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HCID 43672Erstellt: 26. Oktober 2026

[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 · PIPERACILLIN SODIUM · Pipracil · 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 · (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-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

https://huagongshe.com/de/chemical/43672

Molekülstruktur von [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

Identifikatoren & physikalische Daten

CAS No.61477-96-1
SummenformelC23H27N5O7S
Durchschnittliche Molmasse517,6 g/mol
Monoisotopische Masse517,1631192 g/mol
SMILESCCN1CCN(C(=O)N[C@@H](C(=O)N[C@@H]2C(=O)N3[C@@H]2SC(C)(C)[C@@H]3C(=O)O)c2ccccc2)C(=O)C1=O
InChIKeyIVBHGBMCVLDMKU-GXNBUGAJSA-N
PubChem CID43672
ChEMBLCHEMBL702
ChEBICHEBI:8232
EC No.262-811-8
DTXSIDDTXSID2023482
Lokaler Name[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 & physikalische Eigenschaften

XLogP0,5
Polarare Oberfläche (TPSA)182
H-Brücken-Donoren3
H-Brücken-Akzeptoren8
Frei drehbare Bindungen6
Schwere Atome36
Formalladung0
Komplexität982
StoffklassenOther Uses -> Pharmaceuticals
ArzneimittelPharmaceuticals -> AntibioticsPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Used in Switzerland
LogP (Verteilungskoeffizient)0.3
Löslichkeit1.19e-01 g/LFreely soluble in methanol. Only sparingly soluble in aqueous solution at 0.119 mg/mL256.8mg/L at 20℃
Human DrugsBreast FeedingLactationMilk, HumanAnti-Infective AgentsAntibacterial AgentsPenicillins
Physical DescriptionWhite to off-white solid[Bristol-Myers Squibb]
Collision Cross Section227.2 Ų [M+H]+ [CCS Type: TWMethod: calibrated with Waters Major Mix]222.2 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]221.26 Ų [M-H]-
Schmelzpunkt183-185C (dec.)
Dichte1.51±0.1 g/cm3(Predicted)
Dampfdruck0Pa at 20℃
LagerbedingungenSealed in dry,2-8°C
pKa (Säurekonstante)2.44±0.50(Predicted)
AggregatzustandSolid
FarbeWhite to Off-White
StabilitätHygroscopic
InChIKeyIVBHGBMCVLDMKU-GXNBUGAJSA-N
SMILESN12[C@@]([H])([C@H](NC([C@H](NC(N3CCN(CC)C(=O)C3=O)=O)C3=CC=CC=C3)=O)C1=O)SC(C)(C)[C@@H]2C(O)=O
LogP (Verteilungskoeffizient)-1.55 at 20℃
CAS Datenbank61477-96-1(CAS DataBase Reference)

Sicherheit & Vorschriften

GHS-EinstufungDangerH317 (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.
Regulatorische InformationenStatus: Active Update: 15-06-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/27459
Weitere SicherheitsinformationenIMAP assessments - 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-[2.alpha.,5.alpha.,6.beta.(S*)]]-: Environment tier I assessment
GefahrenübersichtA dermal and respiratory sensitizer[Bristol-Myers Squibb] Occupational asthma confirmed in a pharmaceutical worker[Malo] Causes contact urticaria[Kanerva, p. 219]
Hazard Classes and CategoriesSkin Sens. 1 (93.8%)
HepatotoxicityPatients 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.
Unerwünschte WirkungenAsthma - Reversible bronchoconstriction (narrowing of bronchioles) initiated by the inhalation of irritating or allergenic agents.
Drug Induced Liver InjuryDrug-Induced Liver Injury Severity and Toxicity (DILIst)piperacillinDILI NegativeIntravenousDOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
R-Sätze (R)42/43
GefahrensymboleXi
Sicherheitshinweise (S)36/37

Anwendungen & Verwendung

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.