Identification

Name
Azlocillin
Accession Number
DB01061  (APRD00814)
Type
Small Molecule
Groups
Approved
Description

A semisynthetic ampicillin-derived acylureido penicillin. [PubChem]

Structure
Thumb
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
External IDs
J01CA09
Product Ingredients
IngredientUNIICASInChI Key
Azlocillin sodiumDWV1EFW94737091-65-9UVOCNBWUHNCKJM-UHFFFAOYSA-M
International/Other Brands
Azlin / Securopen
Categories
UNII
HUM6H389W0
CAS number
37091-66-0
Weight
Average: 461.492
Monoisotopic: 461.136904183
Chemical Formula
C20H23N5O6S
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

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.

TargetActionsOrganism
APenicillin-binding protein 1A
inhibitor
Clostridium 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
Toxicity
Not Available
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinAzlocillin may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinAzlocillin may increase the anticoagulant activities of (S)-Warfarin.
4-hydroxycoumarinAzlocillin may increase the anticoagulant activities of 4-hydroxycoumarin.
AcemetacinAcemetacin may decrease the excretion rate of Azlocillin which could result in a higher serum level.
AcenocoumarolAzlocillin may increase the anticoagulant activities of Acenocoumarol.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Azlocillin.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Azlocillin.
Anthrax immune globulin humanThe therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Azlocillin.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Azlocillin.
ApramycinThe serum concentration of Apramycin can be decreased when it is combined with Azlocillin.
Food Interactions
Not Available

References

General References
  1. Wright AJ: The penicillins. Mayo Clin Proc. 1999 Mar;74(3):290-307. [PubMed:10090000]
External Links
Human Metabolome Database
HMDB0015194
KEGG Drug
D02339
KEGG Compound
C06839
PubChem Compound
6479523
PubChem Substance
46506654
ChemSpider
4980416
ChEBI
2956
ChEMBL
CHEMBL1537
Therapeutic Targets Database
DAP001169
PharmGKB
PA164749135
Wikipedia
Azlocillin
ATC Codes
J01CR50 — Combinations of penicillinsJ01CA09 — Azlocillin
MSDS
Download (42.1 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySodium salt is soluble in water (50 mg/ml)Not Available
logP0.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.233 mg/mLALOGPS
logP0.2ALOGPS
logP-0.33ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.49ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area148.15 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity111.71 m3·mol-1ChemAxon
Polarizability45.02 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8506
Blood Brain Barrier-0.9946
Caco-2 permeable-0.7255
P-glycoprotein substrateSubstrate0.8133
P-glycoprotein inhibitor INon-inhibitor0.8936
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9277
CYP450 2C9 substrateNon-substrate0.6786
CYP450 2D6 substrateNon-substrate0.8035
CYP450 3A4 substrateNon-substrate0.5342
CYP450 1A2 substrateNon-inhibitor0.7646
CYP450 2C9 inhibitorNon-inhibitor0.8188
CYP450 2D6 inhibitorNon-inhibitor0.9022
CYP450 2C19 inhibitorNon-inhibitor0.7413
CYP450 3A4 inhibitorNon-inhibitor0.8669
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.928
Ames testNon AMES toxic0.7453
CarcinogenicityNon-carcinogens0.9182
BiodegradationReady biodegradable0.8281
Rat acute toxicity2.1838 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9958
hERG inhibition (predictor II)Non-inhibitor0.658
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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 / Penicillin / N-acyl-alpha amino acid or derivatives / N-carbamoyl-alpha-amino acid or derivatives / Alpha-amino acid amide / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / Phenylacetamide / Penam / Imidazolidinone
show 28 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
penicillin (CHEBI:2956)

Targets

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
  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:17139284]
  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:17016423]
  3. Wright AJ: The penicillins. Mayo Clin Proc. 1999 Mar;74(3):290-307. [PubMed:10090000]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 08:39