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-IYZXUIDESA-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 |
|||
Curative | AZACTAM Approved UseAztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms. Launch Date1986 |
|||
Curative | AZACTAM Approved UseAztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms. Launch Date1986 |
|||
Curative | AZACTAM Approved UseAztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms. Launch Date1986 |
|||
Curative | AZACTAM Approved UseAztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms. Launch Date1986 |
|||
Curative | AZACTAM Approved UseAztreonam for Injection is indicated for the treatment of infections caused by susceptible gram-negative microorganisms. Launch Date1986 |
|||
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 |
---|---|---|---|---|
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 |
|
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 |
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 n = 10 Health Status: unhealthy Condition: cystic fibrosis Age Group: 10 - 18 years Sex: unknown Population Size: 10 Sources: |
|
1 g single, intramuscular Recommended Dose: 1 g Route: intramuscular Route: single Dose: 1 g Sources: |
unhealthy, 18 - 75 years n = 102 Health Status: unhealthy Condition: urogenital gonorrhoea Age Group: 18 - 75 years Sex: M+F Population Size: 102 Sources: |
|
1 g 3 times / day steady, intramuscular (median) Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children n = 343 Health Status: unhealthy Condition: infections Age Group: children Sex: unknown Population Size: 343 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%) |
1 g 3 times / day steady, intramuscular (median) Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children n = 612 Health Status: unhealthy Condition: infections Age Group: children Sex: unknown Population Size: 612 Sources: |
Other AEs: Rash, Diarrhea... Other AEs: Rash (4.3%) Sources: Diarrhea (1.4%) Fever (1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Induration | 0.9% | 1 g 3 times / day steady, intramuscular (median) Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children n = 343 Health Status: unhealthy Condition: infections Age Group: children Sex: unknown Population Size: 343 Sources: |
Pain | 12% | 1 g 3 times / day steady, intramuscular (median) Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children n = 343 Health Status: unhealthy Condition: infections Age Group: children Sex: unknown Population Size: 343 Sources: |
Phlebitis | 2.1% | 1 g 3 times / day steady, intramuscular (median) Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children n = 343 Health Status: unhealthy Condition: infections Age Group: children Sex: unknown Population Size: 343 Sources: |
Erythema | 2.9% | 1 g 3 times / day steady, intramuscular (median) Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children n = 343 Health Status: unhealthy Condition: infections Age Group: children Sex: unknown Population Size: 343 Sources: |
Neutropenia | 3.2% | 1 g 3 times / day steady, intramuscular (median) Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children n = 343 Health Status: unhealthy Condition: infections Age Group: children Sex: unknown Population Size: 343 Sources: |
Increased platelets | 3.6% | 1 g 3 times / day steady, intramuscular (median) Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children n = 343 Health Status: unhealthy Condition: infections Age Group: children Sex: unknown Population Size: 343 Sources: |
AST increased | 3.8% | 1 g 3 times / day steady, intramuscular (median) Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children n = 343 Health Status: unhealthy Condition: infections Age Group: children Sex: unknown Population Size: 343 Sources: |
Increased serum creatinine | 5.8% | 1 g 3 times / day steady, intramuscular (median) Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children n = 343 Health Status: unhealthy Condition: infections Age Group: children Sex: unknown Population Size: 343 Sources: |
Blood eosinophils increased | 6.3% | 1 g 3 times / day steady, intramuscular (median) Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children n = 343 Health Status: unhealthy Condition: infections Age Group: children Sex: unknown Population Size: 343 Sources: |
ALT increased | 6.5% | 1 g 3 times / day steady, intramuscular (median) Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children n = 343 Health Status: unhealthy Condition: infections Age Group: children Sex: unknown Population Size: 343 Sources: |
Fever | 1% | 1 g 3 times / day steady, intramuscular (median) Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children n = 612 Health Status: unhealthy Condition: infections Age Group: children Sex: unknown Population Size: 612 Sources: |
Diarrhea | 1.4% | 1 g 3 times / day steady, intramuscular (median) Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children n = 612 Health Status: unhealthy Condition: infections Age Group: children Sex: unknown Population Size: 612 Sources: |
Rash | 4.3% | 1 g 3 times / day steady, intramuscular (median) Recommended Dose: 1 g, 3 times / day Route: intramuscular Route: steady Dose: 1 g, 3 times / day Sources: |
unhealthy, children n = 612 Health Status: unhealthy Condition: infections Age Group: children Sex: unknown Population Size: 612 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 |
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
admin
on
Edited
Sat Dec 16 04:58:04 GMT 2023
by
admin
on
Sat Dec 16 04:58:04 GMT 2023
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Record UNII |
5Q55M3D9UA
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Record Status |
Validated (UNII)
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Record Version |
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-
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