Laninamivir - 10mM in Water , CAS No.203120-17-6

CAS: 203120-17-6 Cat. No.: L654509 Formula: C₁₃H₂₂N₄O₇ Molecular Weight: 346.34

GRADE & PURITY 10mM in Water

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Laninamivir (R 125489) is a potent influenza neuraminidase (NA) inhibitor with IC 50 s of 0.90 nM, 1.83 nM and 3.12 nM for avian H12N5 NA (N5), pH1N1 N1 NA (p09N1) and A/RI/5+/1957 H2N2 N2 (p57N2), respectively

In Vitro

Laninamivir (R 125489) inhibits efficiently common oseltamivir-resistant viruses, including those with the ubiquitous His274Tyr substitution. Laninamivir (R 125489) is potent against p57N2, p09N1 and N5 with a similar binding mode to Zanamivir. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

IC50& Target:IC50: 0.90 nM (N5), 1.83 nM (p09N1), 3.12 nM (p57N2)

Specifications

Specifications & Purity

10mM in Water

Biochemical and Physiological Mechanisms

Laninamivir (R 125489) is a potent influenza neuraminidase (NA) inhibitor with IC 50 s of 0.90 nM, 1.83 nM and 3.12 nM for avian H12N5 NA (N5), pH1N1 N1 NA (p09N1) and A/RI/5+/1957 H2N2 N2 (p57N2), respectively.

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

Names and Identifiers

Isomeric SMILES

CC(=O)N[C@@H]1[C@H](C=C(O[C@H]1[C@@H]([C@@H](CO)O)OC)C(=O)O)N=C(N)N

Molecular Weight

346.34

Reaxy-Rn

24659410

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24659410&ln=

Application Protocols

• Item-specific

  • No tested applications or recommended protocols are provided in the Product Data for this item.

• General guidance (non-item-specific, illustrative only)

  • Enzymatic inhibition assay setup: Prepare fresh inhibitor dilutions in assay buffer, maintain constant DMSO across wells, and follow a standardized substrate incubation/readout schedule as defined by your lab SOPs.
  • Analytical reference use: Prepare calibration curves (e.g., 0.1–50 µg/mL) in your validated diluent; assess linearity, precision, and accuracy per ICH Q2 guidelines.

• Please consult the SDS and CoA/Spec Sheet and validate any protocol under your internal quality system before use.

Biological Roles

• General mechanism and target class (research context)

  • Laninamivir is a small-molecule inhibitor used to study influenza virus neuraminidases (sialidases), enzymes that cleave terminal sialic acids from glycoproteins and glycolipids. Inhibition of neuraminidase is a central tool strategy to interrogate virion release, spread, and glycan-processing pathways in virology and glycobiology experiments.

• Binding interactions (literature/general)

  • Polyhydroxylated, guanidinium-bearing scaffolds mimic sialic-acid transition states and engage neuraminidase via a network of hydrogen bonds and salt bridges in the conserved active site. This underpins potency across influenza A/B neuraminidase subtypes in biochemical assays (specific potency values are assay-dependent and not specified here).

• Research utilities

  • Probe for: substrate specificity, catalytic residue function, and resistance mutations in neuraminidase through kinetic assays and structural studies.
  • Useful control compound when benchmarking new neuraminidase inhibitors or validating phenotypic screening hits.
  • Tool for mapping host–pathogen interactions where sialic acid processing modulates attachment/release cycles.

• Notes and limitations

  • Biological activity profiles can vary with buffer composition, pH, ionic strength, and temperature; standardize assay conditions and include appropriate controls.
  • No clinical/therapeutic claims are made for this catalog item. For research use only as stated in Product Data.

• Item-specific

  • No potency, EC50/IC50, or subtype-selectivity data are provided for this specific item; consult literature or generate under your laboratory conditions.

Buffer Applications

• Applicability

  • Laninamivir is not a buffering agent. However, it is routinely prepared and used in aqueous buffers for biochemical assays (e.g., neuraminidase inhibition).

• Practical buffer choices (general guidance)

  • Common assay buffers: MES (pH 5.5–6.5), HEPES (pH 7.0–7.5), or phosphate-buffered saline (PBS) depending on target enzyme conditions. Maintain ionic strength (e.g., 100–150 mM NaCl) for protein stability when required.
  • Stock solutions: Prepare in water or low-ionic-strength buffer to high concentration, then dilute into final assay buffer. If using DMSO stocks, keep final DMSO ≤1–2%.
  • Stability considerations: Avoid prolonged exposure at high pH; store working solutions on ice during long assay setups. Filter-sterilize if sterility is needed.

• Example preparation (illustrative, not item-specific spec)

  • 10 mM stock in water or DMSO; aliquot and store at −80°C. Thaw immediately before use and discard leftovers after the experimental session to minimize degradation risk.

• Not specified for this item

  • Exact solubility limits, pKa values, and stability half-lives in specific buffers are not provided; refer to CoA/Spec Sheet or determine empirically under your conditions.

Green Alternatives

• Context

  • Laninamivir is a research tool compound rather than a process solvent. “Green alternatives” considerations therefore focus on formulation and assay media rather than replacing the molecule itself.

• Greener handling and formulation options

  • Prefer aqueous buffers (PBS, HEPES, MES) over high percentages of organic co-solvents. Many neuraminidase assays operate effectively with ≤1–2% DMSO, reducing solvent hazards and waste.
  • Use small-volume, high-concentration DMSO stocks followed by immediate aqueous dilution to minimize total DMSO usage.
  • For sterilization, opt for sterile filtration rather than sodium azide (to reduce environmental/toxicity concerns) when compatible with downstream biology.

• Comparison (illustrative)

  • Solvent choice for stock prep:
    • Aqueous buffers: lowest hazard, minimal VOCs, compatible with most enzymatic assays.
    • DMSO: excellent solvency but higher environmental/worker exposure considerations; keep minimal.
    • DMF/MeCN: avoid where possible in bioassays due to toxicity and waste handling.

• Waste minimization

  • Prepare only the amount of stock required for the experimental window; freeze single-use aliquots to avoid repeated thawing and discard of unused solutions.
  • Consolidate and label aqueous and organic waste streams appropriately for institutional disposal.

• Item-specific

  • No process-scale environmental data are provided for this item; recommendations above are general best practices for laboratory-scale work.

Pharmaceutical Uses

• Scope of this catalog item

  • For research use only. Not for human or animal therapeutic use.

• Typical roles in pharmaceutical R&D (non-clinical)

  • Reference standard: Qualitative/quantitative reference in LC–MS/UPLC assays for neuraminidase inhibitors; supports system suitability, retention time locking, and ionization optimization for polyhydroxylated analytes.
  • Method development: Evaluation of extraction, cleanup, and derivatization strategies for highly polar small molecules in complex matrices.
  • Impurity/degradation studies: Benchmarking forced-degradation pathways (acid/base, oxidative, thermal) to design stability-indicating analytical methods.
  • In vitro pharmacology: Positive control in neuraminidase inhibition assays; comparator in SAR campaigns for novel sialidase-targeting chemotypes.

• Quality/documentation considerations

  • Request batch CoA with identity (NMR/MS) and purity (HPLC/UPLC). For regulated labs, retain full chain-of-custody and storage-condition logs (−80°C per Product Data) to support data integrity.

• Formulation science (preclinical tooling)

  • Solubility enhancers (if needed): minimal DMSO co-solvent; cyclodextrin complexation can sometimes aid aqueous formulation for polyols (evaluate empirically).

• Not specified for this item

  • Pharmacopeial monograph status, exact impurity thresholds, and salt form are not listed; consult CoA/Spec Sheet if applicable.

Physical Properties

• Item-specific (from Product Data)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general physicochemical profile (qualitative unless noted)

  • State/form: Typically isolated as a crystalline solid or amorphous powder for carbohydrate-like neuraminidase inhibitors (literature, class-based).
  • Polarity: Highly polar due to multiple hydroxyls and a guanidinium group (literature).
  • Aqueous solubility: Generally good to excellent in water and buffered saline across physiological pH; may form hygroscopic powders (literature, qualitative).
  • Organic solubility: Poor in nonpolar and moderately polar aprotic solvents (e.g., EtOAc, MTBE, toluene, MeCN). DMSO can dissolve many polar actives, but high polarity may still limit solubility (literature, qualitative).
  • Ionization: Guanidinium pKa typically >12; carboxylate/acidic functionality pKa ~2–3 for related sialic-acid analogs, leading to zwitterion/ionic forms depending on pH (literature, typical ranges; exact values for this item not established here).
  • LogP/logD: Expected very low/negative at neutral pH owing to polyol character (literature, qualitative).
  • Hygroscopicity: Polyol-rich actives can be mildly hygroscopic; store tightly sealed under dry conditions (good practice).

• Not provided for this specific item (consult CoA/Spec Sheet if needed)

  • Melting point, refractive index, density, UV cutoff/ε, water or residual solvent content, and specific impurities.

Always verify precise constants from primary references or the CoA before method validation or specification setting.

Quality & Grades

• Item-specific (from Product Data)

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• Interpreting grade and suitability (general guidance)

  • Research-grade small molecules are typically qualified by HPLC purity and identity (NMR/HRMS). When using Laninamivir as a reference material (e.g., enzymology or LC–MS method development), review:
    • HPLC/UPLC purity profile and impurity thresholds
    • Counter-ion or salt form (if applicable)
    • Residual solvents (ICH Q3C) and water content (KF)
    • Documentation of identity (1H/13C NMR, MS, possibly optical rotation for chiral integrity)
  • For analytical applications (calibration standards, system suitability), preference is often given to lots accompanied by detailed chromatographic purity, mass balance, and assay-by-differential scanning calorimetry or qNMR, where available.

• Stabilizers/additives

  • No stabilizer is listed for this item. If stabilizers are present in a given lot, they will be stated on the CoA/Spec Sheet.

• What to request for regulated workflows

  • Batch-specific CoA, SDS, and if needed: impurity profiling, elemental analysis (if relevant), and validated assay method details. Ensure lot traceability and storage history, particularly for materials stored below −20°C/−80°C.

• Note

  • In the absence of an explicit grade on this page, treat this as research-use material; verify suitability against your internal specifications before use.

Reaction & Applications

• Applications in research (non-clinical)

  • Biochemical tool compound for probing influenza neuraminidase (sialidase) activity. Useful in inhibitor titration experiments, competitive binding studies, and kinetic analyses (e.g., Ki/Kd determination) using fluorogenic substrates such as MUNANA.
  • Employed as a positive control or reference inhibitor in high-throughput neuraminidase screening panels and in orthogonal confirmation assays (enzymatic, SPR, ITC).
  • Structural biology: Co-crystallization or soaking experiments with neuraminidase catalytic domains to map active-site interactions and resistance-associated mutations (general practice with neuraminidase inhibitors).
  • Analytical chemistry: Acts as a reference standard for LC–MS/UPLC assay development (retention, ionization optimization, and system suitability) when working with polyhydroxylated actives.

• Practical notes

  • Prepare fresh aqueous or DMSO stocks; aliquot to avoid repeated freeze–thaw. Verify concentration by qNMR or UV (if chromophore permits) for quantitative assays.
  • Ionic strength and pH can influence binding; typical neuraminidase assays use mildly acidic buffers (pH ~5.5–6.5) at 25–37°C. Include controls for substrate turnover and background fluorescence.
  • For HTS, plate-management is critical: limit plate residence time at ambient conditions to reduce evaporation; seal plates between handling steps.

• Noteworthy context (literature)

  • Laninamivir is a long-acting neuraminidase-binding analog in the same mechanistic class as zanamivir; its prodrug forms are known but are outside the scope of this research-use material.

• Item-specific

  • Manufacturer Applications: Not provided in the Product Data for this item.

Reaction Conditions

• Applicability

  • Laninamivir is primarily used as a tool compound in biochemical assays rather than as a reagent. Accordingly, “reaction conditions” here focus on typical neuraminidase inhibition assay conditions (literature-based, illustrative).

• Typical enzymatic assay conditions (literature/general)

  • Buffer: MES, pH 5.5–6.5; alternatives include acetate (pH ~5.5) or HEPES (pH 7.4) depending on enzyme source.
  • Temperature: 25–37°C.
  • Substrate: MUNANA (2′-(4-methylumbelliferyl)-α-D-N-acetylneuraminic acid) for fluorometric readout.
  • Enzyme: Recombinant influenza neuraminidase (subtype-dependent); enzyme concentration titrated to produce linear initial rates.
  • Inhibitor dosing: Serial dilutions of laninamivir to cover expected IC50 range; maintain constant co-solvent (%DMSO) across wells.
  • Readout: Fluorescence increase from 4-methylumbelliferone release; quantify initial velocities and fit to determine IC50/Ki (model selection per mechanism).

• Practical notes

  • Preincubation: 10–20 min preincubation of enzyme with inhibitor at assay temperature can reduce variability for tight-binding inhibitors.
  • Controls: No-inhibitor (100% activity), no-enzyme (background), and known comparator inhibitor.
  • Data quality: Include replicates, verify absence of fluorescence quenching/inner-filter effects by dilution series.

• Not specified for this item

  • Exact IC50/Ki values, stability half-life in buffer, and extinction coefficients are not provided; determine empirically under your lab conditions.

Safety & Handling

• Item-specific (from Product Data)

  • Storage: Store at -80°C. Shipped on dry ice + cold packs to maintain integrity.
  • GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.

• General laboratory safety (defer to SDS for authoritative guidance)

  • PPE: Lab coat, safety glasses, and suitable gloves (e.g., nitrile). Handle powders in a fume hood to minimize dust inhalation.
  • Avoid: Inhalation of dusts/aerosols, contact with eyes/skin, ingestion. Wash thoroughly after handling. Use dedicated, clean tools to prevent cross-contamination.
  • First aid (overview): If inhaled—move to fresh air. Skin/eye contact—rinse with water for several minutes, remove contaminated clothing, seek medical attention if irritation persists. If swallowed—rinse mouth, seek medical advice.
  • Incompatibilities: Strong oxidizers and strong acids/bases may degrade polyhydroxylated actives; avoid prolonged exposure to elevated temperatures and moisture.
  • Thermal/photolytic stability: Neuraminidase-inhibitor analogs can undergo slow hydrolysis/epimerization in aqueous media; protect from excessive heat and store frozen per product data.
  • Environmental: Prevent release to the environment. Collect spills with inert absorbent; dispose according to institutional and local regulations.

• Documentation

  • Always consult the product’s SDS and CoA/Spec Sheet for definitive hazard classification, exposure limits (if any), and recommended handling procedures.

Solvent Selection

• Polarity and dissolution behavior (general, literature-based)

  • Laninamivir is a highly polar, polyhydroxylated small molecule. Practical dissolution hierarchy:
    • Best: Water, physiological buffers (e.g., PBS), mildly acidic buffers (pH 5–7) to enhance protonation of basic sites.
    • Moderate: DMSO (often used to prepare concentrated stocks for screening); DMF can work but is less preferred in bioassays.
    • Poor: Alcohols beyond MeOH, aprotic solvents of moderate polarity (MeCN, acetone), and nonpolar solvents (EtOAc, toluene, MTBE/hexanes).

• Tips for preparing stocks

  • Start with water or buffer; if solubility is insufficient at target concentration, prepare a small-volume DMSO concentrate and dilute into buffer with vigorous mixing, keeping final DMSO ≤1–2% for most biochemical assays.
  • Gentle warming (room temperature to 37°C) and brief sonication can aid dissolution; avoid prolonged heating.
  • Filter sterilize through 0.22 µm PVDF or PES if sterility is required; avoid cellulose acetate with strong DMSO stocks.

• Comparison to alternatives

  • Versus hydrophobic antivirals/tools: Laninamivir’s aqueous solubility simplifies buffer-based work and avoids large co-solvent fractions.
  • Versus zanamivir: Similar aqueous behavior is expected (literature); verify exact solubility numerically from CoA if critical.

• Compatibility considerations

  • Avoid prolonged exposure in high-pH buffers (risk of base-catalyzed degradation for carbohydrate-like scaffolds). Maintain neutral to mildly acidic pH during storage and assays.

• Item-specific

  • No solvent specifications are provided for this item; consult the CoA/Spec Sheet for any lot-specific solubility notes.

Storage & Reconstitution

• Item-specific (from Product Data)

  • Storage conditions: Store at −80°C.
  • Shipping: Dry ice packs + cold packs.

• Reconstitution (general best practices)

  • Solvents: Prefer sterile water or buffer (e.g., PBS, MES) for immediate assay use. If higher concentration is required, dissolve in minimal DMSO, then dilute into aqueous buffer while mixing. Keep final DMSO low (≤1–2%) for most biochemical assays.
  • Concentration and aliquots: Prepare concentrated stock solutions (e.g., 1–10 mM, as solubility permits), sterile-filter if needed (0.22 µm), and dispense into single-use aliquots to avoid repeated freeze–thaw.
  • Labeling: Record solvent, concentration, preparation date, and lot number on each aliquot.

• Stability and handling

  • Working solutions: Keep on ice during use and discard at end of day unless stability has been verified under your conditions.
  • Freeze–thaw: Minimize cycles; multiple thaw–freeze events may promote degradation of polyhydroxylated actives.
  • Light/heat: Protect from excessive heat and direct light. Do not store solutions at room temperature for extended periods.

• Not specified for this item

  • Official shelf life, exact solution stability, and solubility values are not provided; consult the CoA/Spec Sheet and perform stability assessments appropriate to your application.

Structure & Identity

Brief overview: Laninamivir is a polyhydroxylated sialic acid analog and neuraminidase-binding small molecule used as a research tool in influenza glycoprotein studies.

• Item-specific (from Product Data)

  • Product name: Laninamivir (SKU: L654509)
  • CAS: 203120-17-6
  • PubChem CID: 502272
  • Storage: Store at -80°C; shipped on dry ice + cold packs
  • Research use: For research use only
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: 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.

• Literature/structural description (general, non-spec):

  • Core scaffold related to the 2-deoxy-2,3-didehydro-N-acetylneuraminic acid (Neu5Ac2en) motif.
  • Features a highly polar, polyhydroxylated cyclohexene-like sugar ring bearing multiple vicinal diols.
  • Typically contains a strongly basic guanidino functionality at the C-4 position (literature), enhancing electrostatic interaction with neuraminidase active-site residues.
  • Overall presents multiple hydrogen-bond donors/acceptors; net charge expected to be positive/neutral depending on pH due to guanidinium and carboxamide/acidic moieties (literature, qualitative).
  • 2D structure in words: a congested carbohydrate-like ring with pendant hydroxyls, an anomeric side chain terminating in a carboxamide/acidic group, and a cationic guanidino substituent; no stereochemical inversion typical of small lipophiles—rather, several defined chiral centers akin to sialic-acid analogs.

• Notes

  • When exact identifiers (SMILES/InChIKey, MF, MW) are required for regulatory or analytical work, consult the item’s CoA/Spec Sheet for authoritative values.

Synthetic Utility

• Applicability

  • Laninamivir is a complex, polyhydroxylated small molecule designed for target binding; it is not typically employed as a general synthetic reagent or building block.

• Context in synthesis (general)

  • In medicinal chemistry, laninamivir may serve as a comparator or template in the design of neuraminidase inhibitors. Structure–activity relationship (SAR) campaigns often explore modifications to the polyol pattern, guanidino functionality, or side-chain substituents to tune binding and pharmacokinetics (literature context).
  • Derivatization for probes: Installation of reporter handles (e.g., linkers for biotinylation or fluorophores) on peripheral positions has been explored in related scaffolds to create target-engagement probes; such chemistries typically require protecting-group strategies due to the dense polyol array.

• Practical guidance

  • If chemical modification is intended, expect multi-step protecting-group manipulations (acetonides, silyl ethers, carbonate masks) and specialized guanidinylation conditions. Purification relies heavily on HILIC or ion-exchange methods rather than normal-phase chromatography.

• Not provided for this item

  • No item-specific reactivity data, protecting-group maps, or derivatization protocols are provided in the Product Data. Consult the primary literature for synthetic routes and verified transformations.

Target Specificity

• Item-specific

  • Target, epitope, species reactivity, clone/isotype (if antibody), and tested applications are not provided for this item in the Product Data.

• Note

  • While laninamivir is broadly recognized in the literature as a neuraminidase-binding small molecule, any specific target-binding data for this particular catalog lot are not specified. Please consult the CoA/Spec Sheet or perform in-house qualification relevant to your assay system.

Frequently Asked Questions

How should this product be stored?

Store at ?80 °C. Ultra-low temperature storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships frozen with dry ice and cold packs. Unpack on arrival and transfer it to the storage condition stated above; handle dry ice with insulated gloves in a ventilated area.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 203120-17-6, the molecular formula is C13H22N4O7, and the molecular weight is 346.34 g/mol.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.