Cycloheximide

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Structural formula
Structure of cycloheximide
General
Surname Cycloheximide
other names
  • 4 - [(2 R ) -2 - [(1 S , 3 S , 5 S ) -3,5-dimethyl-2-oxocyclohexyl] -2-hydroxyethyl] piperidine-2,6-dione
  • Actidion
  • Naramycin A
  • CHX
Molecular formula C 15 H 23 NO 4
Brief description

colorless crystals

External identifiers / databases
CAS number 66-81-9
EC number 200-636-0
ECHA InfoCard 100,000,578
PubChem 6197
Wikidata Q412895
properties
Molar mass 281.35 g mol −1
Physical state

firmly

Melting point

115-116 ° C

solubility

poor in water (21 g l −1 at 20 ° C)

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
06 - Toxic or very toxic 08 - Dangerous to health 09 - Dangerous for the environment

danger

H and P phrases H: 300-341-360D-411
P: 201-280-301 + 330 + 331 + 310-308 + 313
Toxicological data

2 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cycloheximide is an antibiotic in the broadest sense that is produced by streptomycetes ( Streptomyces griseus ).

It acts as a translation inhibitor in eukaryotes and, by preventing protein synthesis on the ribosomes, leads to growth inhibition and the death of eukaryotic cells. It is a classic translation inhibitor. The mitochondrial and plastid protein synthesis of eukaryotic cells is also disturbed by very high concentrations of cycloheximide, which is why this antibiotic can also be used for the selection of transgenic plants (eukaryote). Cycloheximide is hardly used any more as an antibiotic, since it inhibits mitochondrial protein translation in humans at high doses.

use

  • Selection of prokaryotic cells, suppression of eukaryotic contaminants
  • Selection of resistant cells in transformation and cloning experiments in eukaryotes (fungi)
  • controlled inhibition of protein synthesis in cell cultures and detection of short-lived proteins
  • Initiation of apoptosis u. a.

Individual evidence

  1. ↑ a b c d e Entry on cycloheximide in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
  2. ↑ Entry on Cicloheximide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  3. ↑ Entry on cycloheximide in the ChemIDplus database of the United States National Library of Medicine (NLM) .