Structure via PubChem · Public domain (PubChem)
پیپراسیلین
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, Piperacillin, 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
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1981
- Admin. routes
- parenteral
- Indications
- infection, Pseudomonas infection, abscess, osteomyelitis
via ChEMBL · EBI
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
- Subclass of
- carboxylic acid
- Mass
- 517.163
- Has use
- medication
Show 8 more facts
- found in taxon
- Pseudoalteromonas
- 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
- subject has role
- bactericide
- Commons category
- Piperacillin
via Wikidata · CC0