Glutarimide

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Glutarimide
Glutarimide.svg
Glutarimide-3D-balls.png
Names
Preferred IUPAC name
Piperidine-2,6-dione
Other names
2,6-Diketopiperidine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.038 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C5H7NO2/c7-4-2-1-3-5(8)6-4/h1-3H2,(H,6,7,8)
    Key: KNCYXPMJDCCGSJ-UHFFFAOYSA-N
  • C1CC(=O)NC(=O)C1
Properties
C5H7NO2
Molar mass 113.11 g/mol
Melting point 155-157 °C [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Glutarimide, also known as piperidinedione, is the organic compound with the formula (CH2)3(CO)2NH. It is a white solid. The compound forms upon dehydration of the amide of glutaric acid. [2]

The drug lenalidomide contains the substructure glutarimide (blue) Lenalidomide substructures.svg
The drug lenalidomide contains the substructure glutarimide (blue)

Glutarimide is sometimes called 2,6-piperidinedione. It is the core of a variety of drugs, including lenalidomide, a medication used to treat anemia and multiple myeloma; [3] and cycloheximide, a potent inhibitor of protein synthesis. [4] A group of sedatives and hypnotics that includes glutethimide are derivatives of glutarimide.

References

  1. ↑ Glutarimide - Sigma-Aldrich
  2. ↑ Paris, G.; Berlinguet, L.; Gaudry, R.; English, Jr., J.; Dayan, J. E. (1957). "Glutaric Acid and Glutarimide". Organic Syntheses. 37: 47. doi:10.15227/orgsyn.037.0047.
  3. ↑ "A to Z List of Cancer Drugs: Lenalidomide". National Cancer Institute. 1 September 2022. Retrieved 5 August 2024.
  4. ↑ Sisler, Hugh D.; Siegel, Malcolm R. (1967). "Cycloheximide and Other Glutarimide Antibiotics". Mechanism of Action. pp. 283–307. doi:10.1007/978-3-642-46051-7_21. ISBN   978-3-642-46053-1.
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