239763-M
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:
Molecular Weight:
281.35
UNSPSC Code:
12352111
NACRES:
NA.77
MDL number:
Assay:
≥90% (by assay)
Form:
powder
Storage condition:
OK to freeze
Quality Segment
assay
≥90% (by assay)
form
powder
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze
color
white to brown
storage temp.
room temp
SMILES string
N1C(=O)CC(CC1=O)C[C@@H](O)[C@@H]2C[C@H](C[C@@H](C2=O)C)C
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.
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.
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
Disclaimer
Toxicity: Highly Toxic & Carcinogenic / Teratogenic (I)
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signalword
Danger
hcodes
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
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