46401

Cycloheximide

PESTANAL^®, analytical standard

• Synonym(s): 3-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide, Actidione, Naramycin A
• Empirical Formula (Hill Notation): C₁₅H₂₃NO₄
• CAS Number: 66-81-9
• Molecular Weight: 281.35
• UNSPSC Code: 41116107
• NACRES: NA.24
• PubChem Substance ID: 329757163
• EC Number: 200-636-0
• Beilstein/REAXYS Number: 88868
• MDL number: MFCD00082346

Properties

• grade: analytical standard
• Quality Segment: 100
• description: mixture of stereo isomers
• product line: PESTANAL^®
• assay: ≥95% (HPLC)
• shelf life: limited shelf life, expiry date on the label
• technique(s): HPLC: suitable, gas chromatography (GC): suitable
• solubility: H₂O: slightly soluble
• antibiotic activity spectrum: fungi
• application(s): agriculture; cleaning products; cosmetics; environmental; food and beverages; personal care
• format: neat
• mode of action: protein synthesis | interferes
• storage temp.: −20°C
• SMILES string: [H][C@]1(C[C@@H](C)C[C@H](C)C1=O)[C@H](O)CC2CC(=O)NC(=O)C2
• 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

Description

General description

Cycloheximide is an antibiotic having significant antifungal properties. It is produced by streptomycin-producing strains of Streptomyces griseus and acts by inhibiting protein synthesis. Its main biological activity is translation inhibition in eukaryotes resulting in cell growth arrest and cell death. It is used as a fungicide.
As per Regulation (EC) No 1107/2009, repealing the directive 91/414, cycloheximide is not approved for use in the European Union (EU).

Application

Cycloheximide may find the following uses:

• To evaluate the antifungal efficacy and safety of cycloheximide as a supplement in Optisol-GS
• To study the effect of cycloheximide on leaf-cutting ant workers
• To study the effect of streptomycin, cycloheximide, fungizone, captan, carbofuran, cygon, and pentachloronitrobenzene on soil microorganisms
• To study the fungal control of nitrous oxide production in a semiarid grassland
• To study the activity and degradation of streptomycin and cycloheximide in soil

Biochem/physiol Actions

Mode of Action: Translation inhibition in eukaryotes resulting in cell growth arrest and cell death. CHX is widely used for the selection of CHX-resistant strains of yeast and fungi, controlled inhibition of protein synthesis for detection of short-lived proteins and super-induction of protein expression, and apoptosis induction or facilitation of apoptosis induction by death receptors.

Activity Spectrum: Active against yeast and fungi like Candida, Aspergillus, Saccharomyces, Penicillium

Legal Information

PESTANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• pictograms: GHS06,GHS08,GHS09
• signalword: Danger
• hcodes: H300,H341,H360D,H411
• pcodes: P202 - P264 - P273 - P280 - P301 + P310 - P391
• 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
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges