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Piperacillin

Piperacillin Structure
Piperacillin
  • CAS No.61477-96-1
  • Chemical Name:Piperacillin
  • CBNumber:CB0181853
  • Molecular Formula:C23H27N5O7S
  • Formula Weight:517.55
  • MOL File:61477-96-1.mol
Piperacillin Property
  • Melting point 183-185?C (dec.)
  • Density 1.51±0.1 g/cm3(Predicted)
  • vapor pressure 0Pa at 20℃
  • RTECS XH8952200
  • storage temp. Sealed in dry,2-8°C
  • solubility Freely soluble in methanol. Only sparingly soluble in aqueous solution at 0.119 mg/mL
  • pka 2.44±0.50(Predicted)
  • form Solid
  • color White to Off-White
  • Water Solubility 256.8mg/L at 20℃
  • Stability Hygroscopic
  • LogP -1.55 at 20℃
  • CAS DataBase Reference 61477-96-1(CAS DataBase Reference)
  • FDA UNII 9I628532GX
  • NCI Drug Dictionary piperacillin sodium
  • ATC code J01CA12
Safety
  • Hazard Codes  :Xi
  • Risk Statements  :42/43
  • Safety Statements  :36/37
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H317-H334
  • Precautionary statements P261-P280g-P284-P304+P340-P342+P311a-P501a

Piperacillin Chemical Properties,Usage,Production

  • Chemical Properties 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.
  • Originator Pentcillin, Toyama ,Japan ,1980
  • Uses 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.
  • Definition 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-).
  • brand name Pipracil (Wyeth).
  • Therapeutic Function Antibiotic
  • 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.
  • Acquired resistance 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
    Cmax 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.
  • Side effects 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.
  • Synthesis Piperacillin, (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2R)-2-[(4-ethyl-2,3-dioxo- 1-piperazinyl)formamido]-2-phenylacetamido]-4-thia-1-azabicyclo[3.2.0]-heptan-2-carboxylic acid (32.1.1.30), is also synthesized by acylating ampicillin (32.1.1.16), but with 1-chlorocarbonyl-4-ethylpiperazin-2,3-dione (32.1.1.29). The necessary 1-chlorocarbonyl-4- ethylpiperazin-2,3-dione (32.1.1.29) is synthesized by reacting N-ethylethylenediamine with diethyloxalate, forming 4-ethylpiperazin-2,3-dione (32.1.1.28), and then acylating this with phosgene after initial silylation of the product at the nitrogen atom with trimethylchlorosilane.

    Synthesis_61477-96-1

  • 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.
Piperacillin Preparation Products And Raw materials
Raw materials
Preparation Products
Piperacillin Suppliers
Global(278)Suppliers
  • Supplier：
    Hangzhou ICH Biofarm Co., Ltd
  • Tel：+86-0571-28186870;<br/>+undefined8613073685410
  • Email：sales@ichemie.com
  • Country：China
  • ProdList：1015
  • Advantage：58
  • Supplier：
    Henan Tianfu Chemical Co.,Ltd.
  • Tel：+86-0371-55170693<br/>+86-19937530512
  • Email：info@tianfuchem.com
  • Country：China
  • ProdList：21628
  • Advantage：55
  • Supplier：
    career henan chemical co
  • Tel：+86-0371-86658258<br/>+8613203830695
  • Email：sales@coreychem.com
  • Country：China
  • ProdList：29859
  • Advantage：58

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