Tofimilast , Phosphodiesterase 4 inhibitor, CAS No.185954-27-2, Phosphodiesterase 4 inhibitor

CAS: 185954-27-2 Cat. No.: T669034 Summenformel: C18H21N5S Molekulargewicht: 339.5 PubChem CID: 9896267
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Synonyms
Tofimilast|CP-325366|CP-325,366|9-Cyclopentyl-7-ethyl-3-(thiophen-2-yl)-6,9-dihydro-5H-pyrazolo(3,4-c)-1,2,4-triazolo(4,3-a)pyridine|8-Cyclopentyl-6-ethyl-3-thiophen-2-yl-5,8-dihydro-4H-1,2,3a,7,8-pentaaza-as-indacene|12-cyclopentyl-10-ethyl-5-thiophen-2-yl-3,4,6,11,12-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,10-tetraene|Tofimilast [INN]|Tofimilast [USAN:INN]|Tofimilast (INN/USAN)|TOFIMILAST [USAN]|TOFIMILAST [WHO-DD]|8Cyclopentyl-6-ethyl-3-thiophen-2-yl-5,8-dihydro-4H-1,2,3a,7,8-pentaaza-as-indacene|5H-Pyrazolo(3,4-c)-1,2,4-triazolo(4,3-a)pyridine, 9-cyclopentyl-7-ethyl-6,9-dihydro-3-(2-thienyl)-|9-cyclopentyl-5,6-dihydro-7-ethyl-3-(thien-2-yl)-9H-pyrazolo(3,4-c)-1,2,4-triazolo(4,3-a)pyridine|9-cyclopentyl-5,6-dihydro-7-ethyl-3-(thien-2-yl)-9H-pyrazolo[3,4-c]-1,2,4-triazolo[4,3-alpha]pyridine|9-Cyclopentyl-7-ethyl-6,9-dihydro-3-(2-thienyl)-5H-pyrazolo[3,4-c]-1,2,4-triazolo[4,3-a]pyridine
Storage
Room temperature
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1mg
T669034-1mg
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496,26€

744,43€
Speichern 248,17 € (33.34%)
5mg
T669034-5mg
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2.603,13€
Speichern 867,74 € (33.33%)
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Spezifikationen

Synonyme
Tofimilast | CP-325366 | CP-325,366 | 9-Cyclopentyl-7-ethyl-3-(thiophen-2-yl)-6,9-dihydro-5H-pyrazolo(3,4-c)-1,2,4-triazolo(4,3-a)pyridine | 8-Cyclopentyl-6-ethyl-3-thiophen-2-yl-5,8-dihydro-4H-1,2,3a,7,8-pentaaza-as-indacene | 12-cyclopentyl-10-ethyl-5-thiophen-2-yl-3,4,6,11,12-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,10-tetraene | Tof Show more
Storage
Room temperature
Aktionsart
INHIBITOR
Mechanismus der Wirkung
Phosphodiesterase 4 inhibitor
Produkteigenschaften
ALogP
2.8
Namen und Kennungen
Kanonisches Lächeln
CCC1=NN(C2=C1CCN3C2=NN=C3C4=CC=CS4)C5CCCC5
IUPAC Name
12-cyclopentyl-10-ethyl-5-thiophen-2-yl-3,4,6,11,12-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,10-tetraene
InChIKey
DHCOPPHTVOXDKU-UHFFFAOYSA-N
INCHI
1S/C18H21N5S/c1-2-14-13-9-10-22-17(15-8-5-11-24-15)19-20-18(22)16(13)23(21-14)12-6-3-4-7-12/h5,8,11-12H,2-4,6-7,9-10H2,1H3
Isomere SMILES
CCC1=NN(C2=C1CCN3C2=NN=C3C4=CC=CS4)C5CCCC5
PubChem CID
9896267
Molekulargewicht
339.5

Erweiterte Daten

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
KlasseTriazolopyridines
SubclassNot available
Intermediate Tree Nodes Not available
Direct ParentTriazolopyridines
Alternative Parents Pyridines and derivatives  Triazoles  Thiophenes  Pyrazoles  Heteroaromatic compounds  Azacyclic compounds  Organonitrogen compounds  Hydrocarbon derivatives  
Molecular FrameworkAromatic heteropolycyclic compounds
Substituents Triazolopyridine - Pyridine - Heteroaromatic compound - 1,2,4-triazole - Triazole - Thiophene - Pyrazole - Azole - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Organonitrogen compound - Aromatic heteropolycyclic compound
BeschreibungThis compound belongs to the class of organic compounds known as triazolopyridines. These are compounds containing a triazole ring fused to a pyridine ring. Triazole is a five-membered ring consisting of two carbon atoms and three nitrogen atoms. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center.
External Descriptors Not available
3D-Struktur
Interaktives chemisches Strukturmodell





Zugehörige Ziele (menschlich)
PDE4D Tclin cAMP-specific 3',5'-cyclic phosphodiesterase 4D (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
PDE4A Tclin cAMP-specific 3',5'-cyclic phosphodiesterase 4A (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
PDE4B Tclin cAMP-specific 3',5'-cyclic phosphodiesterase 4B (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
ADORA1 Tclin Adenosine A1 receptor (17603 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA2A Tclin Adenosine A2a receptor (16305 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE4A Tclin Phosphodiesterase 4A (1943 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA3 Tchem Adenosine A3 receptor (15931 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE4B Tclin Phosphodiesterase 4B (2748 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE4C Tclin Phosphodiesterase 4C (258 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U-937 (7138 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Monocyte (474 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Zugehörige Ziele (nicht menschlich)
Pde4d Phosphodiesterase 4D (4 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mustela putorius furo (1007 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Canis familiaris (36305 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Wirkungsmechanismen
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht339.500 g/mol
XLogP32.800
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Exact Mass339.152 Da
Monoisotopic Mass339.152 Da
Topological Polar Surface Area76.800 Ų
Heavy Atom Count24
Formal Charge0
Complexity457.000
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds0
Covalently-Bonded Unit Count1
Lösungsrechner
Bewertungen

Kundenbewertungen

Application Protocols

No tested application protocols are provided for this item.

General lab workflow suggestions for small-molecule research compounds:

  • Stock preparation: Dissolve in an appropriate solvent (commonly anhydrous DMSO) to a convenient concentration (e.g., 10–50 mM). Vortex, sonicate briefly, and filter if necessary (0.2 µm PTFE).
  • Aliquoting: Dispense single-use aliquots to minimize freeze–thaw or ambient exposure. Clearly label with compound name, lot, concentration, solvent, and date.
  • Assay setup: Include vehicle controls matching the highest solvent percentage used. If applicable, perform serial dilutions to establish concentration–response relationships.
  • Analytical verification: Confirm identity and purity of working solutions by LC–MS/HPLC before critical experiments.
  • Documentation: Record lot numbers, preparation details, and storage conditions in your ELN or LIMS for traceability.

For any specific bioassay or analytical protocol, tailor conditions based on validated methods from the literature for compounds of similar class and properties.

Biological Roles

Item-specific biological target data are not provided in this listing. Users intending to employ this compound as a tool in biochemical or cellular studies should consult primary literature via the CAS (185954-27-2) or PubChem CID (9896267) to verify reported targets, potency, and selectivity, and to ensure the identity matches their intended use.

General guidance for small-molecule research compounds (non-clinical, non-medical):

  • Verify identity and purity (e.g., LC–MS, 1H/13C NMR) before biological testing to avoid confounding results from impurities or alternate salt/solvate forms.
  • Establish compound stability in the chosen assay media (buffer composition, pH, presence of serum/proteins, light exposure) and monitor for precipitation over time.
  • Determine practical stock concentration limits in DMSO and perform serial dilutions to minimize cosolvent effects; include vehicle controls.
  • If the literature suggests a molecular target, confirm activity in-house using orthogonal assays and include counter-screens to assess off-target effects.

Research use only: This product is not intended for human or veterinary use, diagnostics, or therapeutic applications. Any biological roles should be validated experimentally under your institutional approvals and biosafety practices.

Buffer Applications

Not typically applicable. Tofimilast is a discrete organic small molecule and is not used as a buffering agent.

Practical notes (general):

  • When preparing assay buffers that will contain small-molecule stocks (e.g., from DMSO), confirm that the final cosolvent percentage is compatible with your buffer system and biological components.
  • Common laboratory buffers (PBS, HEPES, Tris, acetate) may be used as assay media depending on the target biology; optimize ionic strength and pH independently of the compound, which does not provide buffering capacity in the physiological range.
  • Filter-sterilize or use low-protein-binding filters if adsorption is a concern with hydrophobic analytes.

For item-specific pKa or ionization behavior that could influence buffer selection, refer to the CoA/Spec Sheet or primary literature.

Green Alternatives

Green chemistry considerations for handling small organic molecules focus on solvent choices, energy use, and waste minimization rather than the compound itself.

  • Greener solvent swaps (general):
    • Replace dichloromethane with ethyl acetate or cyclopentyl methyl ether (CPME) when feasible for extractions and chromatography.
    • Favor ethanol or isopropanol over acetonitrile/methanol when compatible with the process, particularly for recrystallizations or workups.
    • For reaction media, 2-MeTHF or CPME can sometimes substitute for THF/MTBE, offering lower peroxide formation and improved environmental metrics.
  • Energy minimization: Conduct reactions and dissolutions at ambient temperature when possible; avoid prolonged reflux if unnecessary.
  • Concentration and recovery: Use rotary evaporation with appropriate cold traps and consider solvent recycling where infrastructure allows.
  • Waste segregation: Separate halogenated and non-halogenated waste streams to facilitate appropriate disposal and, where possible, recycling.

Note: No item-specific greener “alternative compound” is proposed because this listing is for a specific, discrete molecule (Tofimilast). Greenness should be addressed via choice of solvent, scale, and purification strategy in your downstream application.

Pharmaceutical Uses

No pharmacopeial status or excipient role is provided for this item. This product is supplied strictly for research use only and is not intended for use in humans or for clinical applications.

Research/manufacturing context (non-clinical):

  • May be used as a reference material in analytical method development (e.g., LC–MS, HPLC) and stability-indicating methods for small-molecule characterization in R&D settings.
  • Can support pre-formulation research such as solubility screening, polymorph/excipient compatibility studies, and forced-degradation profiling—provided identity and purity are confirmed.
  • If used as a system suitability or retention-time marker, document lot number, purity, and preparation to ensure traceability.

Regulatory note:

  • No claims are made regarding compliance with USP/EP/JP or GMP manufacturing. For any regulated work, obtain an appropriate reference standard or GMP-grade material and a comprehensive documentation package.

Always consult your QA/RA teams before employing research-grade compounds in any workflow that intersects with regulated development or QC.

Physical Properties

Item-specific physicochemical specifications have not been provided for this catalog entry.

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: 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 specified for this item; refer to CoA/Spec Sheet.
  • Density: Not specified for this item; refer to CoA/Spec Sheet.
  • Refractive index: Not applicable/not specified for solids; refer to CoA/Spec Sheet if relevant.
  • Solubility: Not specified for this item; refer to CoA/Spec Sheet.
  • LogP/logD, pKa: Not specified for this item; consult literature databases using the CAS or CID if needed.

Practical guidance (general, not item-specific):

  • For drug-like, heteroatom-containing small molecules, DMSO is commonly used to prepare screening stocks (e.g., 10–50 mM), followed by dilution into assay buffers containing cosolvent (0.1–1% v/v). Always verify actual solubility and stability experimentally.
  • If crystalline, gentle warming (≤40 °C) and sonication may assist dissolution; avoid prolonged heating or basic/acidic conditions unless stability is known.
  • For analytical method development (HPLC/LC–MS), start with reversed-phase gradients (C18) and aqueous-organic systems (water with 0.1% formic acid or ammonium formate vs acetonitrile or methanol), then optimize based on response and retention. These are general starting points only.
Quality and Grades
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

How to interpret quality information (general guidance):

  • When purity is provided (e.g., ≥95% or ≥98% by HPLC), it typically reflects area percent by a specified method. Verify the method (HPLC vs GC), detection wavelength(s), and whether salts/solvates are included in the assay.
  • For screening libraries, material is often provided as the free base/neutral form unless otherwise stated. Confirm salt form, solvate content, and water content (Karl Fischer) on the CoA if these are relevant to your application.
  • Low-level impurities can influence biological readouts and analytical baselines. If you require tighter limits (e.g., for quantitative SAR or as a reference standard), request the most recent CoA and consider orthogonal purity checks (NMR, LC–MS, qNMR).
  • Stabilizers/inhibitors: Not specified for this item; most small-molecule library members are shipped without stabilizers. If a stabilizer is present, it will be declared on the CoA.
  • Batch-to-batch documentation: Retain the lot-specific CoA/SDS for traceability and report the lot number in publications to ensure reproducibility.
Reaction and Applications

This product is supplied as a discrete small molecule for research collections and reference use rather than as a general-purpose synthetic reagent. No manufacturer application notes are provided for reactions.

Typical research uses (general, not item-specific):

  • Reference material or tool compound in screening panels, analytical method development (e.g., LC–MS retention time markers), and as a comparator in in vitro assay development where allowed by your protocols.
  • Calibration/QA: Can serve as an internal or external standard in methods tailored to its physicochemical properties, once purity and stability are verified.

If you plan to derivatize or use it in synthesis:

  • Confirm functional groups and reactivity from authoritative structural data before planning transformations.
  • Conduct small-scale feasibility tests to assess chemoselectivity, stability to acids/bases, and compatibility with common coupling/oxidation/reduction conditions.

Practical tips:

  • Dry handling: Hygroscopicity is unknown—work in a dry environment if moisture sensitivity is suspected.
  • Analytical monitoring: Establish an LC–MS method early (e.g., 0.1% formic acid in water/acetonitrile) to track purity and detect degradation.
  • Stability-indicating studies: Subject aliquots to temperature/light/pH stress to understand handling limits for your workflow.

Because reaction-specific guidance requires exact structural knowledge, consult the CoA/SDS and primary literature before any synthetic manipulation.

Reaction Conditions

Not directly applicable. This product is supplied as a standalone small molecule rather than a reagent or catalyst with defined reaction condition use cases.

If performing transformations or stability studies (general guidance only):

  • Solvents: Begin with dry, oxygen-free solvents compatible with anticipated functional groups (e.g., DCM, MeCN, THF, DMF, DMSO), then refine based on observed stability.
  • Temperature: Start at ambient temperature; escalate cautiously. Screen 0–80 °C as needed while monitoring by LC–MS/HPLC for decomposition.
  • Atmosphere: Use inert gas (N2/Ar) if the molecule appears air/moisture sensitive or contains oxidation-prone motifs.
  • Catalysts/additives: Choose only after structural confirmation. Weak bases (DIPEA, NaHCO3) or acids (AcOH, TFA) can be tested for robustness; avoid strong reagents until stability is known.
  • Light sensitivity: If the chromophore is unknown, protect from light during solution handling and storage as a precaution.

Expected yields/times: Not applicable without a defined transformation; perform small-scale scouting experiments to establish feasibility.

Safety and Handling

Safety information specific to this item is not provided in the listing and must be obtained from the SDS.

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

General laboratory precautions (not a substitute for the SDS):

  • Wear appropriate PPE: lab coat, safety glasses, and suitable chemically resistant gloves (e.g., nitrile). Handle in a fume hood to avoid inhalation of dust/aerosols.
  • Avoid contact with skin and eyes; avoid inhalation of dust or vapors. Do not eat, drink, or smoke when using this product.
  • Storage incompatibilities (general): Keep away from strong oxidizers, strong acids/bases, and ignition sources. Ensure containers are tightly closed to minimize moisture/air exposure.
  • First aid overview: If inhaled—move to fresh air; if on skin—wash with soap/water; if in eyes—rinse cautiously with water for several minutes; if ingested—rinse mouth. Seek medical attention as needed. Follow SDS instructions.
  • Spill/cleanup (general): Avoid dust formation. Collect with inert absorbent, place in chemical waste. Decontaminate area per institutional procedures.
  • Waste disposal: Dispose of contents/container in accordance with local/regional/national regulations. Coordinate with your EHS office.

Always defer to the official SDS for authoritative hazard, exposure limits, and emergency procedures.

Solvent Selection

Item-specific solubility data are not provided. The following are general, literature-based practices for drug-like small molecules:

  • Primary stock solvent: High-purity DMSO (anhydrous) is commonly used for preparing concentrated stocks (e.g., 10–50 mM). Verify dissolution visually and analytically; filter through 0.2 µm PTFE if particulates persist.
  • Assay dilution: Dilute DMSO stocks into aqueous buffers maintaining a final DMSO content typically at 0.1–1% v/v to balance solubility with biological assay tolerance (if applicable to your workflow). Confirm compatibility with your assay system.
  • Alternative solvents: Acetonitrile or methanol can be used for analytical stocks and LC–MS sample preparation. For preparative work, consider ethanol, isopropanol, ethyl acetate, or CPME as appropriate for extractions and crystallizations.
  • Polarity/miscibility (general): DMSO and alcohols are miscible with water; acetonitrile is fully miscible and LC–MS friendly; ethyl acetate is immiscible with water and useful for partitioning organics from aqueous media.
  • When to choose alternatives: If compound is unstable in DMSO (rare but possible), consider acetonitrile or dry DMF for stocks, minimizing storage time and protecting from moisture/air.

Because no item-specific solubility profile is provided here, confirm solubility and stability experimentally under your exact conditions.

Storage and Reconstitution
  • Storage conditions (as provided): Room temperature.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General best practices (augmenting the provided storage guidance):

  • Keep container tightly closed in a dry, well-ventilated place. Protect from excessive heat and direct light. Use desiccant if humidity control is needed.
  • If long-term storage is anticipated and the compound is in solution, prefer anhydrous solvents (e.g., DMSO or acetonitrile), fill headspace with inert gas, and store in amber vials. Refrigeration or freezing of solutions may be beneficial but verify stability to temperature cycling.
  • Reconstitution (if supplied as a solid):
    • Choose a high-purity solvent suitable for your application (commonly DMSO for screening stocks). Start with small volumes to reach the desired concentration.
    • Mix by vortexing and brief sonication; gently warm (≤40 °C) if needed. Avoid strong acids/bases unless stability is established.
    • Filter through a 0.2 µm PTFE syringe filter if particulates remain.
  • Aliquoting: Prepare single-use aliquots to avoid repeated exposure to air and moisture. Label with concentration, solvent, date, and lot.

Always consult the lot-specific CoA/SDS for definitive storage, stability, and reconstitution instructions.

Structure and Identity

Brief description: Tofimilast is offered as an individual small-molecule research compound (library/reference use). Detailed structural identifiers are not fully specified in this listing.

  • SKU: T669034
  • Product name: Tofimilast
  • CAS: 185954-27-2 (literature identifier for this compound)
  • PubChem CID: 9896267 (literature)
  • InChIKey: 63311 (as provided in Product Data; appears truncated — verify on CoA/SDS)
  • 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, not item-specific):

  • Tofimilast is referenced in the literature as a drug-like, heteroatom-containing small molecule. Specific functional groups and ring systems should be confirmed from primary references or the certificate of analysis.
  • Stereochemistry: Not specified for this item; refer to CoA/Spec Sheet.

2D structure description (general guidance):

  • Without an item-specific SMILES/InChI, a reliable text description of the exact 2D atom connectivity cannot be provided here. Please consult the CoA/SDS or authoritative databases (linked via CAS/CID) to confirm ring systems, heteroatoms, and substitution pattern before use in design or analytical workflows.
Synthetic Utility

This listing is for a specific, fully formed small molecule typically used as a library member or reference compound, not a general-purpose building block. Without confirmed structural details (SMILES/InChI), synthetic manipulations cannot be advised item-specifically.

General considerations if derivatization is contemplated:

  • Confirm the exact structure, functional groups, and potential protecting-group needs from the CoA and primary literature (CAS 185954-27-2).
  • Map potential sites for chemoselective modification (e.g., aromatic substitution, amide coupling, heteroatom alkylation/oxidation) only after verifying the core scaffold.
  • Conduct micro-scale tests to assess sensitivity to acids/bases, oxidants/reductants, and transition-metal catalysis.
  • Analytical controls: Employ LC–MS and NMR after each step; consider qNMR for assay of isolated products when reference standards are not available.

Retrosynthetic value (general):

  • If the scaffold contains multiple rings or heteroatoms (common in drug-like compounds), convergent routes using late-stage coupling, modern C–H activation, or photoredox strategies may be applicable—but these require confirmed connectivity and functional group tolerance.

In summary, treat this compound primarily as a reference material unless you have definitive structural data and a clear derivatization objective.

Target Specificity

No target/biological specificity information is provided for this item in the Product Data.

  • Antigen/target name: Not specified for this item; refer to CoA/Spec Sheet.
  • Reported mechanism/class (if any): Not specified here. Users should consult peer-reviewed literature using CAS 185954-27-2 or PubChem CID 9896267 for any reported molecular targets and validate in-house.
  • Species reactivity/clone/isotype: Not applicable; this product is a small molecule, not an antibody or protein reagent.

Note: Any use as a biochemical tool should be accompanied by orthogonal assays and appropriate controls to confirm target engagement and selectivity under your laboratory conditions.

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