Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C13H17N5O8S2 |
| Molecular Weight | 435.433 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]1[C@H](NC(=O)C(=N/OC(C)(C)C(O)=O)\C2=CSC(N)=N2)C(=O)N1S(O)(=O)=O
InChI
InChIKey=WZPBZJONDBGPKJ-VEHQQRBSSA-N
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
| Molecular Formula | C13H17N5O8S2 |
| Molecular Weight | 435.433 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 1 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/2244291Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050580s040,050632s013lbl.pdf
https://www.ncbi.nlm.nih.gov/pubmed/27334663
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2244291
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050580s040,050632s013lbl.pdf
https://www.ncbi.nlm.nih.gov/pubmed/27334663
Aztreonam is the first monocyclic beta-lactam antibiotic (monobactam) originally isolated from Chromobacterium violaceum. Aztreonam has a high affinity for the protein-binding protein 3 (PBP-3) of aerobic gram-negative bacteria. Most of these organisms are inhibited and killed at low concentrations of the drug. Aztreonam must be administered as an intravenous or intramuscular injection (AZACTAM®), or inhaled (CAYSTON®). Aztreonam for injection is indicated for the treatment of the following infections caused by susceptible gram-negative microorganisms: urinary tract, lower respiratory tract, skin and skin-structure, intra-abdominal and gynecologic infections as well as for septicemia. Aztreonam for inhalation solution is indicated to improve respiratory symptoms in cystic fibrosis patients with Pseudomonas aeruginosa.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2244291 |
0.03 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | AZACTAM Approved UseAztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms. Launch Date1986 |
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| Curative | AZACTAM Approved UseAztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms. Launch Date1986 |
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| Curative | AZACTAM Approved UseAztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms. Launch Date1986 |
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| Curative | AZACTAM Approved UseAztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms. Launch Date1986 |
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| Curative | AZACTAM Approved UseAztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms. Launch Date1986 |
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| Curative | AZACTAM Approved UseAztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms. Launch Date1986 |
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| Palliative | CAYSTON Approved UseCAYSTON® is indicated to improve respiratory symptoms in cystic fibrosis (CF) patients with Pseudomonas aeruginosa. Launch Date2010 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
54 μg/mL |
500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
AZTREONAM serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
90 μg/mL |
1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered: |
AZTREONAM serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
204 μg/mL |
2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered: |
AZTREONAM serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
208 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3710959 |
1 g 1 times / day steady-state, intravenous dose: 1 g route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
AZTREONAM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.67 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3710959 |
1 g 1 times / day steady-state, intravenous dose: 1 g route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
AZTREONAM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
44% |
500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
AZTREONAM serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
30 mg/kg single, intravenous Recommended Dose: 30 mg/kg Route: intravenous Route: single Dose: 30 mg/kg Sources: |
unhealthy, 10 - 18 years Health Status: unhealthy Age Group: 10 - 18 years Sex: unknown Sources: |
|
1 g single, intramuscular Recommended Dose: 1 g Route: intramuscular Route: single Dose: 1 g Sources: |
unhealthy, 18 - 75 years Health Status: unhealthy Age Group: 18 - 75 years Sex: M+F Sources: |
|
1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: |
Other AEs: Rash, Diarrhea... Other AEs: Rash (4.3%) Sources: Diarrhea (1.4%) Fever (1%) |
1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: |
Other AEs: Pain, Erythema... Other AEs: Pain (12%) Sources: Erythema (2.9%) Induration (0.9%) Phlebitis (2.1%) Blood eosinophils increased (6.3%) Increased platelets (3.6%) Neutropenia (3.2%) AST increased (3.8%) ALT increased (6.5%) Increased serum creatinine (5.8%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Fever | 1% | 1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: |
| Diarrhea | 1.4% | 1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: |
| Rash | 4.3% | 1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: |
| Induration | 0.9% | 1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: |
| Pain | 12% | 1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: |
| Phlebitis | 2.1% | 1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: |
| Erythema | 2.9% | 1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: |
| Neutropenia | 3.2% | 1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: |
| Increased platelets | 3.6% | 1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: |
| AST increased | 3.8% | 1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: |
| Increased serum creatinine | 5.8% | 1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: |
| Blood eosinophils increased | 6.3% | 1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: |
| ALT increased | 6.5% | 1 g 3 times / day steady, intramuscular Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/050814Orig1s000PharmR.pdf#page=3 Page: 3.0 |
unlikely | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/050814Orig1s000PharmR.pdf#page=3 Page: 3.0 |
unlikely |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/050814Orig1s000PharmR.pdf#page=3 Page: 3.0 |
no |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005-06 |
|
| Contribution of beta-lactamases to beta-lactam susceptibilities of susceptible and multidrug-resistant Mycobacterium tuberculosis clinical isolates. | 1998-06 |
|
| In-vitro activity of seventeen antimicrobial compounds against seven species of mycobacteria. | 1988-12 |
|
| Broth microdilution testing of susceptibilities to 30 antimicrobial agents of Mycobacterium avium strains from patients with acquired immune deficiency syndrome. | 1987-10 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050814s007lbl.pdf
Urinary tract infections (adults): 0.5-1 g 2-3 times/day. Moderately severe systemic infections (adults): 1-2 g 2-3 times/day. Severe systemic or life-threatening infections (adults): 2 g 3-4 times/day. Maximum recommended dose for adults is 8 g per day. Mild to moderate infections (pediatric patients): 30 mg/kg 3 times/day
Moderate to severe infections (pediatric patients): 30 mg/kg 3-4 times/day. Maximum recommended dose for pediatric patients is 120 mg/kg/day. Inhalation solution: one dose (one single use vial and one ampule of diluent) 3 times a day for 28 days.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2244291
In vitro, minimum inhibition concentration (MIC) values against almost all of the Enterobacteriaceae, Neisseria and Haemophilus strains were below 1 microgram per milliliter. MIC values against Pseudomonas aeruginosa were about 8 ug/ml.
| Substance Class |
Chemical
Created
by
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on
Edited
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by
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| Record UNII |
G2B4VE5GH8
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| Record Status |
Validated (UNII)
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| Record Version |
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Common Name | English |
| Classification Tree | Code System | Code | ||
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NDF-RT |
N0000011311
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NDF-RT |
N0000011311
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LIVERTOX |
NBK548462
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FDA ORPHAN DRUG |
155002
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NDF-RT |
N0000011311
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NDF-RT |
N0000011311
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NCI_THESAURUS |
C260
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WHO-VATC |
QJ01DF01
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NDF-RT |
N0000011311
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WHO-ATC |
J01DF01
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NDF-RT |
N0000011311
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NDF-RT |
N0000011311
Created by
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NDF-RT |
N0000011311
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FDA ORPHAN DRUG |
266208
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NDF-RT |
N0000175493
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NDF-RT |
N0000011311
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| Code System | Code | Type | Description | ||
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278-839-9
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PRIMARY | |||
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5742832
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m2188
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PRIMARY | Merck Index | ||
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SUB05664MIG
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C28845
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161680
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CHEMBL3545256
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G2B4VE5GH8
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Aztreonam
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78110-38-0
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646279
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G2B4VE5GH8
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DTXSID0022640
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DB00355
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100000091595
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279
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D001398
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1272
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AZTREONAM
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5159
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758913
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1046205
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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TARGET ORGANISM->INHIBITOR |
Indicated for the suppressive therapy of chronic pulmonary infections due to Pseudomonas
aeruginosa in patients with cystic fibrosis (CF) aged 6 years and older.
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLITE INACTIVE -> PARENT |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
Open-ring aztreonam and open-ring desulfated aztreonam coelute. The limit is for the sum of these two impurities (1.0 WEUGHT PERCENT)
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
Open-ring aztreonam and open-ring desulfated aztreonam coelute. The limit is for the sum of these two impurities (1.0 WEIGHT PERCENT)
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
|---|---|---|---|---|---|---|
| Volume of Distribution | PHARMACOKINETIC |
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| Cmax | PHARMACOKINETIC |
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Amount Administered PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC |
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| Biological Half-life | PHARMACOKINETIC |
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