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MedKoo Cat#: 574487 | Name: Piperacillin
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Description:

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

Piperacillin is an antibiotic.

Chemical Structure

Piperacillin
Piperacillin
CAS#61477-96-1

Theoretical Analysis

MedKoo Cat#: 574487

Name: Piperacillin

CAS#: 61477-96-1

Chemical Formula: C23H27N5O7S

Exact Mass: 517.1631

Molecular Weight: 517.56

Elemental Analysis: C, 53.38; H, 5.26; N, 13.53; O, 21.64; S, 6.19

Price and Availability

Size Price Availability Quantity
1g USD 270.00 2 Weeks
5g USD 810.00 2 Weeks
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Related CAS #
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Synonym
Piperacillin; CL 227193; Isipen; Pentcillin; Pipracil; T 1220
IUPAC/Chemical Name
(2S,5R,6R)-6-[[(2R)-2-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid
InChi Key
IVBHGBMCVLDMKU-GXNBUGAJSA-N
InChi Code
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
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)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 is an 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 517.56 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.

Recalculate based on batch purity %
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:
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.
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.