Cefuroxime
🧬 Cross-allergy: Cephalosporins
JFDA label: Zinoxime IV/IM
Mechanism of Action
Inhibits bacterial cell wall synthesis by binding to one or more of the penicillin-binding proteins (PBPs) which in turn inhibits the final transpeptidation step of peptidoglycan synthesis in bacterial cell walls, thus inhibiting cell wall biosynthesis. Bacteria eventually lyse due to ongoing activity of cell wall autolytic enzymes (autolysins and murein hydrolases) while cell wall assembly is arrested.
Indications
Approved
- Acute bacterial exacerbations of chronic bronchitis (tablets only)
- Acute bacterial maxillary sinusitis (tablets and oral suspension only)
- Acute otitis media (tablets and oral suspension only)
- Bone and joint infections (injection only)
- Lower respiratory tract infections (injection only)
- Lyme disease (early) (tablets only)
- Pharyngitis/tonsillitis (tablets and oral suspension only)
- Septicemia (injection only)
- Skin and skin structure infection (impetigo) (oral suspension only)
- Skin and skin structure infection (injection; tablets [uncomplicated infections only])
- Surgical (perioperative) prophylaxis (injection only)
- Urinary tract infections (tablets and injection only)
Off-label
- Bite wounds (animal)
- Intra-abdominal Infections
Antimicrobial Spectrum
Expected / intrinsic spectrum (EUCAST breakpoints & labels) — not local resistance. Source: EUCAST v16 · curated · openfda-label.
Bacteria
| Organism | Activity | MIC |
|---|---|---|
| Borrelia burgdorferi | Active | — |
| Escherichia coli | Susceptible | 8.0 mg/L |
| Haemophilus influenzae | Susceptible | 4.0 mg/L |
| Haemophilus influenzae | Susceptible | 1.0 mg/L |
| Haemophilus parainfluenzae | Active | — |
| Klebsiella pneumoniae | Active | — |
| Moraxella catarrhalis | Susceptible | 4.0 mg/L |
| Morganella morganii | Active | — |
| Neisseria gonorrhoeae | Active | — |
| Proteus inconstans | Active | — |
| Proteus mirabilis | Active | — |
| Providencia rettgeri | Active | — |
| Staphylococcus aureus | Susceptible | 1.0 mg/L |
| Staphylococcus epidermidis | Active | — |
| Staphylococcus saprophyticus | Active | — |
| Streptococcus agalactiae | Active | — |
| Streptococcus pneumoniae | Susceptible | 0.125 mg/L |
| Streptococcus pneumoniae | Susceptible | 0.5 mg/L |
| Streptococcus pyogenes | Active | — |
| Viridans group streptococci | Susceptible | 0.5 mg/L |
| Escherichia coli | Resistant | 8.0 mg/L |
Class profile
| gramStatus | Both |
|---|---|
| spectrumBreadth | Moderate |
| atypicalCoverage | No |
| isBactericidal | 1 |
| moaCategory | Cell wall synthesis inhibitor (beta-lactam, 2nd generation cephalosporin) |
| pdIndex | Time-dependent |
| postAntibioticEffect | None |
| mrsaCoverage | 0 |
| resistanceMechanisms | Beta-lactamase production,PBP mutations |
Contraindications
Source: Lexicomp
- Hypersensitivity to cefuroxime, any component of the formulation, or other beta-lactam antibacterial drugs (eg, penicillins and cephalosporins) Absolute
Adverse Reactions
Cardiac disorders (1)
Common Local thrombophlebitis
Vascular disorders (1)
Common Thrombophlebitis (IV)
Hepatobiliary disorders (3)
Common increased serum alkaline phosphatase · Increased serum transaminases
Uncommon Elevated liver enzymes
Renal and urinary disorders (1)
Common Vaginitis
Blood and lymphatic system disorders (3)
Common Decreased hematocrit · decreased hemoglobin · eosinophilia
Immune system disorders (3)
Common Jarisch-Herxheimer reaction
Uncommon Allergic reaction (cross-reactivity with penicillin ~1–2%) · Hypersensitivity / rash
Metabolism and nutrition disorders (1)
Common Increased lactate dehydrogenase
Gastrointestinal disorders (4)
Common Diarrhoea · Nausea · Nausea and vomiting · unpleasant taste
Skin and subcutaneous tissue disorders (1)
Common Diaper rash
Infections and infestations (1)
Uncommon Clostridioides difficile colitis
Other (1)
Very Common Gastrointestinal: Diarrhea
Dosing
Source: Lexicomp
Warnings & Precautions
Source: Lexicomp
Elevated INR
May be associated with increased INR, especially in nutritionally-deficient patients, prolonged treatment, hepatic or renal disease.
Hypersensitivity reactions
Serious and occasionally severe or fatal hypersensitivity (anaphylactic) reactions have been reported in patients receiving beta-lactam drugs. Before initiating therapy, carefully investigate previous penicillin, cephalosporin, or other allergen hypersensitivity. Use caution if given to a patient with a penicillin or other beta-lactam allergy because cross sensitivity among beta-lactam antibacterial drugs has been established. If an allergic reaction occurs, discontinue and institute appropriate therapy.
Superinfection
Prolonged use may result in fungal or bacterial superinfection, including C. difficile-associated diarrhea (CDAD) and pseudomembranous colitis; CDAD has been observed >2 months postantibiotic treatment. Disease-related concerns:
Gastrointestinal disease
Use with caution in patients with a history of colitis.
Renal impairment
Use with caution in patients with renal impairment; modify dosage in severe impairment.
Seizure disorders
Use with caution in patients with a history of seizure disorder; cephalosporins have been associated with seizure activity, particularly in patients with renal impairment not receiving dose adjustments. Discontinue if seizures occur. Concurrent drug therapy issues:
Drug-drug interactions
Potentially significant interactions may exist, requiring dose or frequency adjustment, additional monitoring, and/or selection of alternative therapy. Consult drug interactions database for more detailed information. Dosage form specific issues:
Benzyl alcohol and derivatives
Some dosage forms may contain sodium benzoate/benzoic acid; benzoic acid (benzoate) is a metabolite of benzyl alcohol; large amounts of benzyl alcohol (≥99 mg/kg/day) have been associated with a potentially fatal toxicity (“gasping syndrome”) in neonates; the “gasping syndrome” consists of metabolic acidosis, respiratory distress, gasping respirations, CNS dysfunction (including convulsions, intracranial hemorrhage), hypotension, and cardiovascular collapse (AAP ["Inactive" 1997]; CDC 1982); some data suggests that benzoate displaces bilirubin from protein binding sites (Ahlfors 2001); avoid or use dosage forms containing benzyl alcohol derivative with caution in neonates. See manufacturer’s labeling.
Phenylalanine
Some products may contain phenylalanine.
Suspension/tablet bioequivalence
Tablets and oral suspension are not bioequivalent; do not substitute on a mg-per-mg basis.
Tablets
Should not be crushed or chewed due to a strong, persistent bitter taste. Patients unable to swallow whole tablets should be prescribed the oral suspension.
Pregnancy & Lactation
Pregnancy
Adverse events were not observed in animal reproduction studies. Cefuroxime crosses the placenta and reaches the cord serum and amniotic fluid. Placental transfer is decreased in the presence of oligohydramnios. Several studies have failed to identify an increased teratogenic risk to the fetus following maternal cefuroxime use. During pregnancy, mean plasma concentrations of cefuroxime are 50% lower, the AUC is 25% lower, and the plasma half-life is shorter than nonpregnant values. At term, plasma half-life is similar to nonpregnant values and peak maternal concentrations after IM administration are slightly decreased. Pregnancy does not alter the volume of distribution. Cefuroxime is one of the antibiotics recommended for prophylactic use prior to cesarean delivery.
Lactation
Cefuroxime is excreted in breast milk. Manufacturer recommendations vary; caution is recommended if cefuroxime IV is given to a nursing woman and it is recommended to consider discontinuing nursing temporarily during treatment following oral cefuroxime. Nondose-related effects could include modification of bowel flora.
Monitoring
| Efficacy | Culture and susceptibility testing; clinical resolution (temperature, WBC, CRP, procalcitonin) |
|---|---|
| Toxicity | Renal function (dose adjustment in renal impairment); hepatic function for hepatically cleared agents; signs of C. difficile infection (diarrhoea) |
| Clinical pearl | Culture results guide de-escalation to narrower-spectrum therapy. Review antibiotic appropriateness at 48–72 h (antimicrobial stewardship). |
| Counseling | Complete the full course. Report persistent diarrhoea, rash, or lack of improvement after 48–72 h. |
Chemistry & Properties
| Formula | C16H16N4O8S |
|---|---|
| Molecular weight | 424.39 g/mol |
| IUPAC name | (6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| CAS | 55268-75-2 |
| PubChem CID | 5479529 |
| InChIKey | JFPVXVDWJQMJEE-IZRZKJBUSA-N |
| logP | -0.54 (XLogP -0.2) |
| Polar surface area | 173.76 Ų |
| H-bond acceptors / donors | 9 / 3 |
| Drug-likeness (QED) | 0.30 |
| Lipinski violations | 0 |
SMILES
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(COC(N)=O)CS[C@H]12)c1ccco1Biology & Pharmacokinetics
Pharmacokinetics
| BBB penetrant | Yes |
|---|
Enzyme interactions
| Enzyme | Role | Detail |
|---|---|---|
| CYP2C8 | Inhibitor | — |
Transporters
BCRP (Inhibitor)BSEP (Inhibitor)BSEP (Inhibitor)MRP1 (Inhibitor)MRP2 (Inhibitor)MRP3 (Inhibitor)MRP4 (Inhibitor)OAT3 (Inhibitor)OATP1B1 (Inhibitor)OATP1B1 (Inhibitor)OATP1B3 (Inhibitor)OATP1B3 (Inhibitor)P-gp (Inhibitor)PEPT1 (Inhibitor)PEPT2 (Inhibitor)P-gp (Substrate)PEPT1 (Substrate)
Drug–drug interactions (33, DDInter)
| Interacting drug | Severity | Management |
|---|---|---|
| Aluminum hydroxide | moderate | |
| Amikacin | moderate | |
| Amikacin (liposome) | moderate | |
| Balsalazide | moderate | |
| Calcium carbonate | moderate | |
| Chloramphenicol | moderate | |
| Cimetidine | moderate | |
| Dexlansoprazole | moderate | |
| Dicoumarol | moderate | |
| Disulfiram | moderate | |
| Esomeprazole | moderate | |
| Ethinylestradiol | moderate | |
| Famotidine | moderate | |
| Gentamicin | moderate | |
| Kanamycin | moderate | |
| Lansoprazole | moderate | |
| Magaldrate | moderate | |
| Magnesium carbonate | moderate | |
| Magnesium hydroxide | moderate | |
| Magnesium oxide | moderate | |
| Mycophenolic acid | moderate | |
| Neomycin | moderate | |
| Nizatidine | moderate | |
| Omeprazole | moderate | |
| Pantoprazole | moderate | |
| Pemetrexed | moderate | |
| Rabeprazole | moderate | |
| Ranitidine | moderate | |
| Ranitidine (bismuth citrate) | moderate | |
| Sodium bicarbonate | moderate | |
| Sodium citrate | moderate | |
| Streptomycin | moderate | |
| Warfarin | moderate |
Registered Products (64)
| Brand | Form / strength | Pack | Agent | Citizen (JOD) |
|---|---|---|---|---|
| ZILISTEN VIAL | Vial 750 mg | 1 vial pack varies | Al Hilal Drug Store | 1.150 |
| Cefuzime | Powder for Injection 750 mg | 1 vial | Professional Drug Store | 1.210 |
| Vaxcel Cefuroxime - | Vial 750 mg | 1 vial | AL Rahma Drug Store | 1.210 |
| Zinoxime IV/IM | Vial 750 mg | One Vial | Sukhtian Group | 1.210 |
| Cefutil + Water for Injection | Injection 750 mg/ml | 1 vial | pharma international | 1.640 |
| Maxil 750 Injection | Powder for Injection (as Sodium)750 mg | 1 vial pack varies | Hikma Pharmaceuticals Co.Ltd/Jordan | 1.640 |
| cefutil | Vial 750 mg/ml | 1 vial | Pharma International Company/ Jordan | 1.640 |
| Zinacef Inj. | Powder for Injection 750 mg | 1 vial pack varies | Suleiman Tannous & Sons Co. Ltd | 1.730 |
| ZILISTEN VIAL | Vial 1.5 g | 1 vial pack varies | Al Hilal Drug Store | 2.040 |
| Zinoxime IV Vial | Vial 1.5 g | One Vial | Sukhtian Group | 2.230 |
| Xorim | Vial 1500 mg | 1 vial | Nabulsi Drug Store | 2.370 |
| Xorim | Vial 250 mg | 5 vial | Nabulsi Drug Store | 2.490 |
| Medo-Axetine | Tablet 250 mg | 10 tab | Khoury Drug Store | 2.510 |
| Cefovex | Tablet 250 mg | 10 tab | Noor Drug Store | 2.630 |
| Maxil 1500 mg Sterile Powder for Injection (I.V) | Powder for Injection 1500 mg | 1 vial pack varies | Hikma Pharmaceuticals Co.Ltd/Jordan | 3.020 |
| Zinacef Inj | Powder for Injection 1.5 g | 1 vial | Suleiman Tannous & Sons Co. Ltd | 3.180 |
| Zinnat Susp. | Suspension 250 mg/5 ml | 50 ml pack varies | Suleiman Tannous & Sons Co. Ltd | 3.210 |
| Ceftal | Tablet 250 mg | 10 tab pack varies | AL-TAQADDOM PHARMACEUTICAL INDUSTRIES/JORDAN | 3.350 |
| Zinnat Susp. | Suspension 125 mg/5 ml | 50 ml pack varies | Suleiman Tannous & Sons Co. Ltd | 3.400 |
| Cefurex Susp | Suspension 125 mg/5 ml | 50 ml | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 3.410 |
| Cefurex Suspension | Suspension 250 mg/5 ml | 50 ml | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 3.410 |
| Cefurex F.C Tablets | Film-Coated Tablet 125 mg | 10 tab | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 3.430 |
| Cefutil tab | Tablet 125 mg | 10 tab | Pharma International Company/ Jordan | 3.500 |
| Xorimax | Suspension 125 mg/5 ml | 70 ml | Nabulsi Drug Store | 3.530 |
| Cefurex Tablets | Tablet 250 mg | 10 tab pack varies | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 3.560 |
| Cefutil tab | Tablet (axetil) 250 mg | 10 tab | Pharma International Company/ Jordan | 3.560 |
| Daroxime 250 TABLETS | Tablet 250 mg | 10 tab pack varies | Dar Al Dawa Development and Investment Co Ltd/Jordan | 3.560 |
| Oraxim Tablets | Tablet 250 mg | 10 tab | UNITED PHARM.MFG.CO.LTD(UPM)/JORDAN | 3.560 |
| U-Cef tablet | Tablet (Axetil) 250 mg | 10 tab | The Arab Pharmaceutical Manufactruing Co. | 3.560 |
| Zinnat Tablets | Tablet 250 mg | 10 tab | Suleiman Tannous & Sons Co. Ltd | 3.650 |
| Zinacef Inj. | Powder for Injection 250 mg | 5 vial | Suleiman Tannous & Sons Co. Ltd | 3.770 |
| Medo-Axetine | Tablet 500 mg | 10 tab | Khoury Drug Store | 3.920 |
| U-cef suspension | Suspension 125 mg/5 ml | 50 ml | Advanced Pharmaceutical Industry | 4.000 |
| Cefovex | Tablet 500 mg | 10 tab | Noor Drug Store | 4.100 |
| Zinnat Tablets | Tablet 125 mg | 10 tab | Suleiman Tannous & Sons Co. Ltd | 4.440 |
| Daroxime 250 TABLETS | Tablet 250 mg | 14 tab pack varies | Dar Al Dawa Development and Investment Co Ltd/Jordan | 4.980 |
| U-Cef Tablet | Tablet ( Axetil)250 mg | 14 tab | The Arab Pharmaceutical Manufactruing Co. | 4.980 |
| Ceftal | Tablet 500 mg | 10 tab pack varies | AL-TAQADDOM PHARMACEUTICAL INDUSTRIES/JORDAN | 5.270 |
| Cefurex Tablets | Tablet 500 mg | 10 tab pack varies | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 5.270 |
| Cefutil tab | Tablet 500 mg | 10 tab pack varies | Pharma International Company/ Jordan | 5.270 |
| Daroxime 500 TABLETS | Tablet 500 mg | 10 tab pack varies | Dar Al Dawa Development and Investment Co Ltd/Jordan | 5.270 |
| Oraxim Tablets | Tablet 500 mg | 10 tab | UNITED PHARM.MFG.CO.LTD(UPM)/JORDAN | 5.270 |
| U-Cef tablet | Tablet (Axetil) 500 mg | 10 tab | The Arab Pharmaceutical Manufactruing Co. | 5.270 |
| Xorim | Vial 750 mg | 5 vial | Nabulsi Drug Store | 5.360 |
| Zinoximor Tabs | Tablet 500 mg | 14 tab | Sukhtian Group | 5.740 |
| Zinnat Tablet | Tablet 500 mg | 10 tab | Suleiman Tannous & Sons Co. Ltd | 5.860 |
| Zinnat Susp. | Suspension 250 mg/5 ml | 100 ml pack varies | Suleiman Tannous & Sons Co. Ltd | 6.120 |
| Zinnat Susp. | Suspension 125 mg/5 ml | 100 ml pack varies | Suleiman Tannous & Sons Co. Ltd | 6.460 |
| Cefutil tab | Tablet 500 mg | 14 tab pack varies | Pharma International Company/ Jordan | 7.370 |
| Daroxime 500 TABLETS | Tablet 500 mg | 14 tab pack varies | Dar Al Dawa Development and Investment Co Ltd/Jordan | 7.380 |
| U-Cef Tablet | Tablet (Axetil)500 mg | 14 tab | The Arab Pharmaceutical Manufactruing Co. | 7.380 |
| Zinacef Inj. | Powder for Injection 750 mg | 5 vial pack varies | Suleiman Tannous & Sons Co. Ltd | 8.010 |
| ZILISTEN VIAL | Vial 750 mg | 10 vial pack varies | Al Hilal Drug Store | 10.350 |
| Maxil 750 Injection | Powder for Injection (as Sodium)750 mg | 10 vial pack varies | Hikma Pharmaceuticals Co.Ltd/Jordan | 14.760 |
| cefutil | Vial 750 mg | 10 vial | Pharma International Company/ Jordan | 14.760 |
| ZILISTEN VIAL | Vial 1.5 g | 10 vial pack varies | Al Hilal Drug Store | 18.370 |
| Maxil 1500 mg Sterile Powder for Injection (I.V) | Powder for Injection 1500 mg | 10 vial pack varies | Hikma Pharmaceuticals Co.Ltd/Jordan | 27.180 |
| ZILISTEN VIAL | Vial 750 mg | 50 vial pack varies | Al Hilal Drug Store | 48.850 |
| ZILISTEN VIAL | Vial 1.5 g | 50 vial pack varies | Al Hilal Drug Store | 86.800 |
| Cefurex Tablets | Tablet 500 mg | 250 tab pack varies | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 111.920 |
| Cefurex Tablets | Tablet 250 mg | 500 tab pack varies | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 151.300 |
| Cefutil tab | Tablet 250 mg | 500 tab | Pharma International Company/ Jordan | 151.300 |
| Ceftal | Tablet 250 mg | 1000 tab pack varies | AL-TAQADDOM PHARMACEUTICAL INDUSTRIES/JORDAN | 284.750 |
| Ceftal | Tablet 500 mg | 1000 tab pack varies | AL-TAQADDOM PHARMACEUTICAL INDUSTRIES/JORDAN | 447.950 |