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Identification
Name Cefuroxime
Accession Number DB01112 (APRD00285)
Type small molecule
Groups approved
Description

Broad-spectrum cephalosporin antibiotic resistant to beta-lactamase. It has been proposed for infections with gram-negative and gram-positive organisms, gonorrhea, and haemophilus. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Cefuroxim
  • Cefuroxime [USAN:BAN:INN]
  • Cefuroximo [INN-Spanish]
  • Cefuroximum [INN-Latin]
Brand names
  • Ancef
  • Biofuroksym
  • Cedax
  • Cefizox
  • Cefobid
  • Cefotan
  • Ceftin
  • Cefurax
  • Cefuril
  • Cefzil
  • Cepazine
  • Cephuroxime
  • Duricef
  • Elobact
  • Kefurox
  • Kefzol
  • Kerurox
  • Mandol
  • Maxipime
  • Mefoxin
  • Monocid
  • Oraxim
  • Rocephin
  • Sharox
  • Velosef
  • Zinacef
  • Zinat
  • Zinnat
Brand name mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Cephalosporins
CAS number 55268-75-2
Weight Average: 424.385
Monoisotopic: 424.068884198
Chemical Formula C16H16N4O8S
InChI Key InChIKey=JFPVXVDWJQMJEE-SWWZKJRFSA-N
InChI
InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9+/t10-,14-/m1/s1
Plain Text
IUPAC Name
(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2E)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(COC(N)=O)=C(N1C(=O)[C@H]2NC(=O)C(=N\OC)\C1=CC=CO1)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Carbamates and Derivatives
  • Carboxylic Acids and Derivatives
  • Cephalosporins
Substructures
  • Hydroxy Compounds
  • Acetates
  • Carbamates and Derivatives
  • Amino Ketones
  • Carboxylic Acids and Derivatives
  • Oximes and Derivatives
  • Ethers
  • Aliphatic and Aryl Amines
  • Beta Lactams
  • Enamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Cephalosporins
  • Lactams
  • Furans
  • Imines
  • Azetidines
Pharmacology
Indication For the treatment of many different types of bacterial infections such as bronchitis, sinusitis, tonsillitis, ear infections, skin infections, gonorrhea, and urinary tract infections.
Pharmacodynamics Cefuroxime is a β-lactam type antibiotic. More specifically, it is a second-generation cephalosporin. Cephalosporins work the same way as penicillins: they interfere with the peptidoglycan synthesis of the bacterial wall by inhibiting the final transpeptidation needed for the cross-links. This effect is bactericidal. Cefuroxime is effective against the following organisms: Aerobic Gram-positive Microorganisms: Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenes. Aerobic Gram-negative Microorganisms: Escherichia coli, Haemophilus influenzae (including beta-lactamase-producing strains), Haemophilus parainfluenzae, Klebsiella pneumoniae, Moraxella catarrhalis (including beta-lactamase-producing strains), Neisseria gonorrhoeae (including beta-lactamase-producing strains). Spirochetes: Borrelia burgdorferi. Cefuroxime axetil is the prodrug
Mechanism of action Cefuroxime, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefuroxime interferes with an autolysin inhibitor.
Absorption Absorbed from the gastrointestinal tract. Absorption is greater when taken after food (absolute bioavailability increases from 37% to 52%).
Volume of distribution Not Available
Protein binding 50% to serum protein
Metabolism

The axetil moiety is metabolized to acetaldehyde and acetic acid.
Route of elimination Not Available
Half life Approximately 80 minutes following intramuscular or intravenous injection.
Clearance Not Available
Toxicity Allergic reactions might be expected, including rash, nasal congestion, cough, dry throat, eye irritation, or anaphylactic shock. Overdosage of cephalosporins can cause cerebral irritation leading to convulsions.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Warner chilcott inc
  • Hoffmann la roche inc
  • Glaxosmithkline
  • Ranbaxy laboratories ltd
  • Alkem laboratories ltd
  • Apotex inc etobicoke site
  • Aurobindo pharma ltd inc
  • Lupin ltd
  • Orchid healthcare
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Wockhardt ltd
  • App pharmaceuticals llc
  • Hikma farmaceutica portugal lda
  • Marsam pharmaceuticals llc
  • Steri pharma llc
  • Acs dobfar spa
  • B braun medical inc
  • Samson medical technologies llc
  • Eli lilly and co
Packagers
Dosage forms
Form Route Strength
Powder, for solution Intravenous
Powder, for solution Oral
Tablet Oral
Prices
Unit description Cost Unit
Rocephin 10 gm vial 478.32 USD vial
Ceftin 20 500 mg tablet Bottle 436.36 USD bottle
Cefuroxime Axetil 250 mg/5ml Suspension 100ml Bottle 121.27 USD bottle
Rocephin 2 gm vial 97.5 USD vial
Cefzil 250 mg/5ml Suspension 100ml Bottle 87.62 USD bottle
Zinacef 7.5 gm vial 65.94 USD vial
Rocephin 1 gm Solution Vial 65.53 USD vial
Rocephin 1 gm vial 62.02 USD vial
Duricef 500 mg/5ml Suspension 100ml Bottle 59.36 USD bottle
Cefzil 125 mg/5ml Suspension 100ml Bottle 48.36 USD bottle
Duricef 500 mg/5ml Suspension 75ml Bottle 46.93 USD bottle
Maxipime 2 gram vial 43.04 USD vial
Velosef 250 mg/5ml Suspension 100ml Bottle 23.99 USD bottle
Maxipime 1 gm piggyback vial 23.24 USD vial
Duricef 250 mg/5ml Suspension 50ml Bottle 22.99 USD bottle
Maxipime 1 gram vial 21.7 USD vial
Ceftin 500 mg tablet 20.98 USD tablet
Cefuroxime 1.5 g/50 ml bag 16.8 USD each
Cedax 400 mg capsule 16.13 USD each
Zinacef 1.5 gm add-vant vial 13.94 USD vial
Zinacef 1.5 gm vial 13.45 USD vial
Cefuroxime sod 1.5 gm vial 13.44 USD vial
Ceftin 250 mg tablet 11.74 USD tablet
Cefzil 500 mg tablet 9.77 USD tablet
Cefuroxime axetil 500 mg tablet 8.11 USD tablet
Duricef 1 gm tablet 7.35 USD tablet
Cefzil 250 mg tablet 4.76 USD tablet
Ceftin 500 mg Tablet 3.61 USD tablet
Cefuroxime axetil 250 mg tablet 2.82 USD tablet
Velosef 500 mg capsule 2.02 USD capsule
Apo-Cefuroxime 500 mg Tablet 2.02 USD tablet
Ratio-Cefuroxime 500 mg Tablet 2.02 USD tablet
Ceftin 250 mg Tablet 1.82 USD tablet
Velosef 250 mg capsule 1.03 USD capsule
Apo-Cefuroxime 250 mg Tablet 1.02 USD tablet
Ratio-Cefuroxime 250 mg Tablet 1.02 USD tablet
Zinacef-water 1.5 gm/50 ml 0.32 USD ml
Patents
Country Patent Number Approved Expires
Canada 2408198 2004-03-09 2022-11-21
Canada 1328405 1994-04-12 2011-04-12
Properties
State solid
Melting point 218-225 oC
Experimental Properties
Property Value Source
water solubility Freely soluble as sodium salt (145 mg/L) PhysProp
logP -0.8 PhysProp
Predicted Properties
Property Value Source
water solubility 2.84e-01 g/l ALOGPS
logP -0.24 ALOGPS
logP -0.90 ChemAxon Molconvert
logS -3.17 ALOGPS
pKa 10.98 ChemAxon Molconvert
hydrogen acceptor count 7 ChemAxon Molconvert
hydrogen donor count 3 ChemAxon Molconvert
polar surface area 173.76 ChemAxon Molconvert
rotatable bond count 8 ChemAxon Molconvert
refractivity 97.17 ChemAxon Molconvert
polarizability 38.85 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Perry CM, Brogden RN: Cefuroxime axetil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1996 Jul;52(1):125-58. Pubmed
External Links
Resource Link
KEGG Drug D00262 Link_out
KEGG Compound C06894 Link_out
PubChem Compound 5361202 Link_out
PubChem Substance 46506681 Link_out
ChemSpider 4514699 Link_out
ChEBI 3515 Link_out
ChEMBL 3515 Link_out
Therapeutic Targets Database DAP000445 Link_out
PharmGKB PA448868 Link_out
HET CES Link_out
Drug Product Database 2242657 Link_out
RxList http://www.rxlist.com/cgi/generic/cefurox.htm Link_out
Drugs.com http://www.drugs.com/cdi/cefuroxime.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/cef1076.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Cefuroxime Link_out
ATC Codes
  • J01DC02
AHFS Codes
  • 08:12.06.08
PDB Entries Not Available
FDA label show (808.6 KB)
MSDS show (52.7 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Take with food to increase absorption.
Targets

1. Penicillin-binding proteins 1A/1B

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q8XJ01 Link_out
Gene: pbpA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Cornaglia G, Ligozzi M, Bauernfeind A, Satta G, Fontana R: PBP binding and periplasmic concentration as determinants of the antibacterial activities of three new oral cephalosporins in Escherichia coli. New Microbiol. 1994 Jul;17(3):203-10. Pubmed
Transporters

1. Oligopeptide transporter, small intestine isoform

Actions: inhibitor

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products

UniProt ID: P46059 Link_out
Gene: SLC15A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed

2. Oligopeptide transporter, kidney isoform

Actions: inhibitor

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides

UniProt ID: Q16348 Link_out
Gene: SLC15A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:08

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.