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药品详细

Cefuroxime(头孢呋辛)

化学结构式图
中文名
头孢呋辛
英文名
Cefuroxime
分子式
C16H16N4O8S
化学名
(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
分子量
Average: 424.385
Monoisotopic: 424.068884198
CAS号
55268-75-2
ATC分类
J01D Other Beta- lactam Antibacterials
药物类型
small molecule
阶段
approved
商品名
Ancef;Biofuroksym;Cedax;Cefizox;Cefobid;Cefotan;Ceftin;Cefurax;Cefuril;Cefzil;Cepazine;Cephuroxime;Duricef;Elobact;Kefurox;Kefzol;Kerurox;Mandol;Maxipime;Mefoxin;Monocid;Oraxim;Rocephin;Sharox;Velosef;Zinacef;Zinat;Zinnat;
同义名
Cefuroxim;Cefuroxime [USAN:BAN:INN];Cefuroximo [INN-Spanish];Cefuroximum [INN-Latin];
基本介绍

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]

生产厂家
  • Acs dobfar spa
  • Alkem laboratories ltd
  • Apotex inc etobicoke site
  • App pharmaceuticals llc
  • Aurobindo pharma ltd inc
  • B braun medical inc
  • Eli lilly and co
  • Glaxosmithkline
  • Hikma farmaceutica portugal lda
  • Hoffmann la roche inc
  • Lupin ltd
  • Marsam pharmaceuticals llc
  • Orchid healthcare
  • Ranbaxy laboratories ltd
  • Samson medical technologies llc
  • Sandoz inc
  • Steri pharma llc
  • Teva pharmaceuticals usa inc
  • Warner chilcott inc
  • Wockhardt ltd
封装厂家
参考
Synthesis Reference Not Available
General Reference
  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
剂型
规格
化合物类型
Type small molecule
Classes Not Available
Substructures Not Available
适应症
antibacterials 抗细菌;
药理
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.
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.
Absorption Absorbed from the gastrointestinal tract. Absorption is greater when taken after food (absolute bioavailability increases from 37% to 52%).
Volume of distribution Not Available
Protein binding 50% to serum protein
Metabolism
The axetil moiety is metabolized to acetaldehyde and acetic acid.

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Cefuroxime
    		Acetic acid Details
    Cefuroxime
      		acetaldehyde Details
      Route of elimination Not Available
      Half life Approximately 80 minutes following intramuscular or intravenous injection.
      Clearance Not 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
      Pathways Not Available
      理化性质
      Properties
      State solid
      Experimental Properties
      Property Value Source
      melting point 218-225 °C Not Available
      water solubility Freely soluble as sodium salt (145 mg/L) Not Available
      logP -0.16 SANGSTER (1993)
      Predicted Properties
      Property Value Source
      water solubility 2.84e-01 g/l ALOGPS
      logP -0.24 ALOGPS
      logP -0.9 ChemAxon
      logS -3.2 ALOGPS
      pKa (strongest acidic) 3.15 ChemAxon
      pKa (strongest basic) -1.1 ChemAxon
      physiological charge -1 ChemAxon
      hydrogen acceptor count 7 ChemAxon
      hydrogen donor count 3 ChemAxon
      polar surface area 173.76 ChemAxon
      rotatable bond count 8 ChemAxon
      refractivity 97.17 ChemAxon
      polarizability 38.75 ChemAxon
      药物相互作用
      Drug Interaction
      Amikacin Increased risk of nephrotoxicity
      Gentamicin Increased risk of nephrotoxicity
      Netilmicin Increased risk of nephrotoxicity
      Probenecid Probenecid may increase the serum level of cefuroxime.
      Tobramycin Increased risk of nephrotoxicity
      食物相互作用
      • Take with food to increase absorption.

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