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a silvery soft waxy metallic element of the alkali metal group; occurs abundantly in natural compounds (especially in salt water); burns with a yellow flame and reacts violently in water; occurs in sea water and in the mineral halite (rock salt) (同)Na, atomic number 11
a synthetic type of penicillin antibiotic (trade name Pipracil) used for moderate to severe infections (同)Pipracil

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ソジウム,ナトリウム(金属元素;化学記号はNa)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/01 16:56:17」(JST)

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Piperacillin is a broad-spectrum β-lactam antibiotic of the ureidopenicillin class.^[1] The chemical structure of piperacillin and other ureidopenicillins incorporates a polar side chain that enhances penetration into Gram-(-) bacteria and reduces susceptibility to cleavage by Gram-(-) 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 pathogen Staphylococcus aureus, as the beta-lactam ring is broken by the bacteria's beta-lactamase.^[2]

Piperacillin is most commonly used in combination with the beta-lactamase inhibitor tazobactam (piperacillin/tazobactam) (tradename "Zosyn"), 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 methicillin-resistant Staphylococcus aureus, however, as penicillins (and most other beta lactams) do not avidly bind to the penicillin-binding proteins of this pathogen.^[3]

Medical uses

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.^[4]

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.^[5] It is also one of several antibacterials recommended for the treatment of infections known to be caused by anaerobic Gram-(-) rods.^[6]

Piperacillin-tazobactam is recommended by the National Institute for Health and Care Excellence as initial empiric treatment for people with suspected neutropenic sepsis.^[7]

Adverse effects

The most common adverse effects associated with piperacillin-tazobactam are diarrhea, constipation, nausea, headache and insomnia. Less commonly, severe adverse effects may include anaphylaxis, Stevens-Johnson syndrome, and Clostridium difficile associated diarrhea.^[8]

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.^[9]

References

^ Tan JS, File TM (1995). "Antipseudomonal penicillins". Med. Clin. North Am. 79 (4): 679–93. PMID 7791416.
^ Hauser, AR Antibiotic Basics for Clinicians, 2nd Ed., Wolters Kluwer, 2013, pg 26-27
^ Zhanel GG, DeCorby M, Laing N, Weshnoweski B, Vashisht R, Tailor F, Nichol KA, Wierzbowski A, Baudry PJ, Karlowsky JA, Lagacé-Wiens P, Walkty A, McCracken M, Mulvey MR, Johnson J, Hoban DJ (2008). "Antimicrobial-resistant pathogens in intensive care units in Canada: results of the Canadian National Intensive Care Unit (CAN-ICU) study, 2005-2006". Antimicrob. Agents Chemother. 52 (4): 1430–7. doi:10.1128/AAC.01538-07. PMC 2292546. PMID 18285482.
^ Schumock GT, Li EC, Suda KJ, Wiest MD, Stubbings J, Matusiak LM, Hunkler RJ, Vermeulen LC (2015). "National trends in prescription drug expenditures and projections for 2015". Am J Health Syst Pharm 72 (9): 717–36. doi:10.2146/ajhp140849. PMID 25873620.
^ Mandell LA, Wunderink R, in Harrison's Principles of Internal Medicine 18th Ed., Chapter 257, pp 2139-2141
^ Kasper DL, Cohen-Poradosu R, in Harrison's Principles of Internal Medicine 18th Ed., Chapter 164, pp 1331-1339
^ "Neutropenic Sepsis: Prevention and Management of Neutropenic Sepsis in Cancer Patients - PubMed - NCBI".
^ "www.accessdata.fda.gov" (PDF).
^ 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.

UpToDate Contents

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1. 基質特異性拡張型β-ラクタマーゼ extended spectrum beta lactamases
2. ペニシリン penicillins
3. β-ラクタマーゼ阻害剤、カルバペネム系、およびモノバクタム系抗菌薬の併用 combination beta lactamase inhibitors carbapenems and monobactams
4. 深頸部の感染症 deep neck space infections
5. 化学療法以外の原因による好中球減少症を有する小児の発熱の評価およびマネージメント evaluation and management of fever in children with non chemotherapy induced neutropenia

English Journal

Epidemiological and bacteriological profiles in children with burns.

Fekih Hassen A1, Ben Khalifa S2, Daiki M2.
Burns : journal of the International Society for Burn Injuries.Burns.2014 Aug;40(5):1040-5. doi: 10.1016/j.burns.2013.10.020. Epub 2013 Dec 9.
OBJECTIVES: The aim of our study is to determine the most prevalent bacteria responsible for nosocomial infection (NI) in burned children.MATERIALS AND METHODS: A prospective analytic study was conducted over a period of 30 months at the Children's Hospital of Tunisia. All burned children were enrol
PMID 24331406

Individualization of Piperacillin Dosing for Critically Ill Patients: Dosing Software To Optimize Antimicrobial Therapy.

Felton TW1, Roberts JA2, Lodise TP3, Van Guilder M4, Boselli E5, Neely MN4, Hope WW6.
Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2014 Jul;58(7):4094-4102. Epub 2014 May 5.
Piperacillin-tazobactam is frequently used for empirical and targeted therapy of infections in critically ill patients. Considerable pharmacokinetic (PK) variability is observed in critically ill patients. By estimating an individual's PK, dosage optimization Bayesian estimation techniques can be us
PMID 24798288

Population Pharmacokinetic Analysis of Piperacillin in Burn Patients.

Jeon S1, Han S1, Lee J1, Hong T1, Paek J1, Woo H2, Yim DS3.
Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2014 Jul;58(7):3744-3751. Epub 2014 Apr 21.
Piperacillin in combination with tazobactam, a β-lactamase inhibitor, is a commonly used intravenous antibiotic for the empirical treatment of infection in intensive care patients, including burn patients. The purpose of this study was to develop a population pharmacokinetic (PK) model for piperaci
PMID 24752260

Japanese Journal

整形外科周術期感染予防抗菌薬としてのピペラシリンナトリウム(ペントシリン)の有用性の検討

市村晴充,上杉雅文,吉井雄一
日本骨・関節感染症学会雑誌 25, 52-54, 2011
NAID 40019193404

日本発・世界のくすり(31)日本生まれのペニシリン系薬TAZ/PIPC ゾシン静注用2.25・ゾシン静注用4.5 一般名:注射用タゾバクタムナトリウム・ピペラシリンナトリウム

大正富山医薬品株式会社
医療 63(7), 450-452, 2009-07
NAID 40016774927

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リンク元

「ピペラシリン」

Piperacillin
Systematic (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
Clinical data
Trade names	Pipracil
AHFS/Drugs.com	Consumer Drug Information
Pregnancy; category	B;
Legal status	UK: POM (Prescription only); US: ℞-only;
Routes of; administration	IV, IM
Pharmacokinetic data
Bioavailability	0% oral
Protein binding	Slightly less than Amoxicillin
Metabolism	largely not metabolized
Biological half-life	36–72 minutes
Excretion	20% in bile, 80% unchanged in urine
Identifiers
CAS Number	61477-96-1
ATC code	J01CA12
PubChem	CID: 43672
IUPHAR/BPS	422
DrugBank	DB00319
ChemSpider	39798
UNII	9I628532GX
KEGG	D08380
ChEBI	CHEBI:8232
ChEMBL	CHEMBL702
Chemical data
Formula	C23H27N5O7S
Molecular mass	517.555 g/mol
	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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　　[★]

英: piperacillin, PIPC
ラ: piperacillinum
化: ピペラシリン水和物 piperacillin hydrate、ピペラシリンナトリウム piperacillin sodium
商: ピシリアント、ピペユンシン、プランジン、タイペラシリン、ピペラシリンナトリウム、ペントシリン、ペンマリン、Pipracil、(タゾバクタム、ピペラシリン)ゾシン
関: 抗菌薬、ピペラシリン-タゾバクタム

特徴

第三世代セフェムに匹敵する抗菌薬
グラム陰性菌に対しても使える。
緑膿菌にも効く

[1] Tan JS, File TM (1995). "Antipseudomonal penicillins". Med. Clin. North Am. 79 (4): 679–93. PMID 7791416.

[2] Hauser, AR Antibiotic Basics for Clinicians, 2nd Ed., Wolters Kluwer, 2013, pg 26-27

[3] Zhanel GG, DeCorby M, Laing N, Weshnoweski B, Vashisht R, Tailor F, Nichol KA, Wierzbowski A, Baudry PJ, Karlowsky JA, Lagacé-Wiens P, Walkty A, McCracken M, Mulvey MR, Johnson J, Hoban DJ (2008). "Antimicrobial-resistant pathogens in intensive care units in Canada: results of the Canadian National Intensive Care Unit (CAN-ICU) study, 2005-2006". Antimicrob. Agents Chemother. 52 (4): 1430–7. doi:10.1128/AAC.01538-07. PMC 2292546. PMID 18285482.

[4] Schumock GT, Li EC, Suda KJ, Wiest MD, Stubbings J, Matusiak LM, Hunkler RJ, Vermeulen LC (2015). "National trends in prescription drug expenditures and projections for 2015". Am J Health Syst Pharm 72 (9): 717–36. doi:10.2146/ajhp140849. PMID 25873620.

[5] Mandell LA, Wunderink R, in Harrison's Principles of Internal Medicine 18th Ed., Chapter 257, pp 2139-2141

[6] Kasper DL, Cohen-Poradosu R, in Harrison's Principles of Internal Medicine 18th Ed., Chapter 164, pp 1331-1339

[7] "Neutropenic Sepsis: Prevention and Management of Neutropenic Sepsis in Cancer Patients - PubMed - NCBI".

[8] "www.accessdata.fda.gov" (PDF).

[9] 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.

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案内

piperacillin sodium