[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

Piperacillin Struktur
61477-96-1
CAS-Nr.
61477-96-1
Bezeichnung:
[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
Englisch Name:
Piperacillin
Synonyma:
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
Summenformel:
C23H27N5O7S
Molgewicht:
517.55
MOL-Datei:
61477-96-1.mol

[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 Eigenschaften

Schmelzpunkt:
183-185?C (dec.)
Dichte
1.51±0.1 g/cm3(Predicted)
Dampfdruck
0Pa at 20℃
RTECS-Nr.
XH8952200
storage temp. 
Sealed in dry,2-8°C
Löslichkeit
Freely soluble in methanol. Only sparingly soluble in aqueous solution at 0.119 mg/mL
pka
2.44±0.50(Predicted)
Aggregatzustand
Solid
Farbe
White to Off-White
Wasserlöslichkeit
256.8mg/L at 20℃
Stabilität:
Hygroscopic
LogP
-1.55 at 20℃
CAS Datenbank
61477-96-1(CAS DataBase Reference)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xi
R-Sätze: 42/43
S-Sätze: 36/37
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H317 Kann allergische Hautreaktionen verursachen. Sensibilisierung der Haut Kategorie 1A Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H334 Kann bei Einatmen Allergie, asthmaartige Symptome oder Atembeschwerden verursachen. Sensibilisierung der Atemwege Kategorie 1 Achtung GHS hazard pictogramssrc="/GHS08.jpg" width="20" height="20" /> P261, P285, P304+P341, P342+P311,P501
Sicherheit
P261 Einatmen von Staub vermeiden.
P284 Atemschutz tragen.
P304+P340 BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen.

[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 Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften

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.

Verwenden

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.

Pharmakokinetik

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.

Nebenwirkungen

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.

[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 Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


[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 Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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61477-96-1([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)Verwandte Suche:


  • 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
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