Structure via PubChem · Public domain (PubChem)
piperacillin
Sign in to saveAlso known as Pipracil, Piperacillin Anhydrous, Piperacillina, (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, Pipéracilline, Piperacilina, Piperacillinum
Piperacillin is a broad-spectrum β-lactam antibiotic of the ureidopenicillin class. The chemical structure of piperacillin and other ureidopenicillins incorporates a polar side chain that enhances penetration into Gram-negative bacteria and reduces susceptibility to cleavage by Gram-negative beta lactamase enzymes. These properties confer activity against the important hospital pathogen Pseudomonas aeruginosa. Thus piperacillin is sometimes referred to as an "anti-pseudomonal penicillin".
Key facts
- Drug.verifiedrevid
- 461746289
- Drug.image
- Piperacillin skeletal formula labelled.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Piperacillin-from-xtal-3D-bs-17.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Pipracil
- Drug.pregnancy_AU
- B1
- Drug.pregnancy_US
- B
- Drug.routes_of_administration
- Intravenous (IV), intramuscular (IM)
- Drug.class
- β-lactam antibiotic
- Drug.ATC_prefix
- J01
- Drug.ATC_suffix
- CA12
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
- Drug.bioavailability
- 0% oral
- Drug.protein_bound
- 30%
- Drug.metabolism
- Largely not metabolized
- Drug.elimination_half life
- 36–72 minutes
via Wikipedia infobox
Chemical data
- Formula
- C23H27N5O7S
- Molecular weight
- 517.6 g/mol
- IUPAC name
- (2S,5R,6R)-6-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- SMILES
- CCN1CCN(C(=O)C1=O)C(=O)N[C@H](C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
- InChIKey
- IVBHGBMCVLDMKU-GXNBUGAJSA-N
- XLogP
- 0.5
- Polar surface area
- 182 Ų
- H-bond donors
- 3
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Research
11,110 papers- Piperacillin/tazobactam: an updated review of its use in the treatment of bacterial infections.Drugs · 1999
- Reevaluating Piperacillin-Tazobactam Mortality.JAMA internal medicine · 2024
- Reevaluating Piperacillin-Tazobactam Mortality-Reply.JAMA internal medicine · 2024
- Reevaluating Piperacillin-Tazobactam Mortality.JAMA internal medicine · 2024
- Piperacillin-tazobactam: a beta-lactam/beta-lactamase inhibitor combination.Expert review of anti-infective therapy · 2007
via PubMed
Wikidata facts
- Mass
- 517.163
Show 6 more facts
- chemical formula
- C₂₃H₂₇N₅O₇S
- canonical SMILES
- CCN1CCN(C(=O)C1=O)C(=O)NC(C2=CC=CC=C2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
- isomeric SMILES
- CCN1CCN(C(=O)C1=O)C(=O)N[C@H](C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
- defined daily dose
- 14
- World Health Organisation international non-proprietary name
- piperacillin
- Commons category
- Piperacillin
via Wikidata · CC0
~21 min read
Article
12 sectionsContents
- Medical uses
- Pneumonia
- Administration
- Adverse effects
- Interactions
- Pharmacology
- Mechanism of action
- Mechanisms of resistance
- Pharmacokinetics
- Pharmacodynamics
- Chemistry
- References
{{Infobox drug | verifiedrevid = 461746289 | drug_name = | INN = | type = | image = Piperacillin skeletal formula labelled.svg | image_class = skin-invert-image | width = | alt = | caption = | image2 = Piperacillin-from-xtal-3D-bs-17.png | image_class2 = bg-transparent | pronounce = | tradename = Pipracil | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = B1 | pregnancy_AU_comment = | pregnancy_US = B | pregnancy_US_comment = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = Intravenous (IV), intramuscular (IM) | class = β-lactam antibiotic | ATC_prefix = J01 | ATC_suffix = CA12 | ATC_supplemental = | legal_AU = | legal_AU_comment = | legal_BR = | legal_BR_comment = | legal_CA = | legal_CA_comment = | legal_DE = | legal_DE_comment = | legal_NZ = | legal_NZ_comment = | legal_UK = POM | legal_UK_comment = | legal_US = Rx-only | legal_US_comment = | legal_EU = | legal_EU_comment = | legal_UN = | legal_UN_comment = | legal_status =
| bioavailability = 0% oral | protein_bound = 30% | metabolism = Largely not metabolized | metabolites = | onset = | elimination_half-life = 36–72 minutes | duration_of_action = | excretion = 20% in bile, 80% unchanged in urine