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Substance Name: Cycloheximide [USAN]
RN: 66-81-9
UNII: 98600C0908
InChIKey: YPHMISFOHDHNIV-FSZOTQKASA-N

Note

  • Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.

Molecular Formula

  • C15-H23-N-O4

Molecular Weight

  • 281.35
 

Classification Codes

Classification Codes

  • Agricultural Chemical
  • Anti-Infective Agents
  • Antifungal Agents
  • Antipsoriatic
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Fungicide, Bactericide, Wood Preservative
  • Growth Regulator / Fertilizer
  • Mutation Data
  • Protein Synthesis Inhibitors
  • Reproductive Effect
  • Skin / Eye Irritant

Superlist Classification Code

  • Threshold Planning Quantity (TPQ) = 100/10000 lb
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Names and Synonyms

Name of Substance

  • Cicloheximide [INN]
  • Cycloheximide
  • Cycloheximide [BSI:ISO]
  • Cycloheximide [USAN]

MeSH Heading

  • Cycloheximide

Synonyms

  • (1S-(1alpha(S*),3alpha,5beta))-4-(2-(3,5-Dimethyl-2-oxo-cyclohexyl))-2-hydroxyethyl-2,6-piperidinedione
  • 2,6-Piperidinedione, 4-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-, (1S-(1alpha(S*),3alpha,5beta))-
  • 3-((R)-2-((1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide
  • 3-(2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide
  • 3-(2R)-2-((1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethylglutarimide
  • 4-((2R)-2-((1S,3S,5S)-(3,5-Dimethyl-2-oxocyclohexyl))-2-hydroxyethyl)piperidine-2,6-dione
  • 5-21-13-00434 (Beilstein Handbook Reference)
  • Acti-Aid
  • Acti-Dione
  • Actidion
  • Actidione
  • Actidione BR
  • Actidione PM
  • Actidione TGF
  • Actidone
  • Actispray
  • AI3-15541
  • Aktidion
  • Aktidion [Czech]
  • beta-(2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide
  • BRN 0088868
  • Caswell No. 270A
  • CBC 500046
  • CCRIS 937
  • Cicloheximida
  • Cicloheximida [INN-Spanish]
  • Cicloheximide
  • Cicloheximidum
  • Cicloheximidum [INN-Latin]
  • CX
  • Cycloheximide
  • EINECS 200-636-0
  • EPA Pesticide Chemical Code 043401
  • Glutarimide, 3-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-
  • Hizarocin
  • HSDB 1552
  • Kaken
  • Naramycin
  • Naramycin A
  • Neocycloheximide
  • NSC 185
  • NSC-185
  • TZA
  • U 4527
  • U-4527
  • UNII-98600C0908

Systematic Names

  • 2,6-Piperidinedione, 4-((2R)-2-((1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-
  • 2,6-Piperidinedione, 4-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-, (1S-(1alpha(S*),3alpha,5beta))-
  • Cicloheximide
  • Cycloheximide
  • Glutarimide, 3-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-

Superlist Names

  • 2,6-Piperidinedione, 4-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-, (1S-(1alpha(S*),3alpha,5beta))-
  • Cycloheximide

Registry Numbers

CAS Registry Number

  • 66-81-9

FDA UNII

  • 98600C0908

System Generated Number

  • 0000066819

Structure Descriptors

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

InChIKey

YPHMISFOHDHNIV-FSZOTQKASA-N

Smiles

C1([C@H]([C@@H](CC2CC(NC(C2)=O)=O)O)C[C@@H](C)C[C@@H]1C)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intraperitoneal 4mg/kg (4mg/kg)   Journal of the American Chemical Society. Vol. 70, Pg. 1223, 1948.
chicken LDLo subcutaneous 2mg/kg (2mg/kg)   Comparative Biochemistry and Physiology, C: Comparative Pharmacology. Vol. 66, Pg. 83, 1980.
dog LD50 intravenous 1mg/kg (1mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 687, 1958.
dog LD50 oral 65mg/kg (65mg/kg)   Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 292, 1966.
guinea pig LD50 intraperitoneal 60mg/kg (60mg/kg)   Antibiotics and Chemotherapy Vol. 10, Pg. 682, 1960.
guinea pig LD50 oral 65mg/kg (65mg/kg)   Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 292, 1966.
guinea pig LD50 subcutaneous 60mg/kg (60mg/kg)   Journal of the American Chemical Society. Vol. 70, Pg. 1223, 1948.
hamster LDLo intraperitoneal 40mg/kg (40mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 162, Pg. 170, 1979.
monkey LD50 oral 60mg/kg (60mg/kg)   Guide to the Chemicals Used in Crop Protection. Vol. 6, Pg. 146, 1973.
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   Cancer Chemotherapy Reports. Vol. 30, Pg. 9, 1963.
mouse LD50 intravenous 150mg/kg (150mg/kg)   Journal of the American Chemical Society. Vol. 69, Pg. 474, 1947.
mouse LD50 oral 133mg/kg (133mg/kg)   "Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." Vol. 2(6), Pg. -, 1971.
mouse LD50 subcutaneous 160mg/kg (160mg/kg)   "Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." Vol. 2(6), Pg. -, 1971.
rabbit LD50 intravenous 17mg/kg (17mg/kg)   Journal of the American Chemical Society. Vol. 70, Pg. 1223, 1948.
rat LD50 intraperitoneal 3700ug/kg (3.7mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Journal of Pharmacology and Experimental Therapeutics. Vol. 136, Pg. 400, 1962.
rat LD50 intravenous 2mg/kg (2mg/kg)   Antibiotics and Chemotherapy Vol. 10, Pg. 682, 1960.
rat LD50 oral 2mg/kg (2mg/kg)   "Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." Vol. 2(6), Pg. -, 1971.
rat LD50 subcutaneous 2500ug/kg (2.5mg/kg)   Antibiotics and Chemotherapy Vol. 10, Pg. 682, 1960.
rat LD50 unreported 133mg/kg (133mg/kg)   Yakkyoku. Pharmacy. Vol. 30, Pg. 397, 1979.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 119 deg C   EXP
log P (octanol-water) 0.55 (none)   EXP
Water Solubility 2.10E+04 mg/L 2 EXP
Vapor Pressure 4.45E-13 mm Hg 25 EST
Henry's Law Constant 3.52E-15 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 6.55E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.