Glutarimide

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
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
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 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
  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. 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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