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Identification
NameAzlocillin
Accession NumberDB01061  (APRD00814)
TypeSmall Molecule
GroupsApproved
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 Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AzlinNot Available
SecuropenNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Azlocillin sodium
Thumb
  • InChI Key: UVOCNBWUHNCKJM-XFAPPKAWSA-M
  • Monoisotopic Mass: 483.118848826
  • Average Mass: 483.473
DBSALT000431
Categories
UNIIHUM6H389W0
CAS number37091-66-0
WeightAverage: 461.492
Monoisotopic: 461.136904183
Chemical FormulaC20H23N5O6S
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentPenicillins
Alternative Parents
Substituents
  • Penicillin
  • N-carbamoyl-alpha-amino acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Phenylacetamide
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Benzenoid
  • Imidazolidinone
  • Monocyclic benzene moiety
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Imidazolidine
  • Urea
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of infections caused by Pseudomonas aeruginosa, Escherichia coli, and Haemophilus influenzae.
PharmacodynamicsAzlocillin, 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 actionBy 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.
Related Articles
AbsorptionNot significantly absorbed from the gastrointestinal tract.
Volume of distributionNot Available
Protein binding20 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 eliminationNot Available
Half lifeMean elimination half-life is 1.3 to 1.5 hours. Longer in neonates, and 2 to 6 hours in patients with renal impairment.
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General References
  1. Wright AJ: The penicillins. Mayo Clin Proc. 1999 Mar;74(3):290-307. [PubMed:10090000 ]
External Links
ATC CodesJ01CA09
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (42.1 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolAzlocillin may increase the anticoagulant activities of Acenocoumarol.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Azlocillin.
BiotinThe therapeutic efficacy of Azlocillin can be decreased when used in combination with Biotin.
DemeclocyclineThe therapeutic efficacy of Azlocillin can be decreased when used in combination with Demeclocycline.
DoxycyclineThe therapeutic efficacy of Azlocillin can be decreased when used in combination with Doxycycline.
GentamicinThe serum concentration of Gentamicin can be decreased when it is combined with Azlocillin.
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Azlocillin.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Azlocillin.
MinocyclineThe therapeutic efficacy of Azlocillin can be decreased when used in combination with Minocycline.
Mycophenolate mofetilThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Azlocillin resulting in a loss in efficacy.
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.
NeomycinThe serum concentration of Neomycin can be decreased when it is combined with Azlocillin.
ProbenecidThe serum concentration of Azlocillin can be increased when it is combined with Probenecid.
StreptomycinThe serum concentration of Streptomycin can be decreased when it is combined with Azlocillin.
TetracyclineThe therapeutic efficacy of Azlocillin can be decreased when used in combination with Tetracycline.
TobramycinThe serum concentration of Tobramycin can be decreased when it is combined with Azlocillin.
WarfarinAzlocillin may increase the anticoagulant activities of Warfarin.
Food InteractionsNot Available

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 strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits) (By similarity).
Gene Name:
pbpA
Uniprot ID:
Q8XJ01
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23