β-lactam

Absorption, Distribution and Excretion
Piperacillin is not absorbed after oral administration. Like other penicillin antibiotics, piperacillin is primarily eliminated via glomerular filtration and tubular secretion; it is rapidly excreted unchanged in high concentrations in the urine. Because piperacillin is excreted via both bile and kidneys, it is safe for use in patients with severely impaired renal function at appropriate doses. 101 mL/kg [50 mg/kg intravenously (5 minutes infusion) for neonates] 32 - 41 mL/min/1.73 m2 124 - 160 mL/min/1.73 m2 [older children] Metabolism/Metabolites Primarily not metabolized. Biological Half-Life 36-72 minutes

Hepatotoxicity
Up to 12% of patients receiving intravenous piperacillin may experience transient, mild to moderate elevations in serum transaminases, but these elevations are clinically insignificant and not more common than with other parenteral antibiotics of the same class. Liver injury was more frequently reported with meropenem (a now discontinued broad-spectrum ureaplasm antibiotic associated with piperacillin). Rare cases of specific liver injury have been reported in patients treated with piperacillin. This liver injury is typically cholestatic and occurs within 1 to 6 weeks of starting treatment. The injury can be severe but usually resolves spontaneously upon discontinuation of piperacillin. Its hepatotoxicity characteristics are similar to those of other penicillins. Cholestatic hepatitis caused by piperacillin and other penicillins can be prolonged and lead to persistent cholestasis (disappearance of bile duct syndrome) or persistently elevated serum alkaline phosphatase, suggesting partial bile duct loss. Most cases of liver injury associated with piperacillin are related to the combined use of piperacillin and the β-lactamase inhibitor tazobactam (Zosyn and its generic versions), which is more common than piperacillin alone.
Probability Score: B (Known rare clinical manifestation of liver injury etiology).

---

Use during pregnancy and lactation
◉ Overview of use during lactation
Limited information suggests that low concentrations of piperacillin in breast milk are not expected to have adverse effects on breastfed infants. There have been reports of penicillin-type drugs occasionally disrupting the infant's gut microbiota, leading to diarrhea or thrush, but these effects have not been fully assessed. Piperacillin can be used in breastfeeding women.
◉ Effects on breastfed infants
No relevant published information found as of the revision date.
◉ Effects on lactation and breast milk
No relevant published information found as of the revision date.

[1]. B. Holmes, et al. A Review of its Antibacterial Activity, Pharmacokinetic Properties and Therapeutic Use.

Piperacillin is a penicillin with a 2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carbamoyl]-2-phenylacetamyl group at the 6-position of its penicillin ring. It is an antibacterial drug. It is both a penicillin and a penicillin allergen. It is the conjugate acid of piperacillin (1-). Piperacillin is a semi-synthetic broad-spectrum urealyticum penicillin antibiotic derived from ampicillin, used to treat Pseudomonas aeruginosa infections. It is also often used in combination with other antibiotics. Anhydrous piperacillin is a penicillin antibacterial drug. Piperacillin is a broad-spectrum urealyticum penicillin used to treat moderate to severe infections caused by susceptible bacteria. Piperacillin has been associated with specific liver injury, but this is very rare, with only case reports. There are reports of liver injury caused by piperacillin in the Chinese honeybee (Apis cerana), and relevant data are available. Anhydrous piperacillin is the anhydrous form of piperacillin, a broad-spectrum semi-synthetic ureapeptide antibiotic. Piperacillin binds to penicillin-binding protein (PBP) located on the inner membrane of bacterial cell walls, thereby interfering with the cross-linking of peptidoglycan chains. This cross-linking is crucial for maintaining the strength and rigidity of the bacterial cell wall. Therefore, cell wall synthesis is disrupted, leading to reduced cell wall strength and ultimately cell lysis. Piperacillin is a broad-spectrum semi-synthetic ampicillin-derived ureapeptide antibiotic. Piperacillin binds to penicillin-binding protein (PBP), an enzyme that catalyzes peptidoglycan synthesis, a key component of the bacterial cell wall. This blocking effect interrupts cell wall synthesis, thereby inhibiting bacterial growth and causing cell lysis. Piperacillin is a semi-synthetic broad-spectrum antibiotic, belonging to the ampicillin-derived ureapeptide class, used to treat Pseudomonas infections. It is also often used in combination with other antibiotics. See also: Piperacillin Sodium (note moved here).

---

Indications
For the treatment of a variety of microbial infections.

---

Mechanism of Action
Piperacillin inhibits the third (and final) stage of bacterial cell wall synthesis by binding to a specific penicillin-binding protein (PBP) located within the bacterial cell wall. Subsequently, bacterial cell wall autolysins (such as autolysins) mediate cell lysis; piperacillin may interfere with the action of autolysin inhibitors.

C23H27N5O7S

517.55

517.163

61477-96-1

Piperacillin sodium;59703-84-3;Piperacillin-d5

43672

White to off-white solid powder

1.5±0.1 g/cm3

139-140ºC

1.678

1.88

3

8

6

36

982

4

CCN1CCN(C(=O)C1=O)C(=O)N[C@H](C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O

IVBHGBMCVLDMKU-GXNBUGAJSA-N

InChI=1S/C23H27N5O7S/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34)/t13-,14-,15+,20-/m1/s1

(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-carboxylic acid

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : 100 mg/mL (193.22 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (4.83 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

---

Solubility in Formulation 2: ≥ 2.5 mg/mL (4.83 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

---

View More

Solubility in Formulation 3: ≥ 2.5 mg/mL (4.83 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

---

 (Please use freshly prepared in vivo formulations for optimal results.)