Piperacillin
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| Category | Antibiotics |
| Catalog number | BBF-03917 |
| CAS | 61477-96-1 |
| Molecular Weight | 517.55 |
| Molecular Formula | C23H27N5O7S |
| Purity | 97% |
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Description
An extended spectrum beta-lactam antibiotic and resistant to many beta-lactamases.
Specification
| Related CAS | 59703-84-3 (monohydrochloride salt) 66258-76-2 (hydrate) |
| Synonyms | CL 227193; Isipen; Pentcillin; Pipracil; 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-; 6α-[[(R)-(4-Ethyl-2,3-dioxo-1-piperazinylcarbonylamino)phenylacetyl]amino]penicillanic acid; 6α-[[(R)-α-Oxo-β-[[(2,3-dioxo-4-ethyl-1-piperazinyl)carbonyl]amino]phenethyl]amino]penicillanic acid; PIPC |
| Storage | Store at -20°C |
| 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 |
| 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 |
| 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 |
| InChI Key | IVBHGBMCVLDMKU-GXNBUGAJSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | White to Off-white Solid |
| Application | Anti-Bacterial Agents |
| Melting Point | 167-169°C |
| Density | 1.510±0.10 g/cm3 (Predicted) |
| Solubility | Soluble in DMSO (Slightly), Methanol (Slightly), Water (Slightly) |
Reference Reading
1.Tazobactam and piperacillin-induced thrombocytopenia: A case report.
Chen H1, Fan Z1, Guo F2, Yang Y1, Li J1, Zhang J1, Wang Y1, LE J1, Wang Z1, Zhu J1. Exp Ther Med. 2016 Apr;11(4):1223-1226. Epub 2016 Feb 9.
The present study reports a case of tazobactam and piperacillin (TZP)-induced thrombocytopenia in an elderly patient, from which complete clinical data and peripheral blood samples were collected. Platelet numbers were decreased 1 day following TZP treatment initiation; however, they were revealed to have increased 1-2 days following withdrawal of TZP, and had reached normal levels 3-5 days later. There was no evidence of bone marrow suppression, antibodies against peripheral plasma platelets were absent and levels of complement C3 were decreased. These results suggested that TZP was able to cause rapid and reversible thrombocytopenia, which was not associated with bone marrow suppression but may have involved activation of complement C3. The results of the present study therefore suggest that doctors should be aware of the risk of thrombocytopenia in patients treated with TZP.
2.Targeted benefits of prolonged-infusion piperacillin-tazobactam in an in vitro infection model of Pseudomonas aeruginosa.
Zelenitsky S1,2, Nash J1, Weber Z1, Iacovides H1,2, Ariano R1,2. J Chemother. 2016 Mar 30:1-5. [Epub ahead of print]
Given the inconsistent clinical findings, our goal was to characterize the pharmacodynamics (PDs) of prolonged-infusion piperacillin-tazobactam (TZP) in an in vitro pharmacodynamic model of Pseudomonas aeruginosa. Specifically, the study was designed to investigate the influence of MIC on the activity of prolonged-infusion TZP using pharmacokinetics (PKs) consistent with a non-critically ill patient population. There was no benefit with prolonged- compared with standard-infusion TZP against isolates with susceptible MICs of 8 or 16 mg/L. However, prolonged-infusion TZP produced more than two times the final bacterial kill against less susceptible isolates with an intermediate MIC of 32 mg/L. The PDs of TZP were well described by a sigmoid Emax model (r2 = 0.84) where %ƒT>MIC thresholds of 27 and 75% were associated with bacteriostatic and bactericidal effects, respectively. However, the well-established PD relationship with %ƒT>MIC was not observed with prolonged-infusion TZP.
3.[Role of bacteriobilia in postoperative complications].
Armiñanzas C, Tigera T, Ferrer D, Calvo J, Herrera LA, Pajarón M, Gómez-Fleitas M, Fariñas MC1. Rev Esp Quimioter. 2016 Apr 8. pii: farinas08apr2016. [Epub ahead of print]
OBJECTIVE: At present there is a controversy regarding the impact of positive bile cultures on morbidity and mortality rates, and on the incidence of readmissions in patients with biliar disease. The aim of this study was to evaluate the role of bacteriobilia in postoperatory infections, mortality or readmissions in these patients.
4.Piperacillin concentration in relation to therapeutic range in critically ill patients - a prospective observational study.
Zander J1, Döbbeler G2, Nagel D1, Maier B1, Scharf C2, Huseyn-Zada M1, Jung J3, Frey L2, Vogeser M1, Zoller M4. Crit Care. 2016 Apr 4;20(1):79. doi: 10.1186/s13054-016-1255-z.
BACKGROUND: Piperacillin levels after standard dosing have been shown frequently to be subtherapeutic, especially when renal clearance was augmented. Here, we aimed to determine if piperacillin was in its therapeutic range in a typically heterogeneous intensive care unit patient group, and also to describe target attainment dependent on daily dosage, creatinine clearance, and renal replacement therapy (RRT).
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
