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Identification
NameCeforanide
Accession NumberDB00923  (APRD00853)
TypeSmall Molecule
GroupsApproved
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
Thumb
Synonyms
(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 acid
7-[O-(Aminomethyl)phenylacetamido]-3-[[[1-(carboxymethyl)-1H-tetrazol-5-yl]thio]methyl]-3-cephem-4-carboxylic acid
7beta-[2-(Aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sulfanyl}methyl-3,4-didehydrocepham-4-carboxylic acid
Ceforanide
Ceforanido
Ceforanidum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
PrecefNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII8M1YF8951V
CAS number60925-61-3
WeightAverage: 519.554
Monoisotopic: 519.099472819
Chemical FormulaC20H21N7O6S2
InChI KeyInChIKey=SLAYUXIURFNXPG-CRAIPNDOSA-N
InChI
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
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
SMILES
[H][C@]12SCC(CSC3=NN=NN3CC(O)=O)=C(N1C(=O)[[email protected]]2NC(=O)CC1=CC=CC=C1CN)C(O)=O
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
  • Phenylacetamide
  • Alpha-amino acid or derivatives
  • Phenylmethylamine
  • Benzylamine
  • Aralkylamine
  • Alkylarylthioether
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Meta-thiazine
  • Heteroaromatic compound
  • Tetrazole
  • Tertiary carboxylic acid amide
  • Azole
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Sulfenyl compound
  • Hemithioaminal
  • Thioether
  • Enamine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of infections caused by susceptible organisms.
PharmacodynamicsCeforanide is a semisynthetic second-generation cephalosporin. The cephalosporins are bactericidal drugs with both gram-positive and gram-negative activity. They inhibit bacterial cell wall synthesis in a way similar to the penicillins.
Mechanism of actionThe bactericidal activity of ceforanide results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
Related Articles
AbsorptionRapidly absorbed following intramuscular injection.
Volume of distributionNot Available
Protein binding80.6%
Metabolism

The major drug elimination route was urinary excretion with 85% of the dose being excreted unchanged in the urine within 12 hr, and no metabolites with antibiotic activity were observed in urine.

Route of eliminationNot Available
Half life2.6 to 2.98 hours
ClearanceNot Available
ToxicityAdverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions.
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5918
Blood Brain Barrier-0.9659
Caco-2 permeable-0.7463
P-glycoprotein substrateSubstrate0.7962
P-glycoprotein inhibitor INon-inhibitor0.8318
P-glycoprotein inhibitor IINon-inhibitor0.9607
Renal organic cation transporterNon-inhibitor0.7981
CYP450 2C9 substrateNon-substrate0.8253
CYP450 2D6 substrateNon-substrate0.8124
CYP450 3A4 substrateNon-substrate0.5421
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.577
Ames testNon AMES toxic0.6325
CarcinogenicityNon-carcinogens0.8446
BiodegradationNot ready biodegradable0.8569
Rat acute toxicity2.3203 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9112
hERG inhibition (predictor II)Non-inhibitor0.7227
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Apothecon inc div bristol myers squibb
  • Bristol laboratories inc div bristol myers co
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP-3.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.197 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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot 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 ]
External Links
ATC CodesJ01DC11
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcenocoumarolCeforanide may increase the anticoagulant activities of Acenocoumarol.
ProbenecidThe serum concentration of Ceforanide can be increased when it is combined with Probenecid.
WarfarinCeforanide may increase the anticoagulant activities of Warfarin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Bacteroides fragilis
Pharmacological action
yes
Actions
inhibitor
General Function:
Penicillin binding
Specific Function:
Not Available
Gene Name:
pbpA
Uniprot ID:
Q70KI2
Molecular Weight:
69434.305 Da
References
  1. Barriere SL, Mills J: Ceforanide: antibacterial activity, pharmacology, and clinical efficacy. Pharmacotherapy. 1982 Nov-Dec;2(6):322-7. [PubMed:6762529 ]
  2. Yotsuji A, Mitsuyama J, Hori R, Yasuda T, Saikawa I, Inoue M, Mitsuhashi S: Mechanism of action of cephalosporins and resistance caused by decreased affinity for penicillin-binding proteins in Bacteroides fragilis. Antimicrob Agents Chemother. 1988 Dec;32(12):1848-53. [PubMed:3266730 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23