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Cycloheximide information


Cycloheximide
Cycloheximide
Names
Preferred IUPAC name
4-{(2R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl}piperidine-2,6-dione
Other names
Naramycin A, hizarocin, actidione, actispray, kaken, U-4527
Identifiers
CAS Number
  • 66-81-9 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:27641 checkY
ChEMBL
  • ChEMBL123292 checkY
ChemSpider
  • 5962 checkY
ECHA InfoCard 100.000.578 Edit this at Wikidata
IUPHAR/BPS
  • 5433
KEGG
  • C06685 ☒N
PubChem CID
  • 6197
RTECS number
  • MA4375000
UNII
  • 98600C0908 checkY
CompTox Dashboard (EPA)
  • DTXSID6024882 Edit this at Wikidata
InChI
  • 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 checkY
    Key: YPHMISFOHDHNIV-FSZOTQKASA-N checkY
  • InChI=1/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
    Key: YPHMISFOHDHNIV-FSZOTQKABD
SMILES
  • O=C2NC(=O)CC(C[C@@H](O)[C@H]1C(=O)[C@@H](C)C[C@H](C)C1)C2
Properties
Chemical formula
C15H23NO4
Molar mass 281.352 g·mol−1
Appearance Colorless crystals
Melting point 119.5 to 121 °C (247.1 to 249.8 °F; 392.6 to 394.1 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Highly toxic
GHS labelling:
Pictograms
GHS06: Toxic
Safety data sheet (SDS) Oxford MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Cycloheximide is a naturally occurring fungicide produced by the bacterium Streptomyces griseus. Cycloheximide exerts its effects by interfering with the translocation step in protein synthesis (movement of two tRNA molecules and mRNA in relation to the ribosome), thus blocking eukaryotic translational elongation. Cycloheximide is widely used in biomedical research to inhibit protein synthesis in eukaryotic cells studied in vitro (i.e. outside of organisms). It is inexpensive and works rapidly. Its effects are rapidly reversed by simply removing it from the culture medium.[1]

Due to significant toxic side effects, including DNA damage, teratogenesis, and other reproductive effects (including birth defects and toxicity to sperm[2]), cycloheximide is generally used only in in vitro research applications, and is not suitable for human use as a therapeutic compound. Although it has been used as a fungicide in agricultural applications, this application is now decreasing as the health risks have become better understood.

Because cycloheximide rapidly breaks down in a basic environment, decontamination of work surfaces and containers can be achieved by washing with a non-harmful alkali solution such as soapy water or aqueous sodium bicarbonate.

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[3]

  1. ^ Müller, Franz; Ackermann, Peter; Margot, Paul (2012). "Fungicides, Agricultural, 2. Individual Fungicides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o12_o06. ISBN 978-3527306732.
  2. ^ "TOXNET". toxnet.nlm.nih.gov. Archived from the original on 2007-05-22. Retrieved 2007-05-03.
  3. ^ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF). Code of Federal Regulations (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011.

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Cycloheximide

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Cycloheximide is a naturally occurring fungicide produced by the bacterium Streptomyces griseus. Cycloheximide exerts its effects by interfering with the...

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Cycloheximide chase

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Cycloheximide chase assays are an experimental technique used in molecular and cellular biology to measure steady state protein stability. Cycloheximide...

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Trichophyton rubrum

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(CEA). T. rubrum cultures can be isolated on both cycloheximide-containing media and cycloheximide-free media. The latter are conventionally used for...

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Glutarimide

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thalidomide, a medication used to treat multiple myeloma and leprosy, and cycloheximide, a potent inhibitor of protein synthesis. Glutarimide - Sigma-Aldrich...

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Bacterivore

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bacterivores, which interfere with the growing of bacteria for study. Adding cycloheximide can inhibit the growth of bacterivores without affecting some bacterial...

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Trichophyton tonsurans

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unaffected by antibiotic treatment with chloramphenicol, as well as by cycloheximide. After 5 days of incubation, CLS production will be evident, suggesting...

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Parthenogenesis

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microinjection of calcium ions, or electrical stimulation. Treatment with cycloheximide, a non-specific protein synthesis inhibitor, enhances parthenote development...

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Streptomyces albulus

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Streptomyces albulus produces acetoxycycloheximide, aciphenol, albanoursin and cycloheximide. List of Streptomyces species LPSN bacterio.net Straininfo of Streptomyces...

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Yeast

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dried malt extract and agar as a solid growth medium. The fungicide cycloheximide is sometimes added to yeast growth media to inhibit the growth of Saccharomyces...

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Imide

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compounds was sparked by the early discovery of the high bioactivity of the Cycloheximide as an inhibitor of protein biosynthesis in certain organisms. Thalidomide...

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Ribosome profiling

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other elongating regions can be detected by adding antibiotics like cycloheximide that inhibit translocation, chloramphenicol that inhibits transfer of...

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CHX

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"Capitán Manuel Niño" International Airport in Changuinola, Panama Cycloheximide, an inhibitor of protein biosynthesis in eukaryotic cells This disambiguation...

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EPA list of extremely hazardous substances

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(E)- Cyanogen bromide Cyanogen iodide Cyanophos Cyanuric fluoride Cycloheximide Cyclohexylamine Decaborane(14) Demeton Demeton-S-methyl Dialifor Diborane...

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Dermatophyte test medium

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medical mycology. It is based on Sabouraud's dextrose agar with added cycloheximide to inhibit saprotrophic growth, antibiotic to inhibit bacterial growth...

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Lymphogranuloma venereum

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culture is often used. Culture is difficult. Requiring a special medium, cycloheximide-treated McCoy or HeLa cells, and yields are still only 30 to 50%. DFA...

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Paraptosis

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induced by IGFIR-IC in 293T cells is deterred by actinomycin D and cycloheximide, thus demonstrating a dependence on transcription and translation. Induction...

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Candida tropicalis

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pyridoxine, V9 without niacin, V10 without PABA, O1 0.01% cycloheximide, O2 0.1% cycloheximide. Positive temperatures from 25–40 °C (77–104 °F). positive...

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Acetoxycycloheximide

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analogue of cycloheximide. It is a potent protein synthesis inhibitor in animal cells and can inhibit the formation of memories. Cycloheximide Mahy, Brian...

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Polysome

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resembling a planar spiral. Polysomal profiling is a technique that uses cycloheximide to arrest translation and a sucrose gradient to separate the resulting...

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List of fungicides

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cuprobam [Wikidata] cyanogen cyazofamid cyclafuramid [Wikidata] cyclobutrifluram cycloheximide cyflufenamid [Wikidata] cymoxanil [Wikidata] cypendazole [Wikidata]...

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Pederin

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selective in targeting solid tumor cells. Psymberin Paederus dermatitis Cycloheximide Christmas eye Bugs Don’t Have to Bite to Do Damage:The Tale of the Paederus...

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Regulation of gene expression

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inhibitors (actinomycin D or α-Amanitin) or translation inhibitors (Cycloheximide), respectively. Artificial transcription factors (small molecules that...

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Penicillium digitatum

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production observed in shake cultures can be inhibited by actinomycin D and cycloheximide and modulated by inorganic phosphate. In addition, aminoethoxyvinyl...

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California Proposition 65 list of chemicals

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135-20-6 Cyanazine 21725-46-2 Cycasin 14901-08-7 Cycloate 1134-23-2 Cycloheximide 66-81-9 Cyclopenta[cd]pyrene 27208-37-3 Cyclophosphamide 50-18-0; 6055-19-2...

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Zygomycota

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induction media can also be used. Most zygomycetes are sensitive to cycloheximide (actidione) and this agent should not be used in culture media. A common...

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Anisomycin

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yeast extract media for the selective isolation of Legionella species. Cycloheximide Anisomycin Archived January 19, 2012, at the Wayback Machine from Sigma...

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Ribosomal pause

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sucrose cushion with translation elongation inhibitors, for example cycloheximide. Ribosome pausing can be detected during preprolactin synthesis on free...

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Eukaryotic ribosome

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of eukaryotic translation elongation is the glutarimide antibiotic cycloheximide (CHX), which has been co-crystallized with the eukaryotic 60S subunit...

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