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Identification
Name Ceforanide
Accession Number DB00923 (APRD00853)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Ceforanido [INN-Spanish]
Ceforanidum [INN-Latin]
Salts Not Available
Brand names
Name Company
Precef
Brand mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Cephalosporins
CAS number 60925-61-3
Weight Average: 519.554
Monoisotopic: 519.099472819
Chemical Formula C20H21N7O6S2
InChI Key InChIKey=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
Plain Text
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)[C@H]2NC(=O)CC1=CC=CC=C1CN)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenethylamines
  • Cephalosporins
Substructures
  • Ethers
  • Hydroxy Compounds
  • Acetates
  • Amino Ketones
  • Carboxylic Acids and Derivatives
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Beta Lactams
  • Enamines
  • Tetrazoles
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Cephalosporins
  • Lactams
  • Azetidines
  • Cyanamides
Pharmacology
Indication For the treatment of infections caused by susceptible organisms.
Pharmacodynamics Ceforanide 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 action The bactericidal activity of ceforanide results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
Absorption Rapidly absorbed following intramuscular injection.
Volume of distribution Not Available
Protein binding 80.6%
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 elimination Not Available
Half life 2.6 to 2.98 hours
Clearance Not Available
Toxicity Adverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Apothecon inc div bristol myers squibb
  • Bristol laboratories inc div bristol myers co
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
logP -3.7 Not Available
Predicted Properties
Property Value Source
water solubility 1.97e-01 g/l ALOGPS
logP -1.4 ALOGPS
logP -3.2 ChemAxon
logS -3.4 ALOGPS
pKa (strongest acidic) 2.55 ChemAxon
pKa (strongest basic) 9.14 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 10 ChemAxon
hydrogen donor count 4 ChemAxon
polar surface area 193.63 ChemAxon
rotatable bond count 10 ChemAxon
refractivity 139.87 ChemAxon
polarizability 49.27 ChemAxon
References
Synthesis Reference Not Available
General Reference
  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
  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
  3. Cone LA, Barton SM, Woodard DR: Treatment of scleroma with ceforanide. Arch Otolaryngol Head Neck Surg. 1987 Apr;113(4):374-6. Pubmed
  4. Barriere SL, Mills J: Ceforanide: antibacterial activity, pharmacology, and clinical efficacy. Pharmacotherapy. 1982 Nov-Dec;2(6):322-7. Pubmed
External Links
Resource Link
KEGG Drug D00259 Link_out
KEGG Compound C06884 Link_out
PubChem Compound 43507 Link_out
PubChem Substance 46504532 Link_out
ChemSpider 39656 Link_out
ChEBI 3495 Link_out
ChEMBL 3495 Link_out
Therapeutic Targets Database DAP001175 Link_out
PharmGKB PA164746057 Link_out
Wikipedia http://en.wikipedia.org/wiki/Ceforanide Link_out
ATC Codes
  • J01DC11
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Amikacin Increased risk of nephrotoxicity
Gentamicin Increased risk of nephrotoxicity
Netilmicin Increased risk of nephrotoxicity
Tobramycin Increased risk of nephrotoxicity
Food Interactions Not Available
Targets

1. Penicillin-binding protein 2

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q70KI2 Link_out
Gene: pbpA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Barriere SL, Mills J: Ceforanide: antibacterial activity, pharmacology, and clinical efficacy. Pharmacotherapy. 1982 Nov-Dec;2(6):322-7. Pubmed
  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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19