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66-81-9

66-81-9 structure
66-81-9 structure
  • Name: Cycloheximide
  • Chemical Name: cicloheximide
  • CAS Number: 66-81-9
  • Molecular Formula: C15H23NO4
  • Molecular Weight: 281.347
  • Catalog: Organic raw materials Organometallic salt
  • Create Date: 2018-03-20 08:00:00
  • Modify Date: 2024-01-05 19:58:11
  • 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.
Name cicloheximide
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
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
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.
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
Water Solubility 2.1 g/100 mL (2 ºC)

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)
Symbol GHS06 GHS08 GHS09
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
HS Code 29419000

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