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药品详细

Piperacillin(哌拉西林)

化学结构式图
中文名
哌拉西林
英文名
Piperacillin
分子式
C23H27N5O7S
化学名
(2S,5R,6R)-6-[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
分子量
Average: 517.555
Monoisotopic: 517.163118933
CAS号
66258-76-2
ATC分类
J01C Beta-lactam Antibacterials, Penicillins
药物类型
small molecule
阶段
approved
商品名
Pipracil;
同义名
Piperacillin Anhydrous;
基本介绍

Semisynthetic, broad-spectrum, ampicillin derived ureidopenicillin antibiotic proposed for pseudomonas infections. It is also used in combination with other antibiotics. [PubChem]

生产厂家
  • Istituto biochimico italiano giovanni lorenzini
  • Wyeth pharmaceuticals inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Lau WK, Mercer D, Itani KM, Nicolau DP, Kuti JL, Mansfield D, Dana A: Randomized, open-label, comparative study of piperacillin-tazobactam administered by continuous infusion versus intermittent infusion for treatment of hospitalized patients with complicated intra-abdominal infection. Antimicrob Agents Chemother. 2006 Nov;50(11):3556-61. Epub 2006 Aug 28. 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 polymicrobial infections.
Pharmacodynamics Piperacillin 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. Piperacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Piperacillin results from the inhibition of cell wall synthesis and is mediated through Piperacillin binding to penicillin binding proteins (PBPs). Piperacillin 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, Piperacillin 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 Piperacillin interferes with an autolysin inhibitor.
Absorption Not absorbed following oral administration.
Volume of distribution
  • 101 mL/kg [intravenous administration of 50 mg/kg (5-minute infusion) in neonates]
Protein binding Not Available
Metabolism
Largely not metabolized.
Route of elimination As with other penicillins, PIPRACIL is eliminated primarily by glomerular filtration and tubular secretion; it is excreted rapidly as unchanged drug in high concentrations in the urine. Because PIPRACIL is excreted by the biliary route as well as by the renal route, it can be used safely in appropriate dosage in patients with severely restricted kidney function.
Half life 36-72 minutes
Clearance
  • 32 - 41 mL/min/1.73 m2
  • 124 - 160 mL/min/1.73 m2 [older pediatric patients]
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
logP 0.3 Not Available
Predicted Properties
Property Value Source
water solubility 1.19e-01 g/l ALOGPS
logP 0.67 ALOGPS
logP -0.26 ChemAxon
logS -3.6 ALOGPS
pKa (strongest acidic) 3.49 ChemAxon
pKa (strongest basic) -4.3 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 7 ChemAxon
hydrogen donor count 3 ChemAxon
polar surface area 156.43 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 126.3 ChemAxon
polarizability 51.77 ChemAxon
药物相互作用
Drug Interaction
Atracurium The agent increases the effect of the muscle relaxant
Demeclocycline Possible antagonism of action
Doxacurium chloride The agent increases the effect of the muscle relaxant
Doxycycline Possible antagonism of action
Ethinyl Estradiol This anti-infectious agent could decrease the effect of the oral contraceptive
Mestranol This anti-infectious agent could decrease the effect of the oral contraceptive
Methacycline Possible antagonism of action
Methotrexate The penicillin increases the effect and toxicity of methotrexate
Metocurine The agent increases the effect of the muscle relaxant
Minocycline Possible antagonism of action
Mivacurium The agent increases the effect of the muscle relaxant
Oxytetracycline Possible antagonism of action
Pancuronium The agent increases the effect of the muscle relaxant
Pipecuronium The agent increases the effect of the muscle relaxant
Rocuronium The agent increases the effect of the muscle relaxant
Rolitetracycline Possible antagonism of action
Succinylcholine The agent increases the effect of the muscle relaxant
Tetracycline Possible antagonism of action
Tubocurarine The agent increases the effect of the muscle relaxant
Vecuronium The agent increases the effect of the muscle relaxant
食物相互作用
Not Available

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