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药品详细

Cefixime(头孢克肟)

化学结构式图
中文名
头孢克肟
英文名
Cefixime
分子式
C16H15N5O7S2
化学名
(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
分子量
Average: 453.45
Monoisotopic: 453.041289239
CAS号
79350-37-1
ATC分类
J01D Other Beta- lactam Antibacterials
药物类型
small molecule
阶段
approved
商品名
Cefixoral;Cefspan;Cephoral;CFIX;Oroken;Suprax;Unixime;
同义名
Cefixim;Cefixima [Spanish];Cefixime Anhydrous;Cefiximum [Latin];
基本介绍

Cefixime, an antibiotic, is a third-generation cephalosporin like ceftriaxone and cefotaxime. Cefixime is highly stable in the presence of beta-lactamase enzymes. As a result, many organisms resistant to penicillins and some cephalosporins due to the presence of beta-lactamases, may be susceptible to cefixime. The antibacterial effect of cefixime results from inhibition of mucopeptide synthesis in the bacterial cell wall.

生产厂家
  • Lederle laboratories div american cyanamid co
  • Lupin ltd
  • Lupin pharmaceuticals inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. McMillan A, Young H: The treatment of pharyngeal gonorrhoea with a single oral dose of cefixime. Int J STD AIDS. 2007 Apr;18(4):253-4. Pubmed
  2. Adam D, Hostalek U, Troster K: 5-day cefixime therapy for bacterial pharyngitis and/or tonsillitis: comparison with 10-day penicillin V therapy. Cefixime Study Group. Infection. 1995;23 Suppl 2:S83-6. 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 use in the treatment of the following infections when caused by susceptible strains of the designated microorganisms: (1) uncomplicated urinary tract infections caused by Escherichia coli and Proteus mirabilis, (2) otitis media caused by Haemophilus influenzae (beta-lactamase positive and negative strains), Moraxella catarrhalis (most of which are beta-lactamase positive), and S. pyogenes, (3) pharyngitis and tonsillitis caused by S. pyogenes, (4) acute bronchitis and acute exacerbations of chronic bronchitis caused by Streptococcus pneumoniae and Haemophilus influenzae (beta-lactamase positive and negative strains), and (5) uncomplicated gonorrhea (cervical/urethral) caused by Neisseria gonorrhoeae (penicillinase- and non-penicillinase-producing strains).
Pharmacodynamics Cefixime, an antibiotic, is a third-generation cephalosporin like ceftriaxone and cefotaxime. Cefixime is highly stable in the presence of beta-lactamase enzymes. As a result, many organisms resistant to penicillins and some cephalosporins due to the presence of beta-lactamases, may be susceptible to cefixime. The antibacterial effect of cefixime results from inhibition of mucopeptide synthesis in the bacterial cell wall.
Mechanism of action Like all beta-lactam antibiotics, cefixime binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of 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 cefixime interferes with an autolysin inhibitor.
Absorption About 40%-50% absorbed orally whether administered with or without food, however, time to maximal absorption is increased approximately 0.8 hours when administered with food.
Volume of distribution Not Available
Protein binding 65% (concentration independent)
Metabolism
Hepatic. Approximately 50% of the absorbed dose is excreted unchanged in the urine in 24 hours.
Route of elimination Not Available
Half life 3-4 hours (may range up to 9 hours). In severe renal impairment (5 to 20 mL/min creatinine clearance), the half-life increased to an average of 11.5 hours.
Clearance Not Available
Toxicity Symptoms of overdose include blood in the urine, diarrhea, nausea, upper abdominal pain, and vomiting.
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 55.11 mg/L Not Available
logP -0.4 Not Available
Predicted Properties
Property Value Source
water solubility 1.04e-01 g/l ALOGPS
logP 0.25 ALOGPS
logP -1.2 ChemAxon
logS -3.6 ALOGPS
pKa (strongest acidic) 3.45 ChemAxon
pKa (strongest basic) 2.92 ChemAxon
physiological charge -2 ChemAxon
hydrogen acceptor count 10 ChemAxon
hydrogen donor count 4 ChemAxon
polar surface area 184.51 ChemAxon
rotatable bond count 8 ChemAxon
refractivity 104.91 ChemAxon
polarizability 41.62 ChemAxon
药物相互作用
Drug Interaction
Probenecid Probenecid may increase the serum level of cefixime.
食物相互作用
  • Preferably on an empty stomach, rate of absorption is decreased but extenet of absorption remains the same: not really problematic.

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