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Identification
NameCefuroxime
Accession NumberDB01112  (APRD00285)
Typesmall molecule
Groupsapproved
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
Synonyms
SynonymLanguageCode
CefuroximeNot AvailableINN, BAN, USAN
CefuroximoSpanishINN
CefuroximumLatinINN
SaltsNot Available
Brand names
NameCompany
CeftinGlaxoSmithKline
CefuraxLindopharm
ElobactGlaxoSmithKline
KefuroxEuroCept
OraximMalesci
SharoxFahrenheit
SupacefGlaxoSmithKline
ZinacefGlaxoSmithKline
ZinnatGlaxoSmithKline
Brand mixturesNot Available
Categories
CAS number55268-75-2
WeightAverage: 424.385
Monoisotopic: 424.068884198
Chemical FormulaC16H16N4O8S
InChI KeyInChIKey=JFPVXVDWJQMJEE-IZRZKJBUSA-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
IUPAC Name
(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassLactams
SubclassBeta Lactams
Direct parentCephalosporins
Alternative parentsN-acyl-alpha Amino Acids and Derivatives; Alpha Amino Acid Amides; 1,3-Thiazines; Furans; Tertiary Carboxylic Acid Amides; Azetidines; Tertiary Amines; Oxime Ethers; Hemiaminals; Secondary Carboxylic Acid Amides; Carbamic Acids and Derivatives; Enolates; Enamines; Carboxylic Acids; Ethers; Polyamines; Aminals; Thioethers; Imines
Substituentsn-acyl-alpha amino acid or derivative; alpha-amino acid amide; alpha-amino acid or derivative; meta-thiazine; furan; tertiary carboxylic acid amide; azetidine; carboxamide group; secondary carboxylic acid amide; carbamic acid derivative; oxime ether; tertiary amine; hemiaminal; carboxylic acid derivative; enolate; ether; enamine; carboxylic acid; aminal; polyamine; thioether; imine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the 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 moeity or a derivative thereof.
Pharmacology
IndicationFor the treatment of many different types of bacterial infections such as bronchitis, sinusitis, tonsillitis, ear infections, skin infections, gonorrhea, and urinary tract infections.
PharmacodynamicsCefuroxime 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 actionCefuroxime, 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.
AbsorptionAbsorbed from the gastrointestinal tract. Absorption is greater when taken after food (absolute bioavailability increases from 37% to 52%).
Volume of distributionNot Available
Protein binding50% to serum protein
Metabolism

The axetil moiety is metabolized to acetaldehyde and acetic acid.

SubstrateEnzymesProduct
Cefuroxime
    Acetic acidDetails
    Cefuroxime
      acetaldehydeDetails
      Route of eliminationNot Available
      Half lifeApproximately 80 minutes following intramuscular or intravenous injection.
      ClearanceNot Available
      ToxicityAllergic 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
      PathwaysNot Available
      SNP Mediated EffectsNot Available
      SNP Mediated Adverse Drug ReactionsNot Available
      ADMET
      Predicted ADMET features
      Property Value Probability
      Human Intestinal Absorption + 0.6504
      Blood Brain Barrier - 0.9863
      Caco-2 permeable - 0.7051
      P-glycoprotein substrate Substrate 0.7253
      P-glycoprotein inhibitor I Non-inhibitor 0.8621
      P-glycoprotein inhibitor II Non-inhibitor 0.8383
      Renal organic cation transporter Non-inhibitor 0.8688
      CYP450 2C9 substrate Non-substrate 0.8686
      CYP450 2D6 substrate Non-substrate 0.8196
      CYP450 3A4 substrate Substrate 0.5051
      CYP450 1A2 substrate Non-inhibitor 0.6957
      CYP450 2C9 substrate Non-inhibitor 0.7771
      CYP450 2D6 substrate Non-inhibitor 0.8707
      CYP450 2C19 substrate Non-inhibitor 0.7064
      CYP450 3A4 substrate Non-inhibitor 0.8308
      CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8916
      Ames test Non AMES toxic 0.7525
      Carcinogenicity Non-carcinogens 0.8816
      Biodegradation Not ready biodegradable 0.9759
      Rat acute toxicity 1.6593 LD50, mol/kg Not applicable
      hERG inhibition (predictor I) Weak inhibitor 0.9724
      hERG inhibition (predictor II) Non-inhibitor 0.8292
      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
      FormRouteStrength
      Powder, for solutionIntravenous
      Powder, for solutionOral
      TabletOral
      Prices
      Unit descriptionCostUnit
      Rocephin 10 gm vial478.32USDvial
      Ceftin 20 500 mg tablet Bottle436.36USDbottle
      Cefuroxime Axetil 250 mg/5ml Suspension 100ml Bottle121.27USDbottle
      Rocephin 2 gm vial97.5USDvial
      Cefzil 250 mg/5ml Suspension 100ml Bottle87.62USDbottle
      Zinacef 7.5 gm vial65.94USDvial
      Rocephin 1 gm Solution Vial65.53USDvial
      Rocephin 1 gm vial62.02USDvial
      Duricef 500 mg/5ml Suspension 100ml Bottle59.36USDbottle
      Cefzil 125 mg/5ml Suspension 100ml Bottle48.36USDbottle
      Duricef 500 mg/5ml Suspension 75ml Bottle46.93USDbottle
      Maxipime 2 gram vial43.04USDvial
      Velosef 250 mg/5ml Suspension 100ml Bottle23.99USDbottle
      Maxipime 1 gm piggyback vial23.24USDvial
      Duricef 250 mg/5ml Suspension 50ml Bottle22.99USDbottle
      Maxipime 1 gram vial21.7USDvial
      Ceftin 500 mg tablet20.98USDtablet
      Cefuroxime 1.5 g/50 ml bag16.8USDeach
      Cedax 400 mg capsule16.13USDeach
      Zinacef 1.5 gm add-vant vial13.94USDvial
      Zinacef 1.5 gm vial13.45USDvial
      Cefuroxime sod 1.5 gm vial13.44USDvial
      Ceftin 250 mg tablet11.74USDtablet
      Cefzil 500 mg tablet9.77USDtablet
      Cefuroxime axetil 500 mg tablet8.11USDtablet
      Duricef 1 gm tablet7.35USDtablet
      Cefzil 250 mg tablet4.76USDtablet
      Ceftin 500 mg Tablet3.61USDtablet
      Cefuroxime axetil 250 mg tablet2.82USDtablet
      Velosef 500 mg capsule2.02USDcapsule
      Apo-Cefuroxime 500 mg Tablet2.02USDtablet
      Ratio-Cefuroxime 500 mg Tablet2.02USDtablet
      Ceftin 250 mg Tablet1.82USDtablet
      Velosef 250 mg capsule1.03USDcapsule
      Apo-Cefuroxime 250 mg Tablet1.02USDtablet
      Ratio-Cefuroxime 250 mg Tablet1.02USDtablet
      Zinacef-water 1.5 gm/50 ml0.32USDml
      DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
      Patents
      CountryPatent NumberApprovedExpires (estimated)
      Canada24081982004-03-092022-11-21
      Canada13284051994-04-122011-04-12
      Properties
      Statesolid
      Experimental Properties
      PropertyValueSource
      melting point218-225 °CNot Available
      water solubilityFreely soluble as sodium salt (145 mg/L)Not Available
      logP-0.16SANGSTER (1993)
      Predicted Properties
      PropertyValueSource
      water solubility2.84e-01 g/lALOGPS
      logP-0.24ALOGPS
      logP-0.9ChemAxon
      logS-3.2ALOGPS
      pKa (strongest acidic)3.15ChemAxon
      pKa (strongest basic)-1.1ChemAxon
      physiological charge-1ChemAxon
      hydrogen acceptor count7ChemAxon
      hydrogen donor count3ChemAxon
      polar surface area173.76ChemAxon
      rotatable bond count8ChemAxon
      refractivity97.17ChemAxon
      polarizability38.75ChemAxon
      number of rings3ChemAxon
      bioavailability1ChemAxon
      rule of fiveYesChemAxon
      Ghose filterNoChemAxon
      Veber's ruleNoChemAxon
      MDDR-like ruleYesChemAxon
      Spectra
      SpectraNot Available
      References
      Synthesis Reference

      Vijay Kumar Handa, Ramesh Dandala, Jag Mohan Khanna, “Process for the preparation of cefuroxime.” U.S. Patent US6235896, issued February, 1976.

      US6235896
      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
      ResourceLink
      KEGG DrugD00262
      KEGG CompoundC06894
      ChEBI3515
      ChEMBLCHEMBL1436
      Therapeutic Targets DatabaseDAP000445
      PharmGKBPA448868
      HETCES
      Drug Product Database2242657
      RxListhttp://www.rxlist.com/cgi/generic/cefurox.htm
      Drugs.comhttp://www.drugs.com/cdi/cefuroxime.html
      PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/cef1076.shtml
      WikipediaCefuroxime
      ATC CodesJ01DC02
      AHFS Codes
      • 08:12.06.08
      PDB EntriesNot Available
      FDA labelshow(809 KB)
      MSDSshow(52.7 KB)
      Interactions
      Drug Interactions
      Drug
      AmikacinIncreased risk of nephrotoxicity
      GentamicinIncreased risk of nephrotoxicity
      NetilmicinIncreased risk of nephrotoxicity
      ProbenecidProbenecid may increase the serum level of cefuroxime.
      TobramycinIncreased risk of nephrotoxicity
      Food Interactions
      • Take with food to increase absorption.

      1. Penicillin-binding protein 1A

      Kind: protein

      Organism: Clostridium perfringens (strain 13 / Type A)

      Pharmacological action: yes

      Actions: inhibitor

      Components

      Name UniProt ID Details
      Penicillin-binding protein 1A Q8XJ01 Details

      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

      1. Solute carrier family 15 member 1

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: inhibitor

      Components

      Name UniProt ID Details
      Solute carrier family 15 member 1 P46059 Details

      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. Solute carrier family 15 member 2

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: inhibitor

      Components

      Name UniProt ID Details
      Solute carrier family 15 member 2 Q16348 Details

      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 September 16, 2013 17:13