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Piperacillin

Piperacillin Structure
CAS No.
61477-96-1
Chemical Name:
Piperacillin
Synonyms
Piperacillin;PIPERACILLIN SODIUM;Pipercillin;(2S,5R,6R)-6-[[(2R)-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)-;PIPC;C14034;Pipraci;Pipracil;Piperacil
CBNumber:
CB0181853
Molecular Formula:
C23H27N5O7S
Molecular Weight:
517.55
MOL File:
61477-96-1.mol
Modify Date:
2024/8/2 18:12:07
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Piperacillin Properties

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)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS08
Signal word  Warning
Hazard statements  H317-H334
Precautionary statements  P261-P280g-P284-P304+P340-P342+P311a-P501a
Hazard Codes  Xi
Risk Statements  42/43
Safety Statements  36/37

Piperacillin Chemical Properties,Uses,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.

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-).

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.

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

6-Aminopenicillanic acid Bromide PHOSGENE Diethyl oxalate Chlorotrimethylsilane
Sodium 2-ethylhexanoate 2-Aminoethyl(ethyl)amine
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Preparation Products

Piperacillin Suppliers

Global( 262)Suppliers
Supplier Tel Country ProdList Advantage Inquiry
CHEMXTREE STANDARDS +919872732255 Punjab, India 96 58 Inquiry
JA Sterile Pvt Ltd +91-9427679998 +91-9427679998 Gujarat, India 21 58 Inquiry
Penam Laboratories Ltd +91-1145084500 +91-1145084500 New Delhi, India 13 58 Inquiry
Nectar Lifesciences Ltd +91-9357244445 +91-9357244445 Punjab, India 29 58 Inquiry
CLEARSYNTH LABS LTD. +91-22-45045900 Hyderabad, India 6351 58 Inquiry
A.J Chemicals 91-9810153283 New Delhi, India 6124 58 Inquiry
Pharmaffiliates Analytics and Synthetics P. Ltd +91-172-5066494 Haryana, India 6773 58 Inquiry
SynZeal Research Pvt Ltd +1 226-802-2078 Gujarat, India 6522 58 Inquiry
Medilink Pharmachem +91 (79) 3007-0133 New Delhi, India 424 50 Inquiry
AUROBINDO PHARMA LTD +91 (40) 6672 1200 New Delhi, India 209 58 Inquiry
Supplier Advantage
CHEMXTREE STANDARDS 58
JA Sterile Pvt Ltd 58
Penam Laboratories Ltd 58
Nectar Lifesciences Ltd 58
CLEARSYNTH LABS LTD. 58
A.J Chemicals 58
Pharmaffiliates Analytics and Synthetics P. Ltd 58
SynZeal Research Pvt Ltd 58
Medilink Pharmachem 50
AUROBINDO PHARMA LTD 58

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Piperacillin Spectrum

Piperacillin(61477-96-1)1HNMR

61477-96-1(Piperacillin)Related Search:

PHENYL VALERATE CARBONYL SULFIDE Penicillin G PYRAZOPHOS ISOXADIFEN-ETHYL
Ethyl acetate PIPERAZINE CITRATE HYDRATE 1,4-Dioxane 2-Ethylhexyl ferulate Ethyl acrylate
Selenium dioxide Ethylparaben N-Aminoethylpiperazine Ethanol 1-Ethyl-2,3-dioxopiperazine
SALOR-INT L169811-1EA Fomidacillin Ampicillin
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PIPERACILLIN EPP(CRM STANDARD) PIPERACILLIN USP(CRM STANDARD) PIPERAILLIN 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)- (9CI) 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-[2a,5a,6b(S*)]]- Piperacillin (base and/or unspecified salts) [2S-[2alpha,5alpha,6beta(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]heptane-2-carboxylic acid Pipracil Piperacillin (Acid) Monohydrate 6α-[[(R)-(4-Ethyl-2,3-dioxo-1-piperazinylcarbonylamino)phenylacetyl]amino]penicillanic acid 6α-[[(R)-α-Oxo-β-[[(2,3-dioxo-4-ethyl-1-piperazinyl)carbonyl]amino]phenethyl]amino]penicillanic acid PIPC C14034 Piperacillin anhydrous Piperacillin solution,100ppm Piperacillin, >=96% PIPERACILLIN NA 3-dioxo-1-piperazinyl)carbonyl)amino)phenylacetyl)amino)-7-oxo-l-(2s-(2-al 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylicacid,3,3-dimethyl-6-(((((4-ethy 6-(d-(-)-alpha-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)phenylacetamido)pe (2S,5R,6R)-6-((R)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid hydrate 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)- (N-CD2CD3) Pipracil USP/EP/BP Pipraci Piperacillin-d5 (phenyl-d5) Piperacillin-d5 (N-ethyl-d5) PiperacillinQ: What is Piperacillin Q: What is the CAS Number of Piperacillin Q: What is the storage condition of Piperacillin (2S,5R,6R)-6-[[(2R)-2-[[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid monohydrate Piperacillin-D5, (N-CD2CD3) Piperacilin Acid (2S,5R,6R)-6-[[(2R)-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Piperacillin 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)- Pipercillin PIPERACILLIN SODIUM (2S,5R,6R)-6-((R)-2-(4-Ethyl-2,3-Dioxopiperazine-1-carboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Piperacil (2S,5R,6R)-6-((R)-2-(4-Ethyl-2,3-dioxopiperazine-1-carboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (Piperacillin Impurity) (2S,5R,6R)-6-[[(2R)-2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)amino]-2-phenyl-acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 61477-96-1 161477-96-1 C23H27N5O7SH2O 51755 Antibiotics N-S Antibiotics A to Z Antibiotics BioChemical Aromatics Heterocycles Intermediates & Fine Chemicals Pharmaceuticals Sulfur & Selenium Compounds Antibiotic Explorer 61477-96-1