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][[email protected]](NC(=O)N1CCNC1=O)(C(=O)N[[email protected]@H]1C(=O)N2[[email protected]@H](C(O)=O)C(C)(C)S[[email protected]]12[H])C1=CC=CC=C1

Pharmacology

Indication

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

Structured Indications
Not Available
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
DrugInteractionDrug group
AcenocoumarolAzlocillin may increase the anticoagulant activities of Acenocoumarol.Approved
AclarubicinThe serum concentration of Aclarubicin can be decreased when it is combined with Azlocillin.Investigational
AldoxorubicinThe serum concentration of Aldoxorubicin can be decreased when it is combined with Azlocillin.Investigational
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Azlocillin.Approved, Vet Approved
AmrubicinThe serum concentration of Amrubicin can be decreased when it is combined with Azlocillin.Approved, Investigational
AnnamycinThe serum concentration of Annamycin can be decreased when it is combined with Azlocillin.Investigational
ApramycinThe serum concentration of Apramycin can be decreased when it is combined with Azlocillin.Experimental, Vet Approved
ArbekacinThe serum concentration of Arbekacin can be decreased when it is combined with Azlocillin.Approved, Investigational
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Azlocillin.Investigational
BekanamycinThe serum concentration of Bekanamycin can be decreased when it is combined with Azlocillin.Experimental
ChlortetracyclineThe therapeutic efficacy of Azlocillin can be decreased when used in combination with Chlortetracycline.Approved, Investigational, Vet Approved
ClorindioneAzlocillin may increase the anticoagulant activities of Clorindione.Experimental
DaunorubicinThe serum concentration of Daunorubicin can be decreased when it is combined with Azlocillin.Approved
DemeclocyclineThe therapeutic efficacy of Azlocillin can be decreased when used in combination with Demeclocycline.Approved
DibekacinThe serum concentration of Dibekacin can be decreased when it is combined with Azlocillin.Experimental
DicoumarolAzlocillin may increase the anticoagulant activities of Dicoumarol.Approved
DihydrostreptomycinThe serum concentration of Dihydrostreptomycin can be decreased when it is combined with Azlocillin.Investigational, Vet Approved
DiphenadioneAzlocillin may increase the anticoagulant activities of Diphenadione.Experimental
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Azlocillin.Approved, Investigational
DoxycyclineThe therapeutic efficacy of Azlocillin can be decreased when used in combination with Doxycycline.Approved, Investigational, Vet Approved
EpirubicinThe serum concentration of Epirubicin can be decreased when it is combined with Azlocillin.Approved
Ethyl biscoumacetateAzlocillin may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FluindioneAzlocillin may increase the anticoagulant activities of Fluindione.Investigational
FramycetinThe serum concentration of Framycetin can be decreased when it is combined with Azlocillin.Approved
GeneticinThe serum concentration of Geneticin can be decreased when it is combined with Azlocillin.Experimental
GentamicinThe serum concentration of Gentamicin can be decreased when it is combined with Azlocillin.Approved, Vet Approved
GENTAMICIN C1AThe serum concentration of GENTAMICIN C1A can be decreased when it is combined with Azlocillin.Experimental
GPX-150The serum concentration of GPX-150 can be decreased when it is combined with Azlocillin.Investigational
Hygromycin BThe serum concentration of Hygromycin B can be decreased when it is combined with Azlocillin.Vet Approved
IdarubicinThe serum concentration of Idarubicin can be decreased when it is combined with Azlocillin.Approved
IsepamicinThe serum concentration of Isepamicin can be decreased when it is combined with Azlocillin.Experimental
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Azlocillin.Approved, Investigational, Vet Approved
MedrogestoneThe serum concentration of Medrogestone can be decreased when it is combined with Azlocillin.Approved
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Azlocillin.Approved
MetrizamideThe serum concentration of Metrizamide can be decreased when it is combined with Azlocillin.Approved
MicronomicinThe serum concentration of Micronomicin can be decreased when it is combined with Azlocillin.Experimental
MinocyclineThe therapeutic efficacy of Azlocillin can be decreased when used in combination with Minocycline.Approved, Investigational
Mycophenolic acidThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Azlocillin resulting in a loss in efficacy.Approved
NeamineThe serum concentration of Neamine can be decreased when it is combined with Azlocillin.Experimental
NeomycinThe serum concentration of Neomycin can be decreased when it is combined with Azlocillin.Approved, Vet Approved
NetilmicinThe serum concentration of Netilmicin can be decreased when it is combined with Azlocillin.Approved, Investigational
ParomomycinThe serum concentration of Paromomycin can be decreased when it is combined with Azlocillin.Approved, Investigational
PhenindioneAzlocillin may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonAzlocillin may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Azlocillin.Approved
PirarubicinThe serum concentration of Pirarubicin can be decreased when it is combined with Azlocillin.Investigational
PlazomicinThe serum concentration of Plazomicin can be decreased when it is combined with Azlocillin.Investigational
PlicamycinThe serum concentration of Plicamycin can be decreased when it is combined with Azlocillin.Approved, Investigational, Withdrawn
ProbenecidThe serum concentration of Azlocillin can be increased when it is combined with Probenecid.Approved
PuromycinThe serum concentration of Puromycin can be decreased when it is combined with Azlocillin.Experimental
RibostamycinThe serum concentration of Ribostamycin can be decreased when it is combined with Azlocillin.Approved, Investigational
SabarubicinThe serum concentration of Sabarubicin can be decreased when it is combined with Azlocillin.Investigational
SisomicinThe serum concentration of Sisomicin can be decreased when it is combined with Azlocillin.Investigational
SP1049CThe serum concentration of SP1049C can be decreased when it is combined with Azlocillin.Investigational
SpectinomycinThe serum concentration of Spectinomycin can be decreased when it is combined with Azlocillin.Approved, Investigational, Vet Approved
StreptomycinThe serum concentration of Streptomycin can be decreased when it is combined with Azlocillin.Approved, Vet Approved
StreptozocinThe serum concentration of Streptozocin can be decreased when it is combined with Azlocillin.Approved
TioclomarolAzlocillin may increase the anticoagulant activities of Tioclomarol.Experimental
TobramycinThe serum concentration of Tobramycin can be decreased when it is combined with Azlocillin.Approved, Investigational
ValrubicinThe serum concentration of Valrubicin can be decreased when it is combined with Azlocillin.Approved
WarfarinAzlocillin may increase the anticoagulant activities of Warfarin.Approved
Zoptarelin doxorubicinThe serum concentration of Zoptarelin doxorubicin can be decreased when it is combined with Azlocillin.Investigational
ZorubicinThe serum concentration of Zorubicin can be decreased when it is combined with Azlocillin.Experimental
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
HMDB15194
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 December 01, 2017 17:14