Cycloheximide

Cycloheximide is a naturally occurring fungicide produced by the bacterium Streptomyces griseus. Cycloheximide exerts its effects by interfering with the translocation step in protein synthesis (movement of two tRNA molecules and mRNA in relation to the ribosome), thus blocking eukaryotic 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.

Cycloheximide
Names
Preferred 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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.578
KEGG
RTECS number
  • MA4375000
UNII
  • 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
  • O=C2NC(=O)CC(C[C@@H](O)[C@H]1C(=O)[C@@H](C)C[C@H](C)C1)C2
Properties
C15H23NO4
Molar mass 281.352 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
Occupational safety and health (OHS/OSH):
Main hazards
 Highly toxic
GHS labelling:
Safety data sheet (SDS) Oxford MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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 rapidly breaks down in a basic environment, decontamination of work surfaces and containers can be achieved by washing with a non-harmful alkali solution such as soapy water or aqueous sodium bicarbonate.

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.

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