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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/07/29 17:16:35」(JST)
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Piperacillin
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| 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 |
| AHFS/Drugs.com |
Consumer Drug Information |
| Pregnancy cat. |
B |
| Legal status |
POM (UK) ℞-only (US) |
| Routes |
IV, IM |
| Pharmacokinetic data |
| Bioavailability |
0% oral |
| Protein binding |
Slightly less than Amoxicillin |
| Metabolism |
largely not metabolized |
| Half-life |
36–72 minutes |
| Excretion |
20% in bile, 80% unchanged in urine |
| Identifiers |
| CAS number |
61477-96-1 Y |
| ATC code |
J01CA12 |
| PubChem |
CID 43672 |
| IUPHAR ligand |
422 |
| DrugBank |
DB00319 |
| ChemSpider |
39798 Y |
| UNII |
9I628532GX Y |
| KEGG |
D08380 Y |
| ChEBI |
CHEBI:8232 Y |
| ChEMBL |
CHEMBL702 Y |
| Chemical data |
| Formula |
C23H27N5O7S |
| Mol. 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 Y
Key:IVBHGBMCVLDMKU-GXNBUGAJSA-N Y
|
| Y (what is this?) (verify) |
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.
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Antibacterials: cell envelope antibiotics (J01C-J01D)
|
|
| Intracellular |
- inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
- DADAL/AR inhibitors (Cycloserine)
- bactoprenol inhibitors (Bacitracin)
|
|
| Glycopeptide |
- inhibit PG chain elongation: Vancomycin# (Oritavancin
- Telavancin)
- Teicoplanin (Dalbavancin)
- Ramoplanin
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|
β-lactams/
(inhibit PBP
cross-links) |
|
Penicillins
(penams)
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Extended sp.
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- aminopenicillins: Amoxicillin#
- Ampicillin# (Pivampicillin
- Hetacillin
- Bacampicillin
- Metampicillin
- Talampicillin)
- Epicillin
- carboxypenicillins: Carbenicillin (Carindacillin)
- Ticarcillin
- Temocillin
- ureidopenicillins: Azlocillin
- Piperacillin
- Mezlocillin
- other: Mecillinam (Pivmecillinam)
- Sulbenicillin
|
|
|
Narrow sp.
|
|
β-lactamase sensitive
|
- Benzylpenicillin (G)#: Clometocillin
- Benzathine benzylpenicillin#
- Procaine benzylpenicillin#
- Azidocillin
- Penamecillin
- Phenoxymethylpenicillin (V)#: Propicillin
- Benzathine phenoxymethylpenicillin
- Pheneticillin
|
|
|
β-lactamase resistant
|
- Cloxacillin# (Dicloxacillin
- Flucloxacillin)
- Oxacillin
- Meticillin
- Nafcillin
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|
|
|
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Penems
|
|
|
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Carbapenems
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- Biapenem
- Ertapenem
- antipseudomonal (Doripenem
- Imipenem
- Meropenem)
- Panipenem
|
|
|
Cephalosporins/Cephamycins
(cephems)
|
|
1st (PEcK)
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- Cefazolin#
- Cefacetrile
- Cefadroxil
- Cefalexin
- Cefaloglycin
- Cefalonium
- Cefaloridine
- Cefalotin
- Cefapirin
- Cefatrizine
- Cefazedone
- Cefazaflur
- Cefradine
- Cefroxadine
- Ceftezole
|
|
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2nd (HEN)
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- Cefaclor
- Cefamandole
- Cefminox
- Cefonicid
- Ceforanide
- Cefotiam
- Cefprozil
- Cefbuperazone
- Cefuroxime
- Cefuzonam
- cephamycin (Cefoxitin
- Cefotetan
- Cefmetazole)
- carbacephem (Loracarbef)
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|
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3rd
|
- Cefixime#
- Ceftriaxone#
- antipseudomonal (Ceftazidime#
- Cefoperazone)
- Cefcapene
- Cefdaloxime
- Cefdinir
- Cefditoren
- Cefetamet
- Cefmenoxime
- Cefodizime
- Cefotaxime
- Cefpimizole
- Cefpiramide
- Cefpodoxime
- Cefsulodin
- Cefteram
- Ceftibuten
- Ceftiolene
- Ceftizoxime
- oxacephem (Flomoxef
- Latamoxef ‡)
|
|
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4th (antipseudomonal)
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- Cefepime
- Cefozopran
- Cefpirome
- Cefquinome
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|
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5th
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- Ceftobiprole
- Ceftaroline fosamil
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|
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Veterinary
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- Ceftiofur
- Cefquinome
- Cefovecin
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Monobactams
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- Aztreonam
- Tigemonam
- Carumonam
- Nocardicin A
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|
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β-lactamase inh.
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- penam (Sulbactam
- Tazobactam)
- clavam (Clavulanic acid)
|
|
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Combinations
|
- Amoxicillin/clavulanic acid#
- Imipenem/cilastatin#
- Ampicillin/flucloxacillin
- Ampicillin/sulbactam (Sultamicillin)
- Piperacillin/tazobactam
|
|
|
| Other |
- polymyxins/detergent (Colistin
- Polymyxin B)
- depolarizing (Daptomycin)
- hydrolyze NAM-NAG (lysozyme)
- Gramicidin
- Isoniazid
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
|
|
gr+f/gr+a (t)/gr-p (c)/gr-o
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drug (J1p, w, n, m, vacc)
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English Journal
- Emergence of antimicrobial resistance to Pseudomonas aeruginosa in the intensive care unit: association with the duration of antibiotic exposure and mode of administration.
- Yusuf E1, Van Herendael B2,3, Verbrugghe W4, Ieven M2, Goovaerts E5, Bergs K4, Wouters K6, Jorens PG4, Goossens H2.
- Annals of intensive care.Ann Intensive Care.2017 Dec;7(1):72. doi: 10.1186/s13613-017-0296-z. Epub 2017 Jun 29.
- PMID 28664350
- Therapeutic drug monitoring of beta-lactam antibiotics - Influence of sample stability on the analysis of piperacillin, meropenem, ceftazidime and flucloxacillin by HPLC-UV.
- Pinder N1, Brenner T2, Swoboda S3, Weigand MA2, Hoppe-Tichy T3.
- Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.2017 Sep 5;143:86-93. doi: 10.1016/j.jpba.2017.05.037. Epub 2017 May 22.
- PMID 28578254
- Visual compatibility of colistin injection with other antibiotics during simulated Y-site administration.
- Katip W1.
- American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists.Am J Health Syst Pharm.2017 Jul 15;74(14):1099-1102. doi: 10.2146/ajhp160216.
- PMID 28687555
Related Links
- Pipracil official prescribing information for healthcare professionals. Includes: indications, dosage, adverse reactions, pharmacology and more. ... A 30-minute infusion of 6 g every 6 h gave, on the fourth day, a mean peak serum ...
- Detailed drug Information for Pipracil. Includes common brand names, drug descriptions, warnings, side effects and dosing information. ... Drugs.com provides accurate and independent information on more than 24,000 prescription ...
Related Pictures
★リンクテーブル★
[★]
- 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