Glutarimide

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Glutarimide
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Piperidine-2,6-dione
Other names
2,6-Diketopiperidine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.038 Edit this at Wikidata
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).
Infobox references

Glutarimide 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]

Glutarimide is sometimes called 2,6-piperidinedione. It is the core of a variety of drugs, including thalidomide, a medication used to treat multiple myeloma[3] and leprosy,[4] and cycloheximide, a potent inhibitor of protein synthesis.[5]

References[edit]

  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: Thalidomide". National Cancer Institute. Retrieved 20 September 2021.
  4. ^ Stolberg SG (17 July 1998). "Thalidomide Approved to Treat Leprosy, With Other Uses Seen". New York Times. Retrieved 20 September 2021.
  5. ^ Hugh D. Sisler, Malcolm R. Siegel; Cycloheximide and Other Glutarimide Antibiotics; Mechanism of Action pp 283-307