Carboxytolbutamide-d , CAS No.1219802-95-5

CAS: 1219802-95-5 Cat. No.: C1449067 Summenformel: C₁₂H₇D₉N₂O₅S Molekulargewicht: 309.39

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

Carboxytolbutamide-d 9 is the deuterium labeled Carboxytolbutamide.

Specifications

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Namen und Kennungen

Molekulargewicht

309.39

Application Protocols

No item-specific, validated protocols are provided in the Product Data. The following is a general LC–MS/MS quantitation workflow for a carboxylated sulfonylurea metabolite using a deuterated internal standard (illustrative, non-item-specific):

• Materials: Deuterated internal standard (this product), methanol, acetonitrile, water (LC–MS grade), volatile buffer (e.g., ammonium acetate), biological matrix (e.g., plasma), C18 column.
• Calibration and QCs: Prepare serial dilutions of unlabeled analyte in matrix (e.g., 1–5000 ng/mL). Spike a fixed concentration of the deuterated standard (e.g., 50 ng/mL) into all calibrators, QCs, and samples pre-extraction.
• Sample prep (protein precipitation): Add 3–5 volumes of cold ACN containing the internal standard to 1 volume of sample; vortex, incubate, and centrifuge. Transfer supernatant, dilute with water, and inject.
• LC conditions (example): Gradient from 95:5 to 5:95 (A:B), where A = water + 5 mM ammonium acetate, B = MeOH or ACN, over 5–10 minutes. Flow 0.3–0.5 mL/min; column temp 30–40°C.
• MS settings: ESI negative; monitor MRM transitions for analyte and corresponding mass-shifted transitions for the deuterated standard. Optimize cone/fragmentor voltage and collision energy empirically.
• Data analysis: Use internal-standard-normalized peak area ratios. Evaluate linearity (weighted regression), accuracy, precision, carryover, recovery, and matrix effects per applicable guidance.

Note: Adjust solvent composition and ionization mode to your specific instrument and labeling pattern (consult CoA for exact mass shift).

Biological Roles

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

• Carboxytolbutamide is reported as an oxidative metabolite of tolbutamide formed via hepatic cytochrome P450–mediated pathways. Introduction of a carboxyl group increases polarity and typically reduces pharmacological activity relative to the parent, facilitating renal and biliary excretion.
• Enzymology: Phase I oxidation (e.g., hydroxylation followed by further oxidation to a carboxylate) is commonly implicated. Subsequent Phase II conjugation (e.g., glucuronidation) may occur, enhancing clearance.
• Research utility: The deuterated analog serves as a tracer/internal standard to quantify endogenous levels of the corresponding unlabeled metabolite in in vitro and ex vivo systems. It supports studies of enzyme kinetics (Km, Vmax), intrinsic clearance, and DDI risk assessment by providing robust quantitative anchors in LC–MS/MS assays.
• Matrix considerations: In plasma or microsomal incubations, matrix proteins and phospholipids can cause ion suppression; using a stable-isotope internal standard compensates for such effects and corrects for extraction variability.

Important note: The above describes general biochemical context for carboxylated sulfonylurea metabolites. No physiological, diagnostic, or therapeutic claims are made for this product. It is designated for research use only, as stated in the Product Data.

Buffer Applications

This product is not a buffering agent and is not typically used to prepare laboratory buffers.

Practical notes for analysts (general):

• For LC–MS assays, choose volatile mobile phase buffers such as 2–10 mM ammonium acetate/formate (negative or positive ESI as appropriate) or 0.1% formic acid (positive ESI). Maintain consistent buffer composition across calibrators, QCs, and samples when using a deuterated internal standard.
• Avoid high ionic strength non-volatile buffers (e.g., phosphate) in ESI–MS workflows, as they reduce sensitivity and can cause source fouling.
• If aqueous solubility is limited, first dissolve the material in a small volume of MeOH or ACN, then dilute with the buffered mobile phase immediately before analysis.

Green Alternatives

While this product is a specialty analytical standard (not readily substituted), greener choices can be made around its use, particularly solvent and consumable selection. General guidance:

Greener solvent choices (for stock/working solutions):

• Prefer methanol or ethanol (when compatible) over chlorinated solvents. Acetonitrile, though petrochemical-derived, is recyclable in many labs and offers lower toxicity than DMF/DMAC.
• For aqueous mobile phases, use volatile ammonium buffers (acetate, formate, bicarbonate) at the lowest effective concentrations to reduce environmental impact.

Comparison (general; not item-specific):

• Methanol vs DMSO: Methanol is less persistent and easier to distill/recover; DMSO enables higher concentrations but can increase ESI ion suppression—use sparingly in final injections.
• ACN vs MeOH: ACN offers sharper peaks and faster drying but has supply-chain sustainability issues; MeOH is widely available from bio-based sources.

Operational improvements:

• Scale down: Use microflow LC or reduced injection volumes to cut solvent consumption.
• Recycle ACN/MeOH via in-house solvent recyclers when possible.
• Minimize single-use plastics by employing glass autosampler vials with reusable caps and PTFE/silicone septa.

Note: Because the analyte is a specific deuterated standard, substituting a different compound may compromise quantitative performance. Greener practice should focus on sample preparation and chromatography rather than replacing the standard itself.

Pharmaceutical Uses

No excipient or pharmacopeial status is specified for this item; it is supplied for research use only.

General roles of deuterated reference standards in pharmaceutical R&D and QC (non-clinical):

• Bioanalytical method development: Serve as internal standards for LC–MS/MS quantitation of drug metabolites (e.g., carboxytolbutamide) in preclinical and clinical study samples under regulated bioanalysis (e.g., guidance-compliant workflows).
• Metabolic profiling: Enable confident identification and quantitation of metabolites in in vitro systems (microsomes, S9, hepatocytes) supporting lead optimization and DMPK characterization.
• Stability-indicating assays: Track degradation pathways and support impurity profiling during forced degradation or stress testing of related substances.
• Manufacturing/QC reference: Used as system suitability checks, calibration standards, and spike-recovery controls in release testing of analytical methods that monitor related compounds.

Important: No therapeutic, diagnostic, or clinical application is claimed or implied for this product. It is not intended for human or veterinary use.

Physical Properties

Item-specific physicochemical data are not provided in the Product Data.

• State/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/Not typically used (likely decomposes before boiling, literature general for sulfonylureas); item-specific value not specified.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
• logP/logD: Not specified for this item; refer to CoA/Spec Sheet.
• pKa: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable for solids; item-specific value not specified.

Literature/general expectations (non-item-specific):

• Sulfonylurea carboxylated metabolites are commonly crystalline solids with low volatility. The added carboxyl group confers higher polarity and acidity relative to the parent, improving solubility in polar organic solvents (e.g., methanol, DMSO) and in aqueous basic media (via carboxylate formation).
• For LC–MS reference standards, analysts often prepare stock solutions at 0.5–10 mM in MeOH, ACN, or DMSO and store at low temperature; aqueous working solutions are prepared immediately prior to use to minimize adsorption or hydrolysis. These are general practices and not specifications for this item.
• Deuterium substitution has negligible impact on bulk physical properties but can slightly affect retention and MS fragmentation (kinetic isotope effect), typically without compromising internal-standard behavior.

Quality and Grades

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

Interpretation and considerations for this product category (general):

• Stable-isotope standards: For MS quantitation, two parameters drive performance—chemical purity and isotopic enrichment/pattern. High isotopic enrichment (e.g., ≥98 atom % D across specified positions) reduces isotopic cross-talk with the analyte channel. The precise labeling scheme (which hydrogens are deuterated) affects mass shift and potential back-exchange; consult the CoA for this item’s labeling map and enrichment.
• Residual solvents/inorganics: For high-sensitivity bioanalytical methods, low residual solvents, salts, and non-volatile impurities are desirable to prevent ion suppression and matrix effects. These are typically controlled in analytical-standard grades; verify on the item’s CoA.
• Documentation: Request the Certificate of Analysis for batch-specific purity (HPLC/UPLC), isotopic enrichment, water content, and residual solvent data, if available.
• Research use only: As stated in Product Data, this item is designated for research use only—no medical, diagnostic, or therapeutic use.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. If none are present, users should minimize freeze–thaw cycles and store as aliquots to maintain integrity.
• Traceability: For regulated workflows (e.g., GLP), ensure internal standards are procured with full traceability and lot-to-lot documentation.

Reaction and Applications

This product is primarily intended as a deuterium-labeled analytical standard rather than as a synthetic reagent. Typical research uses (general, literature-based):

• LC–MS/MS internal standard: Deuterated carboxytolbutamide is well-suited as an internal standard for quantitative analysis of carboxytolbutamide (unlabeled) in biological matrices (plasma, microsomes, hepatocytes) and in in vitro metabolism samples. The isotopic label provides a mass offset while preserving chromatographic behavior, enabling accurate compensation for extraction recovery, matrix effects, and ionization variability.
• Metabolic pathway studies: Used to confirm and quantify formation of carboxytolbutamide from tolbutamide in CYP-mediated oxidation studies. Supports the assessment of intrinsic clearance, enzyme kinetics, and metabolite ID workflows.
• Stability/adsorption controls: Added to stability-indicating assays to monitor losses due to adsorption to glass/plastic or degradation during sample prep and storage.
• GC–MS with derivatization: If volatility is insufficient, derivatization (e.g., methyl ester via diazomethane or acidic MeOH; or silylation with BSTFA) can enable GC–MS analysis; maintain awareness of potential H/D scrambling under strongly protic or acidic conditions.

Practical tips:

• Verify the labeling pattern to ensure the mass shift is retained under your ionization/fragmentation conditions.
• Prepare calibration curves and QCs spanning the expected concentration range of analyte; spike internal standard at a constant level across all samples.
• Use low-adsorption plastics or silanized glass for low-ng/mL assays.

Reaction Conditions

There are no item-specific “reaction” conditions because this product is intended as an analytical standard. The following conditions relate to typical analytical sample preparation and optional derivatization (general literature guidance):

• LC–MS/MS preparation:

  • Stock solution: Dissolve in MeOH, ACN, or DMSO to 1–10 mM; store at −20°C. Prepare intermediate working stocks in MeOH/ACN.
  • Spiking: Add a constant concentration (e.g., 10–100 ng/mL) of the deuterated standard to all calibrators, QCs, and samples before extraction.
  • Extraction: Protein precipitation with ACN or MeOH (3–5× volume) is common. Alternatively, use mixed-mode SPE (anion-exchange/reversed-phase) for cleaner extracts of carboxylates.
  • Chromatography: Reversed-phase C18 or polar-embedded phases; aqueous mobile phase with 2–10 mM ammonium acetate/formate, organic phase MeOH or ACN; gradient to elute moderately polar acids.
  • Ionization: ESI in negative mode typically favors carboxylates; positive mode may be viable depending on adduct/fragment pathways. Optimize source settings empirically.

• GC–MS derivatization (if applicable):

  • Methylation: Diazomethane or TMS-diazomethane in ether/MeOH at 0–25°C; quench excess carefully. Alternatively, BF3–MeOH catalyzed esterification (mild heating) can work but may risk H/D exchange.
  • Silylation: BSTFA (±1% TMCS) in anhydrous solvent at 60–70°C for 15–60 min. Ensure dryness to prevent partial hydrolysis.

Note: All conditions above are general guidance only and not specifications for this item.

Safety and Handling

Use appropriate lab precautions. Item-specific GHS details are not provided here; consult the SDS for authoritative guidance.

• GHS classification: Not specified for this item; refer to SDS.
• Signal word / H-statements / Pictograms: Not specified for this item; refer to SDS.

General laboratory safety (for small organic research standards):

• PPE: Wear lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of dusts or aerosols.
• Handling: Avoid dust generation. Prevent contact with skin and eyes. Do not ingest or inhale. Wash thoroughly after handling.
• Storage: Store at −20°C (per Product Data). Keep container tightly closed, desiccated, and protected from light. Allow vials to equilibrate to room temperature in a desiccator before opening to minimize moisture condensation.
• Incompatibilities (general): Strong oxidizers; strong acids/bases can promote hydrolysis of urea/sulfonylurea linkages. Avoid prolonged exposure to aqueous media, heat, and UV.
• Spills: Collect solids with minimal dust formation; for solutions, absorb on inert material. Dispose according to institutional and local regulations.
• First aid (overview): If inhaled—move to fresh air. Skin/eye contact—rinse with water for several minutes; remove contaminated clothing. If ingested—rinse mouth. Seek medical attention in all cases and provide SDS to responders.
• Waste: Treat as organic laboratory chemical waste. Deuterated compounds follow the same disposal practices as their protiated analogs.

Solvent Selection

Item-specific solubility is not provided. The following guidance reflects common practices for carboxylated sulfonylurea standards and deuterated analogs (general/literature-based):

• Polarity/miscibility: Carboxylated sulfonylureas are moderately polar. They typically dissolve well in methanol, acetonitrile, and DMSO. Aqueous solubility improves with slight basification (e.g., 0.01–0.1% NH4OH) due to carboxylate formation.
• Recommended stock solvents (analytical use):
  • Methanol: Good balance of solubility and LC–MS compatibility; minimizes adduct formation.
  • Acetonitrile: Highly volatile, LC–MS friendly; may reduce adsorption to plastics.
  • DMSO: Excellent solvent for concentrated stocks (e.g., 10–50 mM), then dilute into MeOH/ACN before aqueous buffers.
• Aqueous media: Prepare working solutions in water or mobile phase immediately before use. Addition of 0.1% formic acid (positive ESI) or 2–10 mM ammonium bicarbonate/ammonium acetate (negative ESI) can enhance signal stability; choose buffer to match the ionization mode.
• Avoid: High salt buffers for ESI-MS; prolonged storage in basic aqueous media (risk of hydrolysis). For GC–MS, derivatization (e.g., methylation or silylation) may be necessary due to low volatility.

Quick comparison (general):

• Methanol vs ACN: MeOH enhances solubility for many acids but can increase viscosity; ACN improves chromatographic sharpness and is more volatile. DMSO is best for concentrated master stocks but should be diluted prior to injection to avoid ion suppression.

Storage and Reconstitution

• Storage conditions (from Product Data): Store at −20°C. Shipped in an ice chest with ice pads to maintain cold chain.
• Light/moisture: Protect from light and humidity. Keep tightly sealed with desiccant. Allow vial to reach room temperature in a desiccator before opening to prevent condensation.
• Stability: Item-specific shelf life and stability data are not provided; refer to CoA/Spec Sheet. As general practice, minimize freeze–thaw by aliquoting into single-use vials upon first opening.

Reconstitution (general guidance; not item-specific specifications):

• Solvents: Prepare a concentrated stock in methanol, acetonitrile, or DMSO. Typical concentrations for analytical stocks are 1–10 mM, depending on solubility and assay requirements.
• Working solutions: Dilute stock into mobile phase or water immediately before use. For negative-ion LC–MS, low-strength ammonium acetate/formate can improve signal. Keep organic co-solvent content consistent across standards and samples.
• Containers: Use low-adsorption polypropylene or silanized glass. Rinse vials with a small volume of solvent to recover adsorbed analyte when working at low ng/mL levels.
• Freeze–thaw: Avoid repeated cycles; store aliquots at −20°C or below. For long-term storage, consider −80°C if compatible and if CoA indicates extended stability at lower temperatures.

Documentation:

• Record preparation dates, concentrations, and storage conditions. Verify concentration periodically by UV or LC–MS response against a fresh standard if assay criticality requires.

Structure and Identity

Brief overview: This product name indicates a deuterium-labeled form of carboxytolbutamide (a carboxylated metabolite related to the sulfonylurea scaffold). Item-specific structural identifiers are not provided in the Product Data.

• SKU: C1449067
• Product name: Carboxytolbutamide-d (deuterium-labeled)
• CAS: 1219802-95-5
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

Structural notes (literature/general):

• Carboxytolbutamide is described in the literature as an oxidative carboxylated metabolite of the sulfonylurea tolbutamide, retaining the sulfonylurea linkage and para-substituted benzenesulfonamide core, with a terminal carboxyl functionality increasing polarity and acidity relative to the parent.
• The “-d” suffix denotes incorporation of one or more deuterium atoms. The exact labeling pattern and isotopic enrichment for this catalog item are not specified here (consult CoA), but deuterated analogs are commonly used as stable-isotope internal standards in LC–MS workflows due to co-elution and near-identical ionization behavior with the unlabeled analyte.

2D structure (general description):

• Typical features for carboxylated sulfonylureas include: an aromatic ring bearing a sulfonyl group (–SO2–), a urea linkage (–NH–CO–NH–), and a carboxylate/carboxylic acid moiety on an alkyl/aryl side chain. Deuterium substitution does not change the connectivity, only selected hydrogen isotopes.

Synthetic Utility

As a deuterated analytical standard, this compound is not typically employed as a building block in synthesis. However, general synthetic and mechanistic contexts (literature-based) include:

• Isotope tracing: Deuterium labels can probe mechanisms involving C–H bond cleavage, hydrogen transfer, or tautomerization within sulfonylurea frameworks. Incorporation of deuterium at strategic positions helps quantify kinetic isotope effects and hydrogen–deuterium exchange under reaction conditions.
• Reference for product identification: In synthetic routes generating carboxytolbutamide (unlabeled), the deuterated analog provides retention time alignment and MS/MS spectral confirmation, improving confidence in product assignment during process development or metabolite synthesis.
• Derivatization benchmarking: For GC–MS or enhanced LC–MS detectability, derivatization of the carboxyl group (e.g., methyl/ethyl esters, silyl esters) can be validated using the deuterated standard to assess reaction completeness and artifact formation.

Caveats:

• H/D exchange: Avoid strongly protic/acidic/basic conditions and elevated temperatures that can promote back-exchange of labile deuterium atoms, depending on labeling position. Consult the CoA to identify label locations so you can design conditions that preserve isotopic integrity.
• Not a reagent: This product is not intended for stoichiometric use in transformations; use it sparingly as a standard to preserve material and maintain consistent calibration across studies.

Target Specificity

Not applicable. This product is a small-molecule deuterated standard, not an affinity reagent or biological targeting molecule. There is no antigen/epitope specificity, clone information, isotype, or species reactivity associated with this item.