Ulipristal-d , CAS No.U1440015

CAS: U1440015 Cat. No.: U1440015 Formula: C₂₈H₃₂D₃NO₃ Molecular Weight: 436.60

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Ulipristal-d 3 (CDB-3236-d 3 ) is deuterium labeled Ulipristal. Ulipristal (CDB 3236) is a selective progesterone receptor modulator (SPRM). Ulipristal binds to the progesteron receptor, thereby inhibiting PR-mediated gene expression, and interfering with progesterone activity in the reproductive system.

Specifications

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

Molecular Weight

436.60

Application Protocols

General protocol guidance for using Ulipristal-d as an internal standard in LC-MS/MS (adjust to your instrumentation and regulatory requirements):

• Stock preparation:

  • Dissolve Ulipristal-d in LC-MS grade DMSO or acetonitrile to 1–10 mM. Vortex and, if needed, sonicate briefly. Store small aliquots at −20 °C in amber vials.

• Working solutions:

  • Prepare intermediate solutions in acetonitrile or methanol. For calibration standards and QC samples, spike a constant concentration of IS into all samples, standards, and QCs.

• Sample preparation examples:

  • Protein precipitation: Add 3–4 volumes of cold acetonitrile containing the IS to biological matrix, vortex, centrifuge, and inject supernatant after dilution with mobile phase.
  • SPE: Use reversed-phase or mixed-mode sorbents; elute with ACN or MeOH containing a volatile modifier. Evaporate under N2 and reconstitute in initial mobile phase.

• LC-MS considerations:

  • Use a C18 or phenyl-hexyl column; employ gradients of water/acetonitrile or water/methanol with volatile acids/buffers. Monitor distinct MRM/PRM transitions for analyte and IS with sufficient mass separation to avoid isotopic overlap.

• Documentation:

  • Record IS lot number, concentration, and storage. Verify linearity, accuracy, precision, carryover, and matrix effects during method validation.

Note: No item-specific transitions or retention times are provided; optimize empirically.

Biological Roles

Context (literature, referring to the non-deuterated scaffold):

• Ulipristal is a selective progesterone receptor modulator (SPRM) that binds the progesterone receptor (PR) and can exhibit tissue-selective partial agonist/antagonist behavior in research settings. The steroidal framework with a dimethylaminoaryl substituent underlies receptor affinity and selectivity.

Relevance of deuteration for research:

• Deuterated analogs (such as Ulipristal-d) are chemically and biologically analogous for binding studies while providing mass spectrometric distinguishability. This enables rigorous quantification in receptor-binding assays, distribution studies, and biochemical metabolism experiments without altering target engagement in a meaningful way.

Applications (research use only):

• Reference standard in PR ligand-binding assays to evaluate competitive binding of novel compounds.
• Tracking metabolic fate and distinguishing parent vs. metabolite signals in microsomal/S9 incubations using isotope-dilution LC-MS.

Important notes:

• No medical or clinical claims are made. Usage is restricted to laboratory research.
• Item-specific biological activity metrics (Kd, EC50, etc.) are not provided for this product; consult primary literature for the non-deuterated molecule if such parameters are required for study design.

Buffer Applications

This product is a hydrophobic small-molecule standard rather than a buffering agent. It is not used to control pH or ionic strength.

Practical notes for related workflows:

• For LC-MS sample preparation, pair organic solvents (acetonitrile or methanol) with volatile buffers such as ammonium formate/acetate (pH adjusted with formic or acetic acid) to support electrospray ionization.
• In biochemical assays, dilute DMSO stocks into assay buffers (e.g., HEPES, PBS) keeping final organic content low (≤0.1–0.5% v/v as tolerated). Verify solubility and avoid precipitation.

No item-specific buffer recommendations are provided; optimize conditions for your assay and instrumentation.

Green Alternatives

Although Ulipristal-d is a research analyte rather than a process solvent, greener choices can be made for dissolution, chromatography, and sample preparation.

Greener solvent considerations (general):

• Prefer alcohols (ethanol, isopropanol) over chlorinated solvents where solubility allows.
• For LC, methanol and acetonitrile are standard; methanol is biorenewable in some supply chains and may be favored when performance is acceptable.
• Replace non-volatile buffers (phosphate) with volatile, MS-friendly salts (ammonium formate/acetate) to reduce waste and instrument fouling.

Comparison (general guidance):

• DMSO vs ethanol
  • Pros (DMSO): superior solvating power for hydrophobic steroids; stable stocks.
  • Pros (ethanol): lower persistence and toxicity profile; easier waste handling.
  • Trade-off: ethanol may require larger volumes to fully dissolve analyte; verify assay compatibility.

Operational practices:

• Prepare concentrated master stocks to minimize solvent use; aliquot to reduce freeze–thaw cycles and waste.
• Use micro-scale extractions/SPE to reduce solvent volumes and adopt 96-well plate formats for parallelization and reduced footprint.

Note: No item-specific solvent restrictions are provided; validate greener substitutions for your analytical method.

Pharmaceutical Uses

This catalog item is supplied strictly for research use only; it is not an excipient or a GMP-grade ingredient.

• Formulation role: As a deuterated small-molecule reference standard, Ulipristal-d is not used in pharmaceutical formulations for administration. Instead, it assists analytical development and QC (e.g., stability-indicating methods, impurity profiling) by serving as an internal standard for the corresponding non-deuterated analyte.
• Pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet. Deuterated analogs may not have compendial monographs even when the non-deuterated drug substance does.
• Typical pharma R&D applications (non-clinical):
  • Method validation under ICH guidelines (linearity, accuracy, precision, LOD/LOQ) using isotope-dilution calibration.
  • Stability studies to monitor degradation pathways of the non-deuterated API in dosage forms.
  • Bioanalytical quantitation in non-clinical studies, subject to institutional approvals.

No therapeutic or clinical claims are made for this product.

Physical Properties

Item-specific physicochemical data are not provided for this catalog entry.

• Item-specific values: Not specified for this item; refer to CoA/Spec Sheet.

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Melting point, boiling point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
  • Solubility: Not specified for this item; refer to CoA/Spec Sheet.

• General/literature context for ulipristal-type scaffolds (qualitative):

  • Lipophilic steroidal molecules are typically insoluble in water and soluble in organic solvents such as DMSO, DMF, acetonitrile, methanol, and ethanol.
  • Free-base tertiary amine functionality (dimethylaminoaryl) provides basic character; salts can enhance aqueous compatibility for analytical preparations.
  • Deuteration minimally affects bulk properties (mp, solubility) relative to protiated analogs; minor isotope effects can manifest in vapor pressure and fine details of chromatographic retention but are generally small.

• Analytical handling notes (general):

  • Prepare concentrated stocks in dry, anhydrous DMSO or acetonitrile; store aliquots at low temperature to limit degradation.
  • For LC-MS, typical sample diluents are acetonitrile:water with volatile modifiers (e.g., formic acid or ammonium formate). Optimize empirically for your system.

Always rely on the item’s CoA/SDS for definitive specifications.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for assay, impurity profile, and residual solvent data.

Context for deuterated reference materials:

• Isotopic purity: For deuterated standards, two metrics are important: chemical purity (by HPLC/GC/LC-MS) and isotopic enrichment/distribution (e.g., %D, pattern of D incorporation). These define performance in isotope-dilution LC-MS quantitation. Item-specific values are provided on the CoA when available.
• Identity confirmation: Typically supported by HRMS (accurate mass with isotope pattern), 1H/2H NMR, and sometimes 13C NMR. Retention time matching versus protiated reference is common in validated methods.
• Residual protiated content: Low residual H content reduces bias when used as internal standard; the exact value should be taken from the CoA.

Stabilizers/antioxidants:

• Not specified for this item; refer to CoA/Spec Sheet. If present, stabilizers should be disclosed as they can affect LC-MS background and sample preparation.

Documentation and compliance:

• CoA should include lot-specific purity, isotopic enrichment, and recommended storage.
• For regulated workflows, retain CoA and SDS with method validation documents (linearity, accuracy, precision, matrix effects).

Reaction and Applications

Primary research applications (typical for deuterated small molecules):

• Internal standard for LC-MS/MS: Ulipristal-d is well-suited for isotope-dilution quantification of ulipristal or related metabolites in complex matrices (plasma, tissue extracts, formulations). Deuterium labeling helps correct for extraction recovery, ion suppression, and instrument drift.
• Metabolic and stability studies: Track isotopic shifts to probe biotransformations (oxidation, reduction, dealkylation) and to distinguish endogenous/interfering signals from analyte peaks.
• Method development: Evaluate chromatographic selectivity, retention factor shifts due to kinetic isotope effects, and optimize mobile phase additives for robust quantitation.

Chemical reaction context (general/literature):

• Deuterated analogs are typically prepared via selective hydrogen–deuterium exchange, reduction with deuteride sources, or coupling from deuterated building blocks. The final product is used as a tracer, not as a reagent.

Practical tips:

• Spike internal standard early (pre-extraction) to correct for sample workup losses.
• Verify absence of H/D back-exchange under sample prep and LC conditions; minimize prolonged exposure to protic acids/bases and high temperatures where reversible exchangeable positions exist.
• Monitor both analyte and IS transitions; ensure that the mass shift (Δm/z) is sufficient to avoid overlap with natural isotopologues.

Reaction Conditions

As supplied, Ulipristal-d is intended for use as an analytical/internal standard rather than a synthetic reagent. Nevertheless, practical conditions relevant to its use and integrity are outlined below.

• Solution preparation (general):

  • Dissolve in anhydrous DMSO, acetonitrile, or methanol to prepare concentrated stock solutions. Filter through 0.2 µm PTFE if particulate is present.
  • For LC-MS, dilute stocks into mobile phase (e.g., water/acetonitrile with 0.1% formic acid or 2–10 mM ammonium formate/acetate). Avoid non-volatile salts.

• Stability considerations (general):

  • Store at −20 °C; minimize light and air exposure. Use amber vials when possible.
  • Limit freeze–thaw by aliquoting. Assess stability with periodic QC injections (retention time, response factor).
  • Avoid strongly acidic or basic aqueous conditions and elevated temperatures that can promote H/D back-exchange at labile positions.

• Sample extraction (bioanalytical, general):

  • Protein precipitation: Add acetonitrile or methanol containing a fixed concentration of Ulipristal-d prior to precipitation.
  • SPE: Condition–load–wash–elute workflows with reversed-phase or mixed-mode cation-exchange cartridges can yield clean extracts; elute with MeOH or ACN containing a volatile base or acid as needed.

No item-specific reaction temperatures, catalysts, or yields are applicable; adjust conditions to your analytical platform.

Safety and Handling

Safety information specific to this item is not provided in the Product Data.

• GHS classification and hazard statements: Not specified for this item; refer to SDS.
• Signal word and pictograms: Not specified for this item; refer to SDS.

General laboratory precautions for steroidal ligands and deuterated analytical standards:

• Avoid inhalation, ingestion, and skin contact. Use in a chemical fume hood.
• PPE: lab coat, safety glasses, and suitable chemical-resistant gloves (e.g., nitrile). Change gloves frequently when weighing or preparing solutions.
• Prevent environmental release; dispose of solutions and rinsates as hazardous waste according to institutional and local regulations.
• Incompatibilities (general): strong oxidizers; avoid prolonged exposure to strong acids/bases that may promote hydrolysis or degradation of enone/ester functions (where present in related scaffolds).
• First aid (general guidance; defer to SDS):
  • Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical evaluation.
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

Storage and shipping (from Product Data):

• Storage: Store at −20 °C.
• Shipping: Ice chest + ice pads.

Always consult the product-specific SDS for authoritative safety and emergency procedures.

Solvent Selection

Applicability: As a small-molecule steroidal research reagent, solvent selection pertains to dissolution for analytical use rather than serving as a reaction solvent.

General solvent guidance (literature/context):

• Polarity and miscibility: Ulipristal-type scaffolds are hydrophobic and generally:
  • Soluble: DMSO, DMF, acetonitrile, methanol, ethanol, dichloromethane.
  • Poorly soluble: water and aqueous buffers unless formulated with co-solvent or as a salt.
• LC-MS workflows: Prefer LC-MS grade acetonitrile or methanol with volatile modifiers (e.g., 0.1% formic acid or 5–10 mM ammonium formate) for robust ionization and low background.
• Bioassay stocks: Prepare concentrated stocks in DMSO (e.g., 10–50 mM), then dilute into assay media keeping final DMSO ≤0.1–0.5% v/v to minimize biological confounders. Optimize per assay.

When to choose alternatives:

• Use ethanol or isopropanol when DMSO is undesirable (e.g., certain binding assays) and when solubility allows.
• For solid-phase extraction (SPE) elution, acetonitrile with small amounts of strong base/acid modifiers can improve recovery for basic steroids; tune to matrix and sorbent.

Note: No item-specific solubility or solvent limits are provided; consult the CoA and perform small-scale solubility tests under intended conditions.

Storage and Reconstitution

Storage conditions (from Product Data):

• Store at −20 °C. Ship on ice (ice chest + ice pads). Upon receipt, promptly return to cold storage.

General best practices for this product class:

• Keep container tightly closed in a dry, inert atmosphere (desiccant recommended). Protect from light; use amber glass vials if possible.
• Aliquot upon first opening to avoid repeated freeze–thaw cycles; small single-use aliquots improve consistency in quantitative assays.

Reconstitution and working solution guidance:

• Solvent choice: Use anhydrous DMSO, acetonitrile, or methanol for initial dissolution. If necessary for assay compatibility, further dilute into ethanol or aqueous-organic mixtures.
• Concentration: Select a stock concentration appropriate to your assay (commonly 1–10 mM for small molecules). Verify full dissolution visually and, if needed, by analytical injection.
• Stability monitoring: Periodically check for degradation or H/D back-exchange by LC-MS (mass shift integrity, response factors). Discard aliquots showing significant loss of potency or isotopic purity.

Additional notes:

• Grade/purity, appearance, and any stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
• For long-term storage beyond routine timelines, consider −80 °C if compatible with packaging and lab practices, and validate stability under your specific conditions.

Structure and Identity

Brief overview: Ulipristal-d is a deuterium-labeled analog of ulipristal intended for research use (e.g., analytical/internal-standard applications). Deuteration sites and count are not specified for this catalog item.

• Item-specific identifiers (from Product Data):

  • CAS: U1440015 (internal catalog placeholder)
  • 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 (literature, referring to the non-deuterated scaffold):

  • Ulipristal is a steroidal selective progesterone receptor modulator (SPRM) with a 19-nor steroid backbone, an 11β-para-dimethylaminophenyl substituent, and conjugated enone functionality in the A-ring.
  • The widely referenced pharmaceutical form is ulipristal acetate; “ulipristal” denotes the corresponding aglycone/parent scaffold (literature). Deuterated analogs retain the core steroid framework with isotopic (2H) substitutions at defined positions.

• Stereochemistry (literature):

  • Multiple stereocenters intrinsic to the androstane/19-nor steroid nucleus; configuration matches the native ulipristal scaffold. Deuterium substitution does not alter carbon stereochemistry.

• 2D description (literature):

  • A fused tetracyclic steroid core (three six-membered rings and one five-membered ring), a para-dimethylaminophenyl group at C11β, and enone functionality within the A-ring; the deuterated analog replaces one or more hydrogens with deuterium on the carbon skeleton and/or substituents.

Synthetic Utility

Ulipristal-d is primarily a labeled reference material rather than a building block. Its synthetic relevance lies in the strategies used to access deuterated steroidal frameworks and in its role as a benchmark molecule.

• Strategic deuteration (general/literature):

  • Site-selective H/D exchange at activated positions (allylic/benzylic) under acidic or catalytic conditions.
  • Reductive incorporation using deuteride reagents (e.g., LiAlD4, NaBD4) in steps that set specific C–H bonds.
  • Assembly from deuterated aryl fragments (e.g., para-dimethylaminophenyl-dn) or deuterated acetylating agents to place D at defined loci.

• Utility in synthesis research:

  • Mechanistic probes: Deuterium enables kinetic isotope effect studies on steroidal transformations (e.g., enone reductions, allylic oxidations).
  • Reference in structural elucidation: 2H labeling assists NMR signal assignment and confirms regiochemistry in late-stage modifications of the ulipristal scaffold.

• Downstream transformations:

  • The deuterated product is generally handled under mild conditions to preserve D incorporation; avoid unnecessary steps that can exchange deuterium (strong acids/bases, protic media at elevated temperatures).

Item-specific functional group reactivity parameters are not provided; consult literature for the non-deuterated scaffold when planning synthesis.

Target Specificity

This section is typically applicable to biologics (antibodies, enzymes). Ulipristal-d is a small-molecule standard and does not possess antibody-like target specificity parameters.

• Antigen/epitope, clone, isotype, species reactivity: Not applicable.

Research context (literature): The non-deuterated scaffold binds the progesterone receptor in biochemical studies; however, this product is provided as an analytical standard and no binding specifications or bioactivity claims are provided for this item.

Frequently Asked Questions

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

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

The CAS Number is U1440015, the molecular formula is C28H32D3NO3, and the molecular weight is 436.60 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.