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glutarimide
Sign in to saveAlso known as 2,6-Diketopiperidine, Piperidine-2,6-dione, 2,6-piperidinedione
Glutarimide, also known as piperidine-2,6-dione, is an organic compound with the chemical formula C5H7NO2. It is a white crystalline powder formed by the dehydration of the amide of glutaric acid. Glutarimide serves as a core structural component in several pharmacologically active compounds, including thalidomide, lenalidomide, cycloheximide, and glutethimide, which exhibit immunomodulatory, anticancer, or antibiotic properties. As a standalone compound, glutarimide is used in chemical synthesis and research, with no direct therapeutic applications.
Chemical data
- Formula
- C5H7NO2
- Molecular weight
- 113.11 g/mol
- IUPAC name
- piperidine-2,6-dione
- SMILES
- C1CC(=O)NC(=O)C1
- InChIKey
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N
- XLogP
- -0.7
- Polar surface area
- 46.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
451 papers- Research progress of glutarimide-containing polyketides: Structures, bioactivities and their biosynthesis.Pharmaceutical science advances · 2025
- Gepirone.2006
- Cytotoxic glutarimide-containing polyketides isolated from Streptomyces sp. JCM 4793.The Journal of antibiotics · 2024
- Recent advances in glutarimide chemistry for cereblon-mediated targeted protein degradation: developments in synthesis and diversification.RSC medicinal chemistry · 2025
- The Genomic-Driven Discovery of Glutarimide-Containing Derivatives from Burkholderia gladioli.Molecules (Basel, Switzerland) · 2023
via PubMed
Wikidata facts
- Subclass of
- piperidinedione
- Mass
- 113.048
Show 4 more facts
- chemical formula
- C₅H₇NO₂
- Commons category
- Glutarimide
- canonical SMILES
- C1CC(=O)NC(=O)C1
- subject has role
- protein synthesis inhibitor
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
5 sectionsContents
- Chemical properties
- Pharmacology
- History
- See also
- References
Glutarimide, also known as piperidine-2,6-dione, is an organic compound with the chemical formula C5H7NO2. It is a white crystalline powder formed by the dehydration of the amide of glutaric acid. Glutarimide serves as a core structural component in several pharmacologically active compounds, including thalidomide, lenalidomide, cycloheximide, and glutethimide, which exhibit immunomodulatory, anticancer, or antibiotic properties. As a standalone compound, glutarimide is used in chemical synthesis and research, with no direct therapeutic applications.
thumb|left|class=skin-invert-image|The drug lenalidomide contains the substructure glutarimide (blue).
Excerpted from Wikipedia’s “glutarimide” article, available under the CC BY-SA 4.0 licence.