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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2018-05-20 20:14:04 UTC
HMDB IDHMDB0015059
Secondary Accession Numbers
  • HMDB15059
Metabolite Identification
Common NameCeforanide
DescriptionCeforanide 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
Thumb
Synonyms
ValueSource
(6R,7R)-7-[[2-[2-(Aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-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]sulfanyl}methyl-3,4-didehydrocepham-4-carboxylic acidChEBI
CeforanidoChEBI
CeforanidumChEBI
(6R,7R)-7-[[2-[2-(Aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-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]sulphanylmethyl]-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]sulphanylmethyl]-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]sulfanyl}methyl-3,4-didehydrocepham-4-carboxylateGenerator
7b-[2-(Aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sulfanyl}methyl-3,4-didehydrocepham-4-carboxylic acidGenerator
7b-[2-(Aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sulphanyl}methyl-3,4-didehydrocepham-4-carboxylateGenerator
7b-[2-(Aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sulphanyl}methyl-3,4-didehydrocepham-4-carboxylic acidGenerator
7beta-[2-(Aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sulfanyl}methyl-3,4-didehydrocepham-4-carboxylateGenerator
7beta-[2-(Aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sulphanyl}methyl-3,4-didehydrocepham-4-carboxylateGenerator
7beta-[2-(Aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sulphanyl}methyl-3,4-didehydrocepham-4-carboxylic acidGenerator
7β-[2-(aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sulfanyl}methyl-3,4-didehydrocepham-4-carboxylateGenerator
7β-[2-(aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sulfanyl}methyl-3,4-didehydrocepham-4-carboxylic acidGenerator
7β-[2-(aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sulphanyl}methyl-3,4-didehydrocepham-4-carboxylateGenerator
7β-[2-(aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sulphanyl}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 FormulaC20H21N7O6S2
Average Molecular Weight519.554
Monoisotopic Molecular Weight519.099472819
IUPAC Name(6R,7R)-7-{2-[2-(aminomethyl)phenyl]acetamido}-3-({[1-(carboxymethyl)-1H-1,2,3,4-tetrazol-5-yl]sulfanyl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Nameceforanide
CAS Registry Number60925-61-3
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 KeySLAYUXIURFNXPG-CRAIPNDOSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
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
  • Sulfenyl compound
  • Dialkylthioether
  • Carboxylic acid derivative
  • Azacycle
  • Carboxylic acid
  • Organosulfur 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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.2 g/LNot Available
LogP-3.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity139.87 m³·mol⁻¹ChemAxon
Polarizability49.27 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-2911210000-94842c6c48f8af866276View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-4900065000-48bc8fab1349188d0f0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0600-1139230000-b7881f30886eb07b5a73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0600-3429000000-978a86dae2e1f5eb12d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-2984000000-a73d77d2ff45ca13d283View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0981410000-23f43b60da8facacfff4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-3920000000-b077b8a30406d01b8a45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9421000000-bc8cc3af1f0b3d16b716View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00923 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00923 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00923
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID39656
KEGG Compound IDC06884
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCeforanide
METLIN IDNot Available
PubChem Compound43507
PDB IDNot Available
ChEBI ID3495
References
Synthesis ReferenceNot 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 ]