Posted inUncategorized

Mezlocillin

July 24, 2017
Common Name

Mezlocillin Description

Mezlocillin is only found in individuals that have used or taken this drug. It is a semisynthetic ampicillin-derived acylureido penicillin. It has been proposed for infections with certain anaerobes and may be usefli in inner ear, bile, and CNS infections. [PubChem]By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, mezlocillin 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 mezlocillin interferes with an autolysin inhibitor. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (2S,5R,6R)-3,3-Dimethyl-6-{[(2R)-2-({[3-(methylslifonyl)-2-oxoimidazolidin-1-yl]carbonyl}amino)-2-phenylacetyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI 6beta-{(2R)-2-[3-(methaneslifonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acidChEBI MezlinChEBI MezlocilinaChEBI MezlocillineChEBI MezlocillinumChEBI (2S,5R,6R)-3,3-Dimethyl-6-{[(2R)-2-({[3-(methylslifonyl)-2-oxoimidazolidin-1-yl]carbonyl}amino)-2-phenylacetyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator (2S,5R,6R)-3,3-Dimethyl-6-{[(2R)-2-({[3-(methylsliphonyl)-2-oxoimidazolidin-1-yl]carbonyl}amino)-2-phenylacetyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator (2S,5R,6R)-3,3-Dimethyl-6-{[(2R)-2-({[3-(methylsliphonyl)-2-oxoimidazolidin-1-yl]carbonyl}amino)-2-phenylacetyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidGenerator 6b-{(2R)-2-[3-(methaneslifonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanateGenerator 6b-{(2R)-2-[3-(methaneslifonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acidGenerator 6b-{(2R)-2-[3-(methanesliphonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanateGenerator 6b-{(2R)-2-[3-(methanesliphonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acidGenerator 6beta-{(2R)-2-[3-(methaneslifonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanateGenerator 6beta-{(2R)-2-[3-(methanesliphonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanateGenerator 6beta-{(2R)-2-[3-(methanesliphonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acidGenerator 6β-{(2R)-2-[3-(methaneslifonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanateGenerator 6β-{(2R)-2-[3-(methaneslifonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acidGenerator 6β-{(2R)-2-[3-(methanesliphonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanateGenerator 6β-{(2R)-2-[3-(methanesliphonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acidGenerator Bayf 1353MeSH Curasan brand OF mezlocillin sodium (sterile)MeSH BaypenMeSH MelocinMeSH Sodium, mezlocillinMeSH Mezlocillin sodiumMeSH Bay F 1353MeSH Bay-F 1353MeSH Bayer brand OF mezlocillin sodium (sterile)MeSH MeslocillinMeSH

Chemical Formlia

C21H25N5O8S2 Average Molecliar Weight

539.582 Monoisotopic Molecliar Weight

539.114454181 IUPAC Name

(2S,5R,6R)-6-[(2R)-2-[(3-methaneslifonyl-2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Traditional Name

mezlocillin CAS Registry Number

51481-65-3 SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)N1CCN(C1=O)S(C)(=O)=O)C1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C21H25N5O8S2/c1-21(2)14(18(29)30)26-16(28)13(17(26)35-21)22-15(27)12(11-7-5-4-6-8-11)23-19(31)24-9-10-25(20(24)32)36(3,33)34/h4-8,12-14,17H,9-10H2,1-3H3,(H,22,27)(H,23,31)(H,29,30)/t12-,13-,14+,17-/m1/s1

InChI Key

YPBATNHYBCGSSN-VWPFQQQWSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid moleclies (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Peptides Alternative Parents

  • Penicillins
  • N-carbamoyl-alpha amino acids and derivatives
  • N-acyl-alpha amino acids and derivatives
  • Alpha amino acid amides
  • Phenylacetamides
  • Slifonylureas
  • Imidazolidinones
  • Thiazolidines
  • Tertiary carboxylic acid amides
  • Slifonyls
  • Organoslifonic acids and derivatives
  • Ureas
  • Secondary carboxylic acid amides
  • Azetidines
  • Thiohemiaminal derivatives
  • Azacyclic compounds
  • Carboxylic acids
  • Dialkylthioethers
  • Monocarboxylic acids and derivatives
  • Carbonyl compounds
  • Hydrocarbon derivatives
  • Organic oxides
  • Organopnictogen compounds

    • 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
  • Slifonylurea
  • Monocyclic benzene moiety
  • Imidazolidinone
  • Benzenoid
  • Beta-lactam
  • Imidazolidine
  • Organic slifonic acid or derivatives
  • Organoslifonic acid or derivatives
  • Slifonyl
  • Tertiary carboxylic acid amide
  • Thiazolidine
  • Urea
  • Azetidine
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Hemithioaminal
  • Dialkylthioether
  • Thioether
  • Organoheterocyclic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organoslifur compound
  • Organic oxide
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • penicillin (CHEBI:6919 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Bacterial Agents
  • Penicillins

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility4.71e-01 g/LNot Available LogP0Not Available

    Predicted Properties

    Property Value Source Water Solubility0.47 mg/mLALOGPS logP0.21ALOGPS logP-0.84ChemAxon logS-3.1ALOGPS pKa (Strongest Acidic)3.49ChemAxon pKa (Strongest Basic)-5.9ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count8ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area173.5 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity124.88 m3·mol-1ChemAxon Polarizability51.5 Å3ChemAxon Number of Rings4ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00948

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00948

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00948 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    570894 KEGG Compound ID

    C07221 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Mezlocillin NuGOwiki Link

    HMDB15083 Metagene Link

    HMDB15083 METLIN ID

    Not Available PubChem Compound

    656511 PDB ID

    Not Available ChEBI ID

    6919

    Product: MIM2

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. McCormick PA, Greenslade L, Kibbler CC, Chin JK, Burroughs AK, McIntyre N: A prospective randomized trial of ceftazidime versus netilmicin plus mezlocillin in the empirical therapy of presumed sepsis in cirrhotic patients. Hepatology. 1997 Apr;25(4):833-6. [PubMed:9096584 ]
    2. Rohde B, Werner U, Hickstein H, Ehmcke H, Drewelow B: Pharmacokinetics of mezlocillin and sulbactam under continuous veno-venous hemodialysis (CVVHD) in intensive care patients with acute renal failure. Eur J Clin Pharmacol. 1997;53(2):111-5. [PubMed:9403281 ]
    3. Kristof RA, Clusmann H, Koehler W, Fink KB, Schramm J: Treatment of accidental high dose intraventricular mezlocillin application by cerebrospinal fluid exchange. J Neurol Neurosurg Psychiatry. 1998 Mar;64(3):379-81. [PubMed:9527154 ]

    PMID: 11845213

    Last updated on