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239763-M

Sigma-Aldrich

Cycloheximide

Cycloheximide, CAS 66-81-9, is an antifungal antibiotic that inhibits protein synthesis in eukaryotes but not prokaryotes.

Synonym(s):

Cycloheximide

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About This Item

Empirical Formula (Hill Notation):
C15H23NO4
CAS Number:
66-81-9
Molecular Weight:
281.35
MDL number:
MFCD00082346
UNSPSC Code:
12352111
NACRES:
NA.77

Quality Level

200

Assay

≥90% (by assay)

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

white to brown

storage temp.

room temp

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

General description

An 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. Induces DNA fragmentation in macrophages, however it inhibits DNA cleavage in rat thymocytes treated with thapsigargin, methylprednisolone, and ionomycin. Rapidly destroyed in alkaline solutions.
An antifungal antibiotic that inhibits protein synthesis in eukaryotes but not prokaryotes. Competitively inhibits hFKBP12 (Ki = 3.4 µM). Triggers apoptosis in HL-60 cells, T cell hybridomas, Burkitt’s lymphoma cells, and other cell types. A 100 mg/ml solution of Cycloheximide (Cat. No. 239765) in DMSO (sterile-filtered) is also available.

Warning

Toxicity: Highly Toxic & Carcinogenic / Teratogenic (I)

Other Notes

Christner, C., et al. 1999. J. Med. Chem.42, 3615.
Lu, Q. and Mellgreen,R.L. 1996. Arch. Biochem. Biophys.334, 175.
Chow, S.C., et al. 1995. Exp. Cell Res.216, 149.
Waring, P. 1990. J. Biol. Chem.265, 14476.
Obrig, T.G., et al. 1971. J. Biol. Chem.246, 174.
Pestka, S. 1971. Annu. Rev. Microbiol.25, 487.

Legal Information

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

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

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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