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药品详细

Oxacillin(苯唑西林)

化学结构式图
中文名
苯唑西林
英文名
Oxacillin
分子式
C19H19N3O5S
化学名
(2S,5R,6R)-3,3-dimethyl-6-(5-methyl-3-phenyl-1,2-oxazole-4-amido)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
分子量
Average: 401.436
Monoisotopic: 401.104541423
CAS号
66-79-5
ATC分类
J01C Beta-lactam Antibacterials, Penicillins;J01C Beta-lactam Antibacterials, Penicillins;J01C Beta-lactam Antibacterials, Penicillins;J01C Beta-lactam Antibacterials, Penicillins
药物类型
small molecule
阶段
approved
商品名
Bactocill;
同义名
Oxacillin Sodium;
基本介绍

An antibiotic similar to flucloxacillin used in resistant staphylococci infections. [PubChem]

生产厂家
  • Apothecon inc div bristol myers squibb
  • Apothecon sub bristol myers squibb co
  • Baxter healthcare corp
  • Elkins sinn div ah robins co inc
  • Glaxosmithkline
  • Istituto biochimico italiano spa
  • Marsam pharmaceuticals llc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
封装厂家
参考
Synthesis Reference Not Available
General Reference Not Available
剂型
规格
化合物类型
Type small molecule
Classes
  • Phenylpropenes
  • Penicillins
  • Cinnamaldehydes
Substructures
  • Hydroxy Compounds
  • Acetates
  • Amino Ketones
  • Phenylpropenes
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Isoxazoles
  • Carboxylic Acids and Derivatives
  • Beta Lactams
  • Penicillins
  • Thiazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Cinnamaldehydes
  • Carboxamides and Derivatives
  • Oxazoles
  • Lactams
  • Imines
  • Azetidines
  • Thiazolidines
适应症
antibacterials 抗细菌;
药理
Indication Used in the treatment of resistant staphylococci infections.
Pharmacodynamics Oxacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Oxacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Oxacillin results from the inhibition of cell wall synthesis and is mediated through Oxacillin binding to penicillin binding proteins (PBPs). Oxacillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
Mechanism of action By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Oxacillin 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 Oxacillin interferes with an autolysin inhibitor.
Absorption Not Available
Volume of distribution Not Available
Protein binding 94.2 +/- 2.1% (binds to serum protein, mainly albumin)
Metabolism
Not Available
Route of elimination Oxacillin Sodium is rapidly excreted as unchanged drug in the urine by glomerular filtration and active tubular secretion.
Half life 20 to 30 minutes
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 188 °C PhysProp
water solubility 13.9 mg/L Not Available
logP 2.38 HANSCH,C ET AL. (1995)
pKa 2.72 SANGSTER (1994)
Predicted Properties
Property Value Source
water solubility 8.62e-02 g/l ALOGPS
logP 2.05 ALOGPS
logP 1.7 ChemAxon
logS -3.7 ALOGPS
pKa (strongest acidic) 3.75 ChemAxon
pKa (strongest basic) -0.12 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 112.74 ChemAxon
rotatable bond count 4 ChemAxon
refractivity 101.83 ChemAxon
polarizability 39.61 ChemAxon
药物相互作用
Drug Interaction
Demeclocycline Possible antagonism of action
Doxycycline Possible antagonism of action
Ethinyl Estradiol This anti-infectious agent could decrease the effect of the oral contraceptive
Minocycline Possible antagonism of action
Tetracycline Possible antagonism of action
食物相互作用
Not Available

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