Azlocillin

Identification

Generic Name
Azlocillin
DrugBank Accession Number
DB01061
Background

Azlocillin is a semisynthetic ampicillin-derived acylureido penicillin.

Type
Small Molecule
Groups
Approved
Structure
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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Contraindications & Blackbox Warnings
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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.

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

Adverse Effects
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Toxicity

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.
DrugInteraction
AcemetacinAcemetacin may decrease the excretion rate of Azlocillin which could result in a higher serum level.
AcenocoumarolAzlocillin may increase the anticoagulant activities of Acenocoumarol.
AcetazolamideThe therapeutic efficacy of Acetazolamide can be decreased when used in combination with Azlocillin.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Azlocillin is combined with Ambroxol.
AmifampridineThe risk or severity of seizure can be increased when Azlocillin is combined with Amifampridine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Azlocillin sodiumDWV1EFW94737091-65-9UVOCNBWUHNCKJM-XFAPPKAWSA-M
International/Other Brands
Azlin / Securopen

Categories

ATC Codes
J01CR50 — Combinations of penicillinsJ01CA09 — Azlocillin
Drug Categories
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
  1. Wright AJ: The penicillins. Mayo Clin Proc. 1999 Mar;74(3):290-307. [Article]
Human Metabolome Database
HMDB0015194
KEGG Drug
D02339
KEGG Compound
C06839
PubChem Compound
6479523
PubChem Substance
46506654
ChemSpider
4980416
RxNav
1266
ChEBI
2956
ChEMBL
CHEMBL1537
ZINC
ZINC000003830261
Therapeutic Targets Database
DAP001169
PharmGKB
PA164749135
Wikipedia
Azlocillin
MSDS
Download (42.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableRecruitingNot AvailableNeonatal Early Onset Sepsis1

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
Polarizability44.97 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-MSsplash10-014l-9770100000-8492b9b1630f98f790e8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ik9-0927100000-fc82e7c9717cc3d5eb00
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00lr-0009000000-85537b29aba5f42aa458
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-9006300000-126cf7d1360d5e989b4e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ri-8492000000-306a6e866e0b318c7f53
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-9100000000-825b41dd04c773b2becf
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03xr-2901100000-1841cec91d141127d7b3
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-212.8443661
predicted
DarkChem Lite v0.1.0
[M-H]-199.94762
predicted
DeepCCS 1.0 (2019)
[M+H]+211.9124661
predicted
DarkChem Lite v0.1.0
[M+H]+201.77327
predicted
DeepCCS 1.0 (2019)
[M+Na]+211.8584661
predicted
DarkChem Lite v0.1.0
[M+Na]+207.51369
predicted
DeepCCS 1.0 (2019)

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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  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. [Article]
  3. Wright AJ: The penicillins. Mayo Clin Proc. 1999 Mar;74(3):290-307. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 03, 2024 02:31