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Actidione

CAS No.
66-81-9
Chemical Name:
Actidione
Synonyms
Cycloheximide;cicloheximide;CYCLOHEXIMID;Cycloheximide solution,CHX;Cycloheximide 100mg [66-81-9];Kaken;980U/MG;aktidion;FT 3422-2;Actispray
CBNumber:
CB7311602
Molecular Formula:
C15H23NO4
Molecular Weight:
281.35
MDL Number:
MFCD06202064
MOL File:
66-81-9.mol
Last updated:2024-03-14 15:18:27

Actidione 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)
Flash point 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).
pka 11.61±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 Reference 66-81-9(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 98600C0908
Proposition 65 List Cycloheximide
Pesticides Freedom of Information Act (FOIA) Cycloheximide
EPA Substance Registry System Cycloheximide (66-81-9)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08
Signal word  Danger
Hazard statements  H301-H341-H360D-H412
Precautionary statements  P201-P202-P264-P270-P273-P301+P310
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
Toxicity LD50 i.v. in mice: 150 mg/kg (Leach)
NFPA 704
0
2 0

Actidione price More Price(29)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich C7698 Cycloheximide from microbial, ≥94% (TLC) 66-81-9 5g $226 2024-03-01 Buy
Sigma-Aldrich 239763-M Cycloheximide - CAS 66-81-9 - Calbiochem Cycloheximide, CAS 66-81-9, is an antifungal antibiotic that inhibits protein synthesis in eukaryotes but not prokaryotes. 66-81-9 1G $97.6 2024-03-01 Buy
Sigma-Aldrich 239763-M Cycloheximide - CAS 66-81-9 - Calbiochem Cycloheximide, CAS 66-81-9, is an antifungal antibiotic that inhibits protein synthesis in eukaryotes but not prokaryotes. 66-81-9 5G $312 2024-03-01 Buy
Sigma-Aldrich C1988 Cycloheximide Biotechnology Performance Certified 66-81-9 5g $555 2023-06-20 Buy
Sigma-Aldrich 239763-M Cycloheximide - CAS 66-81-9 - Calbiochem Cycloheximide, CAS 66-81-9, is an antifungal antibiotic that inhibits protein synthesis in eukaryotes but not prokaryotes. 66-81-9 239763-1KG $29540 2023-06-20 Buy
Product number Packaging Price Buy
C7698 5g $226 Buy
239763-M 1G $97.6 Buy
239763-M 5G $312 Buy
C1988 5g $555 Buy
239763-M 239763-1KG $29540 Buy

Actidione Chemical Properties,Uses,Production

Description

Cycloheximide 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.

Description

Cycloheximide 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 Properties

Cycloheximide is a colorless crystalline sub- stance.

Chemical Properties

Off-white to light tan powder

Uses

immunosuppressant

Uses

potent and selective 5-HT uptake inhibitor

Uses

immunomodulator

Uses

Cycloheximide 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.

Uses

Cycloheximide is an antibiotic substance isolated from the beers of streptomycin-producing strains of Streptomyces griseus. Cycloheximide is used as fungicide.

Definition

ChEBI: 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 Description

Colorless crystals. Used as a fungicide and as a anticancer drug.

Air & Water Reactions

Water soluble.

Reactivity Profile

Actidione is an imide. Actidione is incompatible with strong oxidizing agents, acid chlorides and acid anhydrides. Actidione decomposes rapidly in alkali at room temperature.

Health Hazard

Actidione 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 Hazard

When exposed to heat, Actidione emits toxic fumes, including nitrogen oxides.

Agricultural Uses

Fungicide; 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 name

ACTI-AID®[C]; ACTIDIONE®[C]; ACTIDIONE® TGF[C]; ACTIDONE®; ACTIDONE® PM; ACTIDONE® TGF; ACTISPRAY; HIZAROCIN®; KAKEN®; NARAMYCIN®; NARAMYCIN A®; NEOCYCLOHEXIMIDE®; U-4527

Biological Activity

Selective 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.

Pharmacology

Strongly 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 Exposure

A 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 vitro

cycloheximide 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 vivo

cycloheximide 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].

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.Medical observation is recommended for 24-48 h following skin contact.

Carcinogenicity

Cycloheximide 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 Fate

CHX 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.

Metabolism

Rapidly inactivated at room temperature by diluted alkali with the formation of a volatile, fragrant ketone, 2,4- dimethylcyclohexanone. Hazardous to fish and wildlife.

storage

room temperature

Purification Methods

It crystallises from H2O /MeOH (4:1), amyl acetate, isopropyl acetate/isopropyl ether or H2O. [Beilstein 21/13 V 434.]

Toxicity evaluation

Skin 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.

Incompatibilities

Incompatible with oxidizers, acid anhy- drides; strong bases.

Waste Disposal

High-temperature incinerator with flue gas scrubbing equipment.

References

1) Merck 14:2728

1001-75-8
66-81-9
Synthesis of Actidione from 4-Pentenoic acid, 4-methyl-

Actidione Preparation Products And Raw materials

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 β-[2-(3,5-DiMethyl-2-oxocyclohexyl)- 2-hydroxyethyl]glutariMide 980U/MG 3alpha,5beta))-(1alpha(s* 5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-6-piperidinedion(1s-4-(2-(3 Actidionebr Actidionepm Actidionetgf Actispray aktidion cycloheximide(actidione) ethyl-2,6-piperidinedione Hizarocin Kaken Naramycin Neocycloheximide CyclohexiMide(CHX),Actidione Actidione, NaraMycin, U 4527, NSC 185 4-[2-(3,5-dimethyl-2-oxo-cyclohexyl)-2-hydroxy-ethyl]piperidine-2,6-dione CYCLOHEXIMIDE, BIOTECHNOLOGY PERFORMANCE CYCLOHEXIMIDE, 100MG, NEAT CYCLOHEXIMIDE FROM STREPTOMYCES GRISEUS ActidioneGr(Cycloheximide) ActidioneGr Cycloheximide solution 2,6-Piperidinedione, 4-(2R)-2-(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl-2-hydroxyethyl- cycloheximide (bsi,iso) Actidione [1S-[1alpha(S*),3alpha,5beta]]-4-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]-2,6-piperidinedione 3-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide CYCLOHEXIMIDE extrapure Cycloheximide,96% Cycloheximide,95% 3-[(R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]glutarimide 4-[(R)-2-Hydroxy-2-[(1S)-3β,5α-dimethyl-2-oxocyclohexyl]ethyl]piperidine-2,6-dione CYCLOHEXIMIDE CRYST.PURE (ACTIDIONE R) 4-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]piperidine-2,6-dione 4-[2-hydroxy-2-(2-keto-3,5-dimethyl-cyclohexyl)ethyl]piperidine-2,6-quinone D-Isocycloheximide Glutarimide, 3-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-, (+)- LEGIONELLA COMBI PACK Cycloheximide liquor Cycloheximide, >=98% GARDNER COLOUR 14 (GAR14) ((dimethyl-3,5oxo-2cyclohexyl)-2hydroxy-2ethyl)-3glutarimide [1s-[1alpha(s*),3alpha,5beta]]-4-[2-(3,5-dimethyl-2-oxo-cyclohexyl)]-2-hydroxy 3-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-glutarimid Cycloheximide,3-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide, Actidione, Naramycin A GARDNER COLOUR 16 (GAR16) GARDNER COLOUR 2 (GAR02) GARDNER COLOUR 4 (GAR04) POTASSIUM HYDROXIDE 0,5MOL DUTY PAID SALINE PEPTONE WATER 40X90ML