Actidione

Actidione Basic information
Product Name:Actidione
Synonyms:Cycloheximide solution,CHX;Cycloheximide 100mg [66-81-9];Cycloheximide Solution 100ug/ml in Acetonitrile;CYCLOHEXIMIDE READY MADE;4-[(2R)-2-[(1S,3S,5S)-3,5-DiMethyl-2-oxocyclohexyl]-2-hydroxyethyl]-2,6-piperidinedione;FT 3422-2;NaraMycin Microcapsule D 80;NaraMycin NM-MCU 80
CAS:66-81-9
MF:C15H23NO4
MW:281.35
EINECS:200-636-0
Product Categories:Amines, Chiral Reagents, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals;ERGAMISOL;Miscellaneous;Antibiotic Explorer;Antifungal;antibiotic;Signalling;Antibiotics
Mol File:66-81-9.mol
Actidione Structure
Actidione Chemical Properties
Melting point 111-116 °C
alpha -28.5 º (c=1, CHCl3)
Boiling point 492℃
density 1.0867 (rough estimate)
refractive index 1.5000 (estimate)
Fp 87°0°(230°F)
storage temp. 2-8°C
solubility Soluble in Ethanol (up to 14 mg/ml) or in Water (up to 7 mg/ml).
pka11.61±0.40(Predicted)
form Glassy Irregular Shaped Granules
color White
Water Solubility 2.1 g/100 mL (2 ºC)
BRN 88868
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, acid chlorides, acid anhydrides, alkali.
CAS DataBase Reference66-81-9(CAS DataBase Reference)
EPA Substance Registry SystemCycloheximide (66-81-9)
Safety Information
Hazard Codes Xn,T,N,T+
Risk Statements 22-68-61-51/53-28-38-52/53
Safety Statements 53-45-61-36/37-28
RIDADR UN 2811 6.1/PG 1
WGK Germany 3
RTECS MA4375000
HazardClass 6.1(a)
PackingGroup II
HS Code 29419000
Hazardous Substances Data66-81-9(Hazardous Substances Data)
ToxicityLD50 i.v. in mice: 150 mg/kg (Leach)
MSDS Information
Actidione Usage And Synthesis
DescriptionCycloheximide is a glutarimide-type antibiotic produced by Streptomyces griseus. Colorless crystals, C15H23NO4 (281.4), melting point: 115.5–117 ?C, weak acidic substance (pKa 11.2), Soluble in chloroform, isopropanol and methanol; water > 21 g/L (2 ?C). Stable in pH 3–5, but rapidly destroyed in alkaline solutions.
DescriptionCycloheximide is a glutarimide antibiotic produced by S. griseus that inhibits protein synthesis in eukaryotes (IC50 = 5-50 μM) by interfering with translational elongation. Its effects on protein synthesis can either induce or inhibit apoptosis depending on cell type. Cycloheximide is widely used as a tool in molecular biology research for ribosome profiling and translational profiling as well as to determine the half-life of a protein.
Chemical PropertiesOff-white to light tan powder
Chemical PropertiesCycloheximide is a colorless crystalline sub- stance.
Usesimmunomodulator
UsesCycloheximide is an antibiotic substance isolated from the beers of streptomycin-producing strains of Streptomyces griseus. Cycloheximide is used as fungicide.
UsesCycloheximide is the most recognised member of the glutarimide microbial metabolites. Cycloheximide was isolated from Streptomyces griseus in the late 1940s as a potent and broad spectrum antifungal. Cycloheximide inhibits protein synthesis by interfering with translocation. Cycloheximide is an established bioprobe and widely-used antifungal reagent in research with over 25,000 literature citations.
Usespotent and selective 5-HT uptake inhibitor
Usesimmunosuppressant
DefinitionChEBI: Cycloheximide is a dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus. It has a role as a bacterial metabolite, a protein synthesis inhibitor, a neuroprotective agent, an anticoronaviral agent and a ferroptosis inhibitor. It is a member of piperidones, a piperidine antibiotic, an antibiotic fungicide, a dicarboximide, a secondary alcohol and a cyclic ketone. It is functionally related to a piperidine-2,6-dione.
General DescriptionColorless crystals. Used as a fungicide and as a anticancer drug.
Air & Water ReactionsWater soluble.
Reactivity ProfileActidione is an imide. Actidione is incompatible with strong oxidizing agents, acid chlorides and acid anhydrides. Actidione decomposes rapidly in alkali at room temperature.
Health HazardActidione is extremely toxic; the probable oral lethal dose in humans is 5-50 mg/kg, or 7 drops to 1 teaspoonful for a 150-lb. person.
Fire HazardWhen exposed to heat, Actidione emits toxic fumes, including nitrogen oxides.
Agricultural UsesFungicide; plant growth regulator: A U.S. EPA restricted Use Pesticide (RUP). Used as an antibiotic, plant growth regulator, and protein synthesis inhibitor. Inhibits growth of many plant pathogenic fungi. Effective for control of powdery mildew on roses and many other ornamentals, rusts and leaf spots on lawn grasses, and azalea petal blight. Also used as a repellent for rodents and other animal pests and in cancer therapy. Not listed for use in EU countries
Trade nameACTI-AID®[C]; ACTIDIONE®[C]; ACTIDIONE® TGF[C]; ACTIDONE®; ACTIDONE® PM; ACTIDONE® TGF; ACTISPRAY; HIZAROCIN®; KAKEN®; NARAMYCIN®; NARAMYCIN A®; NEOCYCLOHEXIMIDE®; U-4527
Biological ActivitySelective inhibitor of eukaryotic (over prokaryotic) protein synthesis, blocking tRNA binding and release from ribosomes. Induces apoptosis in a variety of transformed and normal cell lines, including T-cells. Competitively inhibits the PPIase hFKBP12 (K i = 3.4 μ M). Antifungal antibiotic.
PharmacologyStrongly inhibits the growth of pathogenic fungi but no effects on bacterial growth, even at 100 mg/ml. Inhibits protein synthesis by interfering with the translocation step in eukaryotes, but not in prokaryotes. When ingested by animals, the agent causes excitement, tremors, salivation, diarrhea, and melena.
Potential ExposureA potential danger to those involved in the manufacture, formulation, or application of this fun- gicide and pesticide. Used as an antibiotic, plant growth regulator, and protein synthesis inhibitor. Used on oranges for processing and to inhibit growth of many pathogenic plant fungi. Also used as a repellent for rodents and other animal pests; and in cancer therapy.
in vitrocycloheximide blocks the movement of peptidyl-trna from acceptor site to the donor site on reticulocyte ribosomes. this translocation reaction is dependent on the transfer enzyme, tf-ii, and gtp hydrolysis. cycloheximide has no effect on the ribosome dependent gtpase activity of tf-ii or peptidyl transferase reaction by which peptides on trna in the donor ribosomal site are transferred to an amino acid on trna in the acceptor site [1].
in vivocycloheximide treatment was effective in attenuating rat brain injury within a 6 hr therapeutic window after hypoxia-ischemia in a newborn rat pup model. these data support the possibility that protein synthesis inhibitors, as well as other anti-apoptotic strategies, may have therapeutic utility in hypoxic-ischemic (hi) events of the developing newborn brain even when treatment is delayed for up to 6 hr after the primary asphyxial insult [2].
CarcinogenicityCycloheximide is genotoxic in Escherichia coli with metabolic activation and in the mouse sperm morphology assay. Carcinogenicity bioassays in the mouse and rat are inconclusive.
Environmental FateCHX is a potent inhibitor of protein synthesis in animals. It binds to E-site of 70S ribosome-mRNA complex, blocking the translational step of protein biosynthesis. It causes an increase in adrenal RNA and increased production of glucocorticoids.
MetabolismRapidly inactivated at room temperature by diluted alkali with the formation of a volatile, fragrant ketone, 2,4- dimethylcyclohexanone. Hazardous to fish and wildlife.
storageroom temperature
Purification MethodsIt crystallises from H2O /MeOH (4:1), amyl acetate, isopropyl acetate/isopropyl ether or H2O. [Beilstein 21/13 V 434.]
Toxicity evaluationSkin irritant. LD50 2 mg/kg (rat, orl); 133 mg/kg (mice, Ipr); 65 mg/kg (guinea pig); 60 mg/kg (monkey). Teratogenic effects.
To remove toxicant from gut, activated charcoal and a catharitic dose of sodium sulfate are effective. Mechanisms of toxicity are not well defined, but hydrocortisone is antidotal, particularly in combination with the adrenergic agent methoxyphenamine.
IncompatibilitiesIncompatible with oxidizers, acid anhy- drides; strong bases.
Waste DisposalHigh-temperature incinerator with flue gas scrubbing equipment.
References1) Merck 14:2728
Actidione Preparation Products And Raw materials
Raw materialstrans-2,4-dimethylcyclohexanone, (2S)-->4-Pentenoic acid, 4-methyl-
TIMTEC-BB SBB005972 Glutarimide N,N-Dimethylformamide streptomyces avermifilis ETHANE 2,5-DIMETHYLCYCLOHEXANONE 3-Ethylglutarimide 3-methylglutarimide Dimethyl fumarate Actidione Dimethyl sulfoxide (S)-2-HYDROXYMETHYLCYCLOHEXANONE Dimethyl ether N,N-Dimethylacetamide Dimethyl carbonate 2-(HYDROXYMETHYL)CYCLOHEXANONE CHLOROPHOSPHONAZO III Dimethyl sulfate

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