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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
(6R,7R)-3-[(Carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidNot AvailableNot Available
CefuroximNot AvailableNot Available
CefuroximeNot AvailableINN, BAN, USAN
CefuroximoSpanishINN
CefuroximumLatinINN
CephuroximeNot AvailableNot Available
SharoxNot AvailableNot Available
Zinacef danmarkNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ceftintablet, film coated250 mgoralGlaxo Smith Kline Llc1989-10-01Not AvailableUs
Ceftintablet, film coated500 mgoralGlaxo Smith Kline Llc1989-10-01Not AvailableUs
Ceftinpowder, for suspension125 mg/5mLoralGlaxo Smith Kline Llc2004-06-02Not AvailableUs
Ceftinpowder, for suspension250 mg/5mLoralGlaxo Smith Kline Llc2004-06-02Not AvailableUs
Zinacefinjection, powder, for solution90 mg/mLintramuscular; intravenousCovis Pharmaceuticals Inc2013-01-15Not AvailableUs
Zinacefinjection, powder, for solution90 mg/mLintravenousCovis Pharmaceuticals Inc2013-01-15Not AvailableUs
Zinacefinjection, powder, for solution90 mg/mLintravenousCovis Pharmaceuticals Inc2013-01-15Not AvailableUs
Zinacefinjection, solution1.5 g/50mLintravenousCovis Pharmaceuticals Inc2012-10-15Not AvailableUs
Zinacefinjection, powder, for solution90 mg/mLintravenousCovis Pharmaceuticals Inc2013-01-15Not AvailableUs
Zinacefinjection, powder, for solution90 mg/mLintravenousCovis Pharmaceuticals Inc2013-01-15Not AvailableUs
Ceftinpowder, for suspension250 mg/5mLoralA S Medication Solutions Llc2004-06-02Not AvailableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cefuroximeinjection7.5 gintravenousWest ward Pharmaceutical Corp2004-01-09Not AvailableUs
Cefuroximeinjection1.5 gintramuscular; intravenousWest ward Pharmaceutical Corp2004-01-09Not AvailableUs
Cefuroximeinjection750 mgintramuscular; intravenousWest ward Pharmaceutical Corp2004-01-09Not AvailableUs
Cefuroximeinjection, powder, for solution90 mg/mLintravenousHospira, Inc.2009-04-27Not AvailableUs
Cefuroximeinjection, powder, for solution7.5 g/82.5mLintravenousSagent Pharmaceuticals2008-05-01Not AvailableUs
Cefuroximeinjection, powder, for solution750 mgintramuscular; intravenousWG Critical Care, LLC2012-10-04Not AvailableUs
Cefuroximeinjection, powder, for solution1.5 g/16mLintravenousWG Critical Care, LLC2012-10-04Not AvailableUs
Cefuroximeinjection, powder, for solution7.5 g/80mLintravenousWG Critical Care, LLC2012-10-04Not AvailableUs
Cefuroximeinjection, powder, for solution750 mg/100mLintravenousWG Critical Care, LLC2012-10-04Not AvailableUs
Cefuroximeinjection, powder, for solution1.5 g/100mLintravenousWG Critical Care, LLC2012-10-04Not AvailableUs
Cefuroximeinjection, powder, for solution750 mgintramuscular; intravenousAPP Pharmaceuticals, LLC2011-05-24Not AvailableUs
Cefuroximeinjection, powder, for solution1.5 gintravenousAPP Pharmaceuticals, LLC2011-05-24Not AvailableUs
Cefuroximeinjection, powder, for solution7.5 g/80mLintravenousAPP Pharmaceuticals, LLC2010-07-30Not AvailableUs
Over the Counter ProductsNot Available
International Brands
NameCompany
CefuraxLindopharm
ElobactGlaxoSmithKline
KefuroxEuroCept
OraximMalesci
SharoxFahrenheit
SupacefGlaxoSmithKline
ZinnatGlaxoSmithKline
Brand mixturesNot Available
SaltsNot 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
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
  • Alpha-amino acid or derivatives
  • Meta-thiazine
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Furan
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Oxime ether
  • Carboxamide group
  • Azetidine
  • Oxacycle
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Enamine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
PropertyValueProbability
Human Intestinal Absorption+0.6504
Blood Brain Barrier-0.9863
Caco-2 permeable-0.7051
P-glycoprotein substrateSubstrate0.7253
P-glycoprotein inhibitor INon-inhibitor0.8621
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.8688
CYP450 2C9 substrateNon-substrate0.8686
CYP450 2D6 substrateNon-substrate0.8196
CYP450 3A4 substrateSubstrate0.5051
CYP450 1A2 substrateNon-inhibitor0.6957
CYP450 2C9 substrateNon-inhibitor0.7771
CYP450 2D6 substrateNon-inhibitor0.8707
CYP450 2C19 substrateNon-inhibitor0.7064
CYP450 3A4 substrateNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8916
Ames testNon AMES toxic0.7525
CarcinogenicityNon-carcinogens0.8816
BiodegradationNot ready biodegradable0.9759
Rat acute toxicity1.6593 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9724
hERG inhibition (predictor II)Non-inhibitor0.8292
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injectionintramuscular; intravenous1.5 g
Injectionintramuscular; intravenous750 mg
Injectionintravenous7.5 g
Injection, powder, for solutionintramuscular; intravenous750 mg
Injection, powder, for solutionintramuscular; intravenous90 mg/mL
Injection, powder, for solutionintravenous1.5 g
Injection, powder, for solutionintravenous1.5 g/100mL
Injection, powder, for solutionintravenous1.5 g/16mL
Injection, powder, for solutionintravenous7.5 g/80mL
Injection, powder, for solutionintravenous7.5 g/82.5mL
Injection, powder, for solutionintravenous750 mg/100mL
Injection, powder, for solutionintravenous90 mg/mL
Injection, solutionintravenous1.5 g/50mL
Powder, for suspensionoral125 mg/5mL
Powder, for suspensionoral250 mg/5mL
Tablet, film coatedoral250 mg
Tablet, film coatedoral500 mg
Prices
Unit descriptionCostUnit
Rocephin 10 gm vial478.32USD vial
Ceftin 20 500 mg tablet Bottle436.36USD bottle
Cefuroxime Axetil 250 mg/5ml Suspension 100ml Bottle121.27USD bottle
Rocephin 2 gm vial97.5USD vial
Cefzil 250 mg/5ml Suspension 100ml Bottle87.62USD bottle
Zinacef 7.5 gm vial65.94USD vial
Rocephin 1 gm Solution Vial65.53USD vial
Rocephin 1 gm vial62.02USD vial
Duricef 500 mg/5ml Suspension 100ml Bottle59.36USD bottle
Cefzil 125 mg/5ml Suspension 100ml Bottle48.36USD bottle
Duricef 500 mg/5ml Suspension 75ml Bottle46.93USD bottle
Maxipime 2 gram vial43.04USD vial
Velosef 250 mg/5ml Suspension 100ml Bottle23.99USD bottle
Maxipime 1 gm piggyback vial23.24USD vial
Duricef 250 mg/5ml Suspension 50ml Bottle22.99USD bottle
Maxipime 1 gram vial21.7USD vial
Ceftin 500 mg tablet20.98USD tablet
Cefuroxime 1.5 g/50 ml bag16.8USD each
Cedax 400 mg capsule16.13USD each
Zinacef 1.5 gm add-vant vial13.94USD vial
Zinacef 1.5 gm vial13.45USD vial
Cefuroxime sod 1.5 gm vial13.44USD vial
Ceftin 250 mg tablet11.74USD tablet
Cefzil 500 mg tablet9.77USD tablet
Cefuroxime axetil 500 mg tablet8.11USD tablet
Duricef 1 gm tablet7.35USD tablet
Cefzil 250 mg tablet4.76USD tablet
Ceftin 500 mg Tablet3.61USD tablet
Cefuroxime axetil 250 mg tablet2.82USD tablet
Velosef 500 mg capsule2.02USD capsule
Apo-Cefuroxime 500 mg Tablet2.02USD tablet
Ratio-Cefuroxime 500 mg Tablet2.02USD tablet
Ceftin 250 mg Tablet1.82USD tablet
Velosef 250 mg capsule1.03USD capsule
Apo-Cefuroxime 250 mg Tablet1.02USD tablet
Ratio-Cefuroxime 250 mg Tablet1.02USD tablet
Zinacef-water 1.5 gm/50 ml0.32USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
Canada13284051994-04-122011-04-12
Canada24081982004-03-092022-11-21
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 Solubility0.284 mg/mLALOGPS
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 Area173.76 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity97.17 m3·mol-1ChemAxon
Polarizability38.75 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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
ATC CodesJ01DC02S01AA27
AHFS Codes
  • 08:12.06.08
PDB EntriesNot Available
FDA labelDownload (809 KB)
MSDSDownload (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
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13