Cycloheximide
Also known as Actidione, Cicloheximide, Naramycin a
Key facts
What buyers check first
- Appearance
- Plates from amyl acetate, water or 30% methanol
- Melting point
- 119.5 to 121
- Solubility
- At 2 °C (g/100 ml): water 2.1, amyl acetate 7, sol in chloroform, ether, methanol, ethan…
- HS code
- 292519
- Category
- Fungicides
- UN number
- UN 2588

What is Cycloheximide?
Plain description, key identifiers and synonyms
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 an anticoronaviral agent, a ferroptosis inhibitor, a protein synthesis inhibitor, a neuroprotective agent and a bacterial metabolite. It is a dicarboximide, a secondary alcohol, a cyclic ketone, a member of piperidones, a piperidine antibiotic and an antibiotic fungicide. It is functionally related to a piperidine-2,6-dione.
Identifiers
Registry numbers, names and line notations, tap to copy
- IUPAC name
- 4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione
- CAS number
- 66-81-9 CAS number cross-checkedOther or deprecated CAS: 1154-57-0, 4630-75-5
- EC number
- 200-636-0
- Molecular formula
- C15H23NO4
- UNII
- 98600C0908
- MDL number
- MFCD00082346
- InChIKey
- YPHMISFOHDHNIV-FSZOTQKASA-N
- 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
- Canonical SMILES
- CC1CC(C)C(=O)C(C(O)CC2CC(=O)NC(=O)C2)C1
- Isomeric SMILES
- C[C@H]1C[C@@H](C(=O)[C@@H](C1)[C@@H](CC2CC(=O)NC(=O)C2)O)C
Synonyms
- Actidione
- Cicloheximide
- Naramycin a
- Actidion
- Hizarocin
- Naramycin
- Kaken
- Acti-Aid
- Actidone
- Neocycloheximide
- Cicloheximida
- Actispray
- Actidione PM
- Cicloheximidum
- Actidione BR
- Actidione TGF
- Aktidion
- 4-[(2R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione
- (-)-Cycloheximide
- NM-MCD 80
- CBC 500046
- 3-((R)-2-((1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide
- 4-{(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl}piperidine-2,6-dione
- 3-(2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide
- beta-(2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide
Show all 35 synonymsShow fewer synonyms
- 2,6-Piperidinedione, 4-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-, (1S-(1alpha(S*),3alpha,5beta))-
- 3-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide
- 2,6-Piperidinedione, 4-((2R)-2-((1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-
- 2,6-Piperidinedione, 4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]-
- 3-[(R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]glutarimide
- 4-((2R)-2-((1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)piperidine-2,6-dione
- Acti-Dione
- Cycloheximid
- Zykloheximid
- Acti-dione BR
Physical and chemical properties
Measured values and descriptors computed from the structure
Physical and chemical properties
Measured values, check the supplier specification for your grade
| Appearance | Plates from amyl acetate, water or 30% methanolexp.Measured value |
|---|---|
| Melting point | 119.5 to 121exp.Measured value |
| Solubility | At 2 °C (g/100 ml): water 2.1, amyl acetate 7, sol in chloroform, ether, methanol, ethanol, insol in saturated hydrocarbonsexp.Measured value |
| Vapour pressure | 0.006 [mm Hg] @25 °Cexp.Measured value |
Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.
Computed descriptors
Calculated from the structure, useful for screening and formulation
| Molecular weight | 281.35 g/molcalc.Computed value |
|---|---|
| Exact mass | 281.1627 Dacalc.Computed value |
| LogP (octanol/water) | 1.04calc.Computed value |
| Topological polar surface area | 83.47 Ųcalc.Computed value |
| Hydrogen bond donors | 2calc.Computed value |
| Hydrogen bond acceptors | 4calc.Computed value |
| Rotatable bonds | 3calc.Computed value |
| Heavy atoms | 20calc.Computed value |
| Rings | 2calc.Computed value |
| Aromatic rings | 0calc.Computed value |
| Fraction sp3 carbons | 0.8calc.Computed value |
| Formal charge | 0calc.Computed value |
| Stereocentres | 4calc.Computed value |
| Lipinski rule of five | Passes (0 violations)calc.Computed value |
Calculated for screening. Confirm critical figures with the supplier.
Murcko scaffold
The ring system that remains when every side chain is removed
Safety and hazards
GHS classification summary, not a safety data sheet
Hazard statements
- H300Fatal if swallowed.
- H341Suspected of causing genetic defects.
- H360DMay damage the unborn child.
- H411Toxic to aquatic life with long lasting effects.
Precautionary statements (12)
- P203Obtain, read and follow all safety instructions before use.
- P264Wash skin thoroughly after handling.
- P270Do not eat, drink or smoke when using this product.
- P273Avoid release to the environment.
- P280Wear protective gloves, protective clothing, eye protection and face protection.
- P301 + P316If swallowed: Get emergency medical help immediately.
- P318If exposed or concerned, get medical advice.
- P321Specific treatment (see supplemental first aid instructions on the label).
- P330Rinse mouth.
- P391Collect spillage.
- P405Store locked up.
- P501Dispose of contents and container in accordance with local regulations.
- UN number
- UN 2588
- Transport hazard class
- 6.1
- Packing group
- I
GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.
Full safety data and first aidCycloheximide suppliers
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- ManufacturerUnclaimed profileCycloheximideGrade, purity and minimum order on requestPrice on request
- United States, San DiegoUnclaimed profileCycloheximideGrade, purity and minimum order on requestPrice on request
- India, MumbaiUnclaimed profileActidioneGrade, purity and minimum order on requestPrice on request
- India ManufacturerUnclaimed profileCycloheximideGrade, purity and minimum order on requestPrice on request
- India ManufacturerUnclaimed profileActidioneGrade, purity and minimum order on requestPrice on request
- United States ManufacturerUnclaimed profileCycloheximideGrade, purity and minimum order on requestPrice on request
- Price on request
- South Africa, Germiston ManufacturerUnclaimed profileActidioneGrade, purity and minimum order on requestPrice on request
- Price on request
- India ManufacturerUnclaimed profileCycloheximideGrade, purity and minimum order on requestPrice on request
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Where suppliers are based
71 suppliers in 14 countries
- United States31
- China11
- India6
- Germany4
- United Kingdom4
- Spain3
- and 8 more countries
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Cycloheximide price
Indicative price range per kg from live supplier offers
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Uses and applications
What the substance is used for, by industry and function
Fungicide, plant growth regulator, as protein synthesis inhibitor.
/Cycloheximide/ is used in laboratory media as a selective agent to permit isolation of pathogenic and non-pathogenic fungi from specimens such as sputa and feces which may be other fungi.
Cycloheximide has a limited application in treatment of downy mildew of onions and shoot blight of Japanese larch.
Pharmacological actions
- Antifungal Agents
- Protein Synthesis Inhibitors
Roles
- anticoronaviral agent
- antimicrobial agent
- antiviral agent
- bacterial metabolite
- enzyme inhibitor
- ferroptosis inhibitor
- metabolite
- neuroprotective agent
- pathway inhibitor
- pharmaceutical
- prokaryotic metabolite
- protective agent
- protein synthesis inhibitor
How it is made
Antibiotic substance isolated from beers of streptomycin-producing strains of Streptomyces griseus: Leach et al, J Am Chem Soc 69, 474 (1947), Ford, Leach, J Am Chem Soc 70, 1223 (1948), Whiffen et al, US patent 2,574,519 (1951 to Upjohn). Production, assay and antibiotic activity: Whiffen, J Bacteriol 56, 283 (1948). Improved production method: Kominek, US patents 3,915,802-3 (both 1975 to Upjohn). ... synthesis of dl- and l-forms: Johnson et al, J Am Chem Soc 88, 149 (1966).
Regulatory status
Inventories, regulations and trade controls that list this substance
Europe
- EU harmonised classification (CLP Annex VI)Index no: 613-140-00-8
Health and food
- EU Cosmetics Regulation Annex II, prohibited in cosmeticsName: Cycloheximide, Ref no: 729, Annex ref: II/729
HS code and trade data
Customs classification and reported world trade statistics
Global trade
World import and export statistics for the HS code Cycloheximide is traded under.
Imides and their derivatives, salts thereof, other
- China29.7%
- Japan22.7%
- United Kingdom10.0%
- United States12.7%
- Brazil12.6%
- China10.5%
The HS code shown for Cycloheximide is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.
Frequently asked questions
Quick answers about Cycloheximide, based on the data on this page
What is Cycloheximide?
What is the CAS number of Cycloheximide?
What is the molecular formula and weight of Cycloheximide?
What is Cycloheximide used for?
Is Cycloheximide hazardous?
What is the HS code of Cycloheximide?
Where can I buy Cycloheximide?
Where can I buy Cycloheximide in India?
What is the price of Cycloheximide?
Guides for buyers
Practical guides that help when you source, ship or handle Cycloheximide
- Guide, SafetyHow to read a safety data sheet in 10 minutesA section by section method to pull the essentials out of any 16 section SDS: identity, hazards, composition, storage, PPE, properties, transport and emergency measures.Read
- Guide, Trade and logisticsShipping dangerous goods: UN numbers, classes and packing groupsHow the UN dangerous goods system works for chemicals, from the nine classes and UN numbers to packing groups, UN packaging marks, labels, documents and segregation.Read
- Guide, SafetyGHS pictograms, signal words and hazard statements explainedA practical guide to the nine GHS pictograms, the signal words Danger and Warning, H and P statements, and how to read a chemical label in seconds.Read
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