Cas no 60113-83-9 (Valproic Acid b-D-Glucuronide)

Valproic Acid β-D-Glucuronide is a glucuronide conjugate of valproic acid, formed via hepatic metabolism by UDP-glucuronosyltransferase enzymes. This metabolite is significant in pharmacokinetic and metabolic studies, as it represents a major elimination pathway for valproic acid, contributing to its clearance. The compound is particularly valuable for research applications, including drug metabolism investigations, biomarker analysis, and enzymatic activity assays. Its high purity and well-characterized structure make it suitable for use as a reference standard in analytical methods such as HPLC, LC-MS, and NMR. The availability of Valproic Acid β-D-Glucuronide facilitates precise quantification and mechanistic studies of valproic acid disposition in biological systems.
Valproic Acid b-D-Glucuronide structure
Valproic Acid b-D-Glucuronide structure
Product Name:Valproic Acid b-D-Glucuronide
CAS No:60113-83-9
MF:C14H24O8
MW:320.335565567017
CID:516491
PubChem ID:88111
Update Time:2025-06-11

Valproic Acid b-D-Glucuronide Chemical and Physical Properties

Names and Identifiers

    • b-D-Glucopyranuronic acid,1-(2-propylpentanoate)
    • Valproic Acid β-D-Glucuronide
    • VALPROIC ACID B-D-GLUCURONIDE
    • Valproic Acid β-D-Gl
    • 1-(2-Propylpentanoate)-D-Glucopyranuronic Acid
    • 1-O-Valproyl-b-D-glucopyranuronic Acid
    • 1-O-Valproyl--D-glucopyranuronic Acid
    • Dipropylacetate Glucuronide
    • Valproate Glucuronide
    • Valproic Acid Glucuronid
    • Valproic acid glucuronide
    • Valproic Acid-D-Glucuronide
    • VPA-G
    • .BETA.-D-GLUCOPYRANURONIC ACID, 1-(2-PROPYLPENTANOATE)
    • (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-propylpentanoyloxy)oxane-2-carboxylic acid
    • (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-((2-propylpentanoyl)oxy)tetrahydro-2H-pyran-2-carboxylic acid
    • (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-((2-propylpentanoyl)oxy)oxane-2-carboxylic acid
    • 3,4,5-trihydroxy-6-(2-propyl-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid
    • 1-(2-propylpentanoate) beta-D-Glucopyranuronic acid
    • NS00003085
    • 1-O-VALPROYL-.BETA.-D-GLUCOPYRANURONIC ACID
    • DTXSID901311881
    • Valproic Acid beta-D-Glucuronide
    • Valproic acid-beta-O-glucuronide
    • VPAG
    • CHEMBL3526941
    • (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylic acid
    • 1-(2-propylpentanoate) beta-delta-Glucopyranuronate
    • UNII-SB05J7266C
    • 1-(2-propylpentanoate) beta-D-Glucopyranuronate
    • SCHEMBL17061412
    • 1-(2-propylpentanoic acid
    • 1-O-Valproyl-beta-delta-glucopyranuronic acid
    • SB05J7266C
    • Valproic Acid ?-D-Glucuronide
    • 1-O-VALPROYL-BETA-D-GLUCOPYRANURONIC ACID
    • 1-(2-propylpentanoate
    • beta-D-Glucopyranuronic acid, 1-(2-propylpentanoate)
    • 3,4,5-trihydroxy-6-(2-propyl-pentanoyloxy)-tetrahydro-pyran-2-carboxylate
    • CHEBI:168243
    • 60113-83-9
    • 1-(2-propylpentanoate) beta-delta-Glucopyranuronic acid
    • Valproic Acid b-D-Glucuronide
    • Inchi: 1S/C14H24O8/c1-3-5-7(6-4-2)13(20)22-14-10(17)8(15)9(16)11(21-14)12(18)19/h7-11,14-17H,3-6H2,1-2H3,(H,18,19)/t8-,9-,10+,11-,14-/m0/s1
    • InChI Key: XXKSYIHWRBBHIC-JVWRJRKNSA-N
    • SMILES: O1[C@H](C(=O)O)[C@H]([C@@H]([C@H]([C@@H]1OC(C(CCC)CCC)=O)O)O)O

Computed Properties

  • Exact Mass: 320.14700
  • Monoisotopic Mass: 320.147
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 8
  • Heavy Atom Count: 22
  • Rotatable Bond Count: 8
  • Complexity: 379
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 5
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 134A^2
  • XLogP3: 1.1

Experimental Properties

  • Density: 1.33
  • Melting Point: 118-120°C
  • Boiling Point: 491.9°C at 760 mmHg
  • Flash Point: 178°C
  • Refractive Index: 1.531
  • PSA: 133.52000
  • LogP: -0.36180

Valproic Acid b-D-Glucuronide Security Information

  • Storage Condition:Hygroscopic, Store under Inert atmosphere -20°C Freezer

Valproic Acid b-D-Glucuronide Pricemore >>

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Additional information on Valproic Acid b-D-Glucuronide

Introduction to Valproic Acid β-D-Glucuronide (CAS No: 60113-83-9)

Valproic Acid β-D-Glucuronide, with the chemical identifier CAS No 60113-83-9, is a significant metabolite of Valproic Acid (VPA), a widely used anticonvulsant and mood-stabilizing drug. This compound has garnered increasing attention in the field of pharmacology and medicinal chemistry due to its unique pharmacokinetic properties and potential therapeutic applications. Understanding its structure, biosynthesis, and biological significance is crucial for optimizing drug formulations and improving patient outcomes.

The chemical structure of Valproic Acid β-D-Glucuronide consists of a carboxylic acid derivative of VPA conjugated with β-D-glucuronic acid through an ester linkage. This glucuronidation process is a major pathway for the detoxification and excretion of VPA in the human body. The conjugation with glucuronic acid enhances the water solubility of VPA, facilitating its renal excretion. This metabolic transformation is catalyzed by UDP-glucuronosyltransferases (UGTs), a family of enzymes that play a pivotal role in drug metabolism.

Recent studies have highlighted the importance of Valproic Acid β-D-Glucuronide in modulating the pharmacokinetics of VPA. Research indicates that variations in UGT enzyme activity can significantly influence the levels of this metabolite, thereby affecting the overall efficacy and side-effect profile of VPA therapy. For instance, patients with reduced UGT activity may exhibit higher plasma concentrations of VPA, increasing the risk of adverse effects such as hyperammonemia and liver dysfunction.

The pharmacological significance of Valproic Acid β-D-Glucuronide extends beyond its role as a mere metabolite. Emerging evidence suggests that this compound may possess independent pharmacological activities. Some preliminary studies have indicated that Valproic Acid β-D-Glucuronide might exhibit neuroprotective properties, potentially contributing to its therapeutic benefits in conditions like epilepsy and bipolar disorder. Additionally, its interaction with various biological targets has been explored, revealing possible mechanisms that could be exploited for novel therapeutic strategies.

In clinical settings, the measurement of Valproic Acid β-D-Glucuronide levels can serve as a valuable biomarker for assessing UGT activity and predicting drug-drug interactions. For example, co-administration of drugs that inhibit UGT enzymes can lead to elevated levels of VPA and its metabolites, necessitating dose adjustments to prevent toxicity. This underscores the importance of monitoring Valproic Acid β-D-Glucuronide levels in patients receiving VPA therapy, particularly those on multiple medication regimens.

The synthesis and characterization of Valproic Acid β-D-Glucuronide have been subjects of extensive research in synthetic chemistry. Advanced techniques such as high-performance liquid chromatography (HPLC) and mass spectrometry (MS) have enabled precise quantification and structural elucidation of this compound. These analytical methods are essential for validating experimental findings and ensuring the quality control of pharmaceutical formulations containing VPA or its derivatives.

Future research directions in this field aim to explore the potential therapeutic applications of Valproic Acid β-D-Glucuronide. Given its unique biochemical properties, this metabolite could serve as a lead compound for developing new drugs targeting neurological disorders. Additionally, investigating the regulatory mechanisms governing UGT-mediated glucuronidation may provide insights into enhancing drug bioavailability and reducing metabolic clearance.

The development of novel drug delivery systems has also opened new avenues for studying Valproic Acid β-D-Glucuronide. Techniques such as prodrug design and targeted nanoparticles have been employed to improve the solubility and bioavailability of VPA, thereby influencing the formation and excretion rates of its metabolites. These innovations hold promise for optimizing VPA therapy while minimizing side effects associated with high plasma concentrations.

In conclusion, Valproic Acid β-D-Glucuronide (CAS No: 60113-83-9) is a multifaceted compound with significant implications in pharmacology and medicinal chemistry. Its role as a major metabolite of VPA underscores its importance in drug metabolism and therapy. Ongoing research continues to uncover novel aspects of its pharmacological activity and potential therapeutic applications, making it a subject of great interest in academic and industrial settings.

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