Piperacillin

그림문자(GHS)

• 그림문자(GHS)

  

• 신호 어

  Warning

• 유해·위험 문구

  H317：알레르기성 피부 반응을 일으킬 수 있음

  H334：흡입 시 알레르기성 반응, 천식 또는 호흡 곤란 등을 일으킬 수 있음

• 예방조치문구

  P261：분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.

  P284：호흡 보호구를 착용하시오.

  P304+P340：흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.

Piperacillin 화학적 특성, 용도, 생산

• 화학적 성질

  White Crystalline Solid; odorless; slightly hygroscopic. It is easily soluble in methanol, soluble in absolute ethanol or acetone, and very slightly soluble in water. It is a semi-synthetic penicillin antibiotic with broad-spectrum antibacterial effect.

• 용도

  Piperacillin is a semisynthetic penicillin with wide spectrum of antimicrobial activity, particularly pseudomonas strains. It is used to treat moderate-to-severe infections due to susceptible organisms.

• 정의

  ChEBI: Piperacillin is a penicillin in which the substituent at position 6 of the penam ring is a 2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-2-phenylacetamido group. It has a role as an antibacterial drug. It is a penicillin and a penicillin allergen. It is a conjugate acid of a piperacillin(1-).

• Antimicrobial activity

  It displays good activity against non-β-lactamaseproducing strains of N. gonorrhoeae, ampicillin-susceptible H. influenzae and many Enterobacteriaceae. It is the most active of the antipseudomonal penicillins against Ps. aeruginosa and retains its activity in the absence of a β-lactamase inhibitor. Synergy with aminoglycosides has been demonstrated against many strains of Enterobacteriaceae and Ps. aeruginosa.

• 원료

  There is complete cross-resistance with other ureidopenicillins, but ticarcillin-resistant strains of Ps. aeruginosa may be susceptible. Piperacillin-resistant strains of B. fragilis and other Bacteroides spp. are common. Because piperacillin is hydrolyzed by most β-lactamases, many β-lactamaseproducing isolates are resistant unless it is protected by β-lactamase inhibitors.

• Pharmacokinetics

  Oral absorption: Negligible
  C_max 2 g (2–3 min intravenous injection): 305 mg/L after 5 min
  Plasma half-life: 0.9 h
  Volume of distribution: 16–24 L/1.73 m2
  Plasma protein binding: 16%
  In patients with meningitis, mean CSF penetration of 30% has been found. The urine is the principal route of excretion, 50–70% of the dose appearing over 12 h, most in the first 4 h. Most is excreted via the tubules, 75–90% in active form. The half-life is prolonged in renal failure but much less than is the case with carboxypenicillins. There is substantial biliary excretion, levels in the common duct bile after a 1 g intravenous dose commonly reaching 500 mg/L or more. During hemodialysis the plasma half-life remains elevated and only 10–15% of the dose is removed.

• Clinical Use

  Piperacillin (Pipracil) is the most generally useful of the extended-spectrum acylureidopenicillins. It is more active thanmezlocillin against susceptible strains of Gram-negativeaerobic bacilli, such as Serratia marcescens, Proteus,Enterobacter, Citrobacter spp., and P. aeruginosa.Mezlocillin, however, appears to be more active againstProvidencia spp. and K. pneumoniae. Piperacillin is alsoactive against anaerobic bacteria, especially B. fragilis andS. faecalis (enterococcus). β-Lactamase–producing strainsof these organisms are, however, resistant to piperacillin,which is hydrolyzed by S. aureus β-lactamase. The β-lactamase susceptibility of piperacillin is not absolute becauseβ-lactamase–producing, ampicillin-resistant strainsof N. gonorrhoeae and H. influenzae are susceptible topiperacillin.
  Piperacillin is destroyed rapidly by stomach acid; therefore,it is active only by intramuscular or intravenousadministration. The injectable form is provided as the white,crystalline, water-soluble sodium salt. Its pharmacokineticproperties are very similar to those of the other acylureidopenicillins.

• 부작용

  Piperacillin is generally well tolerated, with mild to moderate pain on injection, thrombophlebitis and diarrhea in some patients. It otherwise exhibits side effects common to the group, including hypersensitivity, leukopenia and abnormalities of platelet aggregation without coagulation defect, except on prolonged treatment.

• Mode of action

  Piperacillin binds to penicillin binding proteins (PBP) located on the inner membrane of the bacterial cell wall, thereby interfering with the cross-linking of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. As a result, cell wall synthesis is interrupted leading to a weakened cell wall and eventually cell lysis.

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