Hydroxyvardenafil - ≥95% , CAS No.224785-98-2

CAS: 224785-98-2 Cat. No.: H1021770 Summenformel: C₂₃H₃₂N₆O₅S Molekulargewicht: 504.6 PubChem CID: 135487732

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Reinheit

≥95%

Namen und Kennungen

• Kanonisches Lächeln: CCCC1=NC(=C2N1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)CCO)OCC)C
• IUPAC Name: 2-[2-ethoxy-5-[4-(2-hydroxyethyl)piperazin-1-yl]sulfonylphenyl]-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
• InChIKey: KZFHUILKKFVOMB-UHFFFAOYSA-N
• INCHI: 1S/C23H32N6O5S/c1-4-6-20-24-16(3)21-23(31)25-22(26-29(20)21)18-15-17(7-8-19(18)34-5-2)35(32,33)28-11-9-27(10-12-28)13-14-30/h7-8,15,30H,4-6,9-14H2,1-3H3,(H,25,26,31)
• Isomere SMILES: CCCC1=NC(=C2N1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)CCO)OCC)C
• PubChem CID: 135487732
• Molekulargewicht: 504.6

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Benzene and substituted derivatives
      • Subclass Benzenesulfonamides

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Benzenesulfonamides
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzenesulfonamides
• Alternative Parents: Benzenesulfonyl compounds Phenol ethers Phenoxy compounds N-alkylpiperazines Alkyl aryl ethers 1,2,4-triazines Organosulfonamides N-substituted imidazoles Heteroaromatic compounds Sulfonyls 1,2-aminoalcohols Trialkylamines Azacyclic compounds Organic oxides Hydrocarbon derivatives Primary alcohols
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Benzenesulfonamide - Benzenesulfonyl group - Phenoxy compound - Phenol ether - Alkyl aryl ether - N-alkylpiperazine - 1,4-diazinane - N-substituted imidazole - Piperazine - 1,2,4-triazine - Organosulfonic acid amide - Triazine - Azole - Imidazole - Heteroaromatic compound - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Sulfonyl - Tertiary aliphatic amine - Tertiary amine - 1,2-aminoalcohol - Azacycle - Alkanolamine - Organoheterocyclic compound - Ether - Primary alcohol - Alcohol - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organonitrogen compound - Organic nitrogen compound - Amine - Organooxygen compound - Organosulfur compound - Aromatic heteropolycyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemische und physikalische Eigenschaften

• Molekulargewicht: 504.600 g/mol
• XLogP3: 1.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 504.215 Da
• Monoisotopic Mass: 504.215 Da
• Topological Polar Surface Area: 138.000 Ų
• Heavy Atom Count: 35
• Formal Charge: 0
• Complexity: 872.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No tested application protocols are provided in the Product Data for this item. The following are general, non-binding guidelines for typical research uses; validate and optimize for your system.

• LC–MS/MS calibration:
  • Prepare a primary stock in DMSO (e.g., 1–10 mM). Serially dilute into acetonitrile:water (1:1) with 0.1% formic acid to prepare working standards.
  • Construct calibration curves spanning the expected concentration range. Use matrix-matched standards when quantifying in biological matrices.
• Enzyme/binding assays:
  • Dilute DMSO stocks into assay buffer to a final DMSO content ≤0.5–1% v/v. Include vehicle controls and a parent-compound comparator where relevant.
• Stability assessment:
  • Evaluate stability at bench-top and autosampler conditions, and after multiple freeze–thaw cycles, to define handling limits.

Note: These are general laboratory practices offered for convenience and are not item-specific performance claims. Consult your institution’s SOPs and validate all conditions.

Biological Roles

Context (literature/general): Hydroxyvardenafil is a hydroxylated metabolite of the PDE5 ligand vardenafil. Hydroxylation typically increases polarity and can influence target binding, clearance, and distribution. Although no medical or clinical claims are made here, the compound is valuable in biochemical research to understand structure–activity relationships and metabolism.

Potential roles in research:

• Enzyme interaction studies: Serves as a comparator ligand in phosphodiesterase assays to explore how hydroxylation modulates affinity and selectivity profiles across PDE isoforms (e.g., PDE5 vs. other PDEs), without implying any therapeutic utility.
• ADME investigations: Functions as a defined metabolite standard to characterize metabolic pathways (CYP-mediated oxidation), phase II conjugation tendencies (e.g., glucuronide formation), and transport phenomena due to altered polarity and ionization.
• Biomatrix analysis: Employed as a calibration or confirmation standard in LC–MS/MS quantification of vardenafil-related species in in vitro systems (microsomes, S9, hepatocytes) and non-clinical samples.
• Computational/biophysical: Used in docking, free-energy perturbation, and QSAR workflows to quantify the effect of added hydrogen-bond donor capacity on binding and desolvation.

Research caveats:

• Binding and activity can be assay- and isoform-dependent; validate against purified targets and appropriate controls.
• Matrix effects are common in LC–MS/MS bioanalysis; apply stable-isotope internal standards and matrix-matched calibration where possible.

This product is for research use only.

Buffer Applications

Not typically applicable. Hydroxyvardenafil is a small-molecule research standard rather than a buffering agent. It does not form dedicated buffer systems with defined pKa/pH ranges in laboratory practice.

Practical note: When preparing aqueous working solutions for assays, use your assay’s validated buffer (e.g., phosphate, HEPES, or ammonium formate/acetate for LC–MS) and adjust pH to maintain solubility and stability of the analyte. Any pH adjustment or buffer composition should be qualified in your specific method.

Green Alternatives

This product is a target small molecule standard rather than a reaction solvent or bulk auxiliary; “green alternatives” chiefly concern the analytical and preparative solvents you choose around it rather than the compound itself.

Greener choices for common tasks (general guidance):

• LC mobile phases: Favor water–acetonitrile over water–methanol when appropriate energy recovery and solvent recycling is in place; acetonitrile typically affords lower backpressure and may reduce run times, saving energy. Use the minimum organic percentage that achieves required resolution.
• Stock solution solvents: Dimethyl sulfoxide (DMSO) remains common; where feasible, ethanol or water with mild acidification can reduce reliance on high-toxicity solvents. Validate stability and solubility if switching.
• Work-up and cleaning: Replace chlorinated solvents for glassware cleaning with aqueous detergents or alcohols where compatible.

Comparison (illustrative; not product-specific):

• DMSO vs. DMF: DMSO has a more favorable toxicity and environmental profile than DMF; both solubilize heteroaromatic drug-like compounds effectively.
• Acetonitrile vs. Methanol: Both are widely used; acetonitrile can reduce analysis time and energy consumption at comparable resolution, but supply chain impacts vary. Implement solvent-saving gradients and waste minimization regardless of choice.

Adopt microscale methods, efficient gradients, and solvent recycling programs to reduce overall environmental footprint during analytical use of this compound.

Pharmaceutical Uses

No therapeutic or clinical use is claimed or supported for this catalog item.

Non-clinical, research-oriented uses (general):

• Analytical reference standard: Employed in method development and validation for quality research of vardenafil-related materials, including identification and quantification of oxidative degradation products or metabolites.
• Process/forced degradation studies: Used to confirm specificity of stability-indicating analytical methods for research samples containing vardenafil-like structures.
• Formulation research controls: Serves as a comparator in pre-formulation or excipient-compatibility experiments to study oxidative liabilities of analogous scaffolds (research only).

Regulatory/pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet and applicable compendia if relevant to your research context.

Good practices:

• Document reference identity and purity with the accompanying CoA for audit trails in non-clinical laboratories.
• Use bracketed calibration with matrix-matched standards to mitigate matrix effects during quantitative analyses.

Reminder: For research use only. Not for human or veterinary use, diagnostic procedures, or clinical applications.

Physical Properties

Item-specific specifications:

• Appearance: 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.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not applicable/unknown for this solid under ambient pressure; Not specified for this item; refer to CoA/Spec Sheet.
• Density, refractive index, UV cutoff, water content, and inorganic/metal limits: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general expectations (for context only, not item specifications):

• Physical state: typically a solid organic compound (reference standards are commonly supplied as solids or films).
• Solubility profile: analytical reference molecules of this class are commonly soluble in polar aprotic organic solvents (e.g., DMSO, DMF, acetonitrile) and variably soluble in alcohols; aqueous solubility generally improves with cosolvent or acidification when protonatable amines are present.
• Ionization: tertiary amines and basic nitrogens (from the piperazine) can be protonated under acidic conditions, enhancing aqueous solubility (literature, general behavior for vardenafil-class structures).
• LogP/logD: hydroxylation typically reduces logP relative to the parent compound, reflecting increased polarity (literature trend; no numeric value stated here).

Note: For authoritative, lot-specific values, please consult the CoA/Spec Sheet and SDS.

Quality and Grades

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

Context and expectations for small-molecule reference standards (general guidance):

• Reference/analytical grade materials are typically supplied at high chemical purity with rigorous identity confirmation (NMR, LC–MS/HRMS, and/or HPLC purity). When applicable, residual solvent levels and water content may be provided on the CoA.
• Where stated, HPLC/LC–MS suitability indicates low UV-absorbing and nonvolatile impurities within critical chromatographic ranges, enabling robust quantitation and system suitability testing.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. If stabilizers are used in analogous products, they are declared on the label/CoA because they can affect assay response and calibration curves.
• Trace analysis readiness: For quantitative bioanalysis (e.g., LC–MS/MS), customers often require tight specifications on purity, counterion content, and salt/base form. Confirm salt form and any hydration/solvation state on the CoA before preparing standards.

Best practices:

• Verify lot-specific purity, salt form (free base vs. salt), and water content prior to method development.
• Retain CoA and chromatograms in your analytical file for audit-readiness in regulated environments (non-clinical research only, per product use restrictions).

Reaction and Applications

Manufacturer applications: Not specified in Product Data for this item.

Research applications (general, non-clinical):

• Analytical reference standard: Used to develop and validate LC–UV/LC–MS methods for monitoring vardenafil metabolism and to confirm metabolite identity in in vitro/in vivo studies.
• Metabolism and enzymology: Useful as a probe or standard in CYP450-mediated metabolism studies to investigate hydroxylation pathways and kinetics relative to the parent compound (vardenafil), including phase I formation and potential phase II conjugation (e.g., glucuronidation) profiling.
• Binding/biophysics: As a hydroxylated analogue of a PDE5 ligand, it can support structure–activity relationship (SAR) investigations, binding assays, and computational docking as a polarity-modified comparator (no medical claims; research only).
• Stability/degradation studies: Serves as a positive control for oxidative transformation products during forced-degradation assessments of vardenafil-containing research materials.

Practical tips:

• Authenticate identity by orthogonal techniques (HRMS, 1H/13C NMR, LC–MS retention match to literature or reference) prior to quantitative studies.
• Prepare fresh working solutions and evaluate short-term stability in chosen solvent system; include stability-indicating controls in validation batches.
• For LC–MS/MS, monitor multiple transitions to guard against interferences; consider isotope-labeled internal standards when available.

Note: This product is for research use only and is not intended for human or veterinary use.

Reaction Conditions

This product is not typically employed as a reagent or catalyst in synthetic reactions; therefore, defined reaction conditions are not generally applicable.

General guidance related to analytical handling (literature/practice; not product specifications):

• Stock solutions: Prepare at 1–50 mM in dry DMSO or methanol. Filter (0.2 µm PTFE) if particulate is present.
• LC–MS method development: Start with reversed-phase C18, water/acetonitrile with 0.1% formic acid, gradient 5–95% acetonitrile over 10–15 min, monitoring multiple reaction monitoring (MRM) transitions optimized empirically.
• Stability checks: Assess bench-top, autosampler (4–10 °C), and freeze–thaw stability in your matrix, as hydroxylated metabolites may exhibit different stability than parent compounds.

If you intend to transform this molecule chemically (e.g., derivatize the hydroxyl group), select standard conditions for alcohol functionalization (e.g., carbonate formation, Mitsunobu inversion/etherification, or acylation) only after confirming the precise structural isomer and protecting other nucleophilic/basic sites as needed. No specific conditions can be prescribed without the exact structure and compatibility data.

Safety and Handling

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

General laboratory safety (good practice; defer to SDS for authoritative guidance):

• Handle in a chemical fume hood to avoid inhalation of dust or aerosols. Avoid skin and eye contact.
• Personal protective equipment: lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Wash thoroughly after handling.
• Incompatibilities: Strong oxidizing agents and strong acids/bases may lead to degradation; avoid conditions that promote oxidation or hydrolysis unless intended for study.
• First aid (overview): If inhaled, move to fresh air; if on skin, wash with soap and water; if in eyes, rinse cautiously with water for several minutes; if ingested, rinse mouth. Seek medical attention as per SDS.
• Spill/accidental release: Avoid dust formation. Sweep up solids carefully, minimizing aerosolization; place in suitable container for disposal according to institutional and local regulations.
• Thermal/photostability: Many heteroaromatic drug-like molecules exhibit some sensitivity to prolonged heat or strong light; store as directed and minimize unnecessary exposure (general guidance).
• Waste disposal: Dispose of unused material, solutions, and contaminated consumables in accordance with local/regional regulations and institutional policies.

Always consult the product’s SDS for definitive hazard, toxicological, and response information. For research use only.

Solvent Selection

This compound is a hydrophobic, nitrogen- and sulfur-containing heteroaromatic small molecule with a basic piperazine motif (literature, based on the vardenafil scaffold). Practical solvent choices for stock solutions and method development are as follows (general guidance; not product specifications):

• Polar aprotic solvents: DMSO and DMF typically afford high solubility and stability for drug-like heterocycles; commonly used for 10–50 mM stocks.
• Chromatography solvents: Acetonitrile and methanol are preferred for LC–UV/LC–MS mobile phases; combine with water and acid modifiers (e.g., 0.1% formic acid) to improve peak shape and ionization (method-development consideration).
• Aqueous media: Aqueous solubility can improve under mildly acidic conditions due to protonation of basic nitrogens (e.g., pH 2–4 with formic or phosphoric acid). Use minimal organic cosolvent to maintain solubility without precipitation during dilutions.
• Nonpolar solvents: Generally disfavored for assay stocks and analytics due to limited polarity and detector compatibility.

Selection notes:

• For bioassay addition, prepare a concentrated DMSO stock and perform serial aqueous dilutions keeping final DMSO ≤0.5–1% v/v to minimize biological confounding.
• For LC–MS quantitation, DMSO or methanol primary stocks followed by acetonitrile:water (1:1) working solutions with 0.1% formic acid typically yield stable response (general practice).

Always validate solvent choice for your specific assay, instrument, and concentration range.

Storage and Reconstitution

Storage conditions (Product Data):

• Store at room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General handling recommendations (not item specifications; adopt per your QA/SOPs):

• Protect from excessive heat, humidity, and light. Keep container tightly closed to prevent moisture ingress and contamination.
• For long-term analytical consistency, some laboratories aliquot solids upon first opening and store in desiccators or low-humidity cabinets.

Reconstitution (general guidance for small-molecule standards):

• Choose a high-purity solvent such as DMSO or methanol to prepare a concentrated primary stock (e.g., 1–50 mM), based on solubility and assay requirements.
• If aqueous working solutions are needed, dilute the organic stock into buffer slowly with mixing to avoid precipitation; adjust pH if necessary to maintain solubility.
• Filter working solutions through 0.2 µm PTFE or PVDF if particulate is observed.
• Avoid repeated freeze–thaw of solutions; prepare single-use aliquots and store at the lowest practical temperature compatible with your method (e.g., 2–8 °C for short-term autosampler storage or −20 °C for longer-term solutions), validating stability experimentally.

Always consult the product’s CoA and SDS for definitive instructions related to the supplied lot and packaging.

Structure and Identity

Brief overview: Hydroxyvardenafil is a hydroxylated derivative of vardenafil used as a research small molecule standard and probe in metabolism, analytical, and enzymology studies.

• SKU: H1021770
• Product name: Hydroxyvardenafil
• CAS: 224785-98-2
• PubChem CID: 135487732 (literature identifier)
• InChIKey: 193538 (as provided in Product Data)
• 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):

• Hydroxyvardenafil is described in the literature as a phase I metabolite of vardenafil formed by oxidative hydroxylation, increasing polarity relative to the parent compound. The parent scaffold (vardenafil) contains a heteroaromatic bicyclic core, a sulfonyl-substituted piperazine, and an aryl/alkoxy substituent; hydroxylation typically occurs on an aliphatic or aromatic position depending on metabolic route (literature, position may vary by isomer).
• Functional group classes expected (literature, general): heteroaromatic ring system, amide/urea-like carbonyl within a bicyclic lactam, tertiary amine(s) within a piperazine, sulfonyl substituent, and one added hydroxyl group versus vardenafil.

2D description in words (literature/general): a fused heterocycle core bearing a carbonyl, appended via a sulfonyl linker to a piperazine ring, further substituted by an aryl/alkoxy moiety; hydroxyvardenafil contains one additional –OH substituent compared with vardenafil, increasing hydrogen-bonding capacity.

Synthetic Utility

Hydroxyvardenafil is generally used as a defined analyte/standard rather than as a synthetic building block. Nevertheless, in a synthetic chemistry context, hydroxylated analogues of drug-like scaffolds can provide insight into late-stage functionalization and SAR.

General/literature considerations:

• Functional groups: The scaffold class features a heteroaromatic bicyclic core with a lactam-like carbonyl, a sulfonyl-linked piperazine (basic), and an aryl/alkoxy substituent; the hydroxy group introduces an additional hydrogen-bond donor/acceptor site and potential handle for derivatization (e.g., etherification, esterification) if the position is accessible.
• Late-stage diversification: Hydroxyl groups allow prodrug exploration (carbonate/ester formation) and polarity tuning. They can also serve as anchoring points for immobilization on solid supports for affinity or pull-down experiments (research).
• Oxidation state context: Comparison of parent vs. hydroxy analogue aids in mapping metabolic “soft spots” and guiding protective modifications in medicinal chemistry campaigns (no medical claims).

Caveats:

• Without a specified position of hydroxylation for this item, any derivatization strategy is conceptual and should be validated with a fully defined structure (SMILES/InChI and NMR confirmation).
• If synthetic transformations are planned, confirm the compound’s salt/base form and protect sensitive motifs (e.g., piperazine) as needed.

For most customers, the principal value is analytical and biochemical, not as a reagent.

Target Specificity

Item-specific target data (antigen/epitope/clone/isotype) are not applicable to small molecules and are not provided for this product.

General research context (literature): Hydroxyvardenafil is an analogue/metabolite of a known PDE5 ligand. While it may interact with phosphodiesterase isoforms in biochemical assays, no quantitative affinity/selectivity data are provided with this listing. Users should generate or consult literature values specific to their assay system.