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Cefuroxime

Catalog No. DB01112 Name DrugBank
CAS Number 55268-75-2 Website http://www.ualberta.ca/
M. F. C16H16N4O8S Telephone (780) 492-3111
M. W. 424.38524 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 983

SYNONYMS

IUPAC name
(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2E)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
IUPAC Traditional name
cefuroxime
Brand Name
Sharox
Cedax
Cephuroxime
Kefzol
Cefotan
Ceftin
Cefuril
Cepazine
Elobact
Mandol
Maxipime
Velosef
Zinacef
Zinat
Zinnat
Ancef
Biofuroksym
Cefizox
Cefobid
Cefurax
Cefzil
Duricef
Kefurox
Kerurox
Mefoxin
Monocid
Oraxim
Rocephin
Synonyms
Cefuroximum [INN-Latin]
Cefuroxime [USAN:BAN:INN]
Cefuroximo [INN-Spanish]
Cefuroxim

DATABASE IDS

CAS Number 55268-75-2

PROPERTIES

Hydrophobicity(logP) -0.8
Solubility Freely soluble as sodium salt (145 mg/L)

DETAILS

Description (English)
Item Information
Drug Groups approved
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]
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.
Pharmacology 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
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
Biotransformation The axetil moiety is metabolized to acetaldehyde and acetic acid.
Absorption Absorbed from the gastrointestinal tract. Absorption is greater when taken after food (absolute bioavailability increases from 37% to 52%).
Half Life Approximately 80 minutes following intramuscular or intravenous injection.
Protein Binding 50% to serum protein
References
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
Wikipedia
RxList
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REFERENCES

  • 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