Atecegatran TFA , CAS No.433937-75-8

CAS: 433937-75-8 Cat. No.: A1443766 Fórmula: C₂₃H₂₂ClF₅N₄O₆ Peso molecular: 580.89

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

Atecegatran TFA (AR-H067637 TFA) is an anticoagulant with selective direct thrombin inhibitory activity. Atecegatran TFA is commonly used to inhibit cardiovascular diseases. The biotransformation product of Atecegatran TFA, AR-H067637, is its active form and participates in the anticoagulation process.

Specifications

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Tipo de acción

INHIBITOR

Nombres e identificadores

Peso molecular

580.89

Application Protocols

• Item-specific protocols (from Product Data)

  • None provided for this item.

• General handling protocols (literature/general; adapt to your assay)

  • Stock preparation: Dissolve compound in anhydrous DMSO to 10–50 mM, vortex and, if needed, sonicate briefly. Filter (0.2 μm) for sterile applications.
  • Working solutions: Dilute stock into assay buffer with thorough mixing to achieve the desired final concentration while keeping DMSO ≤1% v/v (typical for cell-based assays) or ≤2% v/v (typical for enzyme assays), unless validated otherwise.
  • Controls: Include vehicle controls matched for DMSO and, if relevant, TFA content. Perform serial dilutions freshly to minimize adsorption and carryover.
  • Storage of aliquots: Store small single-use aliquots at −20 °C. Avoid repeated freeze–thaw; record time out of freezer and cumulative thaw cycles.
  • Documentation: Record batch/lot number and reference the CoA for purity and counterion content in reports to ensure reproducibility.

Biological Roles

• Item-specific biological information (from Product Data)

  • None provided for this item.

• General considerations (literature/general)

  • As a catalog small molecule in TFA salt form, this compound does not have an inherent endogenous biological role. Any biological activity is context- and target-dependent and must be verified experimentally by the end user.
  • For in vitro work, confirm purity, identity, and counterion content. Prepare dose–response curves with appropriate vehicle controls (e.g., 0.1–1% DMSO) and verify that TFA does not confound readouts (include TFA-matched controls if necessary).
  • For biochemical assays, consider potential ion-pairing or pH effects introduced by the TFA counterion. Buffer capacity should be sufficient to maintain the desired pH upon addition of compound stocks.
  • If the compound is intended as a probe in cells or lysates, assess permeability and efflux liabilities empirically; salt-to-base conversion or prodrug strategies may alter cellular uptake and should be validated separately.

Buffer Applications

• Applicability to this product

  • This item is a small-molecule TFA salt and is not itself a buffering agent.

• Practical guidance (literature/general)

  • When preparing aqueous stocks, dissolve first in DMSO or a minimal amount of water, then dilute into a pre-equilibrated buffer with sufficient capacity (e.g., 25–50 mM HEPES, PBS) to offset any acidity from the TFA counterion.
  • Avoid high concentrations of TFA in buffers used for enzyme assays sensitive to weak acids. If needed, exchange TFA for a different counterion (acetate/citrate) prior to biological testing.
  • Verify final solution pH after dosing compound stocks into buffer, especially at low buffer strengths or high compound concentrations.

Green Alternatives

• Context

  • This product is a specific small-molecule trifluoroacetate salt; “green alternative” considerations mainly involve solvent choices and counterion selection rather than replacing the active scaffold.

• Greener solvent practices (literature/general)

  • Prefer water/ethanol mixtures for assay buffers or crystallizations when feasible; minimize use of DMF and dichloromethane due to environmental/health profiles.
  • Use 2-MeTHF or CPME instead of THF/Et2O for extractions or crystallizations where compatible.
  • Employ acetonitrile alternatives (e.g., EtOH/H2O or MeOH/H2O) for preparative chromatography where separation allows.

• Counterion considerations

  • TFA is persistent and can complicate waste handling. If application permits, exchange TFA for more environmentally benign counterions (e.g., acetate, citrate) while monitoring impacts on solubility and stability.

• Comparison (general, not item-specific)

  • TFA salt vs. acetate salt:
    • Pros (TFA): often higher crystallinity, improved handling, strong ion pairing.
    • Pros (acetate/citrate): reduced environmental persistence, milder acidity, easier removal in workups.
    • Trade-offs: potential changes in solubility, hygroscopicity, and polymorphism; re-validate analytical profile after exchange.

Pharmaceutical Uses

• Item-specific pharmaceutical/formulation information (from Product Data)

  • None provided for this item.

• General notes (non-clinical; for research/manufacturing context only)

  • Salt forms, including trifluoroacetates, are frequently explored during preformulation to optimize solubility, crystallinity, and processability. In research settings, TFA salts may be convenient for screening and early analytical work.
  • For any development activities, counterion screening (e.g., HCl, sulfate, phosphate, acetate) is recommended to balance hygroscopicity, stability, and manufacturability. Trifluoroacetate is often replaced in later stages due to regulatory and environmental considerations.
  • No pharmacopoeial status is implied. This product is supplied strictly for research use only and is not intended for human or veterinary use.

Physical Properties

• Item-specific facts (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 values and expectations (not item-specific)

  • Trifluoroacetate salts of organic bases are typically solids with relatively high melting points (often >120 °C), though exact MP is structure-dependent.
  • Solubility profile (typical for small-molecule TFA salts): high to moderate solubility in polar protic solvents (water, methanol, ethanol) and polar aprotic solvents (DMSO, DMF); lower solubility in nonpolar solvents. Actual solubility should be verified experimentally for this item.
  • Hygroscopicity: TFA salts can absorb moisture; measured water content should be checked if moisture-sensitive applications are planned.
  • pH behavior: Aqueous solutions of TFA salts may be mildly acidic due to partial dissociation/hydrolysis of TFA; solution pH will depend on concentration and conjugate base strength.

• Not provided for this item; consult CoA/Spec Sheet or determine experimentally

  • Melting point, boiling point, density, refractive index, logP/logD, pKa values, UV–Vis cutoff/ε. These properties are structure-dependent and must not be inferred without data.

Quality and Grades

• Item-specific quality information (from Product Data)

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

• How to interpret grade and analytical controls (general guidance)

  • For screening compounds/small molecules, typical QC packages include identity confirmation (1H/13C NMR, LC–MS/HRMS), purity by HPLC/UPLC (area %), and, where relevant, counterion content and residual solvent levels. When a TFA salt is supplied, counterion stoichiometry may be reported (e.g., 1.0 ± 0.1 eq TFA).
  • If low UV-background applications (e.g., HPLC method development) are intended, request UV trace and purity chromograms; TFA can contribute to UV absorbance below ~220 nm (literature), which may be relevant in analytical contexts.
  • Water content (Karl Fischer), residual TFA, and inorganic ions may be significant for moisture-sensitive or biological assays; verify per batch CoA.
  • If the free base is required, confirm that salt-to-base conversion (neutralization) does not reduce purity; re-check by LC–MS/HPLC after conversion.

• Documentation

  • For this item, specific specifications (purity %/grade, residual solvents, metals, stabilizers) are not provided here. Rely on the batch CoA/Spec Sheet for acceptance criteria and analytical results.

Reaction and Applications

• Item-specific applications (from Product Data)

  • Manufacturer applications: Not provided for this item.

• General research uses for a small-molecule TFA salt (literature/general)

  • Chemical probe screening: Supplied as a salt form to facilitate handling and dissolution for in vitro assays. Users should validate activity and selectivity empirically for their targets of interest.
  • Analytical reference: Can serve as an internal/retention-time reference standard once identity/purity are confirmed by orthogonal methods.
  • Salt exchange or counterion optimization: TFA can be exchanged for other counterions (e.g., HCl, mesylate) to modulate properties such as hygroscopicity or crystallinity.

• Practical considerations

  • If the molecule contains basic nitrogens (typical for TFA salts), activity assays sensitive to pH should control for the slight acidity introduced by the TFA counterion upon dissolution.
  • Avoid high concentrations of TFA in buffered systems where it may interfere with assay readouts (e.g., LC–MS ion suppression or enzyme assays sensitive to weak acids). Dialysis, spin columns, or lyophilization after salt exchange can mitigate interference.
  • For synthetic elaboration, the salt may need conversion to the free base to enable reactions in nonpolar media or with base-sensitive reagents (see Synthetic Utility).

Reaction Conditions

• Item-specific conditions (from Product Data)

  • None provided for this item.

• General guidance (literature/general) relevant to TFA salts of small molecules

  • Salt to free-base conversion: 0–25 °C, aqueous bicarbonate/carbonate, 5–30 minutes agitation; typical isolated yields of the free base are high (>80%) after extraction, contingent on structure and workup.
  • Salt exchange/crystallization: Dissolve the TFA salt in an appropriate solvent (MeOH, EtOH, iPrOH, MeCN, or H2O), introduce the new counterion under controlled addition, and induce crystallization by antisolvent or slow cooling. Seed if necessary to manage polymorphism.
  • Solution preparation for assays: Stock solutions 10–50 mM in anhydrous DMSO, stored at −20 °C and protected from moisture/light. Thaw and use promptly; avoid multiple freeze–thaw cycles to limit degradation and concentration drift.
  • Analytical methods: Calibrate LC–MS and HPLC methods to resolve potential TFA-related peaks; consider volatile modifiers (0.1% formic acid or ammonium acetate) to maintain MS compatibility.

Safety and Handling

• Item-specific hazard data (from Product Data)

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

• General laboratory precautions (literature/general guidance)

  • Handle in a fume hood, avoid inhalation of dust or aerosols, and prevent skin/eye contact. Wear appropriate PPE: lab coat, safety glasses, and chemical-resistant gloves.
  • Trifluoroacetate salts may cause irritation to skin, eyes, and respiratory tract. If contact occurs, rinse with water for 15 minutes and seek medical attention as needed. If inhaled, move to fresh air; if ingested, rinse mouth and obtain medical advice. Always follow your institution’s emergency procedures.
  • Incompatibilities: Strong bases (which will convert the salt to the free base and may liberate heat), strong oxidizers, and reactive acylating agents. Avoid contact with strong reducing agents and moisture for hygroscopic materials.
  • Thermal decomposition can release corrosive/irritant fumes (e.g., HF/TFA-related species). Avoid heating to decomposition.
  • Environmental precautions: Prevent release to the environment; collect spills with inert absorbent and dispose of per local regulations.

• Authoritative source

  • Consult the product SDS for definitive hazard classification, exposure limits, and first-aid/handling instructions.

Solvent Selection

• Item-specific facts (from Product Data)

  • No solvent recommendations are provided for this item; refer to CoA/Spec Sheet.

• General selection guidance for TFA salts of small molecules (literature/general)

  • Preferred solvents for dissolution: DMSO (anhydrous), DMF, water, and aqueous buffers. Co-solvent approaches (DMSO→aqueous buffer) often enable clear solutions at assay-relevant concentrations.
  • Miscibility/polarity: DMSO mixes with water and most organics; for stock solutions, 10–50 mM in dry DMSO is common practice for screening libraries, then dilute into assay buffer to ≤1% DMSO v/v.
  • For preparative work or salt exchange, alcohols (MeOH, EtOH, iPrOH) and acetonitrile are frequently used. Nonpolar solvents (EtOAc, MTBE, hexanes) typically have poor solubility for polar salts.
  • If the free base is needed for nonpolar media, convert the TFA salt to the free base (see Synthetic Utility) prior to use.

• Practical tips

  • Filter solutions (0.2 μm PTFE/nylon) to remove particulates before biological or analytical use.
  • Verify solution stability over time; some salts can show gradual changes in pH or precipitate upon storage/dilution—run a quick solubility/compatibility check in your exact matrix.

Storage and Reconstitution

• Item-specific instructions (from Product Data)

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

• Additional practical guidance (literature/general)

  • Protect from moisture; many TFA salts are hygroscopic. Keep container tightly closed under dry inert atmosphere if possible.
  • Light sensitivity is structure-dependent; in absence of data, store in amber or foil-wrapped containers to limit photodegradation.
  • Reconstitution for research use: Prepare concentrated stocks in dry DMSO (e.g., 10–50 mM). For purely aqueous use, dissolve in minimal water and adjust pH/buffer strength as needed to maintain solubility and stability. Always verify clarity and absence of precipitate after dilution.
  • Aliquoting: Dispense single-use aliquots to minimize freeze–thaw cycles. Thaw on ice, mix gently, and use promptly. Discard aliquots showing precipitation, discoloration, or unexpected LC–MS/HPLC profiles.
  • Stability: Item-specific shelf-life and solution stability are not specified for this item; refer to CoA/Spec Sheet and verify experimentally for critical applications.

Structure and Identity

• Item-specific facts (from Product Data)

  • Product name: Atecegatran TFA (trifluoroacetate salt)
  • CAS: 433937-75-8
  • Storage: Store at −20°C
  • Shipping: Ice chest + ice pads
  • 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.

• Literature/general notes (not item-specific)

  • “TFA” denotes the trifluoroacetate counterion (CF3COO−), commonly used to form salts with basic nitrogen-containing small molecules or peptides.
  • Trifluoroacetate salts often enhance crystallinity and handling vs. the free base; they are typically more water-soluble and can be hygroscopic.
  • Without a provided structure, specific functional groups and stereochemistry cannot be confirmed for this item. Users should consult the CoA/Spec Sheet for structural identifiers and confirm identity by orthogonal analytical methods (e.g., 1H/13C NMR, HRMS, LC–MS, IR).

Synthetic Utility

• Item-specific data (from Product Data)

  • Structural details enabling specific transformations are not provided for this item.

• General synthetic considerations for TFA salts of basic small molecules (literature/general)

  • Free-base generation: Suspend the TFA salt in a biphasic mixture (e.g., water/EtOAc or water/CH2Cl2), basify the aqueous layer (e.g., saturated NaHCO3 or dilute Na2CO3) to pH ~9–10, and extract the liberated free base into the organic layer. Dry and concentrate to obtain the base for further reactions. Confirm identity/purity by NMR and LC–MS post-conversion.
  • Counterion exchange: Dissolve in minimal solvent and treat with a stoichiometric mild base plus the desired acid (e.g., HCl in dioxane, acetic acid) to furnish alternative salt forms, adjusting crystallization solvent to optimize isolation.
  • Protection/derivatization: If the molecule contains amines, standard transformations (acylation, sulfonylation, carbamate formation) are typically carried out on the free base. Avoid conditions that could lead to TFA incorporation unless intended (e.g., excessive TFA in acylations).
  • Purification: Ionizable compounds often purify well by reverse-phase chromatography (H2O/MeCN with volatile buffers). Minimize TFA in mobile phases if downstream MS detection is required (use formic acid or ammonium salts instead).

Target Specificity

• Item-specific information (from Product Data)

  • No target, epitope, or specificity data are provided for this product.

• Note

  • Users should determine biological targets and selectivity empirically using appropriate controls and orthogonal assays. No claims of specificity are made by the supplier for this catalog item.