Piperacillin Sodium - ≥98%(N) , Bacterial penicillin-binding protein inhibitor, CAS No.59703-84-3, Bacterial penicillin-binding protein inhibitor

CAS: 59703-84-3 Cat. No.: P129602 Formula: C₂₃H₂₆N₅NaO₇S Molecular Weight: 539.54 Beilstein Registry Number: 5373920 EC Number: 261-868-6

GRADE & PURITY ≥98%(N)

Synonyms

PIPERACILLIN SODIUM|Opera_ID_1140|Piperacillin (as sodium)|Pipracil|PIPERACILLIN SODIUM (USP MONOGRAPH)|PIPERACILLIN SODIUM [USP MONOGRAPH]|PIPERACILLIN SODIUM [VANDF]|L-a-Aminoglutaric acid|PIPERACILLIN SODIUM SALT|Piperacillin sodium (JP17/USP)|7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate|Piperacillin sodium (USAN:USP:JAN)|Sodium (2S,5R,6R)-6-[(R)-2-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate|CL 227,193|Pentcillin (TN)|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|Salt, Piperacillin Monosodium|Sodium;(2S,5R,6R)-6-[[(2S)-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|Penmalin|PIPERACILLIN SODIUM (EP MONOGRAPH)|sodium (2S,5R,6R)-6-((R)-2-(4-ethyl-2,3-dioxopiperazine-|ZOSYN COMPONENT PIPERACILLIN SODIUM|CL 227193|Pentcillin|PIPERACILLIN SODIUM [EP MONOGRAPH]|Pipracil (TN)|Sodium piperacillin|Piperacillin sodium [USAN:USP:JAN]|PIPERACILLIN SODIUM [WHO-DD]|Pipracil Sterile|Monosodium (2S,5R,6R)-6-((2R)-2-((4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino)-2-phenylacetylamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate|PIPERACILLIN SODIUM [JAN]|Sodium, Piperacillin|1-carboxamido)-2-phenylacetamido)-3,3-dimethyl-|Monosodium Salt, Piperacillin|N-Benzyl-2-(2-nitro-imidazol-1-yl)-acetamide|sodium 6beta-{(2R)-2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-2-phenylacetamido}-2,2-dimethylpenam-3alpha-carboxylate|PIPERACILLIN SODIUM [ORANGE BOOK]|4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)phenylacetyl)amino)-3,3-dimethyl-7-oxo-, monosodium salt, (2S-(2alpha,5alpha,6beta(S*)))-|Cl-227193|4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)phenylacetyl)amino)-3,3-dimethyl-7-oxo-, monosodium salt, (2S-(2alpha,5alpha,6beta(S*)))|PIPERACILLIN SODIUM [USAN]|Sodium (2S,5R,6R)-6-((R)-2-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate|sodium 6beta-((2R)-2-((4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido)-2-phenylacetamido)-2,2-dimethylpenam-3alpha-carboxylate|(.+/-.)-p-Methoxy-.alpha.-methylphenethylamine|Zosyn Sterile|Sodium (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-carboxylate

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

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

Specifications

Synonyms

PIPERACILLIN SODIUM | Opera_ID_1140 | Piperacillin (as sodium) | Pipracil | PIPERACILLIN SODIUM (USP MONOGRAPH) | PIPERACILLIN SODIUM [USP MONOGRAPH] | PIPERACILLIN SODIUM [VANDF] | L-a-Aminoglutaric acid | PIPERACILLIN SODIUM SALT | Piperacillin sodium (JP17/USP) | 7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | Piperacillin sodi Show more

Specifications & Purity

≥98%(N)

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 -20°C,Argon charged

Shipped In

Ice chest + Ice pads

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

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%(N)

Names and Identifiers

Pubchem Sid

504769534

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504769534

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=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 N-acyl-alpha amino acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: N-acyl-alpha amino acids and derivatives
• Alternative Parents: Penams Dioxopiperazines N-acyl ureas N-alkylpiperazines Benzene and substituted derivatives Thiazolidines Tertiary carboxylic acid amides Azetidines Isoureas Azacyclic compounds Thiohemiaminal derivatives Propargyl-type 1,3-dipolar organic compounds Carboximidamides Carboxylic acids Dialkylthioethers Monocarboxylic acids and derivatives Organopnictogen compounds Hydrocarbon derivatives Organic zwitterions Carbonyl compounds Organic sodium salts Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: N-acyl-alpha amino acid or derivatives - Dioxopiperazine - Penam - N-acyl urea - Ureide - N-alkylpiperazine - Monocyclic benzene moiety - 1,4-diazinane - Piperazine - Benzenoid - Beta-lactam - Tertiary carboxylic acid amide - Thiazolidine - Lactam - Isourea - Carboxamide group - Azetidine - Propargyl-type 1,3-dipolar organic compound - Hemithioaminal - Thioether - Carboximidic acid - Carboxylic acid - Organic alkali metal salt - Azacycle - Carboximidic acid derivative - Monocarboxylic acid or derivatives - Carboximidamide - Organoheterocyclic compound - Organic 1,3-dipolar compound - Dialkylthioether - Organic salt - Organic oxide - Organopnictogen compound - Organic oxygen compound - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Organic nitrogen compound - Carbonyl group - Organic sodium salt - Organic zwitterion - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
• External Descriptors: organic sodium salt

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

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

• Solubility: DMSO 100 mg/mL Water 100 mg/mL Ethanol 100 mg/mL Soluble in ethanol, water and methanol
• 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