Cycloheximide

Cycloheximide

Names
IUPAC name 4-[(2R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione
Other names Naramycin A, hizarocin, actidione, actispray, kaken, U-4527
Identifiers
CAS Number	66-81-9 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:27641 Y
ChEMBL	ChEMBL123292 Y
ChemSpider	5962 Y
ECHA InfoCard	100.000.578
IUPHAR/BPS	5433
KEGG	C06685 N
PubChem	6197
RTECS number	MA4375000
UNII	98600C0908 Y
InChI InChI=1S/C15H23NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h8-12,17H,3-7H2,1-2H3,(H,16,18,19)/t8-,9-,11-,12+/m0/s1 Y Key: YPHMISFOHDHNIV-FSZOTQKASA-N Y InChI=1/C15H23NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h8-12,17H,3-7H2,1-2H3,(H,16,18,19)/t8-,9-,11-,12+/m0/s1 Key: YPHMISFOHDHNIV-FSZOTQKABD
SMILES O=C2NC(=O)CC(C[C@@H](O)[C@H]1C(=O)[C@@H](C)C[C@H](C)C1)C2
Properties
Chemical formula	C15H23NO4
Molar mass	281.35 g·mol−1
Appearance	Colorless crystals
Melting point	119.5 to 121 °C (247.1 to 249.8 °F; 392.6 to 394.1 K)
Hazards
Safety data sheet	Oxford MSDS
EU classification (DSD)	Toxic (T)
R-phrases	R26 R27 R28
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Cycloheximide is a eukaryote protein synthesis inhibitor, produced by the bacterium Streptomyces griseus. Cycloheximide exerts its effect by interfering with the translocation step in protein synthesis (movement of two tRNA molecules and mRNA in relation to the ribosome), thus blocking translational elongation. Cycloheximide is widely used in biomedical research to inhibit protein synthesis in eukaryotic cells studied in vitro (i.e. outside of organisms). It is inexpensive and works rapidly. Its effects are rapidly reversed by simply removing it from the culture medium.

Due to significant toxic side effects, including DNA damage, teratogenesis, and other reproductive effects (including birth defects and toxicity to sperm), cycloheximide is generally used only in in vitro research applications, and is not suitable for human use as a therapeutic compound. Although it has been used as a fungicide in agricultural applications, this application is now decreasing as the health risks have become better understood.

Because cycloheximide is degraded by alkaline conditions (pH > 7), decontamination of work surfaces and containers can be achieved by washing with a non-harmful alkali solution such as soap.

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.

Cycloheximide was discovered by Alma Joslyn Whiffen-Barksdale, a professional mycologist working at the Upjohn Company in Kalamazoo, Michigan, between 1943 and 1952.