Pomalidomide-d5

 CAS No.: 1377838-49-7  Cat No.: BP-200078  Purity: 95% by HPLC; 95% atom D 4.5  

Pomalidomide-d5 is a deuterated analog of pomalidomide, specifically engineered for advanced PROTAC research and proteolysis targeting chimera applications. As an E3 ligase ligand, it binds cereblon (CRBN), a key E3 ubiquitin ligase recruiting component, enabling selective ubiquitination and degradation of pathogenic proteins. The incorporation of five deuterium atoms provides enhanced metabolic stability and facilitates quantitative mass spectrometry in tracer studies. Pomalidomide-d5 is ideal for the synthesis of CRBN-recruiting PROTACs in targeted protein degradation, drug discovery, and mechanistic studies on ubiquitin-proteasome system function.

Pomalidomide-d5

Structure of 1377838-49-7

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Category
Ligand for E3 Ligase
Molecular Formula
C13H6D5N3O4
Molecular Weight
278.27

* For research and manufacturing use only. Not for human or clinical use.

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  • Comprehensive PROTAC Platform
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Purity
95% by HPLC; 95% atom D
Solubility
DMF: 10 mg/ml; DMSO: 15 mg/ml
Storage
Store at -20°C
IUPACName
4-amino-2-(3,4,4,5,5-pentadeuterio-2,6-dioxopiperidin-3-yl)isoindole-1,3-dione
Synonyms
Pomalidomide D5
Boiling Point
582.9±45.0 °C at 760 mmHg
Density
1.6±0.1 g/cm3
InChI Key
UVSMNLNDYGZFPF-XHNMXOBISA-N
InChI
InChI=1S/C13H11N3O4/c14-7-3-1-2-6-10(7)13(20)16(12(6)19)8-4-5-9(17)15-11(8)18/h1-3,8H,4-5,14H2,(H,15,17,18)/i4D2,5D2,8D
Canonical SMILES
C1CC(=O)NC(=O)C1N2C(=O)C3=C(C2=O)C(=CC=C3)N

Background Introduction

Pomalidomide-d5 is the deuterated form of pomalidomide, a well-characterized immunomodulatory imide drug (IMiD) that serves as a potent ligand for the Cereblon (CRBN) E3 ubiquitin ligase. This stable isotope-labeled analog contains five deuterium atoms, making it a unique tool for pharmacokinetic studies and tracer experiments as well as an effective building block for proteolysis targeting chimera (PROTAC) design. Leveraging the biological activity of pomalidomide, pomalidomide-d5 supports quantitative analysis and advanced research in targeted protein degradation (TPD) technologies.

Mechanism

Pomalidomide-d5 binds selectively to the CRBN component within the CUL4-CRBN E3 ubiquitin ligase complex. Through this CRBN recognition, it mediates the recruitment of the ligase machinery to the protein of interest when incorporated into a PROTAC construct. This recruitment enables targeted ubiquitination and subsequent degradation of the target protein via the proteasomal pathway. The incorporation of deuterium atoms provides enhanced analytical capabilities for mass spectrometry, offering increased stability and facilitating differentiation in metabolic or in vivo studies compared to non-deuterated forms.

Applications

Pomalidomide-d5 serves as a crucial intermediate in the synthesis of CRBN-recruiting PROTACs and molecular glues. Its deuterated nature is especially valuable for ADME (absorption, distribution, metabolism, and excretion) studies, bioanalytical quantification, and tracking the fate of PROTACs in biological systems. Key applications include:

• Synthesis of CRBN-based PROTACs for targeted protein degradation research
• Use as an internal standard or tracer in LC-MS/MS studies for pharmacokinetic and metabolomic analysis
• Evaluation of metabolic stability and isotope effect studies on degrader molecules
• SAR (structure-activity relationship) and medicinal chemistry optimization projects
• Support for CRO services and academic research requiring stable isotope-labeled E3 ligase ligands
• High-purity compound verified by HPLC, NMR, and LC-MS
• Consistent batch-to-batch reproducibility with complete QC documentation
• Supplied with COA, MSDS, and analytical data for traceability
• Reliable global shipping with stability-guaranteed packaging
• Dedicated technical support and optional custom synthesis service
• Demonstrates strong binding affinity to CRBN, VHL, or other E3 ligases
• Enables stable E3 ligase recruitment for targeted protein degradation
• Deuterium labeling enables precise quantitative analysis in PROTAC research and mass spectrometry applications.
• High purity and structural fidelity make it ideal for synthesizing stable CRBN E3 ligase recruiting elements.

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It is commonly abbreviated as: C1V1 = C2V2

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