Piperacillin sulfoxide | CAS# 67275-27-8 | Semi-synthetic Penicillin derivative

MedKoo Cat#: 574489 | Name: Piperacillin sulfoxide

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Description:

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

Piperacillin sulfoxide is a derivative compound of Piperacilin -- a broad spectrum semi-synthetic antibiotic related to Penicillin.

Chemical Structure

Piperacillin sulfoxide

CAS#67275-27-8

Theoretical Analysis

MedKoo Cat#: 574489

Name: Piperacillin sulfoxide

CAS#: 67275-27-8

Chemical Formula: C23H27N5O8S

Exact Mass: 533.1580

Molecular Weight: 533.56

Elemental Analysis: C, 51.78; H, 5.10; N, 13.13; O, 23.99; S, 6.01

Price and Availability

Size	Price	Availability
10mg	USD 375.00	2 Weeks
25mg	USD 720.00	2 Weeks
100mg	USD 1,265.00	2 Weeks
250mg	USD 2,145.00	2 Weeks

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Synonym

Piperacillin sulfoxide

IUPAC/Chemical Name

(2S,5R,6R)-6-((R)-2-(4-Ethyl-2,3-dioxopiperazine-1-carboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid 4-Oxide

InChi Key

GRUJPMFLVBFNDC-ZBRIBHSASA-N

InChi Code

InChI=1S/C23H27N5O8S/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)37(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-,37?/m1/s1

SMILES Code

O=C([C@@H](C(C)(C)S([C@]1([H])[C@@H]2NC([C@H](NC(N3C(C(N(CC)CC3)=O)=O)=O)C4=CC=CC=C4)=O)=O)N1C2=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:

Piperacillin sulfoxide is a derivative compound of Piperacilin -- a broad spectrum semi-synthetic antibiotic related to Penicillin.

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 533.56 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.

Navle, K., Prasanna, B. L., Dometti, H. S., & Moodu, S. (2017). STABILITY INDICATING RP-HPLC METHOD FOR THE DETERMINATION OF PIPERACILLIN AND TAZOBACTAM AND THEIR RELATED SUBSTANCES IN BULK AND PHARMACEUTICAL FORMULATION.