Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H23N5O6S |
| Molecular Weight | 461.492 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)N3CCNC3=O)C4=CC=CC=C4)C(O)=O
InChI
InChIKey=JTWOMNBEOCYFNV-NFFDBFGFSA-N
InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1
Azlocillin is a semisynthetic penicillin with broad spectrum of anti-bacterial action. The drug is effective against gram-negative and gram-positive infections and acts by inhibition of penicillin-binding protein (PBP)-dependent bacterial cell wall synthesis. Azlocillin was marketed in the USA under the name Azlin (sodium salt), however, its approval was discontinued.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2354204 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | AZLIN Approved UseTreatment of Gram-positive (Streptococcus spp., Enterococcus, Listeria monocytogenes) and Gram-negative (H. influenzae, E. coli, Proteus mirabilis, Salmonella spp., Shigella spp.) infections. Launch Date3.99859188E11 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
414 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3780161 |
4 g 4 times / day multiple, intravenous dose: 4 g route of administration: Intravenous experiment type: MULTIPLE co-administered: |
AZLOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
374 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729353 |
4 g single, intravenous dose: 4 g route of administration: Intravenous experiment type: SINGLE co-administered: |
AZLOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
592 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2751284 |
4 g 4 times / day multiple, intravenous dose: 4 g route of administration: Intravenous experiment type: MULTIPLE co-administered: |
AZLOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
772 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2751284 |
5 g 3 times / day multiple, intravenous dose: 5 g route of administration: Intravenous experiment type: MULTIPLE co-administered: |
AZLOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.26 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729353 |
4 g single, intravenous dose: 4 g route of administration: Intravenous experiment type: SINGLE co-administered: |
AZLOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.29 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2751284 |
4 g 4 times / day multiple, intravenous dose: 4 g route of administration: Intravenous experiment type: MULTIPLE co-administered: |
AZLOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.46 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2751284 |
5 g 3 times / day multiple, intravenous dose: 5 g route of administration: Intravenous experiment type: MULTIPLE co-administered: |
AZLOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3780161 |
4 g 4 times / day multiple, intravenous dose: 4 g route of administration: Intravenous experiment type: MULTIPLE co-administered: |
AZLOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
17 g 1 times / day multiple, intravenous|intramuscular Dose: 17 g, 1 times / day Route: intravenous|intramuscular Route: multiple Dose: 17 g, 1 times / day Sources: |
unhealthy n = 21 |
Disc. AE: Macular rash, Pruritic rash... AEs leading to discontinuation/dose reduction: Macular rash (4 patients) Sources: Pruritic rash (4 patients) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Macular rash | 4 patients Disc. AE |
17 g 1 times / day multiple, intravenous|intramuscular Dose: 17 g, 1 times / day Route: intravenous|intramuscular Route: multiple Dose: 17 g, 1 times / day Sources: |
unhealthy n = 21 |
| Pruritic rash | 4 patients Disc. AE |
17 g 1 times / day multiple, intravenous|intramuscular Dose: 17 g, 1 times / day Route: intravenous|intramuscular Route: multiple Dose: 17 g, 1 times / day Sources: |
unhealthy n = 21 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Broth microdilution testing of susceptibilities to 30 antimicrobial agents of Mycobacterium avium strains from patients with acquired immune deficiency syndrome. | 1987 Oct |
|
| Sensitization to aztreonam and cross-reactivity with other beta-lactam antibiotics in high-risk patients with cystic fibrosis. | 1991 Jan |
|
| Evaluation of the immunologic cross-reactivity of aztreonam in patients with cystic fibrosis who are allergic to penicillin and/or cephalosporin antibiotics. | 1991 May-Jun |
|
| The penicillins. | 1999 Mar |
|
| [Microbiology of open surgical wounds after delivery--episiotomy and cesarean section]. | 2001 |
|
| Effect of beta-estradiol on voltage-gated Ca(2+) channels in rat hippocampal neurons: a comparison with dehydroepiandrosterone. | 2001 Mar 30 |
|
| Natural antibiotic susceptibility of Enterobacter spp., with special reference to Enterobacter aerogenes and Enterobacter intermedius strains. | 2002 Oct |
|
| Evaluation of culture media for the recovery of Mycobacterium avium subsp. paratuberculosis from Cheddar cheese. | 2003 |
|
| Natural antibiotic susceptibility of Ewingella americana strains. | 2003 Oct |
|
| (-)-Epigallocatechin-3-gallate induces contraction of the rat aorta by a calcium influx-dependent mechanism. | 2004 May |
|
| [Enzyme immunoassay of ampicillin in milk]. | 2005 Nov-Dec |
|
| [Bacterial meningitis and Pseudomonas aeruginosa: apropos of a case]. | 2005 Sep-Dec |
|
| Problematic clinical isolates of Pseudomonas aeruginosa from the university hospitals in Sofia, Bulgaria: current status of antimicrobial resistance and prevailing resistance mechanisms. | 2007 Jul |
|
| Effects of treatment with antimicrobial agents on the human colonic microflora. | 2008 Dec |
|
| Mycobacterium ulcerans disease, Peru. | 2008 Mar |
|
| Phylogeography and recolonization of the Swiss Alps by the Valais shrew (Sorex antinorii), inferred with autosomal and sex-specific markers. | 2008 Sep |
|
| How beta-lactam antibiotics enter bacteria: a dialogue with the porins. | 2009 |
|
| Detection of Extended Spectrum β-lactamase Production Among Uropathogens. | 2009 Jan |
|
| Data correction pre-processing for electronically stored blood culture results: implications on microbial spectrum and empiric antibiotic therapy. | 2009 Jun 7 |
|
| Direct susceptibility testing for multi drug resistant tuberculosis: a meta-analysis. | 2009 May 20 |
|
| Role of the BACTEC radiometric method in the evaluation of patients with clinically probable tuberculous meningitis. | 2010 Apr |
|
| Laboratory diagnosis of tuberculous meningitis - is there a scope for further improvement? | 2010 Jan |
|
| In-vitro efficacy of synergistic antibiotic combinations in multidrug resistant Pseudomonas aeruginosa strains. | 2010 Jan |
|
| Pleistocene climatic cycling drives intra-specific diversification in the intermediate horseshoe bat (Rhinolophus affinis) in Southern China. | 2010 Jul |
|
| Contrasting patterns of phylogeographic relationships in sympatric sister species of ironclad beetles (Zopheridae: Phloeodes spp.) in California's Transverse Ranges. | 2010 Jun 24 |
|
| Molecular taxonomy, phylogeny and evolution in the family Stichopodidae (Aspidochirotida: Holothuroidea) based on COI and 16S mitochondrial DNA. | 2010 Sep |
Sample Use Guides
Gram-negative infections: 2 to 5 grams every 8 hours IV. Serious infections: 225 to 300 mg/kg/day IV in 4 to 6 divided doses (usual IV doses 3g q4h or
4g q6h) (up to 18 g/day).
Route of Administration:
Intravenous
In vitro activity of Azlocillin against different bacterial strains was determined. MIC50 values were 2 ugml (Enterococcus), 8 ug/ml (E. coli), 16 ug/ml (Enterobacter spp.), 64 ug/ml (Klebsiella spp.), 4 ug/ml (P. mirabilis), 16 ug/ml (P. aeruginosa, gentamicin susceptible)).
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WHO-ATC |
J01CA09
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NCI_THESAURUS |
C1500
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WHO-VATC |
QJ01CA09
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1266
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HUM6H389W0
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DTXSID1022639
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DB01061
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253-348-2
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SUB05661MIG
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m2178
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CHEMBL1537
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100000086086
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4011
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758227
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277
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AZLOCILLIN
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C293
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6479523
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37091-66-0
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2956
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D001390
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
