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Cephapirin

July 24, 2017
Common Name

Cephapirin Description

Cephapirin is only found in individuals that have used or taken this drug. It is a cephalosporin antibiotic, partly plasma-bound, that is effective against gram-negative and gram-positive organisms. [PubChem]The bactericidal activity of cephapirin reslits from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylslifanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidChEBI CefapirinChEBI CefapirinaChEBI CefapirineChEBI CefapirinumChEBI CefaprinChEBI CephapirineChEBI CEPRChEBI (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylslifanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsliphanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsliphanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidGenerator CefadylMeSH Monosodium salt, cephapirinMeSH Salt, cephapirin monosodiumMeSH BL P 1322MeSH Bristol-myers brand OF cephapirin sodiumMeSH Cephapirin, sodiumMeSH Apothecon brand OF cephapirin sodiumMeSH Cephapirin sodiumMeSH CéfalojectMeSH Sodium cephapirinMeSH BL-P 1322MeSH BrisfirinaMeSH Bristol-myers squibb brand OF cephapirin sodiumMeSH Cephapirin monosodium saltMeSH

Chemical Formlia

C17H17N3O6S2 Average Molecliar Weight

423.463 Monoisotopic Molecliar Weight

423.055876671 IUPAC Name

(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(pyridin-4-ylslifanyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Traditional Name

CEPR CAS Registry Number

21593-23-7 SMILES

[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CSC1=CC=NC=C1)C(O)=O

InChI Identifier

InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1

InChI Key

UQLLWWBDSUHNEB-CZUORRHYSA-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

  • Cephems
  • Alkylarylthioethers
  • 1,3-thiazines
  • Pyridines and derivatives
  • Dicarboxylic acids and derivatives
  • Tertiary carboxylic acid amides
  • Heteroaromatic compounds
  • Azetidines
  • Carboxylic acid esters
  • Thiohemiaminal derivatives
  • Slifenyl compounds
  • Azacyclic compounds
  • Propargyl-type 1,3-dipolar organic compounds
  • Carboximidic acids
  • Dialkylthioethers
  • Carboxylic acids
  • Carbonyl compounds
  • Organonitrogen compounds
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • N-acyl-alpha amino acid or derivatives
  • Cephem
  • Aryl thioether
  • Alkylarylthioether
  • Meta-thiazine
  • Dicarboxylic acid or derivatives
  • Pyridine
  • Heteroaromatic compound
  • Beta-lactam
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid ester
  • Lactam
  • Azetidine
  • Azacycle
  • Organoheterocyclic compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Dialkylthioether
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Slifenyl compound
  • Thioether
  • Hemithioaminal
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organoslifur compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • cephalosporin (CHEBI:554446 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Bacterial Agents
  • Cephalosporins

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.51e-01 g/LNot Available LogP-0.1Not Available

    Predicted Properties

    Property Value Source Water Solubility0.15 mg/mLALOGPS logP0.18ALOGPS logP-2ChemAxon logS-3.5ALOGPS pKa (Strongest Acidic)3.54ChemAxon pKa (Strongest Basic)5ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area125.9 Å2ChemAxon Rotatable Bond Count8ChemAxon Refractivity102.43 m3·mol-1ChemAxon Polarizability40.63 Å3ChemAxon Number of Rings3ChemAxon 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

    • 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 DB01139

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01139

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01139 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

    28486 KEGG Compound ID

    C06896 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB15270 Metagene Link

    HMDB15270 METLIN ID

    Not Available PubChem Compound

    30699 PDB ID

    Not Available ChEBI ID

    554446

    Product: PNPP

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    PMID: 10448131

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