Chemical: Drug
azlocillin

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PharmGKB contains no Clinical Variants that meet the highest level of criteria.

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Overview

Generic Names
  • Azlocilina [INN-Spanish]
  • Azlocillin sodium salt
  • Azlocilline [INN-French]
  • Azlocillinum [INN-Latin]
Trade Names
  • Azlin
  • Bayer Brand of Azlocillin
  • Securopen
Brand Mixture Names

PharmGKB Accession Id

PA164749135

Type(s):

Drug

Description

A semisynthetic ampicillin-derived acylureido penicillin.

Source: Drug Bank

Indication

For the treatment of infections caused by Pseudomonas aeruginosa, Escherichia coli, and Haemophilus influenzae.

Source: Drug Bank

Other Vocabularies

Information pulled from DrugBank has not been reviewed by PharmGKB.

Pharmacology, Interactions, and Contraindications

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.

Source: Drug Bank

Pharmacology

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.

Source: Drug Bank

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Eliminated predominantly by renal mechanisms, but also undergoes biotransformation within body tissues and intraintestinal degradation by bowel bacteria, with high concentrations found in bile.

Source: Drug Bank

Protein Binding

20 to 46% bound to plasma proteins

Source: Drug Bank

Absorption

Not significantly absorbed from the gastrointestinal tract.

Source: Drug Bank

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.

Source: Drug Bank

Chemical Properties

Chemical Formula

C20H23N5O6S

Source: Drug Bank

Isomeric SMILES

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)NC(=O)N4CCNC4=O)C(=O)O)C

Source: Drug Bank

[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

Source: Drug Bank

Canonical SMILES

[H][C@]

Source: Drug Bank

Average Molecular Weight

461.492

Source: Drug Bank

Monoisotopic Molecular Weight

461.136904183

Source: Drug Bank

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

Source: Drug Bank

InChI String

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

Source: Drug Bank

Genes that are associated with this drug in PharmGKB's database based on (1) variant annotations, (2) literature review, (3) pathways or (4) information automatically retrieved from DrugBank, depending on the "evidence" and "source" listed below.

No related genes are available.

Drug Interactions

Interaction Description
demeclocycline - azlocillin Possible antagonism of action (source: Drug Bank)
doxycycline - azlocillin Possible antagonism of action (source: Drug Bank)
ethinyl estradiol - azlocillin This anti-infectious agent could decrease the effect of the oral contraceptive (source: Drug Bank)
minocycline - azlocillin Possible antagonism of action (source: Drug Bank)
tetracycline - azlocillin Possible antagonism of action (source: Drug Bank)
No related diseases are available

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB01061
ChEBI:
2956
KEGG Compound:
C06839
KEGG Drug:
D02339
PubChem Compound:
37625
PubChem Substance:
9057
Therapeutic Targets Database:
DAP001169

Clinical Trials

These are trials that mention azlocillin and are related to either pharmacogenetics or pharmacogenomics.

No trials found.

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Sources for PharmGKB drug information: DrugBank, PubChem.