Fluconazole hydrate - ≥98% , CAS No.155347-36-7

CAS: 155347-36-7 Cat. No.: F1020209 PubChem CID: 9862025

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Specifiche e purezza

≥98%

Condizioni di conservazione di stoccaggio

Room temperature

Tipo di azione

INHIBITOR

Purezza

≥98%

Nomi e identificatori

Sorrisi canonici

C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)O.O

IUPAC Name

2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol;hydrate

InChIKey

QSZFKRINVAUJGQ-UHFFFAOYSA-N

INCHI

1S/C13H12F2N6O.H2O/c14-10-1-2-11(12(15)3-10)13(22,4-20-8-16-6-18-20)5-21-9-17-7-19-21;/h1-3,6-9,22H,4-5H2;1H2

Isomeri SMILES

C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)O.O

PubChem CID

9862025

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Halobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Halobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Fluorobenzenes
• Alternative Parents: Aryl fluorides Triazoles Tertiary alcohols Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organofluorides Organic oxides Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Fluorobenzene - Aryl halide - Aryl fluoride - Heteroaromatic compound - 1,2,4-triazole - Tertiary alcohol - Azole - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Aromatic alcohol - Organooxygen compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Alcohol - Aromatic heteromonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as fluorobenzenes. These are compounds containing one or more fluorine atoms attached 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

Proprietà chimiche e fisiche

• Peso molecolare: 324.290 g/mol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 324.115 Da
• Monoisotopic Mass: 324.115 Da
• Topological Polar Surface Area: 82.700 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 358.000
• 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: 2

XLogP3

Application Protocols

No manufacturer-tested biological application protocols (WB, IHC, IF, FC, etc.) are provided for this small-molecule compound.

General practice examples (literature/practice-based; adapt to your lab SOPs):

• Preparation of 10 mM stock: Weigh appropriate amount of fluconazole hydrate (adjusting for hydrate MW if known), dissolve in DMSO to volume, vortex until clear. Aliquot and store desiccated.
• CYP51 binding assay (difference spectra): Prepare enzyme in phosphate buffer (50 mM, pH 7.4). Record baseline; titrate compound from a concentrated DMSO stock to ≤1% final DMSO while recording spectra; observe type II shift. Fit ΔA vs [ligand] to estimate Kd.
• HPLC reference standard: Prepare primary standard solution in methanol or acetonitrile at ~0.5–1.0 mg/mL. Perform serial dilutions to construct a 5–7 point calibration curve. Filter through 0.2 µm PTFE prior to injection. Validate linearity, precision, and recovery per your method.

These examples are provided for context only; validate and optimize under your specific instrumentation and QA requirements.

Biological Roles

Contextual biochemistry (literature; no clinical claims):

• Molecular pharmacology:

  • Fluconazole is a triazole ligand that coordinates to the heme iron of fungal lanosterol 14α-demethylase (CYP51) via azole nitrogen, inhibiting the oxidative demethylation step in ergosterol biosynthesis.
  • The presence of two 1,2,4-triazole rings and a tertiary alcohol imparts balanced polarity, enabling aqueous compatibility and protein binding in vitro.

• Systems biology relevance:

  • In fungal systems, CYP51 inhibition perturbs sterol homeostasis, leading to accumulation of 14-methyl sterols; this is widely used as a research handle to study sterol pathway regulation, membrane composition, and compensatory responses.
  • In mammalian systems, fluconazole shows comparatively low affinity for many human P450s relative to imidazoles, but interactions can occur; thus, it serves as a tool compound for P450 inhibition profiling and drug–drug interaction models in vitro.

• ADME features (qualitative, literature):

  • Multiple heteroatoms confer hydrogen-bond accepting capacity; relatively low logP supports solubility in polar media.
  • Ionization under acidic conditions increases aqueous solubility and can alter membrane permeability, relevant to transporter and distribution studies in vitro.

This section summarizes general, literature-based biology to inform experimental design; it is not item-specific specification nor a statement of therapeutic use.

Buffer Applications

This compound is not a buffering agent and is not typically used to prepare buffer systems.

Practical notes for buffer-based experiments (general guidance):

• For aqueous assays, dissolve in a small volume of DMSO or alcohol and dilute into phosphate, citrate, or acetate buffers depending on target pH. Slightly acidic buffers (pH 4–6) can improve apparent solubility via azole protonation.
• To prevent precipitation on dilution, add organic stock slowly with vigorous mixing; maintain final organic solvent fraction within the tolerance of your biological system.
• If higher apparent solubility is needed, consider cyclodextrin complexation or cosolvent systems (e.g., 10–20% ethanol) while validating assay integrity.

For true buffer formulations (e.g., PBS, HEPES), follow standard recipes; fluconazole hydrate serves only as a solute of interest within those buffers.

Green Alternatives

Greener practice considerations for handling fluconazole hydrate focus on solvent and process choices rather than replacing the molecule itself (as it is the analyte/tool compound of interest).

• Solvent selection improvements:

  • Prefer water-rich media when compatible with your assay by using mild acidified buffers or co-solvents (≤10–20% MeOH/EtOH) to reduce reliance on high-boiling polar aprotics.
  • When organic is required, ethanol or methanol are generally greener than DMF/NMP; acetonitrile is acceptable for chromatography but manage waste appropriately.

• Stock solution strategy:

  • Prepare a high-concentration DMSO or ethanol master stock and serially dilute into aqueous buffer to minimize total organic solvent volume per experiment.
  • Use mini-aliquots to reduce freeze–thaw and waste.

• Waste and energy:

  • Combine compatible azole-containing waste streams and use appropriate hazardous organic disposal; avoid halogenated solvent systems when not needed.
  • Room-temperature storage (as per Product Data) supports lower energy consumption versus refrigerated storage.

Comparison (literature-based, not specifications):

• DMSO vs Ethanol for stock prep
  • Pros (DMSO): highest solubilizing power, low volatility; Cons: persistence in aqueous assays, potential biological effects at >0.5–1%.
  • Pros (Ethanol): greener profile, rapid evaporation; Cons: lower solubility ceiling, volatility management.

Select the least hazardous solvent that achieves your target concentration and analytical performance.

Pharmaceutical Uses

No therapeutic or clinical claims are made for this catalog item. Research-use context only.

• Typical laboratory/industrial roles (literature/practice):

  • Reference standard for analytical methods (HPLC/UPLC–UV, LC–MS) in quality control laboratories, including assay, identification, and impurity profiling.
  • System suitability and dissolution testing calibrant in method development for azole-class APIs.
  • Forced-degradation and stability-indicating method development: supports determination of degradation pathways (oxidative, photolytic, hydrolytic) and impurity marker tracking.
  • Formulation research: excipient compatibility screening, solubilization strategies (pH adjustment, co-solvents, cyclodextrins) and solid-state studies (hydrate–anhydrate interconversion, cocrystal exploration).

• Pharmacopeial notes (general):

  • Many laboratories reference compendial monographs for the parent compound; hydrate-specific attributes (water content, polymorph) may require internal specifications and validated methods.

All uses described are for laboratory research and analytical purposes. This SKU is labeled “For research use only.”

Physical Properties

• Item-specific (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.
  • Storage conditions: Room temperature (as provided).

• Literature/general properties for context (not specifications for this item):

  • Physical state: crystalline solid (hydrate forms are common for fluconazole standards).
  • Approximate melting point (fluconazole anhydrous, literature): ~139–141 °C; hydrate forms can exhibit onset/DSC events associated with water loss prior to melt.
  • Solubility profile: moderately soluble in DMSO, methanol, ethanol; limited to moderate aqueous solubility at neutral pH, increased solubility in acidic aqueous media due to azole protonation; enhanced in presence of co-solvents or cyclodextrins (literature).
  • logP/logD (literature, anhydrous): reported low to moderate lipophilicity (logP around 0.5–1), reflecting polar azole nitrogens and tertiary alcohol.
  • pKa (literature, anhydrous): multiple basic sites associated with 1,2,4-triazoles (reported conjugate acid pKa values in the acidic range; overall amphoteric behavior; ionization increases in acidic conditions).
  • UV characteristics: π–π* transitions from aromatic and azole chromophores give modest UV absorbance; wavelengths in the 200–260 nm range often used analytically (literature).

Notes:

• Exact hydrate stoichiometry, water content, and analytical constants can vary by batch; consult the CoA/Spec Sheet for item-specific values.

Quality and Grades

• Item-specific (from Product Data):

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

• Guidance on typical quality attributes for library compounds (general context):

  • Small-molecule library materials are often provided at high chemical purity (e.g., ≥95–98% by HPLC/GC) with supporting analytical data (HPLC chromatogram, MS, NMR where applicable). UV cutoff, residual solvents, water content, and salt/hydrate stoichiometry may be reported when relevant.
  • For hydrates, the hydration level can influence both molecular weight used for stoichiometry and the apparent potency in assays; suppliers may include KF water and TGA data. For this item, specific values are not provided here.
  • If labeled as reference standard or analytical grade in documentation, expect tight impurity limits and validated identity (orthogonal methods). If intended for screening, emphasis may be on purity and identity with practical packaging.

• Stabilizers/antioxidants:

  • No stabilizer information is provided for this item. If stabilizers were present, they would be disclosed on the CoA/Spec Sheet; absence typically implies none added.

Please consult the item’s CoA/Spec Sheet for batch-resolved purity, identity confirmation, and any residual solvent or water content data.

Reaction and Applications

As supplied, fluconazole hydrate is most commonly used as a research tool compound and analytical reference rather than as a reagent in synthesis.

• Research applications (general/literature):

  • Target engagement studies: Probe compound for fungal sterol 14α-demethylase (CYP51) biochemistry, ligand-binding assays, and structure–activity investigations of azole–heme interactions.
  • Analytical reference standard: Calibration/validation of HPLC/LC–MS methods in quality control, dissolution testing, and impurity profiling where fluconazole is monitored.
  • Crystallographic/biophysical: Ligand for protein–ligand structural determination (e.g., CYP51 homologs), ITC/SPR binding, and spectroscopic heme titrations.

• Less common synthetic roles:

  • Derivatization studies: Formation of salts, cocrystals, and prodrug-like derivatives for comparative physicochemical evaluation.
  • Coordination/ion-pair complexes: Leveraging azole nitrogens to assemble model complexes for spectroscopic studies (not typically for preparative synthesis).

• Practical tips:

  • Maintain consistent hydrate stoichiometry when weighing for assays; if stoichiometry is uncertain, consider drying to constant weight under mild vacuum and note any mass loss (literature practice; confirm suitability for your protocol).
  • Prepare concentrated DMSO stocks and aliquot to minimize freeze–thaw or moisture uptake.

Note: The above are typical literature/practice-based applications for this chemotype; no specific manufacturer application notes were provided for this SKU.

Reaction Conditions

There are no item-specific reaction conditions for this product, as it is not marketed as a reagent. The following guidance addresses preparation of solutions and common analytical setups (literature/practice-based):

• Stock solution preparation:

  • Dissolve in DMSO at 10–50 mM; vortex and, if needed, warm gently (≤40 °C) to aid dissolution. Filter (0.2 µm PTFE) if particulates remain.
  • For aqueous work, pre-dissolve in DMSO or ethanol, then titrate into buffered water (pH 4–7) with rapid mixing to avoid precipitation.

• Chromatography (general):

  • RP-HPLC: C18 columns with water–acetonitrile or water–methanol gradients; volatile acid modifiers (e.g., 0.1% formic acid) aid peak shape and MS compatibility.
  • Expected retention: moderate due to polar azoles; detection by UV 210–230 nm or LC–MS (ESI+ often suitable).

• Stability testing setups:

  • Forced degradation: oxidative (H2O2), acidic/basic hydrolysis, photolysis per ICH Q1A guidance to establish stability-indicating methods; hydrate form may demonstrate mass changes upon drying/heating.

• Protein binding/biophysical assays:

  • Perform titrations in buffered aqueous media with ≤1–2% DMSO. For CYP binding spectra (type II difference spectra), typical temperatures are ambient and ionic strengths 50–150 mM.

All conditions above are general literature guidance to assist experimental planning and are not product specifications.

Safety and Handling

• Item-specific hazard information (from Product Data):

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

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

  • Handle solid powders in a fume hood or biosafety cabinet to avoid inhalation and dust generation.
  • Recommended PPE: lab coat, safety glasses, nitrile gloves; use respiratory protection if dust/aerosol may form and engineering controls are insufficient.
  • Avoid contact with strong oxidizers and strong acids/bases unless conditions are controlled; azole nitrogens can coordinate metals—avoid unintended contact with reactive metal salts.
  • Hygiene: Wash thoroughly after handling; avoid eating or drinking in work area.

• First aid (overview; follow institutional protocols):

  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical advice if irritation continues.
  • Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel; seek medical advice.

• Fire and stability considerations:

  • Solid organic compound; use CO2, dry chemical, or foam to extinguish small fires; combustion may produce irritating fumes.
  • Store at room temperature, in a tightly closed container, protected from moisture to maintain defined hydrate content.

Always consult the product-specific SDS for complete hazard and response information.

Solvent Selection

Fluconazole hydrate is a neutral, heteroatom-rich aromatic solid with two triazoles and a tertiary alcohol; it is moderately polar and typically formulated in organic or mixed aqueous systems.

• Practical dissolution choices (general guidance):

  • Excellent: DMSO, DMF, NMP — high polarity, strong H-bond accepting media; typical for screening stocks (e.g., 10–50 mM in DMSO).
  • Good: Methanol, ethanol, isopropanol — useful for analytical standards and intermediate stock solutions.
  • Conditional/adjusted: Water — solubility improves in acidified water (e.g., dilute HCl or buffers below neutral pH) due to azole protonation; use co-solvent or cyclodextrins to enhance aqueous delivery when needed.
  • Less suitable: Nonpolar solvents (hexanes, toluene) — poor solubility expected due to polar functionalities.

• Miscibility and handling:

  • DMSO stocks can be diluted into buffered aqueous media; to avoid precipitation, add stock slowly with vigorous mixing, maintaining final DMSO typically ≤1–2% v/v in bioassays.
  • For solid-on-solid operations (e.g., spiking standards), dry the glassware and use volumetric solvents with low water content if you require tight concentration control relative to the hydrate mass.

• When to choose alternatives:

  • For entirely aqueous systems, consider pH adjustment (slightly acidic) or co-solvents to reach target concentrations without exceeding vehicle tolerances.
  • For LC-UV methods, acetonitrile/water or methanol/water with 0.1% acid modifiers are common; verify UV transparency and retention.

All solubility statements are literature/practice-based guidance and not item specifications.

Storage and Reconstitution

• Item-specific storage (from Product Data):

  • Room temperature.

• Packaging/handling:

  • Store in a tightly sealed container to limit moisture exchange, which can alter hydrate stoichiometry and effective assay concentrations.
  • Protect from excess humidity and direct light. Use desiccant in secondary containment if ambient humidity is high.

• Reconstitution guidance (general, not specification):

  • For screening: prepare concentrated DMSO stocks (e.g., 10–50 mM), aliquot into small volumes (e.g., 50–200 µL) to minimize freeze–thaw and headspace moisture.
  • For aqueous use: dissolve first in a miscible organic solvent (DMSO or ethanol), then dilute into buffer. Maintain final organic content within assay tolerance (commonly ≤1–2% v/v DMSO).
  • If exact molarity is critical and hydrate ratio is uncertain, consider determining water content (e.g., Karl Fischer) or calculate based on the declared hydrate stoichiometry on the CoA.

• Stability:

  • Under typical lab conditions, the solid is stable at room temperature. For long-term analytical standards, store in amber vials, minimize repeated opening, and record open dates.

• Research use note:

  • For research use only. Not for human or animal therapeutic or diagnostic use.

Structure and Identity

Brief: Fluconazole hydrate is the hydrated form of the triazole antifungal chemotype, cataloged here for research use in small‐molecule libraries.

• Item-specific (from Product Data):

  • Product Name: Fluconazole hydrate
  • CAS: 155347-36-7 (hydrate)
  • CID: 9862025
  • InChIKey: 305702 (as provided)
  • 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.

• Literature/reference identity (for scientific context; not item specifications):

  • Parent compound (fluconazole, anhydrous) formula: C13H12F2N6O; monohydrate commonly represented as C13H12F2N6O·H2O.
  • Approx. formula mass (monohydrate, literature): ~324.3 g/mol (base 306.3 + 18.0 for H2O).
  • InChIKey (fluconazole, anhydrous, literature): PFWKXMJEWADPNW-UHFFFAOYSA-N.

• Structural features (descriptive, literature):

  • Core: 2,4-difluorophenyl substituted tertiary carbinol (secondary alcohol center bearing two triazolylmethyl substituents).
  • Heterocycles: Two 1,2,4-triazole rings attached via methylene linkers to a benzylic tertiary alcohol center.
  • Functional groups: Alcohol (tertiary); multiple azole nitrogens (Lewis basic); two aryl fluorides.
  • 2D description: A difluorophenyl ring bearing at its benzylic carbon a hydroxylated quaternary carbon connected to two –CH2–triazolyl substituents; no defined stereocenters in the parent (achiral, racemic at a prochiral center).

Synthetic Utility

Fluconazole hydrate is not typically employed as a synthetic reagent; it is the end product of a medicinal chemistry sequence. Nevertheless, some synthetic and analytical contexts are relevant (literature-based):

• Functional group features:

  • Two 1,2,4-triazole rings (multiple ring nitrogens, basic/ligating) and a tertiary alcohol at a benzylic center adjacent to a 2,4-difluorophenyl ring.

• Transformations used in derivatization studies:

  • Esterification/etherification at the tertiary alcohol (often low yielding due to steric hindrance; typically requires activation or carbocation-stabilizing conditions).
  • Salt formation or co-crystal assembly exploiting azole basicity and hydrogen-bonding motifs.
  • Metal–ligand complexation via azole N to probe binding geometries; primarily analytical/biophysical rather than preparative chemistry.

• Retrosynthetic perspective (for context):

  • Assembly from a difluoroacetophenone precursor followed by introduction of two triazolylmethyl groups and tertiary alcohol formation is a common medicinal route; knowledge of this can inform impurity tracking in stability studies.

• Utility in method development:

  • Serves as a probe substrate/ligand for CYP assays, enabling optimization of reductants, co-factors, and spectrophotometric detection.

Because this SKU is offered as a research compound, not a reagent, focus on its use as a tool/reference material rather than as a building block.

Target Specificity

No antibody or biological macromolecule is supplied; this is a small-molecule compound. Therefore, antigen/epitope specificity, clone, isotype, and species reactivity are not applicable to this item.

Literature context (for users planning biochemical assays):

• Fluconazole is widely used as a tool ligand for fungal CYP51 (lanosterol 14α-demethylase) in enzymology and structural biology. Binding involves coordination of an azole nitrogen to the heme iron. Off-target interactions with other P450s may occur in vitro at higher concentrations, but target selectivity varies by species and isoform.

These notes are for general scientific context and are not product-specific test data.