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Merck

01810

Cycloheximide

≥95% (HPLC)

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
PubChem Substance ID:
329747360
UNSPSC Code:
51102829
NACRES:
NA.85
EC Number:
200-636-0
MDL number:
MFCD00082346
Beilstein/REAXYS Number:
88868

Key Documents

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Product Name

Cycloheximide, ≥95% (HPLC)

SMILES string

N1C(=O)CC(CC1=O)C[C@@H](O)[C@@H]2C[C@H](C[C@@H](C2=O)C)C

InChI key

YPHMISFOHDHNIV-FSZOTQKASA-N

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

biological source

microbial

assay

≥95% (HPLC)

form

powder or crystals

color

white to light beige

antibiotic activity spectrum

fungi
yeast

mode of action

protein synthesis | interferes

Quality Level

200

Gene Information

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

Related Categories

Application

Cyclohexamide (CHX) is widely used for selection of CHX-resistant strains of yeast and fungi, controlled inhibition of protein synthesis for detection of short-lived proteins, super-induction of protein expression, and apoptosis induction or facilitation of apoptosis induction by death receptors. It has been shown to selectively clear macrophages in atherosclerotic plaques, activate cumulus-free equine oocytes, and to have neuroprotective properties.

Biochem/physiol Actions

Cyclohexamide inhibits protein biosynthesis in eukaryotic cells by binding with the 80S ribosome.
Cycloheximide (CHX) is an antibiotic produced by Strptomyces sp.. Its main biological activity is translation inhibition in eukaryotes resulting in cell growth arrest and cell death. CHX is widely used for 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.

Other Notes

Conditions for safe storage, including any incompatibilities. Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Packaging

1G, 5G

signalword

Danger

Hazard Classifications

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

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
049M4767V
128M4769V
108M4890V
028M4848V
028M4847V

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Tumor-suppressive functions of long-chain acyl-CoA synthetase 4 in gastric cancer
Ye X, et al.
IUBMB Life, 68(4), 320-327 (2016)
K Furukawa et al.
The Journal of cell biology, 136(5), 1137-1149 (1997-03-10)
The ability of the protein synthesis inhibitor cycloheximide (CHX) to prevent neuronal death in different paradigms has been interpreted to indicate that the cell death process requires synthesis of "killer" proteins. On the other hand, data indicate that neurotrophic factors
Neuronal activity regulates DROSHA via autophagy in spinal muscular atrophy
GG Ines do Carmo, et al.
Scientific Reports, 8(1), 7907-7907 (2018)
Valerie Croons et al.
The Journal of pharmacology and experimental therapeutics, 320(3), 986-993 (2006-12-01)
Macrophages are an essential component of unstable atherosclerotic plaques and play a pivotal role in the destabilization process. We have demonstrated previously that local delivery of the mammalian target of rapamycin (mTOR) inhibitor everolimus selectively clears macrophages in rabbit plaques.
Y H Choi et al.
Reproduction (Cambridge, England), 122(1), 177-183 (2001-06-27)
Two different culture media (TCM-199 and follicular fluid), two activation treatments (10 and 50 micromol calcium ionophore l(-1)) and three culture periods with cycloheximide were evaluated to find effective culture conditions for activation of cumulus-free equine oocytes. Oocytes were collected
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