Piperacillin

Piperacillin
Clinical data

Trade names	Pipracil
AHFS/Drugs.com	Consumer Drug Information
Pregnancy category	B
Routes of administration	IV, IM
ATC code	J01CA12 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	0% oral
Protein binding	30%
Metabolism	Largely not metabolized
Biological half-life	36–72 minutes
Excretion	20% in bile, 80% unchanged in urine
Identifiers
IUPAC name (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
CAS Number	61477-96-1^Y
PubChem (CID)	43672
IUPHAR/BPS	422
DrugBank	DB00319^Y
ChemSpider	39798^Y
UNII	9I628532GX^Y
KEGG	D08380^Y
ChEBI	CHEBI:8232^Y
ChEMBL	CHEMBL702^Y
Chemical and physical data
Formula	C₂₃H₂₇N₅O₇S
Molar mass	517.555 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)NC(=O)N2C(=O)C(=O)N(CC)CC2)[C@H]4SC3(C)C
InChI InChI=1S/C23H27N5O7S/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34)/t13-,14-,15+,20-/m1/s1^Y Key:IVBHGBMCVLDMKU-GXNBUGAJSA-N^Y

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".

When used alone, piperacillin lacks strong activity against the Gram positive pathogens such as Staphylococcus aureus, as the beta-lactam ring is hydrolyzed by the bacteria's beta-lactamase.

Piperacillin is most commonly used in combination with the beta-lactamase inhibitor tazobactam (Piperacillin/Tazobactam) (tradename "Zosyn" or "Tazocin"), which enhances piperacillin's effectiveness by inhibiting many beta lactamases to which it is susceptible. The co-administration of tazobactam does not confer activity against MRSA, however, as penicillins (and most other beta lactams) do not avidly bind to the penicillin-binding proteins of this pathogen.

Piperacillin is used almost exclusively in combination with the beta lactamase inhibitor tazobactam for the treatment of serious, hospital-acquired infections. This combination is among the most widely used drug therapies in United States non-Federal hospitals, accounting for $388M in spending in spite of being a low-cost generic drug.

Piperacillin-tazobactam is recommended as part of a three drug regimen for the treatment of hospital-acquired pneumonia suspected as being due to infection by multi-drug resistant pathogens. It is also one of several antibacterials recommended for the treatment of infections known to be caused by anaerobic Gram negative rods.

Piperacillin-tazobactam is recommended by the National Institute for Health and Care Excellence as initial empiric treatment for people with suspected neutropenic sepsis.

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Wikipedia