Sofosbuvir impurity G , CAS No.1337482-15-1

CAS: 1337482-15-1 Cat. No.: S647272 Summenformel: C₂₂H₂₉FN₃O₉P Molekulargewicht: 529.45 PubChem CID: 58463528

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

Sofosbuvir impurity G, an diastereoisomer of Sofosbuvir, is the impurity of Sofosbuvir. Sofosbuvir (PSI-7977) is an inhibitor of HCV RNA replication, demonstrates potent anti-hepatitis C virus activity.

Form:Solid

Spezifikationen

Biochemische und physiologische Mechanismen

Sofosbuvir impurity G, an diastereoisomer of Sofosbuvir, is the impurity of Sofosbuvir. Sofosbuvir (PSI-7977) is an inhibitor of HCV RNA replication, demonstrates potent anti-hepatitis C virus activity.

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Namen und Kennungen

Kanonisches Lächeln

CC(C)OC(=O)C(C)NP(=O)(OC1C(OC(C1(C)F)N2C=CC(=O)NC2=O)CO)OC3=CC=CC=C3

IUPAC Name

propan-2-yl (2S)-2-[[[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-2-(hydroxymethyl)-4-methyloxolan-3-yl]oxy-phenoxyphosphoryl]amino]propanoate

InChIKey

IBMLPFZASPUMOW-IAAJYNJHSA-N

INCHI

1S/C22H29FN3O9P/c1-13(2)32-19(29)14(3)25-36(31,34-15-8-6-5-7-9-15)35-18-16(12-27)33-20(22(18,4)23)26-11-10-17(28)24-21(26)30/h5-11,13-14,16,18,20,27H,12H2,1-4H3,(H,25,31)(H,24,28,30)/t14-,16+,18+,20+,22+,36?/m0/s1

Isomere SMILES

C[C@@H](C(=O)OC(C)C)NP(=O)(O[C@@H]1[C@H](O[C@H]([C@]1(C)F)N2C=CC(=O)NC2=O)CO)OC3=CC=CC=C3

PubChem CID

58463528

Molekulargewicht

529.45

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Klasse Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Ebene5 Amino acids and derivatives
          • Ebene6 Alpha amino acids and derivatives
            • Ebene7 Alpha amino acid esters

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Klasse: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Alpha amino acid esters
• Alternative Parents: Alanine and derivatives Phenoxy compounds Phosphoric diester monoamides Pyrimidones Hydropyrimidines Organic phosphoramides Oxolanes Vinylogous amides Heteroaromatic compounds Lactams Carboxylic acid esters Ureas Oxacyclic compounds Monocarboxylic acids and derivatives Azacyclic compounds Organonitrogen compounds Organofluorides Alkyl fluorides Organic oxides Hydrocarbon derivatives Carbonyl compounds Primary alcohols
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Alpha-amino acid ester - Alanine or derivatives - Phenoxy compound - Phosphoric diester monoamide - Pyrimidone - Phosphoric acid ester - Pyrimidine - Monocyclic benzene moiety - Benzenoid - Organic phosphoric acid amide - Organic phosphoric acid derivative - Hydropyrimidine - Vinylogous amide - Oxolane - Heteroaromatic compound - Carboxylic acid ester - Lactam - Urea - Oxacycle - Monocarboxylic acid or derivatives - Azacycle - Organoheterocyclic compound - Organofluoride - Alkyl halide - Organohalogen compound - Alkyl fluoride - Alcohol - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Organic nitrogen compound - Primary alcohol - Aromatic heteromonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
• 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

• Löslichkeit: DMSO : 100 mg/mL (188.88 mM; Need ultrasonic)

Application Protocols

No vendor-tested bioassay protocols apply. For analytical use, consider the following general workflows (not item-specific):

• Reference standard preparation
  • Weigh accurately in a dry environment.
  • Dissolve in LC–MS-grade acetonitrile, methanol, or DMSO to prepare a primary stock (e.g., 0.5–2 mg/mL), then dilute with mobile phase to working levels.
• LC–UV/LC–MS method check
  • Run a short scouting gradient on a C18 column; verify retention time, UV spectrum near 260 nm, and MS response.
  • Establish a system suitability test (SST) with criteria for resolution versus neighboring impurities and tailing factor.
• Calibration
  • Prepare multi-point calibration curves bracketing expected impurity levels; assess linearity and residuals.
• Stability
  • Assess short-term autosampler stability (e.g., 24–48 h at 4–8 °C) and bench-top stability; adjust handling accordingly.

These are general suggestions; consult your internal SOPs and the item’s CoA/SDS for authoritative instructions.

Biological Roles

This section provides contextual, non-clinical information.

• General context (not item-specific): Sofosbuvir is a nucleoside phosphoramidate prodrug; its impurities and related substances are structurally similar molecules arising from synthesis, isomerization (e.g., Rp/Sp at phosphorus), or degradation (hydrolysis, oxidation, de-esterification). These compounds do not necessarily share the same biotransformation or activity profiles as the API.
• Research relevance: Characterizing such impurities supports understanding of process robustness, stability-indicating methods, and quality-by-design (QbD) risk assessments.
• Metabolic considerations (literature, general): Phosphoramidate prodrugs typically undergo enzymatic and chemical steps to reveal the monophosphate nucleoside; impurities may bypass, hinder, or mirror parts of these pathways. However, the biological behavior of a specific impurity must be experimentally determined and is not implied by structural similarity.

Important note: No biological activity or clinical claims are made for this item. It is supplied strictly for research use related to analytical characterization and quality control of sofosbuvir-containing materials.

Buffer Applications

Not typically applicable. This product is an organic impurity standard rather than a buffering reagent. For practical laboratory use, buffers are relevant only as mobile-phase components in LC analysis (e.g., ammonium formate/acetate at pH 3–6 for MS compatibility). Choose buffer strength and pH to optimize peak shape and analyte stability for your specific method.

Green Alternatives

Context: As a reference impurity for analytical work, the main environmental impact derives from solvent selection in sample prep and chromatography.

Greener choices (general guidance)

• Prefer acetonitrile over halogenated solvents for stock preparation and sample cleanup. Where feasible, ethanol or IPA may substitute for methanol, balancing solubility and stability.
• For LC, use aqueous mobile phases with volatile, low-toxicity buffers (ammonium acetate/formate) and minimize organic content by optimizing column selectivity (e.g., core–shell C18/C30, polar-embedded phases) to shorten gradients.
• Implement microflow LC or shorter columns to reduce solvent consumption without sacrificing resolution.

Trade-offs

• Ethanol/IPA increase viscosity and backpressure relative to acetonitrile, possibly requiring higher temperatures or reduced flow.
• Lower organic strength may exacerbate peak tailing for phosphate-like analytes; consider ion-pair-free methods first, but low-dose HFIP/TEA systems (though less green) can sometimes be necessary for challenging separations.

Mini-comparison (general)

• MeCN: Low viscosity, strong elution, MS-compatible; petrochemical origin.
• MeOH: Renewable routes exist; higher viscosity; different selectivity.
• EtOH/IPA: Greener profile; may require method re-optimization.

Operational practices

• Scale down assay volumes, employ multi-use vials to cut waste, and segregate solvent waste streams for efficient disposal.

Pharmaceutical Uses

Formulation/excipient roles are not applicable to this item. Sofosbuvir impurity G is intended as a research/analytical reference standard for:

• Establishing and validating impurity profiles in drug substance/product per ICH Q3A/B.
• Serving as a system suitability and identification standard in chromatographic assays.
• Supporting stability-indicating method development and forced-degradation studies.

No therapeutic or clinical use is intended or implied. It is not an excipient or active substance for manufacturing.

Physical Properties

Item-specific values

• 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 applicable/typically not reported for nonvolatile nucleotide-like solids.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
• logP/logD, pKa, refractive index: Not specified for this item; refer to CoA/Spec Sheet.

General/literature guidance (not item-specific)

• Many sofosbuvir-related substances are polar, moderately lipophilic prodrug-like molecules that dissolve in strong organic solvents (DMSO, DMF) and analytical-grade alcohols or acetonitrile; aqueous solubility can vary with pH due to phosphate-like functionality.
• Such compounds often exhibit limited volatility and are amenable to LC-UV and LC–MS analysis using reverse-phase systems. UV absorption commonly arises from the uracil base with typical maxima near 260 nm (literature for uracil chromophore).

Practical notes (general)

• Prepare analytical stocks in dry, LC–MS-grade solvents to minimize hydrolysis of phosphoramidate motifs (if present).
• Evaluate solution stability at room temperature versus refrigerated autosampler conditions; many nucleotide prodrug analogs are more stable when chilled and protected from moisture. Always confirm with a small pilot study specific to this item.

Quality and Grades

Item-specific quality information

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

Context and expectations for impurity standards (general)

• Impurity/reference standards for API-related substances are typically supplied with a Certificate of Analysis (CoA) containing identity confirmation (1H/13C NMR, HRMS/ESI, sometimes 31P NMR for phosphoramidates), chromatographic purity (HPLC/UPLC area %), and water/volatile content (KF/LOD). Exact test set and limits vary by vendor and material.
• Where applicable, chiral and diastereomeric purity may be reported (e.g., Rp/Sp at phosphorus, sugar stereochemistry). If not specified here, consult the CoA for this lot.
• For analytical method development (ICH Q2/Q3), reference standards should have traceable identity and purity assignment; uncertainty of purity may be provided to support quantitative use.

Practical guidance

• Verify lot-specific purity and counterion/solvate state prior to quantitative work (calculation of correction factors may be needed).
• If a stabilizer or salt form is present, implications for mass balance and solubility should be considered; no stabilizer information is specified for this item.

Reaction and Applications

This product is not typically used as a synthetic reagent. Its primary role is as a reference/impurity standard associated with sofosbuvir for analytical purposes.

Analytical applications (general, not item-specific)

• Method development and validation: Establish specificity, linearity, LOD/LOQ, accuracy, and precision for quantifying sofosbuvir-related substances in drug substance/product matrices (ICH Q2).
• System suitability/peak identification: Use as a retention-time and spectral/fragmentation match standard in LC–UV/LC–MS.
• Degradation pathway elucidation: Track formation/consumption during stress studies (acid/base hydrolysis, oxidative, photolytic, and thermal conditions) to map pathways relevant to phosphoramidate prodrugs.
• Response factor assessment: Determine relative response factors versus API for accurate impurity quantitation by LC–UV.

Practical tips

• Prepare fresh working solutions to minimize hydrolysis or transesterification if functional groups are labile; store concentrated stocks at −20 °C in dry organic solvent.
• For LC–MS, optimize source conditions to balance desolvation with minimal in-source fragmentation of phosphate-bearing species.
• Employ orthogonal detection (UV at ~260 nm for uracil chromophore and MS in ESI±) to improve selectivity.

Note: No manufacturer application text is provided for this item; the above reflects common practices for API-related impurity standards.

Reaction Conditions

This material is not intended for preparative reactions. Instead, the most relevant “conditions” are analytical.

General LC conditions for sofosbuvir-related substances (literature, not item-specific):

• Columns: C18 (2.1 × 100 mm, sub-2–3 µm) or polar-embedded phases; temperature 30–45 °C to improve mass transfer.
• Mobile phases: A = water with 0.1% formic acid or 5–10 mM ammonium formate/acetate; B = acetonitrile or methanol. Gradient 5–70% B over 10–20 min for method scouting.
• Detection: UV at ~260 nm (uracil chromophore) and/or ESI–MS in positive and negative modes; monitor characteristic fragments for phosphate-containing analytes.
• Typical injection solvent: ≤5% DMSO in initial mobile phase to avoid distortion.

Forced-degradation stress screens (for method robustness; general)

• Acid/base (e.g., 0.1–0.5 M HCl/NaOH, controlled times/temps), oxidative (e.g., 1–3% H2O2), thermal (40–60 °C), and photolytic (ICH Q1B) to map degradation pathways. Adjust severities cautiously to avoid over-degradation.

Note: The above are literature-style starting points. Optimize to the specific impurity and matrix. No reaction yields or synthesis conditions are provided or implied for this item.

Safety and Handling

Safety information specific to this item

• GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
• Research use: For research use only.
• Storage: Store at −20 °C (per Product Data). Shipped in ice chest with ice pads.

General precautions (not item-specific; defer to SDS)

• Potential hazards: Organic impurity standards for APIs can present unknown acute toxicity and may be irritating to skin/eyes. Handle as a potentially harmful organic compound.
• PPE: Use appropriate laboratory PPE—lab coat, safety glasses, and disposable nitrile gloves; handle powders in a fume hood to avoid inhalation of dust/aerosols.
• Incompatibilities: Avoid strong acids/bases and aqueous conditions if phosphoramidate-like functionalities are present, as hydrolysis may occur. Keep away from oxidizers and reducing agents unless compatibility is known.
• First-aid overview: In case of skin/eye contact, rinse with plenty of water for at least 15 minutes and seek medical attention. If inhaled, move to fresh air. If ingested, rinse mouth and seek medical attention. Consult the SDS for authoritative instructions.
• Spill/cleanup: Avoid dust formation. Absorb small spills with inert material and dispose as organic chemical waste per institutional and local regulations.
• Stability notes: Minimize exposure to moisture and heat; cap vials promptly, purge headspace with inert gas if prolonged storage is expected.

Solvent Selection

Applicability: As an API-related impurity standard, solvent selection primarily concerns analytical stock preparation and chromatographic method development rather than synthetic transformations.

General guidance (not item-specific)

• Likely solvent suitability: DMSO, acetonitrile, and methanol are commonly effective for nucleoside prodrug analogs; water miscibility allows aqueous dilution for LC injection.
• Reverse-phase LC mobile phases: Water with 0.1% formic acid or ammonium formate/acetate buffers paired with acetonitrile or methanol are typical for LC–UV/LC–MS analysis.
• Dielectric/polarity considerations: The polar, partially ionizable nature of phosphoramidate-like impurities often benefits from higher organic strength (MeCN) to limit peak tailing and from volatile buffers to enable MS detection.
• When to choose alternatives: If hydrolysis is a concern, avoid prolonged residence in protic solvents; use anhydrous ACN or DMSO for concentrated stocks and prepare aqueous working solutions immediately prior to use.

Small comparison (general)

• Acetonitrile vs methanol: ACN typically affords sharper peaks and lower backpressure; MeOH can improve selectivity for closely related isomers but may increase run time.
• DMSO: Excellent for concentrated storage stocks but may broaden peaks if injected at high fraction; keep injection DMSO fraction low (<5%) by predilution with mobile phase.

Storage and Reconstitution

Item-specific storage/shipping

• Storage Conditions: Store at −20 °C (per Product Data). Minimize freeze–thaw cycles.
• Shipped In: Ice chest + ice pads (per Product Data).

Reconstitution/handling

• Solvent and concentration: Not specified for this item; refer to CoA/Spec Sheet.
• General guidance (not item-specific): Prepare concentrated primary stocks in dry acetonitrile, methanol, or DMSO using LC–MS-grade solvents. Filter through a low-binding PTFE syringe filter if particulate is observed. For analytical injections, dilute with initial mobile phase to minimize solvent mismatch.
• Aliquoting: Immediately aliquot stock solutions into amber vials or microtubes to avoid repeated freeze–thaw. Purge headspace with inert gas when feasible.
• Light and moisture: Store in tightly sealed, moisture-protective containers. Use desiccant and protect from light if the compound exhibits UV absorption.

Stability

• Long-term stability and solution shelf-life: Not specified for this item; refer to CoA/Spec Sheet. As a precaution, keep solutions refrigerated (autosampler 4–8 °C) and use within a short window unless validated otherwise.

Compliance

• For research use only. Always consult the SDS and CoA for lot-specific instructions before use.

Structure and Identity

Brief overview: This product is a defined related substance of the nucleotide prodrug sofosbuvir, supplied for research and analytical use as an impurity standard.

• Item-specific facts (from Product Data)

  • Product name: Sofosbuvir impurity G (SKU S647272)
  • CAS: 1337482-15-1
  • PubChem CID: 58463528
  • InChIKey: 136609 (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/context (general)

  • Sofosbuvir impurities are structurally related to the phosphoramidate prodrug of a 2′-deoxy-2′-fluoro-2′-C-methyl uridine analog. Impurities may differ in ester, amino acid, phosphate, base, stereochemistry (Rp/Sp), or protecting-group patterns (literature).
  • Typical structural features (literature, not item-specific): ribose-like core bearing 2′-fluoro and 2′-methyl substitution; uracil base; aryl/alkyl phosphate esters; L-alanine isopropyl ester-derived moieties in many related substances.

• 2D structural description (general, not item-specific)

  • Nucleoside base attached to a modified sugar scaffold via a β-N-glycosidic bond; the anomeric position is derivatized as a phosphoramidate/monophosphate ester bearing one aryl and one amino acid ester substituent. Exact substitution pattern and stereochemistry for “impurity G” should be confirmed from the supplied CoA or authoritative databases (e.g., CID 58463528).

Synthetic Utility

Not typically used as a building block or reagent. As a defined related substance of sofosbuvir, it is supplied to support analytical chemistry rather than synthesis.

General insights (not item-specific)

• If structurally bearing a phosphoramidate motif, such compounds can be sensitive to acid/base-catalyzed hydrolysis and nucleophilic substitution at phosphorus. This reactivity is generally a liability for storage but informs stress-testing designs.
• Diastereomeric pairs (Rp/Sp) at phosphorus may interconvert under certain conditions or be produced selectively; chromatographic resolution can require chiral or specially designed phases.

Recommendation

• Use this material to calibrate or challenge analytical separations rather than as a precursor. For synthetic route scouting or impurity fate studies, generate analogs in situ and confirm identity by comparison to this standard where appropriate.

Target Specificity

Not applicable. This product is a small-molecule impurity standard, not a biological reagent or antibody. No antigen/epitope or species reactivity applies.

Häufig gestellte Fragen

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 1337482-15-1, the molecular formula is C22H29FN3O9P, and the molecular weight is 529.45 g/mol. InChIKey IBMLPFZASPUMOW-IAAJYNJHSA-N.

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.