CAS 66-81-9|Cycloheximide

Introduction：Basic information about CAS 66-81-9|Cycloheximide, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Cycloheximide BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles881
8. Synonyms

Common Name	Cycloheximide
CAS Number	66-81-9	Molecular Weight	281.347
Density	1.1±0.1 g/cm3	Boiling Point	491.8±10.0 °C at 760 mmHg
Molecular Formula	C₁₅H₂₃NO₄	Melting Point	111-116 °C
MSDS	ChineseUSA	Flash Point	251.2±19.0 °C
Symbol	GHS06, GHS08, GHS09	Signal Word	Danger

Names

Name	cicloheximide
Synonym	More Synonyms

Cycloheximide BiologicalActivity

Description	Cycloheximide (Naramycin A) is an eukaryote protein synthesis inhibitor, with IC50s of 532.5 nM and 2880 nM for protein synthesis and RNA synthesis in vivo, respectively.
Related Catalog	Signaling Pathways >>Autophagy >>AutophagySignaling Pathways >>Cell Cycle/DNA Damage >>DNA/RNA SynthesisSignaling Pathways >>Anti-infection >>FungalResearch Areas >>InfectionNatural Products >>Others
Target	IC50: 532.5 nM (protein synthesis), 2.88 μM (RNA synthesis)[1]
In Vitro	Cycloheximide (CHX) is the most common laboratory reagent used to inhibit protein synthesis. Cycloheximide has been shown to block the elongation phase of eukaryotic translation. Cycloheximide binds the ribosome and inhibits eEF2-mediated translocation. Surprisingly, Cycloheximide allows one complete translocation cycle to proceed before halting any further elongation. Cycloheximide has been speculated that Cycloheximide requires an E-site bound deacylated tRNA for activity[1].
In Vivo	The mice receive Cycloheximide injections at 30, 60, or 120 mg/kg prior to training with a 200 µA shock. There is a significant effect of Cycloheximide on latencies on the memory test trials (P<0.001). In saline controls, this shock level results in latencies on the test trial that are significantly higher than those at training. Injections of the lowest dose of Cycloheximide tested, 30 mg/kg, results in latencies on the test trial that are significantly higher than those seen in the saline control group. Mice receiving either of the two higher doses of Cycloheximide has latencies on the test trial that are comparable to those of the saline group, i.e., the higher doses neither enhanced nor impaired memory under these conditions, resulting in an inverted-U dose-response curve for Cycloheximide enhancement of memory[2]. Infarct volume, as measured by morphometric analysis of infarct areas with triphenyl tetrazolium chloride (TTC), is significantly reduced by 92% and 61% when Cycloheximide is given 0 or 6 hr after HI respectively, but shows an insignificant trend in infarct reduction if Cycloheximide is administered 12 hr after hypoxia-ischemia (HI) compared to the HI control group, and no protective effect is observed when administration is delayed until 24 hr after HI[3].
Cell Assay	To test cell proliferation, 3000-5000 cells (HeLa, HTB1 and HEK 293T cells; Jurkat, BT 474, HCC 1395, HCC 1937, HCC 2218 and MDA MB231 cells; MCF 10A) per well are plated in a 96-well plate and allowed to adhere overnight. Cycloheximide dissolved in DMSO at the indicated concentrations (0.1 nM-1000μM) are then added and cells are incubated for a further 24 h. [3H]-thymidine is added at 1 μCi per well and incubation is continued for an additional 7 h. Cells are washed twice with PBS and then trypsinized before they are collected with a Tomtec harvester and bound to GF/C filter mats. Thymidine uptake is then measured by scintillation counting[1].
Animal Admin	Mice[2] Male ICR mice (approximately 2 months old) are used in this experiment. Cycloheximide is administered IP at concentrations of 0 (saline controls), 30, 60, or 120 mg/kg. Cycloheximide injections are administered 30 min prior to training. The 120 mg/kg dose is commonly used to study amnesia in mice. Note that amnestic Cycloheximide doses are much lower in rats (1-3 mg/kg) than in mice, consistent with a similar difference in LD50s for rats and mice. Cycloheximide doses of 120-150 mg/kg result in approximately 95% inhibition of brain protein synthesis as measured 30-60 min after injection; the dose of 30 mg/kg produces approximately 80% inhibition of brain protein synthesis. Rats[3] Unilateral carotid artery ligation is performed in 7-day old Sprague Dawley rat pups under methoxyflurane anesthesia. The neck is incised in the midline, and the right common carotid artery is permanently ligated with 4-0 silk. Total time of surgery in each animal never exceeded 5 min. Following surgery, rats are returned to their mother for recovery and feeding for 2 hr. The pups are then exposed to a 100 min-period of hypoxia (8% O2, 92% N2) by placing them in an airtight chamber partially submerged in a temperature controlled water bath to maintain the ambient temperature inside the chamber at a constant 36°C. In the HI with Cycloheximide treatment group, the rat pups receive an intraperitoneal injection of Cycloheximide at a dose of 0.6 mg/kg at 0, 6, 12 or 24 hr of recovery, and an equal volume of normal saline is given to a HI control group. Then, the rat pups are returned to their dam until sacrifice; the whole brain tissue is obtained under deep pentobarbital anesthesia (60 mg/kg, intraperitoneal) for flow cytometry and triphenyl tetrazolium chloride (TTC) at 48 and 72 hr after HI, respectively.
References	[1]. Schneider-Poetsch T, et al. Inhibition of eukaryotic translation elongation by cycloheximide and lactimidomycin. Nat Chem Biol. 2010 Mar;6(3):209-217. [2]. Gold PE, et al. Cycloheximide impairs and enhances memory depending on dose and footshock intensity. Behav Brain Res. 2012 Aug 1;233(2):293-7. [3]. Park W S, et al. Therapeutic window for cycloheximide treatment after hypoxic-ischemic brain injury in neonatal rats. J Korean Med Sci. 2006 Jun;21(3):490-4.

Chemical & Physical Properties

Density	1.1±0.1 g/cm3
Boiling Point	491.8±10.0 °C at 760 mmHg
Melting Point	111-116 °C
Molecular Formula	C₁₅H₂₃NO₄
Molecular Weight	281.347
Flash Point	251.2±19.0 °C
Exact Mass	281.162720
PSA	83.47000
LogP	0.56
Vapour Pressure	0.0±2.8 mmHg at 25°C
Index of Refraction	1.499
InChIKey	YPHMISFOHDHNIV-FSZOTQKASA-N
SMILES	CC1CC(C)C(=O)C(C(O)CC2CC(=O)NC(=O)C2)C1
Water Solubility	2.1 g/100 mL (2 ºC)

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MA4375000

CHEMICAL NAME :: Glutarimide, 3-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-

CAS REGISTRY NUMBER :: 66-81-9

BEILSTEIN REFERENCE NO. :: 0088868

LAST UPDATED :: 199709

DATA ITEMS CITED :: 85

MOLECULAR FORMULA :: C15-H23-N-O4

MOLECULAR WEIGHT :: 281.39

WISWESSER LINE NOTATION :: T6VMVTJ E1YQ- BL6VTJ D1 F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Rinsed with water

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3700 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea Skin and Appendages - hair

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 133 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 133 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 160 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 150 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 65 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1 mg/kg

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 60 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 4 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 17 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 65 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 60 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 60 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 40 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 2 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 mg/kg/4W-I

TOXIC EFFECTS :: Liver - changes in liver weight Endocrine - changes in thymus weight Immunological Including Allergic - decrease in humoral immune response

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 56 mg/kg/7D-I

TOXIC EFFECTS :: Liver - other changes Kidney, Ureter, Bladder - other changes Blood - changes in erythrocyte (RBC) count

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1 mg/kg

SEX/DURATION :: female 4 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 300 ug/kg

SEX/DURATION :: female 13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 250 ug/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1 mg/kg

SEX/DURATION :: female 15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - hepatobiliary system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1 mg/kg

SEX/DURATION :: female 18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Parenteral

DOSE :: 750 ug/kg

SEX/DURATION :: female 18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 30 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 30 mg/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 80 mg/kg

SEX/DURATION :: female 11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 5 mg/kg

SEX/DURATION :: female 11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 5 mg/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 250 ug/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Parenteral

DOSE :: 5 ug/kg

SEX/DURATION :: female 1 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 60 mg/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

TYPE OF TEST :: Morphological transformation

TYPE OF TEST :: Mutation test systems - not otherwise specified

TYPE OF TEST :: DNA inhibition

TYPE OF TEST :: Mutation test systems - not otherwise specified

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: DNA inhibition

TYPE OF TEST :: Mutation test systems - not otherwise specified

TYPE OF TEST :: Cytogenetic analysis

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Mammal - pig Kidney

DOSE/DURATION :: 1 mg/L

REFERENCE :: CYGEDX Cytology and Genetics (English Translation). Translation of TGANAK. (Allerton Press Inc., 150 Fifth Ave., New York, NY 10011) V.8- 1974- Volume(issue)/page/year: 12(1),1,1978 *** REVIEWS *** TOXICOLOGY REVIEW CRTXB2 CRC Critical Reviews in Toxicology. (CRC Press, Inc., 2000 Corporate Blvd., NW, Boca Raton, FL 33431) V.1- 1971- Volume(issue)/page/year: 2,159,1973 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84338 No. of Facilities: 968 (estimated) No. of Industries: 3 No. of Occupations: 6 No. of Employees: 4439 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 84338 No. of Facilities: 234 (estimated) No. of Industries: 2 No. of Occupations: 7 No. of Employees: 3059 (estimated) No. of Female Employees: 2370 (estimated)

Safety Information

Symbol	GHS06, GHS08, GHS09
Signal Word	Danger
Hazard Statements	H300-H341-H360D-H411
Precautionary Statements	Missing Phrase - N15.00950417-P201-P280-P308 + P313
Personal Protective Equipment	Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter
Hazard Codes	T+:Verytoxic;N:Dangerous for the environment;
Risk Phrases	R28;R51/53;R61;R68
Safety Phrases	S53-S45-S61
RIDADR	UN 2811 6.1/PG 1
WGK Germany	3
RTECS	MA4375000
Packaging Group	II
Hazard Class	6.1(a)
HS Code	29419000

Customs

HS Code	29419000

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Synonyms

4-[2-(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-Aid

Actidion

ACTIDIONE

NARAMYCIN A

Actidone

cyclohexamide

MFCD06202064

Hizarocin

cycloheximide

Kaken

4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]-2,6-piperidinedione

EINECS 200-636-0

Cicloheximide

4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione

Recommended......