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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
(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 acid
Cefuroxim
Cefuroxime
Cefuroximo
Cefuroximum
Cephuroxime
Zinacef danmark
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Auro-cefuroximetablet500 mgoralAurobindo Pharma Limited (Unit Vi)2012-01-13Not applicableCanada
Auro-cefuroximetablet250 mgoralAurobindo Pharma Limited (Unit Vi)2012-01-13Not applicableCanada
Ceftintablet, film coated250 mg/1oralGlaxo Smith Kline Llc1989-10-01Not applicableUs
Ceftinpowder, for suspension250 mg/5mLoralA S Medication Solutions Llc2004-06-02Not applicableUs
Ceftinpowder, for suspension250 mg/5mLoralGlaxo Smith Kline Llc2004-06-02Not applicableUs
Ceftinpowder, for suspension125 mg/5mLoralGlaxo Smith Kline Llc2004-06-02Not applicableUs
Ceftintablet, film coated500 mg/1oralGlaxo Smith Kline Llc1989-10-01Not applicableUs
Ceftin - Pwr 250mg/sachetpowder250 mgoralGlaxosmithkline Inc1999-11-102003-02-07Canada
Ceftin - Pws 125mg/5mlpowder for solution125 mgoralGlaxosmithkline Inc1999-09-13Not applicableCanada
Ceftin - Tab 250mgtablet250 mgoralGlaxosmithkline Inc1998-12-31Not applicableCanada
Ceftin - Tab 500mgtablet500 mgoralGlaxosmithkline Inc1998-10-27Not applicableCanada
Ceftin for Oral Suspension-pws 250mg/pckpowder for solution250 mgoralGlaxo Canada Inc1995-12-312000-08-02Canada
Ceftin Pws 125mg/5mlpowder for solution125 mgoralGlaxo Canada Inc1995-12-312000-08-02Canada
Ceftin Tab 250mgtablet250 mgoralGlaxo Canada Inc1990-12-311999-08-12Canada
Ceftin Tab 500mgtablet500 mgoralGlaxo Canada Inc1990-12-311999-08-12Canada
Cefuroxime for Injection USPpowder for solution7.5 gintravenousPharmaceutical Partners Of Canada Inc1998-10-212008-02-15Canada
Cefuroxime for Injection USPpowder for solution1.5 gintravenousPharmaceutical Partners Of Canada Inc1998-10-212008-02-15Canada
Cefuroxime for Injection USPpowder for solution750 mgintramuscular; intravenousPharmaceutical Partners Of Canada Inc1998-10-212008-02-15Canada
Cefuroxime for Injection, USPpowder for solution1.5 gintravenousFresenius Kabi Canada Ltd2002-12-10Not applicableCanada
Cefuroxime for Injection, USPpowder for solution750 mgintravenousSterimax Inc2015-03-24Not applicableCanada
Cefuroxime for Injection, USPpowder for solution7.5 gintravenousFresenius Kabi Canada Ltd2002-12-05Not applicableCanada
Cefuroxime for Injection, USPpowder for solution7.5 gintravenousSterimax Inc2015-05-04Not applicableCanada
Cefuroxime for Injection, USPpowder for solution750 mgintravenousFresenius Kabi Canada Ltd2002-12-05Not applicableCanada
Cefuroxime for Injection, USPpowder for solution1.5 gintravenousSterimax Inc2015-03-24Not applicableCanada
Kefuroxpowder for solution750 mgintravenousPharmaceutical Partners Of Canada Inc1992-12-312008-02-13Canada
Kefuroxpowder for solution1.5 gintravenousPharmaceutical Partners Of Canada Inc1992-12-312008-02-13Canada
Kefuroxpowder for solution7.5 gintravenousPharmaceutical Partners Of Canada Inc1993-12-312008-02-13Canada
Kefurox Inj Pws 1.5gm/add-vantage Vialpowder for solution1.5 gintravenousEli Lilly Canada Inc1991-12-311998-09-15Canada
Kefurox Inj Pws 750mg/add-vantage Vialpowder for solution750 mgintravenousEli Lilly Canada Inc1992-12-311998-08-04Canada
Novo-cefuroximetablet500 mgoralNovopharm LimitedNot applicableNot applicableCanada
Novo-cefuroximetablet250 mgoralNovopharm LimitedNot applicableNot applicableCanada
Novo-cefuroximetablet125 mgoralNovopharm LimitedNot applicableNot applicableCanada
Nu-cefuroximetablet250 mgoralNu Pharm IncNot applicableNot applicableCanada
Nu-cefuroximetablet500 mgoralNu Pharm IncNot applicableNot applicableCanada
Orb-cefuroximetablet250 mgoralOrbus Pharma IncNot applicableNot applicableCanada
Orb-cefuroximetablet500 mgoralOrbus Pharma IncNot applicableNot applicableCanada
Pro-cefuroxime - 500tablet500 mgoralPro Doc Limitee2008-07-04Not applicableCanada
Ratio-cefuroximetablet500 mgoralTeva Canada Limited2001-08-30Not applicableCanada
Ratio-cefuroximetablet250 mgoralTeva Canada Limited2001-08-30Not applicableCanada
Zinacefinjection, powder, for solution90 mg/mLintravenousCovis Pharmaceuticals Inc2013-01-15Not applicableUs
Zinacefinjection, powder, for solution90 mg/mLintravenousCovis Pharmaceuticals Inc2013-01-15Not applicableUs
Zinacefinjection, powder, for solution90 mg/mLintramuscular; intravenousCovis Pharmaceuticals Inc2013-01-15Not applicableUs
Zinacefinjection, powder, for solution90 mg/mLintravenousCovis Pharmaceuticals Inc2013-01-15Not applicableUs
Zinacefinjection, powder, for solution90 mg/mLintravenousCovis Pharmaceuticals Inc2013-01-15Not applicableUs
Zinacefinjection, solution1.5 g/50mLintravenousCovis Pharmaceuticals Inc2012-10-15Not applicableUs
Zinacef Inj 1.5gm/vialpowder for solution1.5 gintramuscular; intravenousGlaxo Canada Inc1980-12-312002-07-31Canada
Zinacef Inj 7.5gm/vialpowder for solution7.5 gintravenousGlaxo Canada Inc1990-12-312002-07-31Canada
Zinacef Inj 750mg/vialpowder for solution750 mgintramuscular; intravenousGlaxo Canada Inc1980-12-312001-08-20Canada
Zinacef Injection - Pws IV 1.5gm/vialpowder for solution1.5 gintravenousGlaxosmithkline Inc2002-01-012007-07-09Canada
Zinacef Injection - Pws Im IV 750mg/vialpowder for solution750 mgintramuscular; intravenousGlaxosmithkline Inc2001-08-202007-11-30Canada
Zinacef Injection - Pws IV 7.5gm/vialpowder for solution7.5 gintravenousGlaxosmithkline Inc2002-01-172007-07-09Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-cefuroximetablet500 mgoralApotex Inc2001-08-29Not applicableCanada
Apo-cefuroximetablet250 mgoralApotex Inc2001-08-29Not applicableCanada
Cefuroximeinjection, powder, for solution1.5 g/1intravenousWest ward Pharmaceutical Corp2004-01-09Not applicableUs
Cefuroximeinjection, powder, for solution90 mg/mLintravenousHospira, Inc.2009-04-27Not applicableUs
Cefuroximeinjection, powder, for solution1.5 g/16mLintravenousWG Critical Care, LLC2012-10-04Not applicableUs
Cefuroximeinjection, powder, for solution750 mg/1intramuscular; intravenousWest ward Pharmaceutical Corp2004-01-09Not applicableUs
Cefuroximeinjection, powder, for solution7.5 g/80mLintravenousAPP Pharmaceuticals, LLC2010-07-30Not applicableUs
Cefuroximeinjection, powder, for solution750 mg/1intramuscular; intravenousWG Critical Care, LLC2012-10-04Not applicableUs
Cefuroximeinjection, powder, for solution1.5 g/1intravenousWest ward Pharmaceutical Corp2004-01-09Not applicableUs
Cefuroximeinjection, powder, for solution1.5 g/1intravenousAPP Pharmaceuticals, LLC2011-05-24Not applicableUs
Cefuroximeinjection, powder, for solution750 mg/8mLintravenousWest ward Pharmaceutical Corp2004-01-09Not applicableUs
Cefuroximeinjection, powder, for solution750 mg/1intramuscular; intravenousAPP Pharmaceuticals, LLC2011-05-24Not applicableUs
Cefuroximeinjection, powder, for solution1.5 g/100mLintravenousWG Critical Care, LLC2012-10-04Not applicableUs
Cefuroximeinjection, powder, for solution7.5 g/1intravenousWest ward Pharmaceutical Corp2004-01-09Not applicableUs
Cefuroximeinjection, powder, for solution750 mg/100mLintravenousWG Critical Care, LLC2012-10-04Not applicableUs
Cefuroximeinjection, powder, for solution7.5 g/82.5mLintravenousSagent Pharmaceuticals2008-05-01Not applicableUs
Cefuroximeinjection, powder, for solution750 mg/1intramuscular; intravenousWest ward Pharmaceutical Corp2004-01-09Not applicableUs
Cefuroximeinjection, powder, for solution7.5 g/80mLintravenousWG Critical Care, LLC2012-10-04Not applicableUs
Cefuroxime Axetiltablet, film coated250 mg/1oralApotex Corp.2002-10-02Not applicableUs
Cefuroxime Axetiltablet250 mg/1oralAurobindo Pharma Limited2006-03-29Not applicableUs
Cefuroxime Axetiltablet500 mg/1oralGen Source Rx2006-03-292015-12-23Us
Cefuroxime Axetiltablet, film coated250 mg/1oralH.J. Harkins Company, Inc.2010-12-01Not applicableUs
Cefuroxime Axetiltablet, film coated250 mg/1oralPd Rx Pharmaceuticals, Inc.2005-07-29Not applicableUs
Cefuroxime Axetiltablet, film coated250 mg/1oralA S Medication Solutions Llc2005-07-29Not applicableUs
Cefuroxime Axetiltablet250 mg/1oralDIRECT RX2014-01-01Not applicableUs
Cefuroxime Axetiltablet, film coated500 mg/1oralMed Vantx, Inc.2009-06-18Not applicableUs
Cefuroxime Axetiltablet, film coated250 mg/1oralWockhardt Limited2005-07-29Not applicableUs
Cefuroxime Axetiltablet, film coated125 mg/1oralWockhardt USA LLC.2005-07-29Not applicableUs
Cefuroxime Axetiltablet500 mg/1oralLupin Pharmaceuticals, Inc.2003-07-25Not applicableUs
Cefuroxime Axetiltablet, film coated500 mg/1oralApotex Corp.2002-10-02Not applicableUs
Cefuroxime Axetiltablet125 mg/1oralAurobindo Pharma Limited2006-03-29Not applicableUs
Cefuroxime Axetiltablet250 mg/1oralGen Source Rx2006-03-292015-12-18Us
Cefuroxime Axetiltablet, film coated500 mg/1oralLucid Pharma Llc2006-03-29Not applicableUs
Cefuroxime Axetiltablet, film coated125 mg/1oralWockhardt Limited2005-07-29Not applicableUs
Cefuroxime Axetiltablet250 mg/1oralLupin Pharmaceuticals, Inc.2003-07-25Not applicableUs
Cefuroxime Axetiltablet250 mg/1oralRebel Distributors Corp2006-03-29Not applicableUs
Cefuroxime Axetiltablet, film coated500 mg/1oralClinical Solutions Wholesale2005-07-29Not applicableUs
Cefuroxime Axetiltablet500 mg/1oralAurobindo Pharma Limited2006-03-292016-01-31Us
Cefuroxime Axetiltablet, film coated500 mg/1oralPreferred Pharmaceuticali Inc.2006-03-29Not applicableUs
Cefuroxime Axetiltablet, film coated250 mg/1oralLucid Pharma Llc2006-03-29Not applicableUs
Cefuroxime Axetiltablet, film coated250 mg/1oralPd Rx Pharmaceuticals, Inc.2005-07-29Not applicableUs
Cefuroxime Axetiltablet, film coated500 mg/1oralAscend Laboratories, LLC2010-12-01Not applicableUs
Cefuroxime Axetiltablet, film coated500 mg/1oralOrchid Pharma Inc2016-04-11Not applicableUs
Cefuroxime Axetiltablet250 mg/1oralPd Rx Pharmaceuticals, Inc.2006-03-29Not applicableUs
Cefuroxime Axetiltablet500 mg/1oralRebel Distributors Corp2006-03-29Not applicableUs
Cefuroxime Axetiltablet, film coated250 mg/1oralClinical Solutions Wholesale2005-07-29Not applicableUs
Cefuroxime Axetiltablet250 mg/1oralAurobindo Pharma Limited2006-03-292016-01-31Us
Cefuroxime Axetiltablet500 mg/1oralPreferred Pharmaceuticals, Inc.2013-03-15Not applicableUs
Cefuroxime Axetiltablet, film coated500 mg/1oralUnit Dose Services2005-07-29Not applicableUs
Cefuroxime Axetiltablet500 mg/1oralPhysicians Total Care, Inc.2004-03-17Not applicableUs
Cefuroxime Axetiltablet, film coated250 mg/1oralAscend Laboratories, LLC2010-12-01Not applicableUs
Cefuroxime Axetiltablet, film coated250 mg/1oralOrchid Pharma Inc2016-04-11Not applicableUs
Cefuroxime Axetiltablet250 mg/1oralPd Rx Pharmaceuticals, Inc.2003-07-25Not applicableUs
Cefuroxime Axetiltablet500 mg/1oralNorth Star Rx Llc2006-03-29Not applicableUs
Cefuroxime Axetiltablet, film coated500 mg/1oralCitron Pharma LLC2006-03-29Not applicableUs
Cefuroxime Axetiltablet125 mg/1oralAurobindo Pharma Limited2006-03-292016-01-31Us
Cefuroxime Axetiltablet250 mg/1oralPreferred Pharmaceuticals, Inc.2013-03-15Not applicableUs
Cefuroxime Axetiltablet250 mg/1oralPhysicians Total Care, Inc.2004-01-30Not applicableUs
Cefuroxime Axetiltablet, film coated250 mg/1oralPd Rx Pharmaceuticals, Inc.2010-12-01Not applicableUs
Cefuroxime Axetiltablet250 mg/1oralPd Rx Pharmaceuticals, Inc.2006-03-29Not applicableUs
Cefuroxime Axetiltablet250 mg/1oralNorth Star Rx Llc2006-03-29Not applicableUs
Cefuroxime Axetiltablet, film coated250 mg/1oralCitron Pharma LLC2006-03-29Not applicableUs
Cefuroxime Axetiltablet, film coated500 mg/1oralWockhardt USA LLC.2005-07-29Not applicableUs
Cefuroxime Axetiltablet500 mg/1oralPreferred Pharmaceuticals, Inc.2014-05-07Not applicableUs
Cefuroxime Axetiltablet500 mg/1oralH.J. Harkins Company, Inc.2006-03-29Not applicableUs
Cefuroxime Axetiltablet250 mg/1oralDIRECT RX2014-01-01Not applicableUs
Cefuroxime Axetiltablet500 mg/1oralAurobindo Pharma Limited2006-03-29Not applicableUs
Cefuroxime Axetiltablet, film coated500 mg/1oralPd Rx Pharmaceuticals, Inc.2005-07-29Not applicableUs
Cefuroxime Axetiltablet, film coated500 mg/1oralA S Medication Solutions Llc2010-12-01Not applicableUs
Cefuroxime Axetiltablet, film coated250 mg/1oralPd Rx Pharmaceuticals, Inc.2010-12-01Not applicableUs
Cefuroxime Axetiltablet, film coated500 mg/1oralSTAT Rx USA LLC2005-07-29Not applicableUs
Cefuroxime Axetiltablet, film coated500 mg/1oralWockhardt Limited2005-07-29Not applicableUs
Cefuroxime Axetiltablet, film coated250 mg/1oralWockhardt USA LLC.2005-07-29Not applicableUs
Cefuroxime Axetiltablet, film coated250 mg/1oralPreferred Pharmaceuticals, Inc.2014-09-18Not applicableUs
Cefuroxime Axetil for Oral Suspensionsuspension250 mg/mLoralRanbaxy Pharmaceuticals Inc2008-02-08Not applicableUs
Cefuroxime Axetil for Oral Suspensionsuspension125 mg/5mLoralRanbaxy Pharmaceuticals Inc2008-02-08Not applicableUs
Cefuroxime Sodiuminjection, powder, for solution1.5 g/16mLintravenousSagent Pharmaceuticals2008-05-01Not applicableUs
Cefuroxime Sodiuminjection, powder, for solution750 mg/1intramuscular; intravenousSagent Pharmaceuticals2008-05-01Not applicableUs
Cefuroxime Sodiuminjection, powder, for solution225 g/1intravenousSamson Medical Technologies, L.L.C.2010-02-01Not applicableUs
Cefuroxime Sodiuminjection, powder, for solution75 g/1intravenousSamson Medical Technologies, L.L.C.2010-02-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CefuraxLindopharm
ElobactGlaxoSmithKline
OraximMalesci
SharoxFahrenheit
SupacefGlaxoSmithKline
ZinnatGlaxoSmithKline
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Cefuroxime axetil
ThumbNot applicableDBSALT001355
Cefuroxime sodium
ThumbNot applicableDBSALT001160
Categories
UNIIO1R9FJ93ED
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)[[email protected]]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.
Related Articles
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 inhibitorNon-inhibitor0.7771
CYP450 2D6 inhibitorNon-inhibitor0.8707
CYP450 2C19 inhibitorNon-inhibitor0.7064
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Powder, for suspensionoral125 mg/5mL
Powder, for suspensionoral250 mg/5mL
Tablet, film coatedoral250 mg/1
Tablet, film coatedoral500 mg/1
Powderoral250 mg
Powder for solutionoral125 mg
Tabletoral250 mg
Tabletoral500 mg
Powder for solutionoral250 mg
Injection, powder, for solutionintramuscular; intravenous750 mg/1
Injection, powder, for solutionintravenous1.5 g/1
Injection, powder, for solutionintravenous1.5 g/100mL
Injection, powder, for solutionintravenous7.5 g/82.5mL
Injection, powder, for solutionintravenous7.5 g/1
Injection, powder, for solutionintravenous7.5 g/80mL
Injection, powder, for solutionintravenous750 mg/8mL
Injection, powder, for solutionintravenous750 mg/100mL
Injection, powder, for solutionintravenous90 mg/mL
Tabletoral125 mg/1
Tabletoral250 mg/1
Tabletoral500 mg/1
Tablet, film coatedoral125 mg/1
Suspensionoral125 mg/5mL
Suspensionoral250 mg/mL
Powder for solutionintravenous1.5 g
Powder for solutionintravenous7.5 g
Powder for solutionintravenous750 mg
Injection, powder, for solutionintravenous1.5 g/16mL
Injection, powder, for solutionintravenous225 g/1
Injection, powder, for solutionintravenous75 g/1
Tabletoral125 mg
Injection, powder, for solutionintramuscular; intravenous90 mg/mL
Injection, solutionintravenous1.5 g/50mL
Powder for solutionintramuscular; intravenous1.5 g
Powder for solutionintramuscular; intravenous750 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
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA1328405 No1994-04-122011-04-12Canada
CA2408198 No2004-03-092022-11-21Canada
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 References
  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:8799689 ]
External Links
ATC CodesJ01DC02J01RA03S01AA27
AHFS Codes
  • 08:12.06.08
PDB EntriesNot Available
FDA labelDownload (809 KB)
MSDSDownload (52.7 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolCefuroxime may increase the anticoagulant activities of Acenocoumarol.
Aluminum hydroxideThe serum concentration of Cefuroxime can be decreased when it is combined with Aluminum hydroxide.
AmikacinCefuroxime may increase the nephrotoxic activities of Amikacin.
ArbekacinCefuroxime may increase the nephrotoxic activities of Arbekacin.
Calcium carbonateThe serum concentration of Cefuroxime can be decreased when it is combined with Calcium carbonate.
CimetidineCimetidine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.
DicoumarolCefuroxime may increase the anticoagulant activities of Dicoumarol.
FamotidineFamotidine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.
FramycetinCefuroxime may increase the nephrotoxic activities of Framycetin.
GentamicinCefuroxime may increase the nephrotoxic activities of Gentamicin.
KanamycinCefuroxime may increase the nephrotoxic activities of Kanamycin.
Magnesium hydroxideThe serum concentration of Cefuroxime can be decreased when it is combined with Magnesium hydroxide.
Magnesium oxideThe serum concentration of Cefuroxime can be decreased when it is combined with Magnesium oxide.
NeomycinCefuroxime may increase the nephrotoxic activities of Neomycin.
NetilmicinCefuroxime may increase the nephrotoxic activities of Netilmicin.
NizatidineNizatidine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Cefuroxime.
ProbenecidThe serum concentration of Cefuroxime can be increased when it is combined with Probenecid.
RanitidineRanitidine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.
RibostamycinCefuroxime may increase the nephrotoxic activities of Ribostamycin.
Sodium bicarbonateThe serum concentration of Cefuroxime can be decreased when it is combined with Sodium bicarbonate.
SpectinomycinCefuroxime may increase the nephrotoxic activities of Spectinomycin.
StreptomycinCefuroxime may increase the nephrotoxic activities of Streptomycin.
TobramycinCefuroxime may increase the nephrotoxic activities of Tobramycin.
WarfarinCefuroxime may increase the anticoagulant activities of Warfarin.
Food Interactions
  • Take with food to increase absorption.

Targets

Kind
Protein
Organism
Clostridium perfringens (strain 13 / Type A)
Pharmacological action
yes
Actions
inhibitor
General Function:
Transferase activity, transferring glycosyl groups
Specific Function:
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits) (By similarity).
Gene Name:
pbpA
Uniprot ID:
Q8XJ01
Molecular Weight:
75176.35 Da
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:17139284 ]
  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:17016423 ]
  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:7968655 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:
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.
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular Weight:
78805.265 Da
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:15567297 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Peptide:proton symporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular Weight:
81782.77 Da
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:15567297 ]
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Drug created on June 13, 2005 07:24 / Updated on November 27, 2015 13:52