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Home > Encyclopedia > Piperacillin

Piperacillin

pharmaceutical raw materials
Piperacillin structure

Piperacillin 

structure
  • CAS No:

    61477-96-1

  • Formula:

    C23H27N5O7S

  • Chemical Name:

    Piperacillin

  • Synonyms:

    4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-,(2S,5R,6R)-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-3,3-dimethyl-7-oxo-,[2S-[2α,5α,6β(S*)]]-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(2R)-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-3,3-dimethyl-7-oxo-,(2S,5R,6R)-;(2S,5R,6R)-6-[[(2R)-2-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;Piperacillin;Pipracil;129043-43-2

  • Categories:

    Active Pharmaceutical Ingredients  >  Antibiotics

Description

Crystalline Solid


Solid


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-).|Semisynthetic, broad-spectrum, ampicillin derived ureidopenicillin antibiotic proposed for pseudomonas infections. It is also used in combination with other antibiotics.|Piperacillin anhydrous is a Penicillin-class Antibacterial.|Piperacillin is an extended spectrum ureidopenicillin and is used to treat moderate-to-severe infections due to susceptible organisms. Piperacillin has been linked with idiosyncratic liver injury, but only rarely and in isolated case reports.|Piperacillin Anhydrous is the anhydrous form of piperacillin, a broad-spectrum semisynthetic ureidopenicillin antibiotic. 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.|Semisynthetic, broad-spectrum, AMPICILLIN derived ureidopenicillin antibiotic proposed for PSEUDOMONAS infections. It is also used in combination with other antibiotics.

Piperacillin Basic Attributes

517.55

517.55

262-811-8

9I628532GX

DTXSID2023482

C61891

J01CR05|J - Antiinfectives for systemic use

2941101900

Characteristics

182

0.3

white crystalline powder

1.5±0.1 g/cm3

180-184 °C

1.678

Freely soluble in methanol. Only sparingly soluble in aqueous solution at 0.119 mg/mL

Hygroscopic, -20°C Freezer, Under Inert Atmosphere

227.2 Ų [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|226.4 Ų [M+Na]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|221.26 Ų [M-H]-

Safety Information

42/43

36/37

XH8952200

Xi

P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, P501

H317

|Danger|H317 (92.31%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P273, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, and P501|Aggregated GHS information provided by 13 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302 (16.67%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P272, P280, P285, P301+P312, P302+P352, P304+P312, P304+P340, P304+P341, P312, P321, P330, P333+P313, P342+P311, P363, and P501|Aggregated GHS information provided by 8 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, and P501|Aggregated GHS information provided by 2 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

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 Information

For the treatment of polymicrobial infections.

Piperacillin is an extended spectrum ureidopenicillin and is used to treat moderate-to-severe infections due to susceptible organisms. Piperacillin has been linked with idiosyncratic liver injury, but only rarely and in isolated case reports.

Antiinfective Agents

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 in vitro 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.

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

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

Largely not metabolized.

36-72 minutes

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.

AB Piperacillin

Piperacillin Use and Manufacturing

Methods of Manufacturing

The β-hydroxyethylamine can be used as the starting material, and after bromination, amination, cyclization, and acid chlorination, EPCP can be prepared. It is then condensed with 6-APA (6-aminopenicillanic acid) to produce piperacillin.

Uses

Broad spectrum semi-synthetic antibiotic related to Penicillin. Antibacterial.

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:517.6
XLogP3:0.5
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:6
Exact Mass:517.16311939
Monoisotopic Mass:517.16311939
Topological Polar Surface Area:182
Heavy Atom Count:36
Complexity:982
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

It inhibits the synthesis of bacterial cell walls by binding to bacterial penicillin-binding proteins (PBPs) and has a bactericidal effect. It has the characteristics of broad spectrum and low toxicity, but it is easily hydrolyzed by β-lactamase produced by bacteria and produces drug resistance.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

  • STERILE INDIA PVT LTD

    United States United States
    Active
  • APITORIA PHARMA PRIVATE LTD

    United States United States
    Active
  • INNER MONGOLIA CHANGSHENG PHARMACEUTICAL CO. LTD.

    Brazil Brazil
    Active

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