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Cefepime

July 24, 2017
Common Name

Cefepime Description

Cefepime is a fourth-generation cephalosporin antibiotic developed in 1994. Cefepime has an extended spectrum of activity against Gram-positive and Gram-negative bacteria, with greater activity against both Gram-negative and Gram-positive organisms than third-generation agents. Cefepime is usually reserved to treat severe nosocomial pneumonia, infections caused by mliti-resistant microorganisms (e.g. Pseudomonas aeruginosa) and empirical treatment of febrile neutropenia. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(1-methylpyrrolidinium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateChEBI CefepimaChEBI CefepimumChEBI (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(1-methylpyrrolidinium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidGenerator Bristol-myers brand OF cefepime dihydrochlorideMeSH Elan brand OF cefepime dihydrochlorideMeSH CefepimMeSH Cefepime hydrochlorideMeSH AxépimMeSH Bristol-myers squibb brand OF cefepime dihydrochlorideMeSH MaxipimeMeSH QuadrocefMeSH

Chemical Formlia

C19H24N6O5S2 Average Molecliar Weight

480.561 Monoisotopic Molecliar Weight

480.124959288 IUPAC Name

1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium Traditional Name

cefepime CAS Registry Number

88040-23-7 SMILES

CON=C(/C(=O)N[C@@H]1C(=O)N2[C@]1([H])SCC(C[N+]1(C)CCCC1)=C2C([O-])=O)C1=CSC(N)=N1

InChI Identifier

InChI=1S/C19H24N6O5S2/c1-25(5-3-4-6-25)7-10-8-31-17-13(16(27)24(17)14(10)18(28)29)22-15(26)12(23-30-2)11-9-32-19(20)21-11/h9,13,17H,3-8H2,1-2H3,(H3-,20,21,22,26,28,29)/b23-12-/t13-,17-/m1/s1

InChI Key

HVFLCNVBZFFHBT-ZKDACBOMSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as 3-quaternary ammonium cephalosporins. These are cephalosporins that are substituted at the 3-position by a quaternary ammonium group. Kingdom

Organic compounds Super Class

Organoheterocyclic compounds Class

Lactams Sub Class

Beta lactams Direct Parent

3-quaternary ammonium cephalosporins Alternative Parents

  • N-acyl-alpha amino acids and derivatives
  • 2,4-disubstituted thiazoles
  • 1,3-thiazines
  • 2-amino-1,3-thiazoles
  • N-alkylpyrrolidines
  • Heteroaromatic compounds
  • Tetraalkylammonium salts
  • Tertiary carboxylic acid amides
  • Carboxylic acid salts
  • Azetidines
  • Secondary carboxylic acid amides
  • Amino acids
  • Carboxylic acids
  • Monocarboxylic acids and derivatives
  • Dialkylthioethers
  • Thiohemiaminal derivatives
  • Azacyclic compounds
  • Carbonyl compounds
  • Hydrocarbon derivatives
  • Organic oxides
  • Organic salts
  • Organic zwitterions
  • Organopnictogen compounds
  • Primary amines

    • Substituents

  • 3'-quaternary ammonium cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • 2,4-disubstituted 1,3-thiazole
  • Meta-thiazine
  • N-alkylpyrrolidine
  • 1,3-thiazol-2-amine
  • Tertiary carboxylic acid amide
  • Thiazole
  • Quaternary ammonium salt
  • Pyrrolidine
  • Tetraalkylammonium salt
  • Azole
  • Heteroaromatic compound
  • Carboxylic acid salt
  • Carboxamide group
  • Amino acid
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Azetidine
  • Azacycle
  • Carboxylic acid derivative
  • Dialkylthioether
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hemithioaminal
  • Thioether
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic salt
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Organic zwitterion
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • cephalosporin (CHEBI:478164 )
  • oxime O-ether (CHEBI:478164 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Bacterial Agents
  • Antibacterial Agents
  • Cephalosporins

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.73e-02 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.017 mg/mLALOGPS logP-0.37ALOGPS logP-4.3ChemAxon logS-4.5ALOGPS pKa (Strongest Acidic)3.25ChemAxon pKa (Strongest Basic)4.06ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count8ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area150.04 Å2ChemAxon Rotatable Bond Count7ChemAxon Refractivity141.98 m3·mol-1ChemAxon Polarizability47.53 Å3ChemAxon Number of Rings4ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

  • 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 DB01413

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01413

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01413 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

    4586395 KEGG Compound ID

    C08111 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Cefepime NuGOwiki Link

    HMDB15483 Metagene Link

    HMDB15483 METLIN ID

    Not Available PubChem Compound

    5479537 PDB ID

    Not Available ChEBI ID

    478164

    Product: DUBs-IN-2

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Chapman TM, Perry CM: Cefepime: a review of its use in the management of hospitalized patients with pneumonia. Am J Respir Med. 2003;2(1):75-107. [PubMed:14720024 ]

    Transporters

    General function:
    Involved in ion transmembrane transporter activity
    Specific function:
    Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
    Gene Name:
    SLC22A5
    Uniprot ID:
    O76082
    Molecular weight:
    62751.1
    References
    1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865 ]
    General function:
    Involved in transporter activity
    Specific function:
    Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
    Gene Name:
    SLC15A1
    Uniprot ID:
    P46059
    Molecular weight:
    78805.3
    References
    1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865 ]
    2. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]
    General function:
    Involved in transporter activity
    Specific function:
    Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
    Gene Name:
    SLC15A2
    Uniprot ID:
    Q16348
    Molecular weight:
    81782.8
    References
    1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865 ]
    2. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]

    PMID: 22267119

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