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Piperacillin Sodium (Synonyms: CL 227,193, T-1220)

Katalog-Nr.GC16755

Piperacillin-Natrium ist ein Breitband-β-Lactam-Antibiotikum.

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Piperacillin Sodium Chemische Struktur

Cas No.: 59703-84-3

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Sample solution is provided at 25 µL, 10mM.

Description of Piperacillin Sodium

Piperacillin Sodium is a broad-spectrum semisynthetic penicillin antibiotic used to treat a variety of infections caused by susceptible bacteria[1]. Piperacillin Sodium exerts its antibacterial action by inhibiting bacterial cell wall synthesis and is effective against a wide range of Gram-positive and Gram-negative bacteria, including some strains that produce β-lactamases[2]. Piperacillin Sodium is often used in combination with other drugs, such as tazobactam, to enhance antibacterial efficacy and broaden the spectrum of activity, better addressing resistant strains[3]. Piperacillin Sodium is commonly used to treat respiratory, urinary, intra-abdominal infections, and skin and soft tissue infections[4].

In vitro, Piperacillin Sodium (2μg/mL) inhibits Staphylococcus aureus with an efficacy rate of up to 93%, and Piperacillin Sodium (4μg/mL) inhibits Escherichia coli with an efficacy rate of up to 90%[5]. Piperacillin Sodium (2–8μg/mL) pre-treatment of various bacteria (Klebsiella pneumoniae, Streptococcus agalactiae, Proteus vulgaris, Haemophilus influenzae) for 18 hours significantly inhibits bacterial growth and reduces resistance[6].

In vivo, Piperacillin Sodium (2.5–5120mg/kg) in combination with the novel β-lactamase inhibitor IID572 (4–640mg/kg) administered subcutaneously three times daily was used in a neutropenic C57BL/6J mouse thigh infection model. The combination of Piperacillin/IID572 significantly reduced the infection burden caused by β-lactamase-producing Enterobacteriaceae and Staphylococcus aureus[7]. Subcutaneous injection of Piperacillin Sodium (10.7mg) in combination with oral β-lactamase (1 or 6mg/kg) was used in CF-1 mice. Compared with mice treated with Piperacillin Sodium alone, the combination with β-lactamase significantly reduced intestinal colonization by Piperacillin-resistant pathogens (including vancomycin-resistant Enterococcus faecium, Klebsiella pneumoniae, and Candida glabrata) and minimized disruption of the indigenous microbiota[8].

References:
[1] Fortner CL, Finley RS, Schimpff SC. Piperacillin sodium: antibacterial spectrum, pharmacokinetics, clinical efficacy, and adverse reactions. Pharmacotherapy. 1982 Nov-Dec;2(6):287-99.
[2] Holmes B, Richards DM, Brogden RN, et al. Piperacillin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use. Drugs. 1984 Nov;28(5):375-425.
[3] Eliopoulos GM, Moellering RC Jr. Azlocillin, mezlocillin, and piperacillin: new broad-spectrum penicillins. Ann Intern Med. 1982 Nov;97(5):755-60.
[4] Russo J Jr, Russo ME. Comparative review of two new wide-spectrum penicillins: mezlocillin and piperacillin. Clin Pharm. 1982 May-Jun;1(3):207-16.
[5] Frank U, Mutter J, Schmidt-Eisenlohr E, et al. Comparative in vitro activity of piperacillin, piperacillin-sulbactam and piperacillin-tazobactam against nosocomial pathogens isolated from intensive care patients. Clin Microbiol Infect. 2003 Nov;9(11):1128-32.
[6] Verbist L. In vitro activity of piperacillin, a new semisynthetic penicillin with an unusually broad spectrum of activity. Antimicrob Agents Chemother. 1978 Mar;13(3):349-57. doi: 10.1128/AAC.13.3.349.
[7] Growcott EJ, Gamboa L, Roth T, et al. Efficacy of piperacillin in combination with novel β-lactamase inhibitor IID572 against β-lactamase-producing strains of Enterobacteriaceae and Staphylococcus aureus in murine neutropenic thigh infection models. J Antimicrob Chemother. 2020 Jun 1;75(6):1530-1536.
[8] Stiefel U, Pultz NJ, Harmoinen J, et al. Oral administration of beta-lactamase preserves colonization resistance of piperacillin-treated mice. J Infect Dis. 2003 Nov 15;188(10):1605-9.

Protocol of Piperacillin Sodium

Cell experiment [1]:

Cell lines

Klebsiella pneumoniae, Streptococcus agalactiae, Proteus vulgaris, Haemophilus influenzae

Preparation Method

The in vitro activity of Piperacillin Sodium was tested against these bacterial strains using agar dilution and broth microdilution methods. The minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs) were determined.

Reaction Conditions

2–8μg/mL; 24h

Applications

Piperacillin Sodium was effective against Haemophilus influenzae and Streptococcus agalactiae at 2μg/mL. Piperacillin Sodium was more active than ampicillin against Klebsiella pneumoniae at 8μg/mL.

Animal experiment [2]:

Animal models

Neutropenic CD-1 mice

Preparation Method

Mice were rendered neutropenic by intraperitoneal injections of cyclophosphamide (150 and 100mg/kg) on days 4 and 1, respectively. Two hours prior to treatment, bacterial inoculum (105–106CFU) was administered into the left gastrocnemius muscle via intramuscular injection. Subcutaneous treatment with Piperacillin Sodium (2.5–5120mg/kg/day)/IID572 (4–640mg/kg/day) or Piperacillin Sodium (5120mg/kg/day) was initiated every 3 hours for 24 hours.

Dosage form

2.5–5120mg/kg/day; s.c.

Applications

IID572 significantly enhances the in vivo bactericidal effect of Piperacillin Sodium.

References:
[1] Verbist L. In vitro activity of piperacillin, a new semisynthetic penicillin with an unusually broad spectrum of activity. Antimicrob Agents Chemother. 1978 Mar;13(3):349-57. doi: 10.1128/AAC.13.3.349.
[2] Growcott EJ, Gamboa L, Roth T, et al. Efficacy of piperacillin in combination with novel ?-lactamase inhibitor IID572 against ?-lactamase-producing strains of Enterobacteriaceae and Staphylococcus aureus in murine neutropenic thigh infection models. J Antimicrob Chemother. 2020 Jun 1;75(6):1530-1536.

Chemical Properties of Piperacillin Sodium

Cas No. 59703-84-3 SDF
Überlieferungen CL 227,193, T-1220
Chemical Name sodium;(2S,5R,6R)-6-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Canonical SMILES CCN1CCN(C(=O)C1=O)C(=O)NC(C2=CC=CC=C2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)[O-].[Na+]
Formula C23H26N5O7S.Na M.Wt 539.54
Löslichkeit ≥ 18.6mg/mL in DMSO Storage Store at 2-8°C, sealed storage, away from moisture
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Piperacillin Sodium

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 1.8534 mL 9.2672 mL 18.5343 mL
5 mM 370.7 μL 1.8534 mL 3.7069 mL
10 mM 185.3 μL 926.7 μL 1.8534 mL
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