Piperacillin Sodium | CAS#59703-84-3 | PBP inactivator

MedKoo Cat#: 318497 | Name: Piperacillin sodium

Featured

Description:

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

Piperacillin sodium is an antibiotic related to penicillin. Piperacillin binds to and inactivates penicillin-binding proteins (PBPs), enzymes located on the inner membrane of the bacterial cell wall, resulting in the weakening of the bacterial cell wall and cell lysis.

Chemical Structure

Piperacillin sodium

CAS#59703-84-3

Theoretical Analysis

MedKoo Cat#: 318497

Name: Piperacillin sodium

CAS#: 59703-84-3

Chemical Formula: C23H26N5NaO7S

Exact Mass: 0.0000

Molecular Weight: 539.54

Elemental Analysis: C, 51.20; H, 4.86; N, 12.98; Na, 4.26; O, 20.76; S, 5.94

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 250.00
10mg	USD 300.00
25mg	USD 350.00
50mg	USD 400.00
100mg	USD 450.00
200mg	USD 500.00
500mg	USD 550.00
1g	USD 650.00
2g	USD 750.00
5g	USD 850.00
10g	USD 1,050.00

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Piperacillin Sodium; PIPERACILLIN SODIUM SALT; Pipracil; Sodium piperacillin; Piperacillin (sodium);curasan Brand of Piperacillin Sodium; Fresenius Brand of Piperacillin Sodium; Hexal Brand of Piperacillin Sodium; Pipera-hameln; Piperacillin; Piperacillin curasan;

IUPAC/Chemical Name

sodium;(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-carboxylate

InChi Key

WCMIIGXFCMNQDS-UHFFFAOYSA-M

InChi Code

InChI=1S/C23H27N5O7S.Na/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);/q;+1/p-1

SMILES Code

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-].[Na+]

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, not in water

Shelf Life

>2 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 sodium is a broad-spectrum 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/

	Solvent	mg/mL	mM
Solubility
	DMF	10.0	18.53
	DMSO	70.0	129.74
	Ethanol	50.5	93.60
	PBS (pH 7.2)	3.0	5.56
	Water	100.0	185.34

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 539.54 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.

1: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Piperacillin and Tazobactam. 2024 Jul 15. PMID: 30000127. 2: Zhang H, Yang L. Adverse reactions of piperacillin: A literature review of case reports. Open Med (Wars). 2024 Apr 10;19(1):20240931. doi: 10.1515/med-2024-0931. PMID: 38623456; PMCID: PMC11017182. 3: Feng Y, Zuo CL, Shi JX. Brucella infection combined with Nocardia infection: A case report and literature review. Open Life Sci. 2024 Feb 3;19(1):20220815. doi: 10.1515/biol-2022-0815. PMID: 38465335; PMCID: PMC10921472. 4: Yin W, Wen B, Wang G, Wang Z, Kong X, Wu Y, Meng X, Ou X, Wei L, Yu P. Clinical characteristics and risk factors analysis of 505 cases of infusion reactions in a tertiary hospital. Front Pharmacol. 2024 Feb 6;15:1292347. doi: 10.3389/fphar.2024.1292347. PMID: 38379900; PMCID: PMC10876897. 5: Zhan Z, Lin X, Li G, Zeng J, Su D, Liao J, Shen Q. Renal abscess complicating acute pyelonephritis in children: Two cases report and literature review. Medicine (Baltimore). 2023 Dec 1;102(48):e36355. doi: 10.1097/MD.0000000000036355. PMID: 38050281; PMCID: PMC10695508. 6: Chuiprasert J, Srinives S, Boontanon N, Polprasert C, Ramungul N, Lertthanaphol N, Karawek A, Boontanon SK. Electrochemical Sensor Based on a Composite of Reduced Graphene Oxide and Molecularly Imprinted Copolymer of Polyaniline-Poly(o-phenylenediamine) for Ciprofloxacin Determination: Fabrication, Characterization, and Performance Evaluation. ACS Omega. 2023 Jan 3;8(2):2564-2574. doi: 10.1021/acsomega.2c07095. PMID: 36687093; PMCID: PMC9850462. 7: Peng J, Li B, He X, Ding C. Lung infection caused by Blastoschizomyces capitatus without immunodeficiency: a case report and review of the literature. Ann Palliat Med. 2022 Dec;11(12):3826-3832. doi: 10.21037/apm-22-1289. PMID: 36636006. 8: Lu HY, Gao YB, Qiu XW, Wang Q, Liu CM, Huang XW, Chen HY, Zeng K, Li CX. Successful surgical treatment of polybacterial gas gangrene confirmed by metagenomic next-generation sequencing detection: A case report. World J Clin Cases. 2022 Dec 16;10(35):13064-13073. doi: 10.12998/wjcc.v10.i35.13064. PMID: 36568998; PMCID: PMC9782953. 9: Pan D, Peng P, Fang Y, Lu J, Fang M. Distribution and Drug Resistance of Pathogenic Bacteria and Prognosis in Patients with Septicemia Bloodstream Infection with Renal Insufficiency. Infect Drug Resist. 2022 Jul 28;15:4109-4116. doi: 10.2147/IDR.S373665. PMID: 35924018; PMCID: PMC9342692. 10: Duan T. Analysis of Microbiological and Clinical Characteristics of Bacterial Infection in Patients with Pulmonary Infection. Comput Intell Neurosci. 2022 Jun 16;2022:5607358. doi: 10.1155/2022/5607358. Retraction in: Comput Intell Neurosci. 2022 Dec 26;2022:9829341. doi: 10.1155/2022/9829341. PMID: 35755768; PMCID: PMC9225854. 11: Zhu C, Lv M, Huang J, Zhang C, Xie L, Gao T, Han B, Wang W, Feng G. Bloodstream infection and pneumonia caused by Chlamydia abortus infection in China: a case report. BMC Infect Dis. 2022 Feb 23;22(1):181. doi: 10.1186/s12879-022-07158-z. PMID: 35197012; PMCID: PMC8867867. 12: Wang XX, Ma CT, Jiang YX, Ge YJ, Liu FY, Xu WG. Cefoperazone sodium/sulbactam sodium vs piperacillin sodium/tazobactam sodium for treatment of respiratory tract infection in elderly patients. World J Clin Cases. 2021 Oct 16;9(29):8694-8701. doi: 10.12998/wjcc.v9.i29.8694. PMID: 34734047; PMCID: PMC8546814. 13: Wang P, Yi ML, Zhang CZ. Nocardiosis with diffuse involvement of the pleura: A case report. World J Clin Cases. 2021 Aug 16;9(23):6824-6831. doi: 10.12998/wjcc.v9.i23.6824. PMID: 34447831; PMCID: PMC8362512. 14: Lan S, Li Z, Su A, Peng Y, Liao Y, Liu X, Tan Q. Study on the mechanisms of the cross-resistance to TET, PIP, and GEN in Staphylococcus aureus mediated by the Rhizoma Coptidis extracts. J Antibiot (Tokyo). 2021 May;74(5):330-336. doi: 10.1038/s41429-021-00407-4. Epub 2021 Jan 26. PMID: 33500562. 15: Geng HJ, Xie YM, Zhang M. [Effect of Xingnaojing Injection in treatment of cerebral hemorrhage based on Tabu search algorithm:a real world study]. Zhongguo Zhong Yao Za Zhi. 2020 Jul;45(14):3316-3323. Chinese. doi: 10.19540/j.cnki.cjcmm.20200314.502. PMID: 32726045. 16: Wang XX, Jin PF, Li PM, Xu S, Kong XD, Qin W, Chen WQ, Qin WJ, Zhang XL. Interlaboratory analysis of teicoplanin plasma concentration assays among Chinese laboratories. J Clin Pharm Ther. 2020 Oct;45(5):983-990. doi: 10.1111/jcpt.13115. Epub 2020 Jan 27. PMID: 31985852. 17: Tartof SY, Kuntz JL, Chen LH, Wei R, Puzniak L, Tian Y, Im TM, Takhar HS, Merchant S, Lodise T. Development and Assessment of Risk Scores for Carbapenem and Extensive β-Lactam Resistance Among Adult Hospitalized Patients With Pseudomonas aeruginosa Infection. JAMA Netw Open. 2018 Oct 5;1(6):e183927. doi: 10.1001/jamanetworkopen.2018.3927. PMID: 30646267; PMCID: PMC6324445. 18: Hernández-Avilés C, Serafini R, Love CC, Teague SR, LaCaze KA, Lawhon SD, Wu J, Blanchard TL, Varner DD. The effects of antibiotic type and extender storage method on sperm quality and antibacterial effectiveness in fresh and cooled- stored stallion semen. Theriogenology. 2018 Dec;122:23-29. doi: 10.1016/j.theriogenology.2018.08.022. Epub 2018 Aug 28. PMID: 30219312. 19: Downes KJ, Cowden C, Laskin BL, Huang YS, Gong W, Bryan M, Fisher BT, Goldstein SL, Zaoutis TE. Association of Acute Kidney Injury With Concomitant Vancomycin and Piperacillin/Tazobactam Treatment Among Hospitalized Children. JAMA Pediatr. 2017 Dec 4;171(12):e173219. doi: 10.1001/jamapediatrics.2017.3219. Epub 2017 Dec 4. PMID: 28973124; PMCID: PMC6583633. 20: Chang X, Xu Y, Liu C. A rapid and sensitive colorimetric measurement of antibiotic efficacy against Escherichia coli in vitro. FEMS Microbiol Lett. 2016 Apr;363(7):fnw037. doi: 10.1093/femsle/fnw037. Epub 2016 Feb 17. PMID: 26892018.