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Merck

239764

Cycloheximide, High Purity

Antifungal antibiotic that inhibits protein synthesis in eukaryotes but not in prokaryotes.

Synonym(s):

Cycloheximide, High Purity

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About This Item

Empirical Formula (Hill Notation):
C15H23NO4
CAS Number:
66-81-9
Molecular Weight:
281.35
UNSPSC Code:
12352200
MDL number:
MFCD00082346
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100
Storage condition:
OK to freeze

Key Documents

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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

assay

≥98% (HPLC)

form

solid

potency

3.4 μM Ki

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

white

solubility

chloroform: soluble, ethanol: soluble, methanol: soluble

shipped in

ambient

storage temp.

10-30°C

Quality Level

100

General description

Antifungal antibiotic that does not inhibit several species of pathogenic bacteria at 100 µg/ml. Inhibits protein synthesis in eukaryotes but not in prokaryotes. Interacts directly with the translocase enzyme, interfering with the translocation step. Inhibits cell-free protein synthesis in eukaryotes. Competitively inhibits hFkBP12 (Ki = 3.4 µM). Triggers apoptosis in HL-60 cells, T-cell hybridomas, Burkitt′s lymphoma cells, and a variety of other cell types, including rodent macrophages. Inhibits DNA cleavage in rat thymocytes treated with thapsigargin, methylprednisolone, and ionomycin. Rapidly destroyed in alkaline solutions.
Antifungal antibiotic that inhibits protein synthesis in eukaryotes but not in prokaryotes. Interacts directly with the translocase enzyme, interfering with the translocation step. Inhibits cell-free protein synthesis in eukaryotes. Competitively inhibits hFKBP12 (Ki = 3.4 µM). Triggers apoptosis in HL-60 cells, T cell hybridomas, Burkitt’s lymphoma cells, and a variety of other cell types including rodent macrophages. However, it inhibits DNA cleavage in rat thymocytes treated with Thapsigargin (Cat. No. 586005 ), methylprednisolone, and Ionomycin (Cat. Nos. 407950 and 407952 ). Rapidly destroyed in alkaline solutions. Also available as a 300 mM solution in DMSO (Cat. No. 508739 ).

Biochem/physiol Actions

Primary Target
hFKBP12

Preparation Note

Following reconstitution, aliquot and freeze (-20°C) for long term storage or refrigerate (4°C) for short term storage. Stock solutions are stable for up to 6 weeks at 4°C, pH 3-5.

Other Notes

Christner, C., et al. 1999. J. Med. Chem. 42, 3615.
Lu, Q., et al. 1996. Arch. Biochem. Biophys.334, 175.
Chow, S.C., et al. 1995. Exp. Cell Res.216, 149.
Cotter, T.G., et al. 1992. Anticancer Res.12, 773.
Takano, Y.S., et al. 1991. J. Pathol.163, 329.
Waring, P. 1990. J. Biol. Chem. 265, 14476.
Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Highly Toxic & Carcinogenic / Teratogenic (I)

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

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.

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

239764-GM: + 239764-100MG: + 239764-1GM: + US2239764-1GM:

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Certificates of Analysis (COA)

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Ashley N Stewart et al.
Biochemistry, 58(6), 727-741 (2018-12-20)
C1q/TNF-related protein 12 (CTRP12) is a secreted regulator of glucose and lipid metabolism. It circulates in plasma as a full-length protein or as a cleaved isoform generated by furin/PCSK3 cleavage. These isoforms preferentially activate different signaling pathways, and their ratio
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The protein arginine methyltransferase 5 (PRMT5) methylates a variety of proteins involved in splicing, multiple signal transduction pathways, epigenetic control of gene expression, and mechanisms leading to protein expression required for cellular proliferation. Dysregulation of PRMT5 is associated with clinical
Raphael Serna et al.
iScience, 25(6), 104325-104325 (2022-05-24)
Metabolic syndrome is associated with obesity, insulin resistance, and the risk of cancer. We tested whether oncogenic transcription factor c-JUN metabolically reprogrammed cells to induce obesity and cancer by reduction of glucose uptake, with promotion of the stemness phenotype leading
Yuan-Lin Kang et al.
bioRxiv : the preprint server for biology (2020-06-09)
Virus entry is a multistep process. It initiates when the virus attaches to the host cell and ends when the viral contents reach the cytosol. Genetically unrelated viruses can subvert analogous subcellular mechanisms and use similar trafficking pathways for successful
Songsong Dan et al.
Scientific reports, 11(1), 10285-10285 (2021-05-15)
Reversible lysine methylation is essential for regulating histones and emerges to critically regulate non-histone proteins as well. Here we show that the master transcription factor OCT4 in pluripotent stem cells (PSCs) was methylated at multiple lysine residues. LSD1 that is
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