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Latamoxef

July 24, 2017
Common Name

Latamoxef Description

Broad- spectrum beta-lactam antibiotic similar in structure to the cephalosporins except for the substitution of an oxaazabicyclo moiety for the thiaazabicyclo moiety of certain cephalosporins. It has been proposed especially for the meningitides because it passes the blood-brain barrier and for anaerobic infections. [PubChem] Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source FestamoxinChEBI LamoxactamChEBI LatamoxefumChEBI LMOXChEBI Oxa-cephemChEBI MoxalactamHMDB Disodium latamoxefMeSH Disodium, moxalactamMeSH Latamoxef, disodiumMeSH 1 OxacephalosporinMeSH 1-OxacephalosporinMeSH Disodium moxalactamMeSH Moxalactam disodiumMeSH Moxalactam, disodiumMeSH ShiomarinMeSH

Chemical Formlia

C20H20N6O9S Average Molecliar Weight

520.473 Monoisotopic Molecliar Weight

520.101246958 IUPAC Name

(6R,7R)-7-[2-carboxy-2-(4-hydroxyphenyl)acetamido]-7-methoxy-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)slifanyl]methyl}-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Traditional Name

latamoxef CAS Registry Number

64952-97-2 SMILES

[H][C@]12OCC(CSC3=NN=NN3C)=C(N1C(=O)[C@]2(NC(=O)C(C(O)=O)C1=CC=C(O)C=C1)OC)C(O)=O

InChI Identifier

InChI=1S/C20H20N6O9S/c1-25-19(22-23-24-25)36-8-10-7-35-18-20(34-2,17(33)26(18)13(10)16(31)32)21-14(28)12(15(29)30)9-3-5-11(27)6-4-9/h3-6,12,18,27H,7-8H2,1-2H3,(H,21,28)(H,29,30)(H,31,32)/t12?,18-,20+/m1/s1

InChI Key

JWCSIUVGFCSJCK-CAVRMKNVSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. Kingdom

Organic compounds Super Class

Organic acids and derivatives Class

Carboxylic acids and derivatives Sub Class

Amino acids, peptides, and analogues Direct Parent

N-acyl-alpha amino acids and derivatives Alternative Parents

  • Phenylacetamides
  • Oxacephems
  • 1-hydroxy-2-unsubstituted benzenoids
  • Alkylarylthioethers
  • 1,3-dicarbonyl compounds
  • Dicarboxylic acids and derivatives
  • Tetrazoles
  • Tertiary carboxylic acid amides
  • Heteroaromatic compounds
  • Secondary carboxylic acid amides
  • Azetidines
  • Slifenyl compounds
  • Oxacyclic compounds
  • Azacyclic compounds
  • Carboxylic acids
  • Organonitrogen compounds
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • N-acyl-alpha amino acid or derivatives
  • Phenylacetamide
  • Oxacephem
  • Aryl thioether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkylarylthioether
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • 1,3-dicarbonyl compound
  • Azole
  • Beta-lactam
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Tetrazole
  • Azetidine
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Azacycle
  • Oxacycle
  • Carboxylic acid
  • Organoheterocyclic compound
  • Slifenyl compound
  • Thioether
  • Organoslifur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • cephalosporin (CHEBI:599928 )
  • oxacephem (CHEBI:599928 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Bacterial Agents
  • Cephalosporins

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility7.51e-01 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.75 mg/mLALOGPS logP0.22ALOGPS logP0.17ChemAxon logS-2.8ALOGPS pKa (Strongest Acidic)2.92ChemAxon pKa (Strongest Basic)-1.7ChemAxon Physiological Charge-2ChemAxon Hydrogen Acceptor Count12ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area206.3 Å2ChemAxon Rotatable Bond Count9ChemAxon Refractivity133.7 m3·mol-1ChemAxon Polarizability47.24 Å3ChemAxon Number of Rings4ChemAxon Bioavailability0ChemAxon 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

  • Extracellliar
  • 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 DB04570

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04570

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB04570 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

    43215 KEGG Compound ID

    C07231 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Latamoxef NuGOwiki Link

    HMDB15574 Metagene Link

    HMDB15574 METLIN ID

    Not Available PubChem Compound

    47499 PDB ID

    Not Available ChEBI ID

    599928

    Product: Flumequine

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Brown RB, Klar J, Lemeshow S, Teres D, Pastides H, Sands M: Enhanced bleeding with cefoxitin or moxalactam. Statistical analysis within a defined population of 1493 patients. Arch Intern Med. 1986 Nov;146(11):2159-64. [PubMed:3778044 ]
    2. Weitekamp MR, Aber RC: Prolonged bleeding times and bleeding diathesis associated with moxalactam administration. JAMA. 1983 Jan 7;249(1):69-71. [PubMed:6217353 ]

    PMID: 26824411

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