aztreonam indications/contra

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

Drug dosage:

DoseUnitRoute
0.23 g Inhal.solution
4 g P

Approvals:

DateAgencyCompanyOrphan
Dec. 31, 1986 FDA BRISTOL MYERS SQUIBB

FDA Adverse Event Reporting System

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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
Death 724.41 62.48 272 932 152052 3232603
Cystic fibrosis 681.13 62.48 96 1108 480 3384175
Infective pulmonary exacerbation of cystic fibrosis 461.96 62.48 68 1136 477 3384178
Respiratory failure 363.57 62.48 104 1100 23037 3361618
Lung transplant 330.96 62.48 53 1151 678 3383977
Lung disorder 179.91 62.48 49 1155 8868 3375787
Off label use 171.76 62.48 74 1130 53903 3330752
Haemoptysis 159.37 62.48 42 1162 6689 3377966
Cough 111.31 62.48 50 1154 39808 3344847
Bronchiectasis 108.78 62.48 22 1182 1079 3383576
Pseudomonas infection 101.99 62.48 23 1181 1898 3382757
Dyspnoea 78.60 62.48 55 1149 102879 3281776
Pulmonary function test decreased 76.21 62.48 15 1189 638 3384017

Pharmacologic Action:

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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)

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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:2527
Disease of liver contraindication 235856003 DOID:409
Pseudomembranous enterocolitis contraindication 397683000 DOID:0060185

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 -1.05 acidic
pKa2 3.44 acidic
pKa3 2.83 Basic

Orange Book patent data (new drug applications)

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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:

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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:

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IDSource
DB00355 DRUGBANK_ID
C2746099 UMLSCUI
D00240 KEGG_DRUG
CHEMBL158 ChEMBL_ID
1272 RXNORM
387386004 SNOMEDCT_US
69918003 SNOMEDCT_US
4239 MMSL
d00067 MMSL
4017762 VANDF
167898 MMSL
N0000146126 NDFRT
N0000005876 NDFRT
002807 NDDF
5742832 PUBCHEM_CID
G2B4VE5GH8 UNII
5159 INN_ID
827611-49-4 SECONDARY_CAS_RN
CHEMBL3833340 ChEMBL_ID
D001398 MESH_DESCRIPTOR_UI
CHEBI:161680 CHEBI

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
AZACTAM HUMAN PRESCRIPTION DRUG LABEL 1 0003-2230 INJECTION, SOLUTION 1 g INTRAVENOUS NDA 11 sections
AZACTAM HUMAN PRESCRIPTION DRUG LABEL 1 0003-2240 INJECTION, SOLUTION 2 g INTRAVENOUS NDA 11 sections
AZACTAM HUMAN PRESCRIPTION DRUG LABEL 1 0003-2560 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR NDA 13 sections
AZACTAM HUMAN PRESCRIPTION DRUG LABEL 1 0003-2570 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR NDA 13 sections
Cayston HUMAN PRESCRIPTION DRUG LABEL 1 61958-0901 KIT 75 mg None NDA 20 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