) [M+H]+ 195.0775472 predictedDarkChem Lite v0.1.0 [M+H]+ 192.89366 predictedDeepCCS 1.0 (2019) [M+Na]+ 196.5564472 predictedDarkChem Lite v0.1.0 [M+Na]+ 199.22261 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Bacillus subtilis (strain 168)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Penicillin-binding proteins (PBPs) function in the late steps of murein biosynthesis (Probable). Probably required for both cortical and vegetative peptidoglycan synthesis (Probable). Although not usually required for cell division, in the absence of PBP 2B (pbpB) it becomes essential. Confers resistance to oxacillin and cephalexin (PubMed:28792086).
- Specific Function
- penicillin binding
- Gene Name
- pbpC
- Uniprot ID
- P42971
- Uniprot Name
- Penicillin-binding protein 3
- Molecular Weight
- 74405.915 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Rittenbury MS: How and why aztreonam works. Surg Gynecol Obstet. 1990;171 Suppl:19-23. [Article]
- Mock CN, Jurkovich GJ, Dries DJ, Maier RV: Clinical significance of antibiotic endotoxin-releasing properties in trauma patients. Arch Surg. 1995 Nov;130(11):1234-40; discussion 1240-1. [Article]
- Fung-Tomc J, Bush K, Minassian B, Kolek B, Flamm R, Gradelski E, Bonner D: Antibacterial activity of BMS-180680, a new catechol-containing monobactam. Antimicrob Agents Chemother. 1997 May;41(5):1010-6. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Binder
- General Function
- Essential cell division protein that catalyzes cross-linking of the peptidoglycan cell wall at the division septum (PubMed:1103132, PubMed:3531167, PubMed:6450748, PubMed:7030331, PubMed:9614966). Required for localization of FtsN (PubMed:9282742).
- Specific Function
- penicillin binding
- Gene Name
- ftsI
- Uniprot ID
- P0AD68
- Uniprot Name
- Peptidoglycan synthase FtsI
- Molecular Weight
- 63876.925 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Citrobacter freundii
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- This protein is a serine beta-lactamase with a substrate specificity for cephalosporins.
- Specific Function
- beta-lactamase activity
- Gene Name
- ampC
- Uniprot ID
- P05193
- Uniprot Name
- Beta-lactamase
- Molecular Weight
- 41974.99 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Poirel L, Brinas L, Fortineau N, Nordmann P: Integron-encoded GES-type extended-spectrum beta-lactamase with increased activity toward aztreonam in Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2005 Aug;49(8):3593-7. [Article]
- Diaz N, Suarez D, Sordo TL: Molecular dynamics simulations of class C beta-lactamase from Citrobacter freundii: insights into the base catalyst for acylation. Biochemistry. 2006 Jan 17;45(2):439-51. [Article]
- Mirelis B, Rivera A, Miro E, Mesa RJ, Navarro F, Coll P: A simple phenotypic method for differentiation between acquired and chromosomal AmpC beta-lactamases in Escherichia coli. Enferm Infecc Microbiol Clin. 2006 Jun-Jul;24(6):370-2. [Article]
- Kind
- Protein
- Organism
- Escherichia coli
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Has strong cefotaxime-hydrolyzing activity.
- Specific Function
- beta-lactamase activity
- Gene Name
- bla
- Uniprot ID
- Q47066
- Uniprot Name
- Beta-lactamase Toho-1
- Molecular Weight
- 31446.6 Da
References
- Ishii Y, Ohno A, Taguchi H, Imajo S, Ishiguro M, Matsuzawa H: Cloning and sequence of the gene encoding a cefotaxime-hydrolyzing class A beta-lactamase isolated from Escherichia coli. Antimicrob Agents Chemother. 1995 Oct;39(10):2269-75. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 07, 2024 17:57