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Ceforanide

July 24, 2017
Common Name

Ceforanide Description

Ceforanide is a second-generation parenteral cephalosporin antibiotic. It has a longer elimination half-life than any currently available cephalosporin. Its activity is very similar to that of cefamandole, a second-generation cephalosporin, except that ceforanide is less active against most gram-positive organisms. Many coliforms, including Escherichia coli, Klebsiella, Enterobacter, and Proteus, are susceptible to ceforanide, as are most strains of Salmonella, Shigella, Hemophilus, Citrobacter and Arizona species. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (6R,7R)-7-[[2-[2-(Aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]slifanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidChEBI 7-[O-(Aminomethyl)phenylacetamido]-3-[[[1-(carboxymethyl)-1H-tetrazol-5-yl]thio]methyl]-3-cephem-4-carboxylic acidChEBI 7beta-[2-(Aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]slifanyl}methyl-3,4-didehydrocepham-4-carboxylic acidChEBI CeforanidoChEBI CeforanidumChEBI (6R,7R)-7-[[2-[2-(Aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]slifanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator (6R,7R)-7-[[2-[2-(Aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]sliphanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator (6R,7R)-7-[[2-[2-(Aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]sliphanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidGenerator 7-[O-(Aminomethyl)phenylacetamido]-3-[[[1-(carboxymethyl)-1H-tetrazol-5-yl]thio]methyl]-3-cephem-4-carboxylateGenerator 7b-[2-(Aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]slifanyl}methyl-3,4-didehydrocepham-4-carboxylateGenerator 7b-[2-(Aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]slifanyl}methyl-3,4-didehydrocepham-4-carboxylic acidGenerator 7b-[2-(Aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sliphanyl}methyl-3,4-didehydrocepham-4-carboxylateGenerator 7b-[2-(Aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sliphanyl}methyl-3,4-didehydrocepham-4-carboxylic acidGenerator 7beta-[2-(Aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]slifanyl}methyl-3,4-didehydrocepham-4-carboxylateGenerator 7beta-[2-(Aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sliphanyl}methyl-3,4-didehydrocepham-4-carboxylateGenerator 7beta-[2-(Aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sliphanyl}methyl-3,4-didehydrocepham-4-carboxylic acidGenerator 7β-[2-(aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]slifanyl}methyl-3,4-didehydrocepham-4-carboxylateGenerator 7β-[2-(aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]slifanyl}methyl-3,4-didehydrocepham-4-carboxylic acidGenerator 7β-[2-(aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sliphanyl}methyl-3,4-didehydrocepham-4-carboxylateGenerator 7β-[2-(aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sliphanyl}methyl-3,4-didehydrocepham-4-carboxylic acidGenerator 7-(alpha-(2-Aminomethylphenyl)acetamido)-3-((1-carboxymethyltetrazol-5-ylthio)methyl)-3-cephem-4-carboxylic acidMeSH CefaronideMeSH BL-S786RMeSH Ceforanide, monosodium saltMeSH BL-S 786MeSH

Chemical Formlia

C20H21N7O6S2 Average Molecliar Weight

519.554 Monoisotopic Molecliar Weight

519.099472819 IUPAC Name

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

ceforanide CAS Registry Number

60925-61-3 SMILES

[H][C@]12SCC(CSC3=NN=NN3CC(O)=O)=C(N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1CN)C(O)=O

InChI Identifier

InChI=1S/C20H21N7O6S2/c21-6-11-4-2-1-3-10(11)5-13(28)22-15-17(31)27-16(19(32)33)12(8-34-18(15)27)9-35-20-23-24-25-26(20)7-14(29)30/h1-4,15,18H,5-9,21H2,(H,22,28)(H,29,30)(H,32,33)/t15-,18-/m1/s1

InChI Key

SLAYUXIURFNXPG-CRAIPNDOSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof. Kingdom

Organic compounds Super Class

Organoheterocyclic compounds Class

Lactams Sub Class

Beta lactams Direct Parent

Cephalosporins Alternative Parents

  • N-acyl-alpha amino acids and derivatives
  • Phenylacetamides
  • Benzylamines
  • Phenylmethylamines
  • Alkylarylthioethers
  • Aralkylamines
  • 1,3-thiazines
  • Dicarboxylic acids and derivatives
  • Tertiary carboxylic acid amides
  • Tetrazoles
  • Heteroaromatic compounds
  • Secondary carboxylic acid amides
  • Amino acids
  • Azetidines
  • Dialkylthioethers
  • Carboxylic acids
  • Slifenyl compounds
  • Azacyclic compounds
  • Thiohemiaminal derivatives
  • Carbonyl compounds
  • Organic oxides
  • Organopnictogen compounds
  • Monoalkylamines
  • Hydrocarbon derivatives

    • Substituents

  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • Phenylmethylamine
  • Aryl thioether
  • Benzylamine
  • Alkylarylthioether
  • Aralkylamine
  • Meta-thiazine
  • Benzenoid
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Tertiary carboxylic acid amide
  • Tetrazole
  • Heteroaromatic compound
  • Azole
  • Amino acid or derivatives
  • Azetidine
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Thioether
  • Hemithioaminal
  • Slifenyl compound
  • Dialkylthioether
  • Carboxylic acid derivative
  • Azacycle
  • Carboxylic acid
  • Organoslifur compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Primary amine
  • Organooxygen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • cephalosporin (CHEBI:3495 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Bacterial Agents
  • Cephalosporins

    • Application

  • Pharmaceutical

    • Cellliar locations

    Not Available Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.97e-01 g/LNot Available LogP-3.7Not Available

    Predicted Properties

    Property Value Source Water Solubility0.2 mg/mLALOGPS logP-1.4ALOGPS logP-3.2ChemAxon logS-3.4ALOGPS pKa (Strongest Acidic)2.55ChemAxon pKa (Strongest Basic)9.14ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count10ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area193.63 Å2ChemAxon Rotatable Bond Count10ChemAxon Refractivity139.87 m3·mol-1ChemAxon Polarizability49.27 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

    Not Available 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 DB00923

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00923

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00923 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

    39656 KEGG Compound ID

    C06884 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Ceforanide NuGOwiki Link

    HMDB15059 Metagene Link

    HMDB15059 METLIN ID

    Not Available PubChem Compound

    43507 PDB ID

    Not Available ChEBI ID

    3495

    Product: Pneumocandin B1

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Crowle AJ, Sbarbaro JA, May MH: Effects of isoniazid and of ceforanide against virulent tubercle bacilli in cultured human macrophages. Tubercle. 1988 Mar;69(1):15-25. [PubMed:3140456 ]
    2. Campoli-Richards DM, Lackner TE, Monk JP: Ceforanide. A review of its antibacterial activity, pharmacokinetic properties and clinical efficacy. Drugs. 1987 Oct;34(4):411-37. [PubMed:3315624 ]
    3. Cone LA, Barton SM, Woodard DR: Treatment of scleroma with ceforanide. Arch Otolaryngol Head Neck Surg. 1987 Apr;113(4):374-6. [PubMed:3814386 ]
    4. Barriere SL, Mills J: Ceforanide: antibacterial activity, pharmacology, and clinical efficacy. Pharmacotherapy. 1982 Nov-Dec;2(6):322-7. [PubMed:6762529 ]

    PMID: 22274912

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