Glutarimide

Glutarimide
Names
	Preferred IUPAC name Piperidine-2,6-dione
	Other names 2,6-Diketopiperidine
Identifiers
CAS Number	1121-89-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	63891;
ECHA InfoCard	100.013.038
PubChem CID	70726;
UNII	MV728O9612 ;
CompTox Dashboard (EPA)	DTXSID7074452 ;
	InChI InChI=1S/C5H7NO2/c7-4-2-1-3-5(8)6-4/h1-3H2,(H,6,7,8) Key: KNCYXPMJDCCGSJ-UHFFFAOYSA-N;
	SMILES C1CC(=O)NC(=O)C1;
Properties
Chemical formula	C5H7NO2
Molar mass	113.11 g/mol
Melting point	155-157 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Glutarimide, also known by its chemical name 2,6-piperidinedione, is the organic compound with the formula (CH₂)₃(CO)₂NH. It is a white solid compound that forms upon dehydration of the amide of glutaric acid.^[2]

Glutaramide is at the core of numerous medical drugs and substances, including lenalidomide (a medication used to treat anemia and multiple myeloma),^[3] cycloheximide (a potent inhibitor of protein synthesis),^[4] and fluoxetine (an SSRI); as well as the sedative/"tranquilizer" hypnotic drugs glutethimide (branded "Doriden" until 1993 (in the US) and 2006 (in Hungary) and aminoglutethimide.

References

^ Glutarimide - Sigma-Aldrich
^ 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.
^ "A to Z List of Cancer Drugs: Lenalidomide". National Cancer Institute. 1 September 2022. Retrieved 5 August 2024.
^ 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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[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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