You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
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 KeyJFPVXVDWJQMJEE-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
Not Available
Acetic acidDetails
Cefuroxime
Not Available
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.

Targets

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

Transporters

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
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13