[2S-[2α,5α,6β(S*)]]-6-[[[[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino]phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-carbonsure

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals -> Antibiotics

White to off-white solid; [Bristol-Myers Squibb]

Solid

227.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]

222.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

221.26 Ų [M-H]-

Danger

H317 (93.8%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P233, P260, P261, P271, P272, P273, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 16 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Patients on intravenous piperacillin may have transient and mild-to-moderate serum aminotransferase elevations in up to 12% of patients, but these are of little clinical significance and not more common than with comparative parenteral antibiotics. Hepatic injury was more commonly reported with mezlocillin, a related extended spectrum ureidopenicillin which has been withdrawn from use. Rare instances of idiosyncratic liver injury have been reported in persons receiving piperacillin. The liver injury is typically cholestatic arising within 1 to 6 weeks of starting therapy. The injury can be severe, but is generally self-limited once piperacillin is stopped. The features of the hepatotoxicity resemble those of other penicillins. The cholestatic hepatitis caused by piperacillin and other penicillins can be prolonged and lead to persistent cholestasis (vanishing bile duct syndrome) or persistent elevations in serum alkaline phosphatase suggestive of partial bile duct loss. Most cases of liver injury related to piperacillin are linked to the combination of piperacillin with the beta-lactamase inhibitor tazobactam (Zosyn and generics), which is more commonly used than piperacillin alone.

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

piperacillin

DILI Negative

Intravenous

DOI:10.1016/j.drudis.2019.09.022

J01CR05

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

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 <i>in vitro</i> 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.

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.

9I628532GX

PIPERACILLIN ANHYDROUS

Established Pharmacologic Class [EPC] - Penicillin-class Antibacterial

Chemical Structure [CS] - Penicillins

Piperacillin anhydrous is a Penicillin-class Antibacterial.

Not absorbed following oral administration.

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.

101 mL/kg [intravenous administration of 50 mg/kg (5-minute infusion) in neonates]

32 - 41 mL/min/1.73 m2

A beta-lactam antibiotic; [Bristol-Myers Squibb]

Use (kg) in Switzerland (2009): >1000