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Identification
Name Azlocillin
Accession Number DB01061 (APRD00814)
Type small molecule
Groups approved
Description

A semisynthetic ampicillin-derived acylureido penicillin. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Azlocilina [INN-Spanish]
  • Azlocillin sodium salt
  • Azlocilline [INN-French]
  • Azlocillinum [INN-Latin]
Brand names
  • Azlin
  • Bayer Brand of Azlocillin
  • Securopen
Brand name mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Penicillins
CAS number 37091-66-0
Weight Average: 461.492
Monoisotopic: 461.136904183
Chemical Formula C20H23N5O6S
InChI Key InChIKey=JTWOMNBEOCYFNV-XQERAMJGSA-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
Plain Text
IUPAC Name
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C(NC(=O)N1CCNC1=O)C1=CC=CC=C1)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Penicillins
  • Phenethylamines
  • Polypeptides
Substructures
  • Hydroxy Compounds
  • Acetates
  • Amino Ketones
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Ureas and Derivatives
  • Carboxylic Acids and Derivatives
  • Beta Lactams
  • Penicillins
  • Thiazoles
  • Phenethylamines
  • Polypeptides
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Lactams
  • Azetidines
  • Thiazolidines
  • Imidazolidines
Pharmacology
Indication For the treatment of infections caused by Pseudomonas aeruginosa, Escherichia coli, and Haemophilus influenzae.
Pharmacodynamics Azlocillin, similar to mezlocillin and piperacillin, is an acylampicillin with an extended spectrum of activity and greater in vitro potency than the carboxy penicillins. Azlocillin demonstrates antibacterial activity against a broad spectrum of bacteria, including Pseudomonas aeruginosa, and, in contrast to most cephalosporins, exhibits activity against 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.
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
Toxicity Not Available
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Bayer pharmaceuticals corp
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
water solubility Sodium salt is soluble in water (50 mg/ml) PhysProp
logP 0.2 PhysProp
Predicted Properties
Property Value Source
water solubility 2.33e-01 g/l ALOGPS
logP 0.20 ALOGPS
logP -0.33 ChemAxon Molconvert
logS -3.30 ALOGPS
pKa 8.90 ChemAxon Molconvert
hydrogen acceptor count 6 ChemAxon Molconvert
hydrogen donor count 4 ChemAxon Molconvert
polar surface area 148.15 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 111.71 ChemAxon Molconvert
polarizability 44.73 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Wright AJ: The penicillins. Mayo Clin Proc. 1999 Mar;74(3):290-307. Pubmed
External Links
Resource Link
KEGG Drug D02339 Link_out
KEGG Compound C06839 Link_out
PubChem Compound 37625 Link_out
PubChem Substance 46506654 Link_out
ChemSpider 34512 Link_out
ChEBI 2956 Link_out
ChEMBL 2956 Link_out
Therapeutic Targets Database DAP001169 Link_out
PharmGKB PA448522 Link_out
Drug Product Database 0 Link_out
Wikipedia http://en.wikipedia.org/wiki/Azlocillin Link_out
ATC Codes
  • J01CA09
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (42.1 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Penicillin-binding proteins 1A/1B

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q8XJ01 Link_out
Gene: pbpA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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. Pubmed
  3. Wright AJ: The penicillins. Mayo Clin Proc. 1999 Mar;74(3):290-307. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:08

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.