L-Piperacillin , CAS No.2743427-34-9

CAS: 2743427-34-9 Cat. No.: L964650 Formula: C₂₃H₂₇N₅O₇S Molecular Weight: 517.600

Storage

Room temperature

Specifications

Storage

Room temperature

Names and Identifiers

Canonical 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

IUPAC Name

(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-carboxylic acid

InChIKey

IVBHGBMCVLDMKU-LDNFRZNASA-N

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+/m0/s1

Molecular Weight

517.600

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Not available
• Direct Parent: Peptides
• Alternative Parents: Penicillins N-acyl-alpha amino acids and derivatives N-carbamoyl-alpha amino acids and derivatives Alpha amino acid amides Phenylacetamides Piperazine carboxamides Dioxopiperazines N-acyl ureas N-alkylpiperazines Tertiary carboxylic acid amides Thiazolidines Dicarboximides Secondary carboxylic acid amides Azetidines Azacyclic compounds Thiohemiaminal derivatives Monocarboxylic acids and derivatives Dialkylthioethers Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds Organonitrogen compounds Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Alpha peptide - Penicillin - N-acyl-alpha amino acid or derivatives - N-carbamoyl-alpha-amino acid or derivatives - Alpha-amino acid amide - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Phenylacetamide - Piperazine-1-carboxamide - Dioxopiperazine - Penam - N-alkylpiperazine - Ureide - N-acyl urea - Benzenoid - Monocyclic benzene moiety - 1,4-diazinane - Piperazine - Beta-lactam - Dicarboximide - Thiazolidine - Tertiary carboxylic acid amide - Azetidine - Urea - Carboxamide group - Secondary carboxylic acid amide - Lactam - Carbonic acid derivative - Monocarboxylic acid or derivatives - Azacycle - Thioether - Hemithioaminal - Carboxylic acid - Dialkylthioether - Organoheterocyclic compound - Hydrocarbon derivative - Carbonyl group - Organic oxygen compound - Organopnictogen compound - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
• External Descriptors: Not available

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

Chemical and Physical Properties

• Molecular Weight: 517.600 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 517.163 Da
• Monoisotopic Mass: 517.163 Da
• Topological Polar Surface Area: 182.000 Ų
• Heavy Atom Count: 36
• Formal Charge: 0
• Complexity: 982.000
• 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: 1

Application Protocols

No tested application protocols (e.g., WB, IHC, IF, FC) apply to this small-molecule product, and none are provided in the product data. For general laboratory use:

• Solution preparation (general): Dissolve the compound in an appropriate solvent (e.g., water for salts; DMSO for free acid or for stock solutions), then dilute into buffer immediately prior to use. Filter-sterilize if needed.
• Analytical assay setup: Develop a stability-indicating HPLC method to confirm concentration and integrity prior to quantitative experiments.

Refer to your internal SOPs and method development data for application-specific parameters.

Biological Roles

The following describes general biochemical roles of ureidopenicillins and is provided for research context only; it does not imply clinical use.

• Molecular target class (literature): Penam beta-lactams acylate active-site serine residues of bacterial D,D-transpeptidases (also known as penicillin-binding proteins, PBPs), transiently forming acyl-enzyme complexes that block peptidoglycan crosslinking.
• Structure–function: The strained beta-lactam ring is essential for acylation kinetics; the urea-extended side chain of ureidopenicillins improves access/affinity to certain PBPs, particularly in Gram-negative organisms.
• Resistance mechanisms: Hydrolysis by class A/C/D beta-lactamases, decreased outer-membrane permeability, and altered PBPs can reduce apparent activity (mechanistic overview only).
• Physicochemical determinants: Ionization state (carboxylate and basic nitrogens) controls membrane passage and target engagement; stereochemistry at the penam core is required for productive binding.
• In vitro assay use: Common in enzyme kinetics to probe PBP acylation/deacylation rates, and in beta-lactamase turnover studies to map substrate scope.

Item-specific biological data (potency, spectrum, MICs, target preferences) are not provided for this SKU and should not be inferred. For quantitative or comparative studies, establish your own reference curves and confirm identity/purity by LC–MS prior to use.

Buffer Applications

This compound is not a buffer reagent. However, buffer choice is important when preparing solutions for in vitro research with beta-lactams.

General guidance (literature; not item-specific):

• pH window: Beta-lactams show improved stability in mildly acidic to neutral conditions. Buffers around pH 5.5–6.5 (e.g., citrate, MES, phosphate) are commonly used to balance solubility and stability.
• Ionic strength: Moderate ionic strength (10–50 mM buffer) is usually sufficient for kinetic or binding assays without promoting hydrolysis.
• Additives: Avoid primary amines (e.g., Tris) if acylation side reactions are a concern over long incubations. Use low-binding plastics to minimize adsorption for dilute solutions.
• Preparation: If using DMSO stocks, add to vigorously stirred buffer to achieve final DMSO ≤1–2% v/v. Filter (0.22 µm) if sterility is required for cell-free systems.

Item-specific buffer compatibility, buffer recipes, and pKa values are not provided and should be confirmed experimentally for your assay conditions.

Green Alternatives

Greener chemistry discussion is only partially applicable because L-Piperacillin is a target molecule rather than a process solvent or reagent. Nonetheless, sustainability considerations can be applied to its handling and formulation.

Considerations (general):

• Aqueous-first workflows: Prefer water or buffered aqueous media over organic solvents whenever solubility allows (particularly for sodium salts). This reduces VOC emissions and waste hazard classification.
• Minimal organic cosolvent: If DMSO is required to dissolve the material, prepare concentrated stocks and dilute immediately into aqueous buffer to keep final DMSO below 1–2% v/v.
• Avoid halogenated solvents: Use acetonitrile or ethanol (if compatible) instead of dichloromethane or chloroform for analytical sample prep.
• Solid-state processing: For stability studies or formulations, employ dry blending or aqueous granulation in place of solvent-intensive steps when feasible.

Illustrative comparison (literature, qualitative; not item-specific):

• DMSO vs. 2-propanol: DMSO offers higher solubility but is less desirable from a green metrics standpoint; 2-propanol or ethanol may suffice for short exposures if solubility permits.
• Buffer at pH ~6 vs. basic aqueous media: Comparable performance for many in vitro assays with improved chemical stability and reduced degradant formation.

Waste management:

• Collect beta-lactam-containing waste separately to prevent unintended exposure; treat as hazardous organic aqueous waste per institutional policy.

Pharmaceutical Uses

No clinical or therapeutic claims are made for this research-use product. The following notes describe formulation/manufacturing context for the compound class (literature; not item-specific to this SKU).

• Role: Ureidopenicillins (e.g., piperacillin salts) are active pharmaceutical ingredients (APIs) used in parenteral dosage forms. For research, the substance may serve as a reference standard in QC methods or formulation development studies.
• Common form: The sodium salt is typically used for aqueous solubility and parenteral compatibility; free acid forms may be used as intermediates or for salt screening.
• Compendial status: Specific salt/hydrate forms may have USP/EP/JP monographs. Verify whether the exact substance offered (free acid vs. sodium salt; hydrate state) corresponds to a pharmacopeial monograph before adopting compendial methods.
• Excipients and compatibility (general): pH-adjusting agents (e.g., sodium citrate), antioxidants minimizing oxidative degradants, and cryoprotectants for lyophilization may be explored in development studies.
• Stability concerns: Hydrolysis and beta-lactam ring opening are the primary degradation pathways; stability-indicating methods (HPLC with gradient elution, MS detection) are standard for monitoring.

For regulated work, ensure sourcing of appropriate GMP/compliant grade with full impurity and residual solvent profiles. This catalog item is designated “For research use only.”

Physical Properties

Item-specific specifications are not provided in the product data. Where useful, representative literature values for piperacillin or its salts are noted for context and must not be treated as specifications.

Item-specific (this SKU):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point/boiling point: Not specified for this item; refer to CoA/Spec Sheet.
• Density, refractive index, UV cutoff, water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general context (non-spec):

• Piperacillin free acid is typically sparingly soluble in water; its sodium salt is freely soluble in water and poorly soluble in most nonpolar organics.
• pKa values (penicillins, general): carboxylate pKa ~2–3; additional basic nitrogens in the ureido/heterocycle can affect net charge and solubility depending on pH.
• LogP/logD: ureidopenicillins tend to be polar with low logP; effective partitioning depends strongly on ionization state.

Practical notes (general):

• Hygroscopicity can be formulation dependent (free acid vs. sodium salt). Handle quickly in ambient air if material is hygroscopic; confirm with CoA.
• For analytical characterization, HPLC with aqueous buffers is commonly used; UV absorbance arises mainly from amide/urea chromophores (no strong chromophore).

Quality & Grades

Product-specific grade and purity are not provided in the listing and must be confirmed on the CoA/Spec Sheet for SKU L964650.

Guidance on typical grades for this compound class (general):

• Research grade: Suitable for non-GLP discovery work, method development, and mechanistic studies. May not include pharmacopeial testing.
• USP/EP/JP compendial grade (when applicable to a given API or salt form): Meets identity, purity, impurities profile, and performance tests defined in the pharmacopeia. If required, verify whether the exact substance (free acid vs. sodium salt, hydrate state) has a monograph.
• Sterile/pharmaceutical grade: Additional sterility, endotoxin, and bioburden controls; often provided for formulation or fill-finish workflows. Not implied for this item absent explicit labeling.

Stabilizers and form (general):

• Some beta-lactam materials are offered as sodium salts or as sterile powders; stabilizers, if any, should be declared on the CoA. For this item, stabilizers and exact form are not specified; refer to CoA/Spec Sheet.

What to check on receipt:

• Identity by HPLC/LC–MS and NMR (where feasible).
• Water content (KF) and residual solvents (GC) if your application is moisture-sensitive.
• Potency/content assay vs. reference standard when quantitative use is intended.

Note: The catalog states “For research use only.” This item is not supplied for human or veterinary use.

Reaction & Applications

As a complex beta-lactam API-class molecule, L-Piperacillin is generally used as a reference standard, analytical substrate, or for mechanistic/biochemical research rather than as a generic building block. No manufacturer application text is provided for this SKU; the notes below expand on general research uses (literature) without implying clinical use.

Representative research applications (general):

• Analytical standards: method development and validation for impurity profiling, stability-indicating HPLC assays, and LC–MS quantitation in complex matrices.
• Degradation studies: hydrolysis kinetics of beta-lactams under varying pH/temperature; identification of ring-opened products and urea side-chain transformations.
• Beta-lactamase interaction studies: enzyme kinetics, inhibition, and turnover measurements in purified systems (non-clinical mechanistic research).
• Formulation science: excipient compatibility, lyophilization cycle development, and solid-state stability screening (salt vs. free acid, hydrate states).

Practical tips (general):

• Minimize exposure to basic media and elevated temperatures to preserve the intact beta-lactam.
• Prepare aqueous solutions fresh; filter-sterilize through low-protein-binding membranes if sterility is required for in vitro assays.
• Use amber containers or minimize light exposure if photo-degradation is suspected; confirm via forced-degradation studies.
• Track pH drift during experiments; buffering near pH 6 typically gives improved chemical stability compared to alkaline conditions.

Note: Without item-specific purity/grade, application suitability should be confirmed by in-house analytical qualification prior to quantitative studies.

Reaction Conditions

There are no item-specific reaction conditions provided for this SKU. For researchers performing stability or derivatization studies on beta-lactams, the following literature-based guidance may be useful (non-spec):

• Hydrolysis kinetics (general):
  • Aqueous buffers, pH 5–7, 20–25°C: relatively slow ring opening; suitable for short-term experiments with minimal degradation.
  • pH > 8 or elevated temperature (>40°C): accelerated hydrolysis; useful for forced-degradation studies.
• Oxidation studies: Mild oxidants (e.g., H2O2, peracids) at low temperature generate sulfoxides; stronger/longer conditions lead to sulfones and additional fragmentation. Quench and neutralize promptly; analyze by LC–MS.
• Solvent systems: Water, phosphate/citrate buffers, and mixtures with acetonitrile are common for HPLC and sample prep. DMSO stocks can be diluted into buffer for biochemical assays.
• Typical timelines: Fresh solutions are preferably used within hours at ambient temperature; for overnight incubations, maintain 2–8°C or pH near 6 to limit degradation.
• Analytical monitoring: Use gradient RP-HPLC (C18) with UV 210–220 nm detection and MS confirmation to track intact compound and degradants. Validate mass balance during stress testing.

These conditions are general guidelines. Optimize experimentally for your matrix and target endpoints. Always defer to your method development data and the item’s CoA/SDS for constraints.

Safety & Handling

Authoritative safety information must be taken from the product’s SDS. The following are general considerations for penam beta-lactams.

Item-specific:

• Signal word, H-statements, GHS classification, pictograms: Not specified for this item; refer to SDS.
• Storage conditions (from Product Data): Room temperature.

General hazards (literature; not item-specific):

• Sensitization: Beta-lactam compounds are well-known skin and respiratory sensitizers. Trace exposure may elicit allergic reactions in sensitized individuals. Use containment and avoid aerosol formation.
• Irritation: Dust may cause eye, skin, and respiratory tract irritation.
• Decomposition: Beta-lactams may hydrolyze in aqueous/basic conditions; thermal decomposition may release nitrogen oxides and sulfur-containing compounds.

PPE and handling:

• Wear lab coat, gloves (nitrile), and safety glasses. Work in a chemical fume hood or ventilated enclosure, especially when weighing powders.
• Avoid inhalation and skin contact; use disposable weigh boats and bench protection.
• Prevent cross-contamination of balances and communal areas if personnel with known penicillin allergies are present.

Incompatibilities and stability (general):

• Avoid strong bases and prolonged exposure to water at elevated temperature (beta-lactam hydrolysis).
• Avoid oxidizing agents that can modify sulfur-containing motifs.

First aid (overview; defer to SDS):

• Skin/eye contact: Rinse with water for ≥15 min; remove contaminated clothing.
• Inhalation: Move to fresh air; seek medical attention if symptoms persist.
• Ingestion: Rinse mouth; seek medical advice. Bring SDS.

Solvent Selection

This product is a solid small-molecule beta-lactam, not a solvent. Solvent selection here pertains to dissolving/processing the compound for analytical or research workflows.

Item-specific solubility is not provided and must be confirmed on the CoA. The following are literature-based guidelines for ureidopenicillins:

• Aqueous systems:
  • Free acid form: typically sparingly soluble in neutral water; improved solubility in mildly basic aqueous media can accelerate hydrolysis—use caution.
  • Sodium salt: readily soluble in water and many aqueous buffers; prepare fresh solutions to minimize hydrolysis.
• Organic solvents:
  • Polar aprotic solvents (DMF, DMSO) can dissolve both free acid and salts; small DMSO stocks (e.g., 10–50 mg/mL) are commonly used and then diluted into buffer immediately before use.
  • Alcohols (methanol, ethanol) may offer limited solubility; monitor for transesterification/hydrolysis under basic conditions.
• pH considerations:
  • Maintain pH ~5–7 during aqueous handling to balance solubility and beta-lactam stability. Strongly basic conditions accelerate ring opening.

Comparison (literature, qualitative):

• Water (neutral): best for sodium salt; limited for free acid; highest chemical compatibility.
• DMSO: broad solvating power; use minimal volumes; avoid prolonged storage in solution.
• Buffer with stabilizers: phosphate or citrate buffers near pH 6 can improve stability vs. alkaline media.

Always verify the supplied form (acid vs. sodium) and follow the CoA for solvent compatibility.

Storage & Reconstitution

Item-specific storage from Product Data:

• Storage conditions: Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

General guidance (literature; not item-specific):

• Solid storage: Keep tightly closed in original container, protected from moisture and excessive heat. If the material is hygroscopic, minimize exposure time when weighing. Consider desiccant and light protection.
• Reconstitution: Determine the supplied form (free acid vs. sodium salt) from the CoA.
  • Aqueous reconstitution (typical for sodium salts): Use cold, degassed water or buffer at pH ~6. Prepare fresh solutions and use promptly.
  • Organic reconstitution (for free acid or concentrated stocks): Use DMSO or DMF to prepare a stock solution; dilute into buffer immediately before use to limit beta-lactam hydrolysis.
• Solution stability: Beta-lactams are prone to hydrolysis in aqueous/basic media. If solution storage is unavoidable, refrigerate (2–8°C), protect from light, and verify integrity by HPLC before use. Avoid freezing–thawing cycles; aliquot stocks to single-use volumes.

Research use only: Not for human or veterinary use. Always consult the CoA and SDS for definitive storage and handling instructions.

Structure & Identity

Brief overview: L-Piperacillin is a ureidopenicillin (beta-lactam/penam scaffold) bearing an extended urea side chain that enhances Gram-negative spectrum (general chemical classification; literature). For this catalog item, detailed identifiers are not provided.

• SKU: L964650
• Product name: L-Piperacillin
• CAS: 2743427-34-9 (as provided)
• InChIKey: 151280 (as provided; note: non-standard length, verify on CoA/SDS)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (literature/general):

• Core: penam bicyclic system (fused beta-lactam and thiazolidine rings) with a thioether bridge.
• Functional groups: beta-lactam amide (strained four-membered lactam), secondary amide(s), urea (–NH–CO–NH–), carboxylic acid (or carboxylate in salt form), and thioether sulfur.
• Side chain: ureido substituent terminating in a piperazine-/piperazine-like moiety; enhances polarity and spectrum relative to benzylpenicillin (general description).
• Stereochemistry: penicillins possess defined stereocenters at C-2, C-5, and C-6 of the penam core; configuration is critical to biological recognition (literature). Exact stereochemical descriptors for this item are not specified here; refer to CoA.

2D structure in words (literature): a bicyclic beta-lactam fused to a five-membered thiazolidine, bearing a carboxylate at C-3 and an acylamino side chain at C-6 that is further extended via a urea linkage to a nitrogen-containing heterocycle.

Synthetic Utility

L-Piperacillin is a complex, densely functionalized beta-lactam and is not typically employed as a generic synthetic building block. Nonetheless, understanding its reactivity is valuable for degradation mapping, prodrug design, or derivatization studies (literature; not item-specific).

Key functional groups and behaviors:

• Beta-lactam ring: Nucleophile-induced ring opening (e.g., hydroxide, amines) leading to penicilloate/penicillanate derivatives; rate increases with pH and temperature.
• Carboxylic acid (or carboxylate): Salt formation and ion-pairing influence solubility/crystallinity; esterification can be used for prodrug analogs under carefully controlled conditions to avoid beta-lactam cleavage.
• Urea side chain: Potential site for hydrogen-bonding interactions; can be modified in structure–activity relationship (SAR) studies on related scaffolds.
• Thioether: Susceptible to oxidation to sulfoxide/sulfone under strong oxidants, useful for forced-degradation studies.

Applications in the lab:

• Reference impurities: Intentional hydrolysis/oxidation to produce known degradants for system suitability and peak identification in stability-indicating methods.
• Derivatization: Transient protection strategies (e.g., silylation of acids) are possible but must be carefully tuned to preserve the beta-lactam.

Caveats:

• Strong bases, prolonged heating, and nucleophilic reagents typically compromise the beta-lactam; low-temperature, neutral to mildly acidic conditions are preferred when handling the intact molecule.

Target Specificity

Not applicable. This product is a small-molecule beta-lactam, not an antibody or affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information applies. For mechanistic details on molecular targets relevant to this compound class, see the Biological Roles section.