An inhibitor of eukaryotic protein synthesis
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Enantiomer(s)
13998(−)-Methamphetamine (hydrochloride)
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Cycloheximide

Item No. 14126

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]-2,6-piperidinedione
CAS Number
66-81-9
Synonyms
  • Naramycin A
  • NSC 185
Molecular Formula
C15H23NO4
Formula Weight
281.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 25 mg/mlEthanol: 25 mg/mlWater: 20 mg/ml
SMILES
O=C1[C@@]([C@H](O)CC2CC(NC(C2)=O)=O)([H])C[C@@H](C)C[C@@H]1C
InChi Code
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
InChi Key
YPHMISFOHDHNIV-FSZOTQKASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Cycloheximide is a glutarimide antibiotic produced by S. griseus that inhibits protein synthesis in eukaryotes (IC50 = 5-50 μM) by interfering with translational elongation.1 Its effects on protein synthesis can either induce or inhibit apoptosis depending on cell type.2 Cycloheximide is widely used as a tool in molecular biology research for ribosome profiling and translational profiling as well as to determine the half-life of a protein.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Obrig, T.G., Culp, W.J., McKeehan, W.L., et al. The mechanism by which cycloheximide and related glutarimide antibiotics inhibit peptide synthesis on reticulocyte ribosomes. The Journal of Biological Chemisty 246, 174-181 (1971).

    2. Baskic, D., Popovic, S., Ristic, P., et al. Analysis of cycloheximide-induced apoptosis in human leukocytes: Fluorescence microscopy using annexin V/propidium iodide versus acridin orange/ethidium bromide. Cell Biol. Int. 30, 924-932 (2006).

    3. Lee, S., Liu, B., Lee, S., et al. Global mapping of translation initiation sites in mammalian cells at single-nucleotide resolution. Proc. Natl. Acad. Sci. USA 109(37), E2424-E2432 (2012).

    4. Jiang, X., Coffino, P., and Li, X. Development of a method for screening short-lived proteins using green fluorescent protein. Genome Biol. 5(10), R81 (2004).

    Product Citations

    Liu, F., Zuo, X., Liu, Y., et al. Suppression of membranous LRP5 recyling, Wnt/β-catenin signaling, and colon carcinogenesis by 15-LOX-1 peroxidation of linoleic acid in PI3P. Cell Rep. 32(7), 108049 (2020).