Piperacilloic Acid | CAS# 64817-22-7 | Antibiotic

MedKoo Cat#: 574488 | Name: Piperacilloic Acid

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Piperacilloic Acid is a degradation product of Piperacillin -- a new β-lactam antibiotic.

Chemical Structure

Piperacilloic Acid

CAS#64817-22-7

Theoretical Analysis

MedKoo Cat#: 574488

Name: Piperacilloic Acid

CAS#: 64817-22-7

Chemical Formula: C23H29N5O8S

Exact Mass: 535.1737

Molecular Weight: 535.57

Elemental Analysis: C, 51.58; H, 5.46; N, 13.08; O, 23.90; S, 5.99

Price and Availability

Size	Price	Availability
1mg	USD 340.00	2 Weeks
10mg	USD 1,715.00	2 Weeks
25mg	USD 3,125.00	2 Weeks

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Synonym

Piperacilloic Acid, Piperacillin EP Impurity B

IUPAC/Chemical Name

(2R,4S)-2-((R)-carboxy((R)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-2-phenylacetamido)methyl)-5,5-dimethylthiazolidine-4-carboxylic acid

InChi Key

OKSUEATVFIVTFV-ARAOSMHQSA-N

InChi Code

InChI=1S/C23H29N5O8S/c1-4-27-10-11-28(19(31)18(27)30)22(36)25-13(12-8-6-5-7-9-12)16(29)24-14(20(32)33)17-26-15(21(34)35)23(2,3)37-17/h5-9,13-15,17,26H,4,10-11H2,1-3H3,(H,24,29)(H,25,36)(H,32,33)(H,34,35)/t13-,14?,15?,17-/m1/s1

SMILES Code

CCN1CCN(C(N[C@H](C2=CC=CC=C2)C(N[C@H](C(O)=O)[C@]3([H])N[C@@H](C(O)=O)C(C)(C)S3)=O)=O)C(C1=O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Piperacilloic Acid is a degradation product of Piperacillin -- a new β-lactam antibiotic.

In vitro activity:

This study shows that clinically relevant doses of piperacillin induce apoptosis in SH-SY5Y and human primary neuron cells through activating caspase-3 activity and decreasing Mcl-1 and Bcl-2 levels. In addition, piperacillin causes mitochondrial dysfunction in neuron cells as shown by the reduction of mitochondrial respiration, membrane potential, and ATP production. This study further demonstrates that piperacillin increases accumulation of mitochondrial superoxide and reactive oxygen species, suggesting the oxidative stress in neuron cells. Reference: Can J Physiol Pharmacol. 2018 Jun;96(6):562-568. https://pubmed.ncbi.nlm.nih.gov/28759731/

In vivo activity:

The effects of the administration piperacillin on bile flow and biliary lipid secretion were studied in male Wistar rats. Intravenous injection of piperacillin at doses ranging from 0.3 to 3.0 mmol/kg bodyweight led to an increase in its biliary concentration and excretion rate. Maximal biliary excretion was reached at a dose of 2.0 mmol/kg piperacillin. Continuous i.v. infusion of piperacillin at 2.0 mmol/100 g per min did not result in significant changes in bile acid or cholesterol secretion, but biliary phospholipid secretion was markedly reduced. The inhibitory effect on phospholipid secretion was also present when biliary lipid output had been previously increased by an infusion of taurocholate (200 nmol/100 g per min). Addition of taurocholate did not reverse the impairment of phospholipid secretion induced by piperacillin. Reference: Clin Exp Pharmacol Physiol. 2002 Oct;29(10):880-4. https://pubmed.ncbi.nlm.nih.gov/12207566/

Preparing Stock Solutions

The following data is based on the product molecular weight 535.57 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Jiang S, Li T, Zhou X, Qin W, Wang Z, Liao Y. Antibiotic drug piperacillin induces neuron cell death through mitochondrial dysfunction and oxidative damage. Can J Physiol Pharmacol. 2018 Jun;96(6):562-568. doi: 10.1139/cjpp-2016-0679. Epub 2017 Jul 31. PMID: 28759731. 2. Morikawa Y, Kitazato M, Mitsuyama J, Mizunaga S, Minami S, Watanabe Y. In vitro activities of piperacillin against beta-lactamase-negative ampicillin-resistant Haemophilus influenzae. Antimicrob Agents Chemother. 2004 Apr;48(4):1229-34. doi: 10.1128/AAC.48.4.1229-1234.2004. PMID: 15047524; PMCID: PMC375295. 3. González P, Mauriz JL, Jiménez R, González-Gallego J, Tuñón MJ. Choleresis and inhibition of biliary lipid secretion induced by piperacillin in the rat. Clin Exp Pharmacol Physiol. 2002 Oct;29(10):880-4. doi: 10.1046/j.1440-1681.2002.03744.x. PMID: 12207566.

In vitro protocol:

In vivo protocol:

1. González P, Mauriz JL, Jiménez R, González-Gallego J, Tuñón MJ. Choleresis and inhibition of biliary lipid secretion induced by piperacillin in the rat. Clin Exp Pharmacol Physiol. 2002 Oct;29(10):880-4. doi: 10.1046/j.1440-1681.2002.03744.x. PMID: 12207566.