4-cis-Hydroxy Cilostazol-d , CAS No.C1449787

CAS: C1449787 Cat. No.: C1449787 Fórmula: C₂₀H₂₂D₅N₅O₃ Peso molecular: 390.49

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Visão geral

4-cis-Hydroxy Cilostazol-d 5 is the deuterium labeled 4'-trans-Hydroxy Cilostazol.

Specifications

Condições de armazenamento de armazenamento

Store at -20°C

Enviado em

Ice chest + Ice pads

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Nomes e identificadores

• Peso molecular: 390.49

Application Protocols

No vendor-tested antibody/ELISA/IHC/IF protocols apply to this small-molecule standard. For analytical use, the following general LC–MS/MS workflow (literature guidance) may be adapted and validated:

• Stock preparation: Dissolve accurately weighed material in DMSO or MeOH to 1–10 mg/mL. Vortex until fully dissolved. Aliquot and store at -20°C.
• Internal standard working solution: Dilute stock to 10–1000 ng/mL in 50:50 ACN:H2O with 0.1% FA.
• Sample spiking: Add internal standard to biological samples at a fixed concentration prior to extraction (e.g., 10–50 ng/mL final; adjust to your calibration range).
• Extraction: Precipitate proteins with 3–4 volumes of cold ACN or MeOH. Centrifuge and collect supernatant. Optionally, clean up by SPE.
• Chromatography: Inject onto a C18 UPLC column; use a water/ACN + 0.1% FA gradient. Monitor MRM for analyte and IS.
• Quantitation: Construct calibration curves with matrix-matched standards, 1/x weighting, and include QCs at LLOQ/low/mid/high.

These steps are general recommendations and must be proven suitable for your specific matrix and instrumentation.

Biological Roles

Context (literature/general knowledge; not item-specific claims):

• Cilostazol is a phosphodiesterase 3 (PDE3) inhibitor; hepatic metabolism produces hydroxylated metabolites among others. Hydroxylation at certain ring positions can modulate potency and pharmacokinetics compared to the parent compound.
• “4-cis-hydroxy” denotes a regio- and stereochemical hydroxylation on the cilostazol scaffold. Deuterated analogs are typically used as tracers/internal standards and do not imply altered biological activity beyond subtle kinetic isotope effects.
• In biochemical research, such metabolite standards support studies of:
  • Enzymatic pathways (e.g., cytochrome P450–mediated oxidation) and metabolite identification.
  • Distribution and clearance profiling in preclinical systems.
  • Matrix effects and stability during sample processing for quantitation.

Important limitations:

• This product is supplied strictly for research use, not for human or veterinary applications, diagnostics, or therapeutic use.
• No biological activity, ADME, or toxicity data specific to this deuterated compound are provided here; consult primary literature if biological testing is intended.

Buffer Applications

Not typically applicable. This product is a small-molecule analytical standard rather than a buffering agent.

Practical note:

• When preparing LC–MS working solutions, volatile buffers (e.g., 0.1% formic acid, 2–10 mM ammonium formate/acetate) are commonly used to aid ionization and chromatographic performance. Selection should be driven by your analytical method rather than any intrinsic buffering capacity of the compound.

Green Alternatives

Although the compound itself is fixed, greener choices can be made for solvents and sample preparation in analytical workflows.

Greener solvent considerations (literature-based):

• Replace acetonitrile where feasible with ethanol or methanol produced via low-impact routes; note that ACN often affords better peak shape and lower backpressure—tradeoffs must be evaluated.
• For protein precipitation, consider ethanol (EtOH) as a partial substitute for ACN/MeOH while monitoring recovery and matrix effects.
• Mobile phases: Employ aqueous buffers at the lowest effective ionic strength; use formic acid or ammonium formate (readily biodegradable) instead of nonvolatile salts.

Comparison (general guidance, not item-specific):

• ACN vs MeOH: ACN offers lower viscosity and sharper peaks but has higher life-cycle impact; MeOH is more benign but can increase pressure and sometimes peak tailing.
• DMSO vs PEG-400 for stocks: DMSO provides superior solvency and is widely accepted in LC–MS; PEG-400 is greener but viscous and ionization-suppressing—generally not recommended for trace LC–MS work.

Operational improvements:

• Minimize solvent volumes by micro-sampling and micro-extraction.
• Use reusable glass vials/syringes where compatible.
• Consolidate methods to reduce gradient length and flushing volumes.

All changes should be validated to ensure no compromise in analyte recovery, stability, or detection limits.

Pharmaceutical Uses

Formulation/excipient roles are not applicable to this product. It is intended as a research/analytical reference standard.

Regulatory/analytical context (general guidance):

• Stable-isotope-labeled reference standards are frequently used to support bioanalytical assays in drug development (e.g., GLP/non-GLP studies). For regulated work, maintain traceability via CoA/Spec Sheet, lot records, and stability data.
• Pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet. Deuterated metabolite standards are typically not compendial.

No clinical or therapeutic claims are made for this product.

Physical Properties

Item-specific physicochemical properties are not provided in the Product Data. For rigorous work, please refer to the product’s CoA/Spec Sheet and SDS.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not applicable/rarely reported for complex, nonvolatile standards; Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable to solids; Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (literature expectations, not specifications):
  • Commonly supplied as a solid reference standard, soluble for analytical use in polar aprotic organic solvents such as DMSO, acetonitrile, methanol, or mixtures with water containing acid modifiers (e.g., 0.1% formic acid) for LC–MS. Actual solubility for this lot is not specified; verify experimentally.
• LogP/logD, pKa (literature context): Hydroxylated cilostazol metabolites are generally lipophilic but less so than the parent; ionization may stem from heteroaryl nitrogens and phenolic OH (if present). Exact values for this item are not specified.

Note: Deuteration minimally affects bulk properties but can subtly influence chromatographic retention and MS response; use matrix-matched validation.

Quality and Grades

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

Interpretation and guidance (general for isotope-labeled small-molecule standards):

• Isotopic labeling: The “-d” suffix indicates deuterium incorporation. CoA typically specifies the deuterium number (e.g., d3, d5, d7) and isotopic enrichment (atom % D). Higher enrichment and fixed label positions improve internal standard performance by coeluting closely with the analyte while remaining baseline-resolved by MS.
• Chemical purity vs. isotopic purity: Chemical purity (e.g., HPLC area %) and isotopic purity (D incorporation level and pattern) are distinct. For quantitative LC–MS, both matter. Review CoA chromatograms and HRMS if available.
• Residual solvents, counter-ions, and water: Not specified for this item; refer to CoA/Spec Sheet. These can impact accurate gravimetric preparation of standards—use mass-correction if %water or salt form is declared.
• UV background/LC compatibility: If HPLC/LC–MS grade is indicated on the CoA, it typically implies low UV-absorbing impurities and low inorganic residue, aiding baseline stability and ionization.

Documentation to request for regulated workflows:

• CoA with structure confirmation (NMR/HRMS), isotopic distribution, assay by HPLC/UPLC, residual solvents, and storage recommendations matching your method validation plan.

Reaction and Applications

This material is best viewed as an isotopically labeled analytical standard rather than a synthetic reagent. The most relevant applications are in bioanalytical and metabolic studies.

Analytical/bioanalytical applications (literature context):

• Internal standard in LC–MS/MS quantitation of 4-hydroxylated cilostazol metabolites in biological matrices (plasma, urine, microsomal incubations), improving accuracy by compensating for ion suppression and extraction variability.
• Method development: Used for calibrator/quality-control (QC) preparation, stability studies (bench-top, autosampler, freeze–thaw), recovery experiments, and matrix effect assessments per regulatory guidance (FDA/EMA bioanalytical method validation guidelines).
• Metabolite profiling: Enables unambiguous identification via isotopic pattern and coelution behavior, supporting CYP-mediated metabolism studies of cilostazol in liver microsomes/S9/hepatocytes.

Practical tips:

• Prepare a concentrated master stock (e.g., 1–10 mg/mL in DMSO or MeOH), aliquot, and store at -20°C or below, minimizing freeze–thaw cycles.
• For protein-precipitation workflows, spike internal standard into organic precipitant (ACN or MeOH) at a fixed concentration to standardize recovery.
• Validate linearity over relevant ranges (e.g., low ng/mL) and monitor for carryover; include stable-isotope-labeled IS in all calibrators and QCs.

This product is not typically used as a reagent in chemical transformations; see Synthetic Utility for brief context.

Reaction Conditions

This product is not primarily used in preparative synthetic reactions. The most relevant “conditions” are analytical method conditions for LC–MS/MS quantitation (literature guidance; not item-specific specifications):

• Column: C18 or phenyl-hexyl, 2.1 × 50–100 mm, sub-2–3 µm particles for UPLC.
• Mobile phase: A = water + 0.1% formic acid (or 2–10 mM ammonium formate); B = acetonitrile or methanol. Typical gradient 10–90% B in 3–6 min; adapt for resolution from isobaric metabolites.
• Flow/Temp: 0.3–0.5 mL/min; 30–45°C to improve peak shape and reproducibility.
• Detection: ESI(+), MRM transitions tailored to the hydroxylated cilostazol core; deuterated IS monitored at +n Da. Optimize cone voltage/collision energy empirically.
• Sample prep examples: protein precipitation with ACN/MeOH (3:1 to sample), SPE on reversed-phase cartridges, or liquid–liquid extraction with MTBE/EtOAc followed by reconstitution in 50:50 ACN:H2O.
• Stability checks: Assess bench-top (4–6 h), autosampler (4–24 h at 4–10°C), freeze–thaw (≥3 cycles), and long-term (-20°C) stability per bioanalytical validation practices.

Note: If any chemical derivatization is used to enhance response or volatility, verify absence of D/H exchange and maintain mass balance with internal standards.

Safety and Handling

Safety information specific to this item is not listed in the provided Product Data. Always review the SDS prior to use.

• GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
• Likely hazards (general for small-molecule analytical standards): May cause irritation to skin, eyes, and respiratory tract. Avoid dust/aerosol formation and ingestion. Handle in a fume hood.
• Personal protective equipment (PPE):
  • Laboratory coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile).
  • Use respiratory protection if aerosols or powders cannot be controlled by engineering measures.
• Handling guidance:
  • Minimize exposure; weigh quickly using antistatic tools and weigh boats with covers.
  • Avoid contact with strong oxidizers and strong acids/bases unless procedure dictates and hazards are assessed.
  • For LC–MS stock solutions, use anhydrous high-purity solvents; filter if necessary through PTFE (chemical compatibility dependent).
• First-aid overview (general):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation continues.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Waste: Collect solutions and solids as organic hazardous waste compliant with local regulations.

Defer to the SDS for authoritative safety and exposure limits.

Solvent Selection

This compound is a deuterated, hydroxylated cilostazol analog used predominantly as an analytical reference standard. Solvent choice is driven by LC–MS compatibility and compound stability.

General/literature guidance (not item-specific specifications):

• Primary diluents for stock solutions (1–10 mg/mL):
  • DMSO (high solvency; excellent freeze–thaw stability; dilute into ACN/H2O for working solutions).
  • Methanol or acetonitrile (LC–MS friendly; moderate solvency for lipophilic analytes). Add 0.1% formic acid for positive-ion ESI.
• Working solutions for LC–MS/MS (1–1000 ng/mL):
  • 50:50 ACN:H2O or MeOH:H2O with 0.1% FA (positive mode) or 5–10 mM ammonium acetate/formate (neutral/negative mode) to balance ionization and peak shape.
• Miscibility and polarity:
  • Expected to be sparingly soluble in water alone; substantially more soluble in polar organic solvents. Employ co-solvent approaches for aqueous matrices.

Small comparison (literature-based):

• DMSO: highest solvency; may suppress ESI at high %; keep <5% in final autosampler vials.
• MeOH: good for phenolic/heteroaromatic analytes; can increase peak tailing if silanol interactions dominate.
• ACN: sharper peaks on RP columns; lower viscosity; may reduce solubility for highly lipophilic standards compared to MeOH.

Always verify actual solubility and stability for this lot; consult CoA/Spec Sheet.

Storage and Reconstitution

Item-specific storage conditions (from Product Data):

• Storage: Store at -20°C.
• Shipping: Shipped in ice chest with ice pads.

Additional handling guidance (general best practice for small-molecule standards):

• Protect from light and moisture. Use desiccant and store in an airtight container or sealed vial. Allow vials to equilibrate to room temperature before opening to prevent condensation.
• Upon first use, prepare concentrated stock solutions (e.g., 1–10 mg/mL in DMSO or MeOH), aliquot into low-bind vials, and refreeze at -20°C or below. Avoid repeated freeze–thaw cycles.
• For LC–MS working solutions, store at 2–8°C (short term, up to several days) or at -20°C (longer term). Verify stability via system suitability/QC checks.
• Reconstitution solvent: Choose LC–MS–grade DMSO, MeOH, or ACN as appropriate for your method. If aqueous composition is required, prepare as an organic-rich solution first, then dilute with water/buffer to prevent precipitation.
• If a solid form is supplied, note the exact net mass and any correction factors from the CoA (water/solvent content, salt form) when preparing calibrators.

Always consult the product’s CoA and SDS for definitive guidance on stability and handling.

Structure and Identity

Brief overview: This product name indicates a deuterium-labeled analog of the 4-cis-hydroxylated metabolite of cilostazol, intended for research use (e.g., analytical/internal standard applications). Item-specific identifiers are not provided in the Product Data.

• Product name: 4-cis-Hydroxy Cilostazol-d (deuterium-labeled standard)
• SKU: C1449787
• CAS: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• 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 (general/literature context):

• Core scaffold of cilostazol derivatives typically includes a quinolinone/quinolin-4-one-like bicyclic system tethered to a substituted tetrazole or heteroaryl ether and a cycloalkyl/alkoxy side chain. The “4-cis-hydroxy” designation denotes regio- and stereospecific hydroxylation of a ring position relative to a reference substituent, with cis stereochemistry at the pertinent centers (literature description; exact stereochemical descriptors for this catalog item are not provided).
• “-d” suffix indicates one or more nonexchangeable deuterium atoms incorporated as isotopic labels (label positions and D-count are not specified here; consult CoA/Spec Sheet).

2D structure description (general): fused aromatic/heteroaromatic ring bearing a carbonyl (lactam-like), a hydroxyl substituent at the 4-position (cis-related), and side chains including heteroatoms (N, O). Deuterium substitution replaces certain hydrogens without altering valence structure.

Synthetic Utility

As a deuterium-labeled, hydroxylated cilostazol analog, this compound is not generally used as a synthetic building block. However, it offers utility in method development and mechanistic studies:

• Isotopic tracer: The deuterium label enables mass spectral differentiation for recovery tracking, degradation pathway elucidation, and isotope-dilution quantitation.
• Reaction benchmarking: In oxidative metabolism simulations (e.g., chemical oxidation screens), a deuterated standard can serve as a reference peak to verify formation of the nondeuterated metabolite and to control for in-source fragmentation.
• Stability-indicating methods: Useful for validating stress conditions (acid/base, oxidative, thermal, photolytic) and ensuring separation of degradants in RP-HPLC/UPLC.

If chemical transformations are attempted (not typical), the phenolic/benzylic hydroxyl and heteroaromatic nitrogens (general features of hydroxylated cilostazol metabolites) could, in principle, undergo derivatization (e.g., silylation, acylation) for GC–MS or improved chromatographic behavior. Such derivatizations must be validated to avoid deuterium/hydrogen exchange at labile positions—consult CoA for labeling sites before any chemistry.

Target Specificity

Not applicable. This product is a small-molecule reference standard, not an antibody, enzyme, or affinity reagent. No antigen/epitope/clone/isotype information applies.