34017-15-7

Basic information

• Product Name: Probenecid Acyl -D-Glucuronide
• Synonyms: 1-[4-[(DipropylaMino)sulfonyl]benzoate];1-[4-[(Dipropylamino)sulfonyl]benzoate] -D-Glucopyranuronic Acid;1-[p-(Dipropylsulfamoyl)benzoate] -D-Glucopyranuronic Acid;Probenecid Acyl -D-Glucuronide;Probenecid Glucuronide
• CAS NO: 34017-15-7
• Molecular Formula: C₁₉H₂₇NO₁₀S
• Molecular Weight: 461.48
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 34017-15-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 153-160?C
• Boiling Point: 688.3°Cat760mmHg
• Flash Point: 370°C
• Appearance: /
• Density: 1.49g/cm³
• Vapor Pressure: 6.87E-20mmHg at 25°C
• Refractive Index: 1.614
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: 2.65±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Probenecid Acyl -D-Glucuronide(CAS DataBase Reference)
• NIST Chemistry Reference: Probenecid Acyl -D-Glucuronide(34017-15-7)
• EPA Substance Registry System: Probenecid Acyl -D-Glucuronide(34017-15-7)

Safety Data

• Hazardous Substances Data: 34017-15-7(Hazardous Substances Data)

Usage

Description

Probenecid Acyl -D-Glucuronide is a major metabolite of Probenecid, a medication primarily used as a uricosuric agent to treat gout and hyperuricemia. It is a white solid with specific chemical properties that make it a significant compound in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
Probenecid Acyl -D-Glucuronide is used as a metabolite for understanding the metabolic pathways and pharmacokinetics of Probenecid. This knowledge aids in optimizing drug dosages, minimizing side effects, and enhancing the therapeutic efficacy of Probenecid in treating gout and hyperuricemia.
Used in Research and Development:
In the field of drug development, Probenecid Acyl -D-Glucuronide serves as a crucial compound for studying the mechanisms of drug metabolism, excretion, and potential drug-drug interactions. This information is vital for designing safer and more effective medications.
Used in Quality Control and Analysis:
Probenecid Acyl -D-Glucuronide is utilized as a reference compound in the quality control and analysis of Probenecid-containing pharmaceutical products. It helps ensure the accuracy, reliability, and consistency of drug formulations, contributing to patient safety and compliance.

InChI:InChI=1/C19H27NO10S/c1-3-9-20(10-4-2)31(27,28)12-7-5-11(6-8-12)18(26)30-19-15(23)13(21)14(22)16(29-19)17(24)25/h5-8,13-16,19,21-23H,3-4,9-10H2,1-2H3,(H,24,25)/t13-,14-,15+,16-,19-/m0/s1

Downstream Products

• 57-66-9 4-[(dipropylamino)sulfonyl]benzoic acid 

Relevant articles and documents

Rapid internal acyl migration and protein binding of synthetic probenecid glucuronides

Internal acyl migration reactions of drug 1-O-acyl-β-D-glucopyranuronates (1β-acyl glucuronides) are of interest because of their possible role in covalent binding to proteins and consequent adverse effects. The reactivity of the synthetic probenecid 1β-acyl glucuronide (PRG), the principal metabolite of probenecid (PR) in humans, has been investigated in terms of acyl migration, hydrolysis, and covalent binding to proteins in phosphate buffer (pH 7.4) and human plasma at 37 °C. PRG primarily degraded by acyl migration according to apparent first-order kinetics and the 2-, 3-, and 4-acyl isomers sequentially appeared as both α- and β-anomeric forms. In addition, small amounts of PRG and extremely labile 1α-acyl isomer existed in the equilibrated mixture favoring the 2α/β-acyl isomer, that provided significant information regarding the mechanism of acyl migration. All of the positional isomers and anomers were characterized using preparative HPLC and NMR spectroscopy. Acyl migration was observed to predominate over hydrolysis in both media although the extent of hydrolysis in plasma was larger than that in the buffer. The overall degradation half-lives (h) in the buffer and plasma were 0.27 ± 0.003 and 0.17 ± 0.007, respectively. The covalent binding rapidly proceeded mainly via the Schiff's base mechanism and reached a plateau after 2 h of incubation. The maximal binding was 146 ± 4.8 pmol/mg of protein, and ca. 10% of the initial concentration of PRG. These results indicated that PRG is most labile and susceptible to acyl migration of all the drug acyl glucuronides reported to date in the physiological conditions, and highly reactive to plasma proteins, that could provide a possible explanation for the immunologically based adverse effects of PR.