aztreonam Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
monobactam antibiotics 279 78110-38-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cayston
  • aztreonam
  • azonam
  • azthreonam
  • aztreon
  • monobactam
  • nebactam
  • primbactam
  • aztreonam lysine
  • azactam
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.
  • Molecular weight: 435.43
  • Formula: C13H17N5O8S2
  • CLOGP: 0.34
  • LIPINSKI: 1
  • HAC: 13
  • HDO: 4
  • TPSA: 201.58
  • ALOGS: -3.34
  • ROTB: 6

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.23 g Inhal.solution
4 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 10 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 68 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 305.44 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 1 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.18 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1.50 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.40 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.50 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 31, 1986 FDA BRISTOL MYERS SQUIBB

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Cystic fibrosis 787.78 53.90 108 852 402 2356723
Death 581.71 53.90 200 760 81268 2275857
Infective pulmonary exacerbation of cystic fibrosis 462.01 53.90 73 887 815 2356310
Lung transplant 255.00 53.90 42 918 608 2356517
Respiratory failure 213.71 53.90 62 898 13466 2343659
Off label use 189.09 53.90 88 872 73510 2283615
Haemoptysis 178.74 53.90 41 919 3486 2353639
Lung disorder 131.95 53.90 36 924 6176 2350949
Pseudomonas infection 118.07 53.90 24 936 1142 2355983
Cough 117.69 53.90 50 910 33067 2324058
Pulmonary function test decreased 111.58 53.90 20 940 481 2356644
Bronchiectasis 104.54 53.90 21 939 940 2356185
Pneumonia 75.82 53.90 42 918 49254 2307871
Dyspnoea 71.92 53.90 48 912 78685 2278440
Cystic fibrosis respiratory infection suppression 53.96 53.90 8 952 54 2357071

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Cystic fibrosis 579.27 56.25 83 661 336 1745701
Death 367.54 56.25 156 588 87287 1658750
Infective pulmonary exacerbation of cystic fibrosis 289.92 56.25 49 695 650 1745387
Lung transplant 205.30 56.25 34 710 391 1745646
Respiratory failure 130.60 56.25 46 698 14459 1731578
Haemoptysis 113.47 56.25 32 712 4844 1741193
Off label use 87.24 56.25 46 698 38525 1707512
Lung disorder 85.50 56.25 26 718 5093 1740944
Sputum increased 76.62 56.25 13 731 172 1745865
Cough 73.80 56.25 33 711 19164 1726873
Dyspnoea 71.80 56.25 45 699 52014 1694023

Pharmacologic Action:

SourceCodeDescription
ATC J01DF01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER BETA-LACTAM ANTIBACTERIALS
Monobactams
FDA EPC N0000175493 Monobactam Antibacterial
FDA Chemical/Ingredient N0000011311 Monobactams
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
CHEBI has role CHEBI:88188 drug allergen
CHEBI has role CHEBI:36047 antibacterial drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Septicemia due to Escherichia coli indication 9323009
Infection due to Pseudomonas aeruginosa indication 11218009
Infection of skin AND/OR subcutaneous tissue indication 19824006
Pneumonia due to Pseudomonas indication 41381004
Peritonitis indication 48661000
Lower respiratory tract infection indication 50417007
Pneumonia due to Escherichia coli indication 51530003
Klebsiella cystitis indication 60867007
Urinary tract infectious disease indication 68566005
Haemophilus influenzae pneumonia indication 70036007
Infection due to Escherichia coli indication 71057007
Bacterial infection due to Serratia indication 71120004
Rhinoscleroma indication 72409005 DOID:11336
Endometritis indication 78623009 DOID:1002
Septicemia due to Serratia indication 82091000
Female genital tract infection indication 125585007
Infectious disease of abdomen indication 128070006
Infection due to Enterobacteriaceae indication 128945009
Bacterial infection due to Klebsiella pneumoniae indication 186435004
Proteus pneumonia indication 195888009
Bacterial peritonitis indication 197171003
Proteus septicemia indication 300986008
Escherichia coli urinary tract infection indication 301011002
Proteus urinary tract infection indication 301012009
Bacterial urinary infection indication 312124009
Sepsis due to Pseudomonas indication 448813005
Sepsis due to Gram negative bacteria indication 449082003
Gram-Negative Aerobic Bacillary Pneumonia indication
Serratia Urinary Tract Infection indication
E. Coli Pelvic Inflammatory Disease indication
Enterobacter Pneumonia indication
Citrobacter Urinary Tract Infection indication
Skin and Skin Structure Proteus Infection indication
Skin and Skin Structure Pseudomonas Aeruginosa Infection indication
Haemophilus Influenzae Bronchitis indication
E. Coli Bronchitis indication
Respiratory Cystic Fibrosis with Pseudomonas aeruginosa Colonization indication
Skin and Skin Structure Serratia Infection indication
Inflammatory Disease of Female Pelvic Organs indication
Proteus Pelvic Inflammatory Disease indication
E. Coli Endometritis indication
Enterobacter Cloacae Bronchitis indication
Serratia Bronchitis indication
Pseudomonas Aeruginosa Bronchitis indication
Citrobacter Peritonitis indication
Aerobic Gram-Negative Bacteremia indication
E. Coli Peritonitis indication
Enterobacter Endometritis indication
Skin and Skin Structure Citrobacter Infection indication
Serratia Peritonitis indication
Enterobacter Pelvic Inflammatory Disease indication
Klebsiella Endometritis indication
Pseudomonas Aeruginosa Urinary Tract Infection indication
Klebsiella Pelvic Inflammatory Disease indication
Bacterial Exacerbation of Acute Bronchitis indication
Proteus Bronchitis indication
Proteus Endometritis indication
Klebsiella Pneumoniae Peritonitis indication
Bronchospasm contraindication 4386001
Kidney disease contraindication 90708001 DOID:557
Disease of liver contraindication 235856003 DOID:409
Pseudomembranous enterocolitis contraindication 397683000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.44 acidic
pKa2 2.83 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
75MG/VIAL CAYSTON GILEAD N050814 Feb. 22, 2010 RX FOR SOLUTION INHALATION 7208141 Dec. 20, 2021 IMPROVE RESPIRATORY SYMPTOMS IN CYSTIC FIBROSIS IN PATIENTS WITH PSEUDOMONAS AERUGINOSA
75MG/VIAL CAYSTON GILEAD N050814 Feb. 22, 2010 RX FOR SOLUTION INHALATION 7427633 Dec. 20, 2021 IMPROVE RESPIRATORY SYMPTOMS IN CYSTIC FIBROSIS IN PATIENTS WITH PSEUDOMONAS AERUGINOSA
75MG/VIAL CAYSTON GILEAD N050814 Feb. 22, 2010 RX FOR SOLUTION INHALATION 8399496 Dec. 20, 2021 IMPROVE RESPIRATORY SYMPTOMS IN CYSTIC FIBROSIS IN PATIENTS WITH PSEUDOMONAS AERUGINOSA

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Penicillin-binding protein 1B Enzyme INHIBITOR IC50 4.32 WOMBAT-PK CHEMBL
Penicillin-binding protein 1A Enzyme INHIBITOR IC50 5.32 WOMBAT-PK CHEMBL
Peptidoglycan synthase FtsI Enzyme INHIBITOR IC50 5.74 WOMBAT-PK CHEMBL
Penicillin-binding protein 1A Enzyme IC50 5.48 CHEMBL
Beta-lactamase Enzyme IC50 7.49 CHEMBL
Beta-lactamase Enzyme Ki 5.70 CHEMBL
AmpC Unclassified IC50 7.22 CHEMBL
Beta-lactamase Enzyme Ki 8.15 CHEMBL
Beta-lactamase Enzyme Ki 5.52 CHEMBL
Efflux transporter; SugE Unclassified IC50 8.22 CHEMBL
Beta-lactamase Enzyme IC50 8.22 CHEMBL

External reference:

IDSource
D001398 MESH_DESCRIPTOR_UI
C2746099 UMLSCUI
D00240 KEGG_DRUG
69918003 SNOMEDCT_US
1272 RXNORM
387386004 SNOMEDCT_US
4239 MMSL
d00067 MMSL
4017762 VANDF
167898 MMSL
002807 NDDF
CHEMBL158 ChEMBL_ID
DB00355 DRUGBANK_ID
G2B4VE5GH8 UNII
5159 INN_ID
AZR PDB_CHEM_ID
CHEBI:161680 CHEBI
827611-49-4 SECONDARY_CAS_RN
CHEMBL3833340 ChEMBL_ID
5742832 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
AZACTAM HUMAN PRESCRIPTION DRUG LABEL 1 0003-2560 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR NDA 12 sections
AZACTAM HUMAN PRESCRIPTION DRUG LABEL 1 0003-2570 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR NDA 12 sections
Cayston HUMAN PRESCRIPTION DRUG LABEL 1 61958-0901 KIT 75 mg None NDA 21 sections
Aztreonam HUMAN PRESCRIPTION DRUG LABEL 1 63323-401 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 14 sections
Aztreonam HUMAN PRESCRIPTION DRUG LABEL 1 63323-402 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 14 sections