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 IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Cefuroxime axetilZ49QDT0J8Z 64544-07-6KEJCWVGMRLCZQQ-YJBYXUATSA-NDetails
Cefuroxime sodiumR8A7M9MY61 56238-63-2URDOHUPGIOGTKV-JTBFTWTJSA-MDetails
Product Images
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Auro-cefuroximeTablet250 mgOralAurobindo Pharma Limited (Unit Vi)2012-01-13Not applicableCanada
Auro-cefuroximeTablet500 mgOralAurobindo Pharma Limited (Unit Vi)2012-01-13Not applicableCanada
CeftinPowder, for suspension125 mg/5mLOralGlaxosmithkline Inc2004-06-02Not applicableUs
CeftinTablet, film coated500 mg/1OralGlaxosmithkline Inc1989-10-012017-04-30Us00173 0394 00 nlmimage10 7d18beb5
CeftinPowder, for suspension250 mg/5mLOralA S Medication Solutions2004-06-022017-06-20Us
CeftinPowder, for suspension250 mg/5mLOralGlaxosmithkline Inc2004-06-02Not applicableUs
CeftinTablet, film coated250 mg/1OralGlaxosmithkline Inc1989-10-012018-04-30Us00173 0387 00 nlmimage10 8018c066
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 gIntravenousPartners Health Care, Inc.1998-10-212008-02-15Canada
Cefuroxime for Injection USPPowder, for solution750 mgIntramuscular; IntravenousPartners Health Care, Inc.1998-10-212008-02-15Canada
Cefuroxime for Injection USPPowder, for solution1.5 gIntravenousPartners Health Care, Inc.1998-10-212008-02-15Canada
Cefuroxime for Injection, USPPowder, for solution1.5 gIntravenousFresenius Kabi2002-12-10Not applicableCanada
Cefuroxime for Injection, USPPowder, for solution750 mgIntravenousSterimax Inc2015-03-24Not applicableCanada
Cefuroxime for Injection, USPPowder, for solution7.5 gIntravenousFresenius Kabi2002-12-05Not applicableCanada
Cefuroxime for Injection, USPPowder, for solution7.5 gIntravenousSterimax Inc2015-05-04Not applicableCanada
Cefuroxime for Injection, USPPowder, for solution750 mgIntravenousFresenius Kabi2002-12-05Not applicableCanada
Cefuroxime for Injection, USPPowder, for solution1.5 gIntravenousSterimax Inc2015-03-24Not applicableCanada
KefuroxPowder, for solution7.5 gIntravenousPartners Health Care, Inc.1993-12-312008-02-13Canada
KefuroxPowder, for solution750 mgIntravenousPartners Health Care, Inc.1992-12-312008-02-13Canada
KefuroxPowder, for solution1.5 gIntravenousPartners Health Care, Inc.1992-12-312008-02-13Canada
Kefurox Inj Pws 1.5gm/add-vantage VialPowder, for solution1.5 gIntravenousEli Lilly & Co. Ltd.1991-12-311998-09-15Canada
Kefurox Inj Pws 750mg/add-vantage VialPowder, for solution750 mgIntravenousEli Lilly & Co. Ltd.1992-12-311998-08-04Canada
Novo-cefuroximeTablet500 mgOralNovopharm LimitedNot applicableNot applicableCanada
Novo-cefuroximeTablet125 mgOralNovopharm LimitedNot applicableNot applicableCanada
Novo-cefuroximeTablet250 mgOralNovopharm LimitedNot applicableNot applicableCanada
Nu-cefuroximeTablet500 mgOralNu Pharm IncNot applicableNot applicableCanada
Nu-cefuroximeTablet250 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 mgOralTeva2001-08-30Not applicableCanada
Ratio-cefuroximeTablet250 mgOralTeva2001-08-30Not applicableCanada
ZinacefInjection, powder, for solution90 mg/mLIntramuscular; IntravenousCovis Pharmaceuticals, Inc.2013-01-15Not applicableUs
ZinacefInjection, solution1.5 g/50mLIntravenousCovis Pharmaceuticals, Inc.2012-10-15Not applicableUs
ZinacefInjection, powder, for solution90 mg/mLIntravenousCovis Pharmaceuticals, Inc.2013-01-15Not applicableUs
ZinacefInjection, powder, for solution90 mg/mLIntravenousCovis Pharmaceuticals, Inc.2013-01-15Not applicableUs
ZinacefInjection, powder, for solution90 mg/mLIntravenousCovis Pharmaceuticals, Inc.2013-01-15Not applicableUs
ZinacefInjection, powder, for solution90 mg/mLIntravenousCovis Pharmaceuticals, Inc.2013-01-15Not 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-cefuroximeTablet250 mgOralApotex Corporation2001-08-29Not applicableCanada
Apo-cefuroximeTablet500 mgOralApotex Corporation2001-08-29Not applicableCanada
CefuroximeInjection, powder, for solution1.5 g/1IntravenousWest Ward Pharmaceutical2004-01-09Not applicableUs
CefuroximeInjection, powder, for solution7.5 g/80mLIntravenousAPP Pharmaceuticals, Inc.2010-07-30Not applicableUs
CefuroximeInjection, powder, for solution750 mg/8mLIntravenousWest Ward Pharmaceutical2004-01-09Not applicableUs
CefuroximeInjection, powder, for solution1.5 g/1IntravenousAPP Pharmaceuticals, Inc.2011-05-24Not applicableUs
CefuroximeInjection, powder, for solution750 mg/1Intramuscular; IntravenousWG Critical Care, LLC2012-10-04Not applicableUs
CefuroximeInjection, powder, for solution90 mg/mLIntravenousHospira, Inc.2009-04-272016-10-13Us
CefuroximeInjection, powder, for solution750 mg/100mLIntravenousWG Critical Care, LLC2012-10-04Not applicableUs
CefuroximeInjection, powder, for solution750 mg/1Intramuscular; IntravenousWest Ward Pharmaceutical2004-01-09Not applicableUs
CefuroximeInjection, powder, for solution1.5 g/1IntravenousWest Ward Pharmaceutical2004-01-09Not applicableUs
CefuroximeInjection, powder, for solution1.5 g/16mLIntravenousWG Critical Care, LLC2012-10-04Not applicableUs
CefuroximeInjection, powder, for solution1.5 g/100mLIntravenousWG Critical Care, LLC2012-10-04Not applicableUs
CefuroximeInjection, powder, for solution7.5 g/1IntravenousWest Ward Pharmaceutical2004-01-09Not applicableUs
CefuroximeInjection, powder, for solution750 mg/1Intramuscular; IntravenousAPP Pharmaceuticals, Inc.2011-05-24Not applicableUs
CefuroximeInjection, powder, for solution7.5 g/82.5mLIntravenousSagent Pharmaceuticals2008-05-012016-10-13Us
CefuroximeInjection, powder, for solution7.5 g/80mLIntravenousWG Critical Care, LLC2012-10-04Not applicableUs
CefuroximeInjection, powder, for solution750 mg/1Intramuscular; IntravenousWest Ward Pharmaceutical2004-01-09Not applicableUs
Cefuroxime AxetilTablet500 mg/1OralA S Medication Solutions2003-07-252017-06-20Us
Cefuroxime AxetilTablet, film coated500 mg/1OralPd Rx Pharmaceuticals, Inc.2005-07-29Not applicableUs
Cefuroxime AxetilTablet500 mg/1OralAurobindo Pharma2006-03-29Not applicableUs
Cefuroxime AxetilTablet, film coated250 mg/1OralAscend Laboratories, LLC2010-12-01Not applicableUs
Cefuroxime AxetilTablet500 mg/1OralRebel Distributors2006-03-29Not applicableUs
Cefuroxime AxetilTablet, film coated250 mg/1OralH.J. Harkins Company2010-12-01Not applicableUs
Cefuroxime AxetilTablet500 mg/1OralGen Source Rx2006-03-292015-12-23Us
Cefuroxime AxetilTablet250 mg/1OralPhysicians Total Care, Inc.2004-01-30Not applicableUs
Cefuroxime AxetilTablet, film coated250 mg/1OralApotex Corporation2002-10-022016-12-13Us
Cefuroxime AxetilTablet500 mg/1OralGolden State Medical Supply2016-02-22Not applicableUs
Cefuroxime AxetilTablet, film coated500 mg/1OralLucid Pharma Llc2006-03-29Not applicableUs
Cefuroxime AxetilTablet, film coated500 mg/1OralA S Medication Solutions2010-12-012017-06-20Us
Cefuroxime AxetilTablet, film coated250 mg/1OralPd Rx Pharmaceuticals, Inc.2010-12-01Not applicableUs
Cefuroxime AxetilTablet, film coated250 mg/1OralWockhardt2005-07-29Not applicableUs
Cefuroxime AxetilTablet500 mg/1OralPreferreed Pharmaceuticals Inc.2013-03-15Not applicableUs
Cefuroxime AxetilTablet, film coated500 mg/1OralWockhardt2005-07-29Not applicableUs
Cefuroxime AxetilTablet, film coated250 mg/1OralA S Medication Solutions2010-12-012017-06-20Us
Cefuroxime AxetilTablet250 mg/1OralNorth Star Rx Llc2006-03-29Not applicableUs16714 0400 02 nlmimage10 8c44c616
Cefuroxime AxetilTablet, film coated500 mg/1OralApotex Corporation2002-10-022016-12-13Us
Cefuroxime AxetilTablet250 mg/1OralGolden State Medical Supply2016-02-22Not applicableUs
Cefuroxime AxetilTablet250 mg/1OralGen Source Rx2006-03-292015-12-18Us
Cefuroxime AxetilTablet, film coated250 mg/1OralLucid Pharma Llc2006-03-29Not applicableUs
Cefuroxime AxetilTablet, film coated500 mg/1OralUnit Dose Services2005-07-29Not applicableUs
Cefuroxime AxetilTablet, film coated250 mg/1OralPd Rx Pharmaceuticals, Inc.2005-07-29Not applicableUs
Cefuroxime AxetilTablet, film coated500 mg/1OralOrchid Pharma Inc2016-04-11Not applicableUs
Cefuroxime AxetilTablet, film coated500 mg/1OralCitron Pharma LLC2006-03-29Not applicableUs
Cefuroxime AxetilTablet500 mg/1OralAurobindo Pharma2006-03-292016-01-31Us
Cefuroxime AxetilTablet125 mg/1OralAurobindo Pharma2006-03-29Not applicableUs
Cefuroxime AxetilTablet250 mg/1OralAvera Mc Kennan Hospital2016-06-06Not applicableUs
Cefuroxime AxetilTablet, film coated125 mg/1OralWockhardt2005-07-29Not applicableUs
Cefuroxime AxetilTablet250 mg/1OralDirectrx2014-01-01Not applicableUs
Cefuroxime AxetilTablet250 mg/1OralA S Medication Solutions2003-07-252017-06-20Us
Cefuroxime AxetilTablet, film coated250 mg/1OralClinical Solutions Wholsesale2005-07-292017-06-24Us
Cefuroxime AxetilTablet250 mg/1OralLupin Pharmaceuticals2003-07-25Not applicableUs
Cefuroxime AxetilTablet250 mg/1OralPd Rx Pharmaceuticals, Inc.2003-07-25Not applicableUs
Cefuroxime AxetilTablet500 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2006-03-29Not applicableUs
Cefuroxime AxetilTablet, film coated500 mg/1OralAscend Laboratories, LLC2010-12-01Not applicableUs67877 0216 60 nlmimage10 d807ec3f
Cefuroxime AxetilTablet250 mg/1OralRebel Distributors2006-03-29Not applicableUs
Cefuroxime AxetilTablet500 mg/1OralH.J. Harkins Company2006-03-29Not applicableUs
Cefuroxime AxetilTablet500 mg/1OralPhysicians Total Care, Inc.2004-03-17Not applicableUs
Cefuroxime AxetilTablet, film coated250 mg/1OralPreferreed Pharmaceuticals Inc.2014-09-18Not applicableUs
Cefuroxime AxetilTablet, film coated250 mg/1OralPd Rx Pharmaceuticals, Inc.2010-12-01Not applicableUs
Cefuroxime AxetilTablet, film coated500 mg/1OralWockhardt2005-07-29Not applicableUs
Cefuroxime AxetilTablet, film coated500 mg/1OralPreferreed Pharmaceuticals Inc.2006-03-29Not applicableUs
Cefuroxime AxetilTablet125 mg/1OralAurobindo Pharma2006-03-292016-01-31Us
Cefuroxime AxetilTablet250 mg/1OralLupin Pharmaceuticals2003-07-25Not applicableUs68180 0302 60 nlmimage10 813a40c2
Cefuroxime AxetilTablet500 mg/1OralNorth Star Rx Llc2006-03-29Not applicableUs
Cefuroxime AxetilTablet, film coated500 mg/1OralMed Vantx, Inc.2009-06-18Not applicableUs16714 0233 02 nlmimage10 d307e9ff
Cefuroxime AxetilTablet250 mg/1OralAurobindo Pharma2006-03-29Not applicableUs
Cefuroxime AxetilTablet500 mg/1OralAvera Mc Kennan Hospital2016-06-20Not applicableUs
Cefuroxime AxetilTablet, film coated500 mg/1OralStat Rx USA2005-07-29Not applicableUs64679 0922 01 nlmimage10 651332c9
Cefuroxime AxetilTablet250 mg/1OralDirectrx2014-01-01Not applicableUs
Cefuroxime AxetilTablet250 mg/1OralA S Medication Solutions2003-07-252017-06-20Us
Cefuroxime AxetilTablet, film coated125 mg/1OralWockhardt2005-07-29Not applicableUs
Cefuroxime AxetilTablet250 mg/1OralPreferreed Pharmaceuticals Inc.2013-03-15Not applicableUs
Cefuroxime AxetilTablet, film coated250 mg/1OralWockhardt2005-07-29Not applicableUs
Cefuroxime AxetilTablet, film coated500 mg/1OralA S Medication Solutions2010-12-012017-06-20Us
Cefuroxime AxetilTablet, film coated250 mg/1OralA S Medication Solutions2010-12-012017-06-20Us
Cefuroxime AxetilTablet, film coated500 mg/1OralClinical Solutions Wholsesale2005-07-292017-06-24Us
Cefuroxime AxetilTablet500 mg/1OralLupin Pharmaceuticals2003-07-25Not applicableUs
Cefuroxime AxetilTablet250 mg/1OralPd Rx Pharmaceuticals, Inc.2006-03-29Not applicableUs
Cefuroxime AxetilTablet500 mg/1OralPreferreed Pharmaceuticals Inc.2014-05-072017-02-09Us
Cefuroxime AxetilTablet250 mg/1OralPd Rx Pharmaceuticals, Inc.2006-03-292016-12-23Us
Cefuroxime AxetilTablet250 mg/1OralNucare Pharmaceuticals, Inc.2006-03-29Not applicableUs
Cefuroxime AxetilTablet, film coated250 mg/1OralA S Medication Solutions2005-07-292017-06-20Us64679 0921 01 nlmimage10 eb3475b3
Cefuroxime AxetilTablet, film coated250 mg/1OralOrchid Pharma Inc2016-04-11Not applicableUs
Cefuroxime AxetilTablet, film coated250 mg/1OralCitron Pharma LLC2006-03-29Not applicableUs
Cefuroxime AxetilTablet250 mg/1OralAurobindo Pharma2006-03-292016-01-31Us
Cefuroxime AxetilTablet500 mg/1OralLupin Pharmaceuticals2003-07-25Not applicableUs68180 0303 20 nlmimage10 7132b8c5
Cefuroxime AxetilTablet, film coated250 mg/1OralPd Rx Pharmaceuticals, Inc.2005-07-29Not applicableUs
Cefuroxime Axetil for Oral SuspensionSuspension125 mg/5mLOralRanbaxy Inc.2008-02-08Not applicableUs
Cefuroxime Axetil for Oral SuspensionSuspension250 mg/mLOralRanbaxy Inc.2008-02-08Not applicableUs
Cefuroxime SodiumInjection, powder, for solution1.5 g/16mLIntravenousSagent Pharmaceuticals2008-05-01Not applicableUs
Cefuroxime SodiumInjection, powder, for solution75 g/1IntravenousSamson Medical Technologies, L.L.C.2010-02-01Not applicableUs
Cefuroxime SodiumInjection, powder, for solution1.5 g/16mLIntravenousSagent Pharmaceuticals2016-09-01Not applicableUs
Cefuroxime SodiumInjection, powder, for solution225 g/1IntravenousSamson Medical Technologies, L.L.C.2010-02-01Not applicableUs
Cefuroxime SodiumInjection, powder, for solution750 mg/1Intramuscular; IntravenousSagent Pharmaceuticals2008-05-01Not applicableUs
Cefuroxime SodiumInjection, powder, for solution750 mg/1Intramuscular; IntravenousSagent Pharmaceuticals2016-09-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CefuraxLindopharm
ElobactGlaxoSmithKline
OraximMalesci
SharoxFahrenheit
SupacefGlaxoSmithKline
ZinnatGlaxoSmithKline
Brand mixturesNot Available
Categories
UNIIO1R9FJ93ED
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)[[email protected]]2NC(=O)C(=N/OC)\C1=CC=CO1)C(O)=O
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.

Structured Indications
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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Penicillin-binding protein 1AProteinyes
inhibitor
Clostridium perfringens (strain 13 / Type A)Q8XJ01 details
Related Articles
Absorption

Absorbed from the gastrointestinal tract. Absorption is greater when taken after food (absolute bioavailability increases from 37% to 52%).

Volume of distributionNot Available
Protein binding

50% 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 life

Approximately 80 minutes following intramuscular or intravenous injection.

ClearanceNot 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
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcenocoumarolCefuroxime may increase the anticoagulant activities of Acenocoumarol.Approved
Aluminum hydroxideThe serum concentration of Cefuroxime can be decreased when it is combined with Aluminum hydroxide.Approved
AsenapineAsenapine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
BCG vaccineThe therapeutic efficacy of Bcg can be decreased when used in combination with Cefuroxime.Investigational
Bismuth SubcitrateThe serum concentration of Cefuroxime can be decreased when it is combined with Bismuth Subcitrate.Approved
Calcium CarbonateThe serum concentration of Cefuroxime can be decreased when it is combined with Calcium carbonate.Approved
CimetidineCimetidine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DicoumarolCefuroxime may increase the anticoagulant activities of Dicoumarol.Approved
DoxepinDoxepin can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
EpinastineEpinastine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
Ethyl biscoumacetateCefuroxime may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FamotidineFamotidine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
FluindioneCefuroxime may increase the anticoagulant activities of Fluindione.Investigational
MagaldrateThe serum concentration of Cefuroxime can be decreased when it is combined with Magaldrate.Withdrawn
Magnesium carbonateThe serum concentration of Cefuroxime can be decreased when it is combined with Magnesium carbonate.Approved
Magnesium HydroxideThe serum concentration of Cefuroxime can be decreased when it is combined with Magnesium hydroxide.Approved
Magnesium oxideThe serum concentration of Cefuroxime can be decreased when it is combined with Magnesium oxide.Approved
Magnesium TrisilicateThe serum concentration of Cefuroxime can be decreased when it is combined with Magnesium Trisilicate.Approved
MethanthelineMethantheline can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
MetiamideMetiamide can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental
NizatidineNizatidine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
OlanzapineOlanzapine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
PhenindioneCefuroxime may increase the anticoagulant activities of Phenindione.Approved
PhenprocoumonCefuroxime may increase the anticoagulant activities of Phenprocoumon.Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Cefuroxime.Approved
ProbenecidThe serum concentration of Cefuroxime can be increased when it is combined with Probenecid.Approved
RanitidineRanitidine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Roxatidine acetateRoxatidine acetate can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
WarfarinCefuroxime may increase the anticoagulant activities of Warfarin.Approved
Food Interactions
  • Take with food to increase absorption.
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 CodesS01AA27 — CefuroximeJ01DC02 — CefuroximeJ01RA03 — Cefuroxime and metronidazole
AHFS Codes
  • 08:12.06.08
PDB EntriesNot Available
FDA labelDownload (809 KB)
MSDSDownload (52.7 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingPreventionComplications of Surgical Procedures1
0RecruitingTreatmentOsteomyelitis1
2WithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections / Sinusitis1
3CompletedPreventionAcute Appendicitis / Perforated Gastroduodenal Ulcer / Small intestinal obstruction1
3CompletedTreatmentPneumonia1
3RecruitingTreatmentEnterobacteriaceae Infections1
4Active Not RecruitingTreatmentInfection NOS1
4CompletedPreventionInfection NOS1
4CompletedPreventionInfection Prophylaxis in Colo Rectal Surgery1
4CompletedPreventionInfection, Postoperative Wound1
4CompletedPreventionPostoperative Infections1
4CompletedPreventionSurgical Site Infections1
4CompletedTreatmentCommunity Acquired Pneumonia (CAP)1
4CompletedTreatmentComplications; Cesarean Section / Infection, Postoperative Wound / Infection; Cesarean Section1
4CompletedTreatmentErythema Chronicum Migrans / Post-Lyme Disease Symptoms1
4CompletedTreatmentOsteoarthritis of the Knees1
4CompletedTreatmentWound Infections1
4RecruitingPreventionInfection, Postoperative Wound1
4RecruitingPreventionObesity; Drug1
4WithdrawnTreatmentPostoperative Infections1
Not AvailableCompletedPreventionEndophthalmitis1
Not AvailableCompletedSupportive CarePost-traumatic; Arthrosis / Synovitis of osteoarthritis1
Not AvailableCompletedTreatmentCataracts / Endophthalmitis1
Not AvailableCompletedTreatmentUlcerative Colitis (UC)1
Not AvailableNot Yet RecruitingNot AvailableCardiovascular Events1
Not AvailableUnknown StatusPreventionCystocele / Enterocele / Rectocele / Uterine Prolapse1
Not AvailableUnknown StatusPreventionInfection NOS1
Not AvailableUnknown StatusPreventionPeristomal Wound Infection After the Operation of PEG / Prophylactic Antibiotics Before PEG / The Patients Who Receive Percutaneous Endoscopic Gastrostomy1
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Powder, for suspensionOral125 mg/5mL
Powder, for suspensionOral250 mg/5mL
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 solutionIntravenous1.5 g/16mL
Injection, powder, for solutionIntravenous7.5 g/80mL
Injection, powder, for solutionIntravenous7.5 g/82.5mL
Injection, powder, for solutionIntravenous7.5 g/1
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
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
SuspensionOral125 mg/5mL
SuspensionOral250 mg/mL
Powder, for solutionIntravenous7.5 g
Powder, for solutionIntravenous750 mg
Injection, powder, for solutionIntravenous225 g/1
Injection, powder, for solutionIntravenous75 g/1
Powder, for solutionIntravenous1.5 g
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 point (°C)218-225 °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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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 )
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cephalosporin 3'-carbamates. These are cephalosporins that are substituted at the 3'-position by a carbamate group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporin 3'-carbamates
Alternative ParentsN-acyl-alpha amino acids and derivatives / 1,3-thiazines / Tertiary carboxylic acid amides / Carbamate esters / Furans / Heteroaromatic compounds / Secondary carboxylic acid amides / Azetidines / Organic carbonic acids and derivatives / Thiohemiaminal derivatives
SubstituentsCephalosporin 3'-carbamate / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Meta-thiazine / Furan / Heteroaromatic compound / Carbamic acid ester / Tertiary carboxylic acid amide / Azetidine / Carboxamide group
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorsoxime O-ether, furans, 3-(carbamoyloxymethyl)cephalosporin (CHEBI:3515 )

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 ]
Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 16:56