aztreonam ๐Ÿถ Veterinary Use | 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: -0.36
  • 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 ยตM/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
Infective pulmonary exacerbation of cystic fibrosis 1676.40 24.32 346 6253 7563 50590962
Cystic fibrosis 421.16 24.32 93 6506 2771 50595754
Death 259.26 24.32 261 6338 325118 50273407
Lung transplant 215.92 24.32 54 6545 2771 50595754
Pulmonary function test decreased 211.00 24.32 55 6544 3333 50595192
Haemoptysis 207.19 24.32 89 6510 25484 50573041
Hospitalisation 194.70 24.32 117 6482 67820 50530705
Cystic fibrosis respiratory infection suppression 125.33 24.32 23 6576 257 50598268
Respiratory failure 110.68 24.32 93 6506 91088 50507437
Cough 98.36 24.32 138 6461 241126 50357399
Pseudomonas infection 97.15 24.32 39 6560 9391 50589134
Lung disorder 81.18 24.32 58 6541 44741 50553784
Off label use 78.46 24.32 183 6416 474243 50124282
Sputum increased 64.06 24.32 19 6580 1848 50596677
Infection 60.26 24.32 92 6507 172862 50425663
Bronchial secretion retention 54.55 24.32 16 6583 1497 50597028
Distal intestinal obstruction syndrome 54.42 24.32 12 6587 353 50598172
Sinus operation 52.74 24.32 16 6583 1680 50596845
Bacterial disease carrier 49.67 24.32 13 6586 798 50597727
Bronchiectasis 49.52 24.32 25 6574 10258 50588267
Eosinophilia 47.86 24.32 30 6569 18622 50579903
Pneumonia 45.78 24.32 130 6469 378271 50220254
Drug reaction with eosinophilia and systemic symptoms 45.13 24.32 34 6565 28390 50570135
Forced expiratory volume decreased 44.65 24.32 18 6581 4376 50594149
Pancreatic failure 43.95 24.32 12 6587 866 50597659
Transplant 42.62 24.32 11 6588 639 50597886
Pulmonary haemorrhage 37.89 24.32 18 6581 6474 50592051
Nonspecific reaction 35.59 24.32 12 6587 1767 50596758
Chest discomfort 34.61 24.32 51 6548 92671 50505854
Superinfection 33.89 24.32 12 6587 2044 50596481
Bronchospasm 33.43 24.32 22 6577 14832 50583693
Treatment noncompliance 32.93 24.32 29 6570 30121 50568404
Productive cough 32.23 24.32 37 6562 52657 50545868
Pathogen resistance 27.88 24.32 14 6585 5675 50592850
Drug resistance 26.40 24.32 21 6578 18968 50579557
Pneumothorax 25.00 24.32 18 6581 14016 50584509

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
Infective pulmonary exacerbation of cystic fibrosis 889.77 24.65 205 4581 6031 29563710
Cystic fibrosis 350.48 24.65 74 4712 1418 29568323
Lung transplant 277.98 24.65 63 4723 1693 29568048
Hospitalisation 135.02 24.65 87 4699 45901 29523840
Death 114.49 24.65 200 4586 341884 29227857
Pulmonary function test decreased 88.47 24.65 31 4755 4132 29565609
Cystic fibrosis respiratory infection suppression 87.93 24.65 17 4769 203 29569538
Haemoptysis 80.30 24.65 54 4732 30496 29539245
Pseudomonas infection 74.61 24.65 36 4750 10816 29558925
Eosinophilia 72.60 24.65 45 4741 22116 29547625
Respiratory failure 61.46 24.65 77 4709 97054 29472687
Sputum increased 55.35 24.65 18 4768 1909 29567832
Cystic fibrosis related diabetes 50.65 24.65 10 4776 134 29569607
Productive cough 49.99 24.65 41 4745 31218 29538523
Infection 48.75 24.65 61 4725 76690 29493051
Hepatic cytolysis 46.46 24.65 24 4762 8323 29561418
Pathogen resistance 41.36 24.65 22 4764 8094 29561647
Infective exacerbation of bronchiectasis 39.90 24.65 10 4776 414 29569327
Lung disorder 38.73 24.65 35 4751 30327 29539414
Leukocytosis 38.63 24.65 30 4756 21112 29548629
Rash maculo-papular 34.97 24.65 30 4756 24259 29545482
Condition aggravated 34.28 24.65 74 4712 146221 29423520
Distal intestinal obstruction syndrome 33.76 24.65 8 4778 261 29569480
Off label use 32.14 24.65 114 4672 300686 29269055
Forced expiratory volume decreased 31.05 24.65 13 4773 2800 29566941
Drug reaction with eosinophilia and systemic symptoms 29.43 24.65 29 4757 27963 29541778
Cough 27.28 24.65 62 4724 126665 29443076

FDA Adverse Event Reporting System (Geriatric)

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
Infective pulmonary exacerbation of cystic fibrosis 1984.85 20.89 437 9182 11359 64477754
Cystic fibrosis 569.02 20.89 126 9493 3308 64485805
Lung transplant 395.37 20.89 97 9522 4011 64485102
Pulmonary function test decreased 244.15 20.89 73 9546 6388 64482725
Haemoptysis 223.69 20.89 120 9499 48928 64440185
Death 210.22 20.89 305 9314 482400 64006713
Hospitalisation 198.02 20.89 129 9490 75078 64414035
Cystic fibrosis respiratory infection suppression 149.73 20.89 29 9590 382 64488731
Pseudomonas infection 129.64 20.89 60 9559 17823 64471290
Eosinophilia 124.49 20.89 75 9544 38001 64451112
Sputum increased 103.19 20.89 33 9586 3602 64485511
Respiratory failure 89.48 20.89 115 9504 161068 64328045
Off label use 88.21 20.89 249 9370 632557 63856556
Distal intestinal obstruction syndrome 81.75 20.89 19 9600 619 64488494
Cough 74.82 20.89 149 9470 301999 64187114
Lung disorder 74.34 20.89 66 9553 60634 64428479
Drug reaction with eosinophilia and systemic symptoms 72.53 20.89 62 9557 54155 64434958
Forced expiratory volume decreased 65.70 20.89 28 9591 6839 64482274
Infective exacerbation of bronchiectasis 63.58 20.89 16 9603 732 64488381
Pancreatic failure 61.70 20.89 18 9601 1442 64487671
Bronchiectasis 57.18 20.89 32 9587 14108 64475005
Pathogen resistance 55.16 20.89 30 9589 12513 64476600
Pneumonia 53.75 20.89 194 9425 559382 63929731
Productive cough 51.58 20.89 59 9560 73144 64415969
Sinus operation 50.63 20.89 16 9603 1679 64487434
Bacterial disease carrier 45.25 20.89 13 9606 986 64488127
Hepatic cytolysis 44.15 20.89 27 9592 14022 64475091
Cystic fibrosis related diabetes 43.32 20.89 9 9610 172 64488941
Transplant 42.35 20.89 12 9607 866 64488247
Bronchial secretion retention 40.65 20.89 15 9604 2512 64486601
Rash maculo-papular 40.25 20.89 42 9577 46984 64442129
Drug resistance 38.70 20.89 36 9583 35066 64454047
Pneumonia pseudomonal 37.23 20.89 17 9602 4886 64484227
Toxic epidermal necrolysis 36.95 20.89 36 9583 37130 64451983
Nonspecific reaction 32.62 20.89 12 9607 1991 64487122
Condition aggravated 32.19 20.89 125 9494 372301 64116812
Leukocytosis 31.03 20.89 33 9586 37707 64451406
Toxicity to various agents 31.02 20.89 8 9611 363505 64125608
Chest discomfort 30.74 20.89 59 9560 116047 64373066
Disease complication 29.96 20.89 14 9605 4241 64484872
Pneumothorax 28.89 20.89 26 9593 24272 64464841
Bronchospasm 27.36 20.89 24 9595 21658 64467455
Toxic skin eruption 25.66 20.89 22 9597 19262 64469851
Treatment noncompliance 25.60 20.89 32 9587 43450 64445663
Sputum discoloured 25.05 20.89 21 9598 17835 64471278
Superinfection 24.95 20.89 12 9607 3874 64485239
Fall 24.56 20.89 16 9603 416810 64072303
Bronchopulmonary aspergillosis allergic 23.79 20.89 9 9610 1613 64487500
Dyspnoea 23.48 20.89 185 9434 718489 63770624
Cystic fibrosis hepatic disease 21.75 20.89 4 9615 39 64489074
Pain in extremity 21.74 20.89 9 9610 303076 64186037
Fatigue 20.89 20.89 51 9568 748679 63740434

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J01DF01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER BETA-LACTAM ANTIBACTERIALS
Monobactams
FDA CS M0014030 Monobactams
FDA EPC N0000175493 Monobactam Antibacterial
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
CHEBI has role CHEBI:36047 antibacterial drugs
CHEBI has role CHEBI:50696 PBP3 inhibitor
CHEBI has role CHEBI:88188 allergenic drug

Drug Use | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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

External reference:

IDSource
D00240 KEGG_DRUG
827611-49-4 SECONDARY_CAS_RN
1272 RXNORM
C0004521 UMLSCUI
CHEBI:161680 CHEBI
CHEMBL158 ChEMBL_ID
CHEMBL3833340 ChEMBL_ID
D001398 MESH_DESCRIPTOR_UI
DB00355 DRUGBANK_ID
10763 IUPHAR_LIGAND_ID
5159 INN_ID
G2B4VE5GH8 UNII
5742832 PUBCHEM_CID
167898 MMSL
170132 MMSL
2813 MMSL
4239 MMSL
d00067 MMSL
002807 NDDF
013342 NDDF
4017762 VANDF
4037186 VANDF
AZR PDB_CHEM_ID
373297006 SNOMEDCT_US
387386004 SNOMEDCT_US
409132008 SNOMEDCT_US
409133003 SNOMEDCT_US
69918003 SNOMEDCT_US
734461007 SNOMEDCT_US
90614001 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
AZACTAM HUMAN PRESCRIPTION DRUG LABEL 1 0003-2560 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR NDA 21 sections
AZACTAM HUMAN PRESCRIPTION DRUG LABEL 1 0003-2570 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR NDA 21 sections
Aztreonam HUMAN PRESCRIPTION DRUG LABEL 1 0409-0829 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 23 sections
Aztreonam HUMAN PRESCRIPTION DRUG LABEL 1 0409-0830 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 g INTRAVENOUS ANDA 23 sections
Aztreonam HUMAN PRESCRIPTION DRUG LABEL 1 63323-401 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 24 sections
Aztreonam HUMAN PRESCRIPTION DRUG LABEL 1 63323-401 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 24 sections
Aztreonam HUMAN PRESCRIPTION DRUG LABEL 1 63323-401 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 24 sections
Aztreonam HUMAN PRESCRIPTION DRUG LABEL 1 63323-401 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 24 sections
Aztreonam HUMAN PRESCRIPTION DRUG LABEL 1 63323-401 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 24 sections
Aztreonam HUMAN PRESCRIPTION DRUG LABEL 1 63323-401 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 24 sections
Aztreonam HUMAN PRESCRIPTION DRUG LABEL 1 63323-402 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 24 sections
Aztreonam HUMAN PRESCRIPTION DRUG LABEL 1 63323-402 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 24 sections
Aztreonam HUMAN PRESCRIPTION DRUG LABEL 1 63323-402 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 24 sections
Aztreonam HUMAN PRESCRIPTION DRUG LABEL 1 63323-402 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 24 sections
Aztreonam HUMAN PRESCRIPTION DRUG LABEL 1 63323-402 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 24 sections
Aztreonam HUMAN PRESCRIPTION DRUG LABEL 1 63323-402 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 24 sections