Cefuroxime is a 3-(carbamoyloxymethyl)cephalosporin compound having a 7-(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido side chain. It has a role as a drug allergen. It is a member of furans, a 3-(carbamoyloxymethyl)cephalosporin and an oxime O-ether.
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification · 4 items
Danger
H317 (31%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P319, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Cefuroxime: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[2-furanyl(methoxyimino)acetyl]amino]-8-oxo-, [6R-[6.alpha.,7.beta.(Z)]]-: Human health tier I assessment
Hazard Classes and CategoriesSkin Sens. 1 (31%)
Toxicology
Adverse Effects · 1 item
Similar to penicillins and most β-lactam antibiotics, cefuroxime is generally well-tolerated. However, cefuroxime may potentially lead to adverse drug reactions in some patients, as seen with other medications. The most commonly reported adverse drug reactions are gastrointestinal disturbances, including nausea, vomiting, and diarrhea. Additional gastrointestinal adverse drug reactions include anorexia, abdominal pain, dizziness, and headache. In cases of parenteral administration, local reactions at the injection site, including thrombophlebitis, can occur.
Chemistry & industry
Pharmacology
ATC Code · 6 items
J - Antiinfectives for systemic use
S - Sensory organs
QJ - Antiinfectives for systemic use
QS - Sensory organs
QJ - Antiinfectives for systemic use
J01DC02
Protein Binding50% to serum protein
Pharmacodynamics · 1 item
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: <i>Staphylococcus aureus</i>, <i>Streptococcus pneumoniae</i>, <i>Streptococcus pyogenes</i>. Aerobic Gram-negative Microorganisms: <i>Escherichia coli</i>, <i>Haemophilus influenzae</i> (including beta-lactamase-producing strains), <i>Haemophilus parainfluenzae</i>, <i>Klebsiella pneumoniae</i>, <i>Moraxella catarrhalis</i> (including beta-lactamase-producing strains), <i>Neisseria gonorrhoeae</i> (including beta-lactamase-producing strains). Spirochetes: <i>Borrelia burgdorferi</i>. Cefuroxime axetil is the prodrug
Mechanism of Action · 1 item
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.
Biological Half-LifeApproximately 80 minutes following intramuscular or intravenous injection.
Metabolism/MetabolitesThe axetil moiety is metabolized to acetaldehyde and acetic acid.
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
cefuroxime
DILI Positive
Oral
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
EPA Human Health Benchmarks for Pharmaceuticals · 6 items
Cefuroxime
11.7
49.3
For pharyngitis/tonsillitis (mild to moderate), dosage is 250 mg every 12 hours.
Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 500 mg/day, Lowest Therapeutic Dose (LTD): 6.3 mg/kg-day, and Screening Dose: 0.002 mg/kg-day.
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Chemical Structure [CS] - Cephalosporins
Cefuroxime is a Cephalosporin Antibacterial.
CEFUROXIME
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and ExcretionAbsorbed from the gastrointestinal tract. Absorption is greater when taken after food (absolute bioavailability increases from 37% to 52%).
Cellular LocationsCytoplasm
Uses & manufacturing
UsesUse (kg) in Switzerland (2009): >100
Use ClassificationVeterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes
Applications · 3 items
DescriptionCefuroxime axetil is the acetoxyethyl ester and oral prodrug of cefuroxime, a second-generation cephalosporin. It has a broad spectrum of action and is resistant to most P-lactamases. Cefuroxime axed is indicated for serious bacterial infections, especially where no identification of organism(s) has been made.
UsesCefuroxime is a second-generation cephalosporin antibiotic.