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C7698

Sigma-Aldrich

Cycloheximide

from microbial, ≥94% (TLC)

Synonym(s):

3-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide, Actidione, Naramycin A

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About This Item

Empirical Formula (Hill Notation):
C15H23NO4
CAS Number:
66-81-9
Molecular Weight:
281.35
Beilstein:
88868
EC Number:
200-636-0
MDL number:
MFCD00082346
UNSPSC Code:
12352111
PubChem Substance ID:
24892981
NACRES:
NA.77

biological source

microbial

Quality Level

200

Assay

≥94% (TLC)

form

powder

storage condition

(Tightly closed. Dry. Keep in a well-ventilated place. Keep locked up or in an area accessible
only to qualified or authorized persons.)

color

white to off-white

solubility

ethanol: soluble, clear to hazy

antibiotic activity spectrum

fungi
yeast

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

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

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

Gene Information

human ... FKBP1A(2280) , PIN1(5300)

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General description

Cycloheximide, also known as Actidione, is a glutarimide antibiotic commonly derived from the bacterium Streptomyces griseus. It acts as a potent inhibitor of protein biosynthesis in eukaryotic cells by disrupting the translocation step during translation, effectively blocking translational elongation. In microbiology, it plays a crucial role as a selection agent for resistant strains of yeast and fungi, proving invaluable in controlled experimental environments.

In cell biology and biochemical research, Cycloheximide showcases a dual nature concerning Apoptosis Induction, inducing or inhibiting apoptosis depending on the cell type. Its rapid and reversible effects make it an ideal choice for studying cellular processes and determining protein half-life. Cycloheximide also finds extensive applications in biomedical research, where it inhibits protein synthesis in eukaryotic cells studied in vitro (outside of organisms) and its effects are rapidly reversed by simply removing it. This makes Cycloheximide a go-to choice for exploring cell biology, biomedical and biochemical research, offering precise control and versatility in experiments.

Application

  • In yeast strains, cycloheximide has been used as a protein synthesis inhibitor in the cycloheximide chase experiment.
  • It has been used to inhibit translation in mammalian cells.
  • It has been used to suppress fungal growth.

Biochem/physiol Actions

Mode of Action: Translation inhibition in eukaryotes resulting in cell growth arrest and cell death. CHX is widely used for the selection of CHX-resistant strains of yeast and fungi, controlled inhibition of protein synthesis for detection of short-lived proteins and super-induction of protein expression, and apoptosis induction or facilitation of apoptosis induction by death receptors.

Activity Spectrum: Active against yeast and fungi like Candida, Aspergillus, Saccharomyces, Penicillium

Features and Benefits

  • High-quality antibiotic suitable for multiple research applications
  • Commonly used in Cell Biology and Biochemical applications

Other Notes

For additional information on our range of Biochemicals, please complete this form.
Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Oral - Aquatic Chronic 2 - Muta. 2 - Repr. 1B

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

EU REACH Annex XVII (Restriction List)

CAS No.

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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