Piperacillin Sodium - 10mM in DMSO , Bacterial penicillin-binding protein inhibitor, CAS No.59703-84-3, Bacterial penicillin-binding protein inhibitor

CAS: 59703-84-3 Cat. No.: P424968 Molecular Weight: 539.54 Beilstein Registry Number: 5373920 EC Number: 261-868-6

GRADE & PURITY 10mM in DMSO

Synonyms

PIPERACILLIN SODIUM | CL 227, 193 | Opera_ID_1140 | NSC 757277 | Piperacillin (as sodium) | Pipracil | T 1220 | PIPERACILLIN SODIUM (USP MONOGRAPH) | HMS1570G12 | PIPERACILLIN SODIUM [USP MONOGRAPH] | Q27108010 | PIPERACILLIN SODIUM [VANDF] | WCMIIGXFCMNQ

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Piperacillin is a semisynthetic, broad-spectrum, ampicillin derived ureidopenicillin antibiotic proposed for pseudomonas infections.
An antibiotic related to penicillin

Specifications

Synonyms

PIPERACILLIN SODIUM | CL 227, 193 | Opera_ID_1140 | NSC 757277 | Piperacillin (as sodium) | Pipracil | T 1220 | PIPERACILLIN SODIUM (USP MONOGRAPH) | HMS1570G12 | PIPERACILLIN SODIUM [USP MONOGRAPH] | Q27108010 | PIPERACILLIN SODIUM [VANDF] | WCMIIGXFCMNQ

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Piperacillin is anantibiotic. It is an extended-spectrum beta-lactam of the ureidopenicillin class.The chemical structure of Piperacillin and other ureidopenicillins incorporates a polar side chain that enhances penetration into Gram-(-) bacteria and redu

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Mechanism of action

Bacterial penicillin-binding protein inhibitor

Names and Identifiers

• 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-].[Na+]
• IUPAC 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
• InChIKey: WCMIIGXFCMNQDS-IDYPWDAWSA-M
• 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/t13-,14-,15+,20-;/m1./s1
• Isomeric SMILES: CCN1CCN(C(=O)C1=O)C(=O)N[C@H](C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)[O-].[Na+]
• Molecular Weight: 539.54
• Beilstein: 5373920
• Reaxy-Rn: 5714109
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=5714109&ln=

Associated Targets(Human)

HEK293 (82097 Activities)

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ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)

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ABCB11 Tchem Bile salt export pump (2311 Activities)

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ABCC3 Tbio Canalicular multispecific organic anion transporter 2 (718 Activities)

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MBNL1 Tbio Muscleblind-like protein 1 (34431 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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ABCC4 Tchem Multidrug resistance-associated protein 4 (785 Activities)

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Associated Targets(non-human)

ampC Beta-lactamase AmpC (62480 Activities)

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Cruzipain (33337 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Streptococcus (3973 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Enterococcus faecalis (29875 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Streptococcus sp. 'group A' (3417 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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ska Streptokinase A (5805 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: heat & moisture sensitive
• Specific Rotation[α]: 180° (C=0.8,H2O)
• Boil Point(°C): 793°C
• Melt Point(°C): 183-185°C
• Molecular Weight: 539.500 g/mol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 539.145 Da
• Monoisotopic Mass: 539.145 Da
• Topological Polar Surface Area: 185.000 Ų
• Heavy Atom Count: 37
• Formal Charge: 0
• Complexity: 989.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

References

1. Lan Sugui, Li Zhirong, Su Aiqiu, Peng Yanhong, Liao Yanke, Liu Xuemei, Tan Qiang.  (2021)  Study on the mechanisms of the cross-resistance to TET, PIP, and GEN in Staphylococcus aureus mediated by the Rhizoma Coptidis extracts.  JOURNAL OF ANTIBIOTICS,  74  (5): (330-336).  [PMID:33500562] [10.1038/s41429-021-00407-4]

2. Jie Jing, Chunlan Zeng, Long Tian, Jiaqi Han, Longming Chen, Taoran Wang, Zhao Meng, Qingbin Meng.  (2025)  The α-Helical Antibacterial Peptides Derived from Mastoparan with Broad-Spectrum Activity against Multidrug-Resistant Pathogens.  ACS Infectious Diseases,      [PMID:40248899] [10.1021/acsinfecdis.4c00944]

3. Zhou Li, Jia Zeng, Min Wang, Die Gao, Deng Li, Yingxi Zhu, Jiahao Lin, Zhiyu Chen, Famin Ke, Lixian Li, Dandan Wang.  (2025)  Enhanced specificity in molecular imprinting: A dual-role chitosan-bentonite substrate coupled with hierarchical monomers for ultrasensitive diclofenac potassium and metabolite enrichment.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:41067339] [10.1016/j.ijbiomac.2025.148144]