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Cycloheximide

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

RTECS number

MA4375000

SMILES

C[C@H]1C[C@H](C)C(=O)[C@@H]
(C1)[C@@H](O)CC2CC(=O)NC(=O)C2

Properties

Molecular formula

C₁₅H₂₃NO₄

Molar mass

281.35

Appearance

colourless crystals

Melting point

119.5-121°C

Hazards

EU classification

T+, N

Main hazards

Highly toxic

NFPA 704

S-phrases

S7/9, S26, S36/37/39, S45

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Cycloheximide is an inhibitor of protein biosynthesis in eukaryotic organisms, 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.

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Due to significant toxic side effects, including DNA damage, teratogenesis, and other reproductive effects (including birth defects and toxicity to sperm^[1]), cycloheximide is generally used only in in vitro research applications, and is not suitable for human use as a therapeutic antibiotic 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.

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

In vitro applications

Cycloheximide can be used as an experimental tool in molecular biology to determine the half-life of a protein (enzyme). Treating cells with cycloheximide in a time-course experiment followed by Western blotting of the cell lysates for the protein of interest can show differences in protein expression due to interference with translation.