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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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€111.00

5 G

€333.00

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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)

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1 of 4

This Item
C198818079C4859
Cycloheximide ≥95% (HPLC)

Sigma-Aldrich

01810

Cycloheximide

Cycloheximide Biotechnology Performance Certified

Sigma-Aldrich

C1988

Cycloheximide

Cycloheximide solution 0.1%, suitable for microbiology

Millipore

18079

Cycloheximide solution

Cycloheximide solution Ready-Made Solution, microbial, 100 mg/mL in DMSO, Suitable for cell culture

Sigma-Aldrich

C4859

Cycloheximide solution

mode of action

protein synthesis | interferes

mode of action

protein synthesis | interferes

mode of action

-

mode of action

protein synthesis | interferes

antibiotic activity spectrum

fungi, yeast

antibiotic activity spectrum

fungi, yeast

antibiotic activity spectrum

fungi

antibiotic activity spectrum

fungi, yeast

assay

≥90% (HPLC)

assay

-

assay

-

assay

-

form

powder or crystals

form

powder

form

liquid

form

solution

biological source

microbial

biological source

-

biological source

-

biological source

microbial

color

white to light beige

color

-

color

-

color

-

Application

Cyclohexamide (CHX) is widely used for selection of CHX-resistant strains of yeast and fungi, controlled inhibition of protein synthesis[1][2] 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,[3] activate cumulus-free equine oocytes,[4] and to have neuroprotective properties.[5]

Biochem/physiol Actions

Cyclohexamide inhibits protein biosynthesis in eukaryotic cells by binding with the 80S ribosome.[6]
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
0000505076
0000505076
0000451278
0000451278
0000430586

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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
Tumor-suppressive functions of long-chain acyl-CoA synthetase 4 in gastric cancer
Ye X, et al.
IUBMB Life, 68(4), 320-327 (2016)
Neuronal activity regulates DROSHA via autophagy in spinal muscular atrophy
GG Ines do Carmo, et al.
Scientific Reports, 8(1), 7907-7907 (2018)
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
The mechanism by which cycloheximide and related glutarimide antibiotics inhibit peptide synthesis on reticulocyte ribosomes.
T G Obrig et al.
The Journal of biological chemistry, 246(1), 174-181 (1971-01-10)
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Questions

  1. What is the minimum shelf life of the product that should be considered if the certificate of analysis only indicates the quality release date?

    1 answer

    1. The product specification sheet for this product contains a recommended retest date period of two years after the quality release date. A recommended retest date is the period of time during which the product is expected to remain within established stability specifications, provided that it has been stored under defined conditions. After the Retest Date, product samples should be examined to ensure that the product is still in compliance with the established specifications. For more information, you may access the "Product Dating Information" document under "ADDITIONAL USEFUL DOCUMENTS ABOUT OUR PRODUCTS" at the bottom of the Quality Services page with this link: https://www.sigmaaldrich.com/US/en/life-science/quality-and-regulatory-management/quality-services

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