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
Sept. 21, 2009 EMA GILEAD SCIENCES IRELAND UC
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 1732.65 24.19 363 7973 8454 63472232
Cystic fibrosis 418.16 24.19 95 8241 3201 63477485
Death 254.26 24.19 277 8059 374104 63106582
Lung transplant 229.73 24.19 58 8278 3070 63477616
Pulmonary function test decreased 216.35 24.19 58 8278 3889 63476797
Haemoptysis 212.55 24.19 94 8242 28632 63452054
Hospitalisation 201.07 24.19 130 8206 84951 63395735
Bacterial disease carrier 194.02 24.19 43 8293 1288 63479398
Bronchial secretion retention 181.94 24.19 47 8289 2726 63477960
Superinfection 160.46 24.19 42 8294 2565 63478121
Eosinophilia 144.61 24.19 67 8269 22689 63457997
Pseudomonas infection 131.42 24.19 51 8285 11162 63469524
Cystic fibrosis respiratory infection suppression 129.89 24.19 24 8312 277 63480409
Bronchospasm 116.43 24.19 53 8283 17227 63463459
Respiratory failure 115.01 24.19 100 8236 101758 63378928
Sinus operation 113.87 24.19 32 8304 2554 63478132
Scoliosis 103.63 24.19 39 8297 7849 63472837
Sleep disorder due to a general medical condition 96.93 24.19 42 8294 12146 63468540
Treatment noncompliance 90.39 24.19 58 8278 37267 63443419
Cough 86.64 24.19 145 8191 292598 63188088
Atelectasis 82.56 24.19 45 8291 21438 63459248
Off label use 82.23 24.19 233 8103 674229 62806457
Nonspecific reaction 77.07 24.19 23 8313 2269 63478417
Aggression 70.84 24.19 42 8294 23456 63457230
Lung disorder 67.93 24.19 60 8276 62201 63418485
Rib fracture 67.10 24.19 40 8296 22557 63458129
Sputum increased 62.87 24.19 20 8316 2439 63478247
Drug reaction with eosinophilia and systemic symptoms 59.14 24.19 43 8293 33793 63446893
Illness 54.95 24.19 48 8288 49011 63431675
Distal intestinal obstruction syndrome 52.71 24.19 12 8324 406 63480280
Wheezing 51.34 24.19 63 8273 95532 63385154
Forced expiratory volume decreased 49.14 24.19 20 8316 4948 63475738
Pancreatic failure 46.84 24.19 13 8323 990 63479696
Bronchiectasis 46.43 24.19 28 8308 16114 63464572
Impaired quality of life 45.13 24.19 26 8310 13757 63466929
Infection 42.27 24.19 93 8243 229080 63251606
Transplant 40.30 24.19 11 8325 787 63479899
Sinus disorder 40.19 24.19 30 8306 24523 63456163
Agranulocytosis 39.56 24.19 30 8306 25104 63455582
Pneumonia 39.05 24.19 140 8196 456627 63024059
Pulmonary haemorrhage 39.03 24.19 19 8317 7162 63473524
Anxiety 37.56 24.19 86 8250 217455 63263231
Pathogen resistance 34.98 24.19 17 8319 6381 63474305
Dyspnoea 33.54 24.19 173 8163 661140 62819546
Heart rate increased 32.28 24.19 50 8286 94188 63386498
Productive cough 31.27 24.19 40 8296 63168 63417518
Drug resistance 30.96 24.19 25 8311 22908 63457778
Atrial fibrillation 30.73 24.19 55 8281 116581 63364105
Chest discomfort 30.45 24.19 53 8283 109916 63370770
Drug ineffective 29.63 24.19 58 8278 1044707 62435979
Asthma 26.05 24.19 54 8282 127507 63353179

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 907.10 23.74 208 4940 6593 34945190
Cystic fibrosis 355.34 23.74 75 5073 1583 34950200
Lung transplant 307.43 23.74 69 5079 1955 34949828
Death 140.38 23.74 226 4922 397823 34553960
Hospitalisation 125.57 23.74 87 5061 56815 34894968
Eosinophilia 95.21 23.74 55 5093 26167 34925616
Pulmonary function test decreased 89.69 23.74 32 5116 4943 34946840
Cystic fibrosis respiratory infection suppression 87.70 23.74 17 5131 228 34951555
Haemoptysis 80.60 23.74 55 5093 34951 34916832
Pseudomonas infection 79.35 23.74 38 5110 12344 34939439
Respiratory failure 65.20 23.74 80 5068 108492 34843291
Rash maculo-papular 54.56 23.74 40 5108 28411 34923372
Sputum increased 53.35 23.74 18 5130 2352 34949431
Cystic fibrosis related diabetes 49.04 23.74 10 5138 176 34951607
Infection 48.20 23.74 63 5085 90852 34860931
Productive cough 46.54 23.74 41 5107 37772 34914011
Hepatic cytolysis 46.27 23.74 28 5120 14468 34937315
Pathogen resistance 45.71 23.74 24 5124 9458 34942325
Leukocytosis 42.04 23.74 32 5116 24033 34927750
Off label use 41.17 23.74 145 5003 419379 34532404
Infective exacerbation of bronchiectasis 40.44 23.74 10 5138 431 34951352
Lung disorder 39.49 23.74 36 5112 34660 34917123
Drug reaction with eosinophilia and systemic symptoms 35.14 23.74 33 5115 32979 34918804
Rash morbilliform 34.46 23.74 14 5134 3073 34948710
Distal intestinal obstruction syndrome 32.28 23.74 8 5140 348 34951435
Toxic epidermal necrolysis 31.81 23.74 26 5122 21620 34930163
Forced expiratory volume decreased 30.60 23.74 13 5135 3190 34948593
Condition aggravated 28.60 23.74 77 5071 192119 34759664
Cough 27.38 23.74 65 5083 150075 34801708
Cystic fibrosis hepatic disease 23.97 23.74 4 5144 21 34951762

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 2039.29 21.05 450 10874 12401 79720663
Cystic fibrosis 565.17 21.05 127 11197 3753 79729311
Lung transplant 405.04 21.05 100 11224 4461 79728603
Eosinophilia 243.91 21.05 122 11202 45223 79687841
Pulmonary function test decreased 239.82 21.05 74 11250 7563 79725501
Haemoptysis 222.41 21.05 123 11201 55876 79677188
Death 216.17 21.05 328 10996 566186 79166878
Hospitalisation 205.14 21.05 141 11183 94095 79638969
Bacterial disease carrier 184.23 21.05 43 11281 1503 79731561
Bronchial secretion retention 164.42 21.05 48 11276 4056 79729008
Cystic fibrosis respiratory infection suppression 148.90 21.05 29 11295 415 79732649
Pseudomonas infection 138.75 21.05 65 11259 20838 79712226
Superinfection 130.97 21.05 42 11282 4860 79728204
Sinus operation 112.13 21.05 32 11292 2493 79730571
Bronchospasm 102.44 21.05 56 11268 24803 79708261
Sputum increased 100.98 21.05 34 11290 4579 79728485
Scoliosis 99.14 21.05 38 11286 7426 79725638
Respiratory failure 94.17 21.05 122 11202 180789 79552275
Drug reaction with eosinophilia and systemic symptoms 92.32 21.05 75 11249 64169 79668895
Sleep disorder due to a general medical condition 87.40 21.05 42 11282 14235 79718829
Off label use 81.17 21.05 297 11027 906918 78826146
Distal intestinal obstruction syndrome 78.71 21.05 19 11305 768 79732296
Treatment noncompliance 75.04 21.05 61 11263 52207 79680857
Nonspecific reaction 73.03 21.05 23 11301 2509 79730555
Forced expiratory volume decreased 70.06 21.05 30 11294 7784 79725280
Atelectasis 67.09 21.05 47 11277 32210 79700854
Pathogen resistance 66.63 21.05 35 11289 14307 79718757
Cough 66.59 21.05 155 11169 366634 79366430
Pancreatic failure 65.02 21.05 19 11305 1609 79731455
Infective exacerbation of bronchiectasis 63.81 21.05 16 11308 758 79732306
Lung disorder 63.01 21.05 67 11257 80490 79652574
Rash maculo-papular 55.51 21.05 53 11271 56025 79677039
Wheezing 51.97 21.05 73 11251 116591 79616473
Rib fracture 51.87 21.05 38 11286 27909 79705155
Bronchiectasis 49.80 21.05 34 11290 22352 79710712
Productive cough 49.72 21.05 62 11262 88269 79644795
Pneumonia 48.89 21.05 204 11120 660042 79073022
Toxic epidermal necrolysis 45.77 21.05 43 11281 44538 79688526
Impaired quality of life 42.21 21.05 26 11298 14360 79718704
Drug resistance 41.97 21.05 40 11284 42173 79690891
Cystic fibrosis related diabetes 41.76 21.05 9 11315 217 79732847
Transplant 41.30 21.05 12 11312 996 79732068
Aggression 40.92 21.05 43 11281 50915 79682149
Illness 40.51 21.05 41 11283 46470 79686594
Sinus disorder 40.46 21.05 30 11294 22434 79710630
Pneumonia pseudomonal 38.03 21.05 18 11306 5893 79727171
Hepatic cytolysis 37.51 21.05 31 11293 27120 79705944
Agranulocytosis 36.16 21.05 38 11286 44992 79688072
Toxicity to various agents 35.88 21.05 8 11316 421532 79311532
Dyspnoea 33.60 21.05 222 11102 856803 78876261
Leukocytosis 31.95 21.05 35 11289 43420 79689644
Rash morbilliform 31.41 21.05 16 11308 6134 79726930
Chest discomfort 29.07 21.05 62 11262 137982 79595082
Acute generalised exanthematous pustulosis 28.76 21.05 22 11302 17232 79715832
Disease complication 28.63 21.05 14 11310 4923 79728141
Pneumothorax 28.46 21.05 27 11297 28296 79704768
Fatigue 28.26 21.05 56 11268 929671 78803393
Toxic skin eruption 27.80 21.05 24 11300 22269 79710795
Asthma 26.54 21.05 59 11265 135036 79598028
Tracheostomy 26.36 21.05 9 11315 1263 79731801
Blood alkaline phosphatase increased 25.64 21.05 38 11286 63626 79669438
Sputum discoloured 24.30 21.05 22 11302 21721 79711343
Heart rate increased 24.02 21.05 53 11271 120671 79612393
Joint swelling 23.51 21.05 6 11318 288640 79444424
Anxiety 23.38 21.05 83 11241 248429 79484635
Diarrhoea 22.68 21.05 58 11266 880431 78852633
Pain in extremity 22.29 21.05 12 11312 364526 79368538
Cystic fibrosis hepatic disease 21.95 21.05 4 11320 39 79733025
Bronchopulmonary aspergillosis allergic 21.80 21.05 10 11314 3051 79730013
Peripheral swelling 21.21 21.05 6 11318 269611 79463453

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
Penicillin-binding protein 1A Enzyme INHIBITOR IC50 5.32 WOMBAT-PK CHEMBL
Penicillin-binding protein 1B Enzyme INHIBITOR IC50 4.32 WOMBAT-PK CHEMBL
Peptidoglycan synthase FtsI Enzyme INHIBITOR IC50 5.74 WOMBAT-PK CHEMBL
Beta-lactamase Enzyme IC50 7.49 CHEMBL
AmpC Unclassified IC50 7.22 CHEMBL
Efflux transporter; SugE Transporter IC50 8.22 CHEMBL
Beta-lactamase Enzyme IC50 8.22 CHEMBL
Beta-lactamase Enzyme Ki 8.15 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
T6O PDB_CHEM_ID
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
373297006 SNOMEDCT_US
387386004 SNOMEDCT_US
409132008 SNOMEDCT_US
409133003 SNOMEDCT_US
69918003 SNOMEDCT_US
734461007 SNOMEDCT_US
90614001 SNOMEDCT_US
4017762 VANDF
4037186 VANDF
002807 NDDF
013342 NDDF

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 0003-2560 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR NDA 21 sections
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
AZACTAM HUMAN PRESCRIPTION DRUG LABEL 1 0003-2570 INJECTION, POWDER, FOR SOLUTION 2 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