Piperacillin

Piperacillin
Clinical data
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	Slightly less than Amoxicillin
Metabolism	largely not metabolized
Elimination 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 ;
PubChem CID	43672;
IUPHAR/BPS	422;
DrugBank	DB00319 ;
ChemSpider	39798 ;
UNII	9I628532GX;
KEGG	D08380 ;
ChEBI	CHEBI:8232 ;
ChEMBL	ChEMBL702 ;
CompTox Dashboard (EPA)	DTXSID2023482 ;
ECHA InfoCard	100.057.083
Chemical and physical data
Formula	C23H27N5O7S
Molar mass	517.555 g/mol g·mol−1
3D model (JSmol)	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 ; Key:IVBHGBMCVLDMKU-GXNBUGAJSA-N ;
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Piperacillin is an extended spectrum beta-lactam antibiotic of the ureidopenicillin class. It is normally used together with a beta-lactamase inhibitor, notably in the combination piperacillin/tazobactam.

Administration

Piperacillin is not absorbed orally, and must therefore be given by intravenous or intramuscular injection. It has been shown that the bacteriocidal actions of the drug do not increase with concentrations of piperacillin higher than 4-6xMIC, which means that the drug is concentration-independent in terms of its actions. Piperacillin has instead shown to offer higher bacteriocidal activity when its concentration remains above the MIC for longer periods of time (50% time>MIC showing the highest activity). This higher activity (present in continuous dosing) has not been directly linked to clinical outcomes, but however does show promise of lowering possibility of resistance and decreasing mortality.^[1]

References

^ Lau W, Mercer D, Itani K; et al. (2006). "Randomized, open-label, comparative study of piperacillin-tazobactam administered by continuous infusion versus intermittent infusion for treatment of hospitalized patients with complicated intra-abdominal infection". Antimicrob Agents Chemother. 50 (11): 3556–61. doi:10.1128/AAC.00329-06. PMC 1635208. PMID 16940077. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)

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[1] Lau W, Mercer D, Itani K; et al. (2006). "Randomized, open-label, comparative study of piperacillin-tazobactam administered by continuous infusion versus intermittent infusion for treatment of hospitalized patients with complicated intra-abdominal infection". Antimicrob Agents Chemother. 50 (11): 3556–61. doi:10.1128/AAC.00329-06. PMC 1635208. PMID 16940077. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)

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