Identification
- Generic Name
- Azlocillin
- DrugBank Accession Number
- DB01061
- Background
Azlocillin is a semisynthetic ampicillin-derived acylureido penicillin.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Azlocillin (DB01061)
- Weight
- Average: 461.492
Monoisotopic: 461.136904183 - Chemical Formula
- C20H23N5O6S
- Synonyms
- (2S,5R,6R)-3,3-dimethyl-7-oxo-6-{[(2R)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- Azlocilina
- Azlocillin
- Azlocilline
- Azlocillinum
Pharmacology
- Indication
For the treatment of infections caused by Pseudomonas aeruginosa, Escherichia coli, and Haemophilus influenzae.
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Similar to mezlocillin and piperacillin, azlocillin is an acylampicillin that exhibits an extended-spectrum of activity and in vitro potency that is greater than that of the carboxy penicillins. Azlocillin is shown to be effective against a broad spectrum of bacteria, including Pseudomonas aeruginosa and enterococci.
- Mechanism of action
By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, azlocillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that azlocillin interferes with an autolysin inhibitor.
Target Actions Organism APenicillin-binding protein 1A inhibitorClostridium perfringens (strain 13 / Type A) - Absorption
Not significantly absorbed from the gastrointestinal tract.
- Volume of distribution
Not Available
- Protein binding
20 to 46% bound to plasma proteins
- Metabolism
Eliminated predominantly by renal mechanisms, but also undergoes biotransformation within body tissues and intraintestinal degradation by bowel bacteria, with high concentrations found in bile.
- Route of elimination
Not Available
- Half-life
Mean elimination half-life is 1.3 to 1.5 hours. Longer in neonates, and 2 to 6 hours in patients with renal impairment.
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcemetacin Acemetacin may decrease the excretion rate of Azlocillin which could result in a higher serum level. Acenocoumarol Azlocillin may increase the anticoagulant activities of Acenocoumarol. Acetazolamide The therapeutic efficacy of Acetazolamide can be decreased when used in combination with Azlocillin. Amifampridine The risk or severity of seizure can be increased when Azlocillin is combined with Amifampridine. Amikacin The serum concentration of Amikacin can be decreased when it is combined with Azlocillin. Amobarbital The therapeutic efficacy of Amobarbital can be decreased when used in combination with Azlocillin. Articaine The risk or severity of methemoglobinemia can be increased when Azlocillin is combined with Articaine. Atracurium The therapeutic efficacy of Atracurium can be increased when used in combination with Azlocillin. Atracurium besylate The therapeutic efficacy of Atracurium besylate can be increased when used in combination with Azlocillin. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Azlocillin. 
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- Not Available
Products
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Ingredient UNII CAS InChI Key Azlocillin sodium DWV1EFW947 37091-65-9 UVOCNBWUHNCKJM-XFAPPKAWSA-M - International/Other Brands
- Azlin / Securopen
Categories
- ATC Codes
- J01CR50 — Combinations of penicillins
- J01CR — Combinations of penicillins, incl. beta-lactamase inhibitors
- J01C — BETA-LACTAM ANTIBACTERIALS, PENICILLINS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Agents that reduce seizure threshold
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Beta-Lactam Antibacterials
- beta-Lactams
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Penicillin G
- Penicillins
- Penicillins With Extended Spectrum
- Sulfur Compounds
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Peptides
- Alternative Parents
- Penicillins / N-acyl-alpha amino acids and derivatives / N-carbamoyl-alpha amino acids and derivatives / Alpha amino acid amides / Phenylacetamides / Imidazolidinones / Tertiary carboxylic acid amides / Thiazolidines / Ureas / Azetidines show 11 more
- Substituents
- Alpha peptide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Benzenoid / Beta-lactam / Carbonic acid derivative / Carbonyl group show 28 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- penicillin (CHEBI:2956)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- HUM6H389W0
- CAS number
- 37091-66-0
- InChI Key
- JTWOMNBEOCYFNV-NFFDBFGFSA-N
- InChI
- 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
- IUPAC Name
- (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetamido]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- SMILES
- [H][C@](NC(=O)N1CCNC1=O)(C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@]12[H])C1=CC=CC=C1
References
- General References
- Wright AJ: The penicillins. Mayo Clin Proc. 1999 Mar;74(3):290-307. [Article]
- External Links
- Human Metabolome Database
- HMDB0015194
- KEGG Drug
- D02339
- KEGG Compound
- C06839
- PubChem Compound
- 6479523
- PubChem Substance
- 46506654
- ChemSpider
- 4980416
- 1266
- ChEBI
- 2956
- ChEMBL
- CHEMBL1537
- ZINC
- ZINC000003830261
- Therapeutic Targets Database
- DAP001169
- PharmGKB
- PA164749135
- Wikipedia
- Azlocillin
- MSDS
- Download (42.1 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count Not Available Recruiting Not Available Neonatal Early Onset Sepsis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Sodium salt is soluble in water (50 mg/ml) Not Available logP 0.2 Not Available - Predicted Properties
Property Value Source Water Solubility 0.233 mg/mL ALOGPS logP 0.2 ALOGPS logP -0.33 Chemaxon logS -3.3 ALOGPS pKa (Strongest Acidic) 3.49 Chemaxon pKa (Strongest Basic) -5.9 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 148.15 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 111.71 m3·mol-1 Chemaxon Polarizability 44.97 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8506 Blood Brain Barrier - 0.9946 Caco-2 permeable - 0.7255 P-glycoprotein substrate Substrate 0.8133 P-glycoprotein inhibitor I Non-inhibitor 0.8936 P-glycoprotein inhibitor II Non-inhibitor 1.0 Renal organic cation transporter Non-inhibitor 0.9277 CYP450 2C9 substrate Non-substrate 0.6786 CYP450 2D6 substrate Non-substrate 0.8035 CYP450 3A4 substrate Non-substrate 0.5342 CYP450 1A2 substrate Non-inhibitor 0.7646 CYP450 2C9 inhibitor Non-inhibitor 0.8188 CYP450 2D6 inhibitor Non-inhibitor 0.9022 CYP450 2C19 inhibitor Non-inhibitor 0.7413 CYP450 3A4 inhibitor Non-inhibitor 0.8669 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.928 Ames test Non AMES toxic 0.7453 Carcinogenicity Non-carcinogens 0.9182 Biodegradation Ready biodegradable 0.8281 Rat acute toxicity 2.1838 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9958 hERG inhibition (predictor II) Non-inhibitor 0.658
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Clostridium perfringens (strain 13 / Type A)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Transferase activity, transferring glycosyl groups
- Specific Function
- Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
- Gene Name
- pbpA
- Uniprot ID
- Q8XJ01
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 75176.35 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Wright AJ: The penicillins. Mayo Clin Proc. 1999 Mar;74(3):290-307. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 03, 2023 08:14