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シクロヘキシミド

Cycloheximide

HCID 6197
ノート反応
基本情報名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
4630-75-5
標準SMILES
C[C@@H]1C[C@@H]([C@H](O)CC2CC(=O)NC(=O)C2)C(=O)[C@@H](C)C1
InChIKey
YPHMISFOHDHNIV-FSZOTQKASA-N
分子式
C15H23NO4
平均分子量
281.35 g/mol
単同位体質量
281.16270821

名称と識別子

優先名称
Cycloheximide
IUPAC
4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione
現地名
シクロヘキシミド
英語名
Actidione
分子式
C15H23NO4
分子量
281.35

名称と別名

cycloheximide66-81-9ACTIDIONECicloheximideNARAMYCIN AActidionHizarocinNaramycinKakenActi-AidActidoneNeocycloheximide
名称をさらに表示
ヒザロシン3-[(R)-2-[(1S,3S,5S)-3,5-ジメチル-2-オキソシクロヘキシル]-2-ヒドロキシエチル]グルタルイミドシクロヘキシミドアクチ-ジオンBRナラマイシンマイクロカプセルD804-[(R)-2-ヒドロキシ-2-[(1S)-3β,5α-ジメチル-2-オキソシクロヘキシル]エチル]ピペリジン-2,6-ジオンアクチ-ジオンPMアクチ-エイドアクチ-ジオンアクチジオンナラマイシンアクチ-ジオンTGFナラマイシンNM-MCU80ナラマイシンAβ-[2-(3,5-ジメチル-2-オキソシクロヘキシル)-2-ヒドロキシエチル]グルタルイミドシクロヘキシイミドシクロヘキシイミド標準品シクロヘキシミド STANDARDシクロヘキシミド, CRYST. PUREシクロヘキシミド 溶液CYCLOHEXIMIDCycloheximide solution,CHXCycloheximide 100mg [66-81-9]980U/MGaktidionFT 3422-2
CicloheximidaActisprayActi-DioneActidione PMCicloheximidumNSC-185Actidione BRActidione TGF

データベース識別子

CAS
4630-75-5、66-81-9
PubChem CID
6197
DTXSID
DTXSID6024882
ChEMBL
CHEMBL123292
ChEBI
CHEBI:27641
UNII
98600C0908
EC Number
200-636-0
Nikkaji
J107.994H

物性

構造計算による物性

XLogP
0.5
極性表面積
83.5 Ų
水素結合供与体数
2
水素結合受容体数
4
回転可能結合数
3
重原子数
20
形式電荷
0
複雑度
404

実験および物理化学的性質

LogP · 2 件

log Kow = 0.55

0.55

Color/Form · 2 件

Plates from amyl acetate, water or 30% methanol

Crystals

Solubility · 6 件

10 to 50 mg/mL at 68 °F (NTP, 1992)

At 2 °C (g/100 ml): water 2.1; amyl acetate 7; sol in chloroform, ether, methanol, ethanol; insol in saturated hydrocarbons

INSOL IN PETROLEUM ETHER

Isopropyl alcohol 5.5 g/100 ml; acetone 33.0 g/100 ml; cyclohexanone 19.0 g/100 ml (@ 20 °C)

In water, 2.1X10-4 mg/l @ 25 °C

Solubility in water, g/100ml at 2 °C: 2.1

CorrosivityNONCORROSIVE
DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Melting Point · 4 件

247 to 250 °F (EPA, 1998)

119.5-121 °C; also listed as 115-16 °C

Glistening plates from methanol; mp: 148-149; specific optical rotation: +22 deg @ 25 °C/D (2.3% in methanol) /Cycloheximide acetate/

119.5-121 °C

Vapor Pressure0.006 [mm Hg] @25 °C
Optical Rotation · 2 件

Specific optical rotation: -3.38 deg @ 29 °C/D (9.47% in methanol); +6.8 deg @ 25 °C/D (2% in water)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral];H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity];H360D ***: May damage the unborn child [Danger Reproductive toxicity];H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P203, P264, P270, P273, P280, P301+P316, P318, P321, P330, P391, P405, and P501 (click each P-code to see the statement)

Danger

危険有害性情報

Regulatory Information · 4 件

Chemical: 2,6-Piperidinedione, 4-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]-, [1S-[1.alpha.(S*),3.alpha.,5.beta.]]-

Hazard Traits - Developmental Toxicity; Reproductive Toxicity;Authoritative List - EC Annex VI CMRs - Cat. 1B; Prop 65;Report - regardless of intended function of ingredient in the product

Cycloheximide: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison
Fire Hazards · 2 件

When exposed to heat, it emits toxic fumes, including nitrogen oxides. (EPA, 1998)

Gives off irritating or toxic fumes (or gases) in a fire.

Health HazardsThis material is extremely toxic; the probable oral lethal dose in humans is 5-50 mg/kg, or 7 drops to 1 teaspoonful for a 150-lb. person. (EPA, 1998)
Hazards Summary · 1 件

A skin and eye irritant; May be very toxic by ingestion; [ICSC] A skin irritant; At lethal doses, causes bloody diarrhea, tremors, excitement, coma, and cardiovascular collapse; LD50 = 500 mg/kg in monkeys and dogs, but only 2 mg/kg in rats; [HSDB] Extremely toxic (probable oral lethal dose in humans is 5-50 mg/kg, or 7 drops to 1 teaspoonful for a 150-lb. person); [CAMEO] An irritant; May cause skin sensitization; May cause damage to liver and spleen, and have effects on the blood; [MSDSonline] Toxic to embryo of mice at a maternal dose of 30 mg/kg; Inhibits maturation of amphibian spermatocytes; [REPROTOX]

化学と産業

薬理情報

Mechanism of Action · 3 件

STIMULATED TRANSPORT OF NUCLEAR RIBONUCLEOPROTEIN COMPLEXES TO CYTOPLASM AFTER ADMIN CYCLOHEXIMIDE TO RATS WAS STUDIED. ADMIN OF 2 MG/KG CYCLOHEXIMIDE CAUSED A DECR IN CONTENT OF TOTAL LIVER NUCLEAR RIBONUCLEOPROTEIN COMPLEX WITHIN 2 HR. THE OVERALL DECR WAS DUE TO AN INCREASED TRANSPORT INTO THE CYTOPLASM, NOT DECREASED SYNTHESIS. OTHER RESULTS SUGGEST THAT DURING INHIBITORY PHASE OF PROTEIN SYNTHESIS, GENE TRANSCRIPTION CONTINUES & GENE PRODUCT IS TRANSPORTED TO CYTOPLASM FOR TRANSLATION.

CYCLOHEXIMIDE (2-5 MG/KG BODY WT) CAUSED COMPLETE INHIBITION OF PROTEIN SYNTHESIS IN RAT LIVER WITHIN 30 MIN, & THE LABELING OF NUCLEAR PROTEINS WAS STRONGLY INHIBITED. UNDER THESE CONDITIONS, THE AMT OF NUCLEOLAR 45 S PRE-rRNA & ITS OROTATE-(14)C LABELING REMAINED UNAFFECTED FOR AT LEAST 4 HR, INDICATING THAT INITIALLY THE RATES OF SYNTHESIS & PROCESSING OF 45 S PRE-rRNA WERE NOT APPRECIABLY ALTERED. DRASTIC ALTERATIONS IN THE 45 S PRE-rRNA PROCESSING PATHWAYS OCCURRED AT THE EARLY STAGES OF CYCLOHEXIMIDE ACTION. THE CHANNELING OF NUCLEAR PRE-rRNA ALONG ALTERNATIVE PROCESSING PATHWAYS IS UNDER STRINGENT CONTROL BY THE CONTINUOUS SUPPLY OF CRITICAL PROTEINS.

CYCLOHEXIMIDE IS A POTENT INHIBITOR OF PROTEIN SYNTHESIS IN FUNGI & ANIMALS. IT CAUSES AN INCREASE IN ADRENAL RNA, INCREASED PRODUCTION OF GLUCOCORTICOIDS ... & DECREASE IN PYRUVATE UTILIZATION IN ISOLATED ADIPOSE TISSUE.

MeSH Pharmacological Classification · 2 件

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.

用途と製造

Uses · 6 件

Antibiotic compound isolated from Streptomyces griseus; [Merck Index] Used as a fungicide, plant growth regulator, protein synthesis inhibitor, and to stimulate the natural abscission process (pre-harvest use on citrus); [HSDB]

関連反応

1 件
反応記録を作成
HRID 1198264 の反応式
HRID 1198264反応物としてuspto-grants-1994_01

化合物ノート

読み込み中…

このページの内容基本情報名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

Specific optical rotation: -33 deg @ 25 °C/D (1% in chloroform)

Physical Description · 3 件

Cycloheximide appears as colorless crystals. Used as a fungicide and as a anticancer drug. (EPA, 1998)

Colorless solid; [ICSC] White to beige powder; [MSDSonline]

COLOURLESS CRYSTALS.

Stability/Shelf LifeRELATIVELY HEAT AND ACID STABLE; RAPIDLY INACTIVATED AT ROOM TEMP BY DIL ALKALI WITH FORMATION OF A VOLATILE, FRAGRANT KETONE, 2,4-DIMETHYLCYCLOHEXANONE
Collision Cross Section · 2 件

170.1 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID6024882];169.4 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID6024882]

160.7 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];170.77 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];165.69 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];170.47 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Other Experimental Properties · 3 件

Elemental composition: C: 64.04%; H: 8.24%; N: 4.98%; O: 22.75%

/Cycloheximide/ activity is destroyed by boiling in aqueous soln at pH 7 for 1 hr, but shows no loss of activity after 15 min boiling. At pH 2 /cycloheximide/ activity is not degraded by boiling for 1 hr.

IT HAS INTERESTING PROPERTY OF FORMING STABLE DERIV SUCH AS THE ACETATE, OXIME, & SEMICARBAZONE THAT ARE ACTIVE AS FUNGICIDES.

物理化学的性質

融点
111 · 111-116 °C
比旋光度
-28.5 · -28.5 º (c=1, CHCl3)
沸点
492 ℃ · 492℃
比重(密度)
1.0867 · 1.0867 (rough estimate)
屈折率
1.5 · 1.5000 (estimate)
闪点
87 °0° · 87°0°(230°F)
貯蔵温度
2 · 2-8°C
溶解性
エタノール (最大 14mg/ml) または水 (最大 7mg/ml) に可溶。
酸解離定数(Pka)
11.61 · 11.61±0.40(Predicted)
外見
ガラス状の不定形顆粒
色
白い
由来生物
microbial
水溶解度
2.1 g/100mL · 2.1g/100mL(2℃)
BRN
88868 · 88868
Henry's Law Constant
2.8 · 2.8×109 mol/(m3Pa) at 25℃, HSDB (2015)
安定性
安定。可燃性。強酸化剤、酸塩化物、酸無水物、アルカリと相容れない。
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
CAS データベース
66 · 66-81-9(CAS DataBase Reference)
EPAの化学物質情報
Cycloheximide (66-81-9)

化学的性質

化学的特性Off-white to light tan powder

Reactive GroupAmides and Imides;Ketones
EC ClassificationSymbol: T+, N; R: 61-28-51/53-68; S: 53-45-61
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: I
FIFRA Requirements · 1 件

In 1988, Congress amended FIFRA to strengthen and accelerate EPA's reregistration program. The nine-year reregistration scheme mandated by "FIFRA 88" applies to each registered pesticide product containing an active ingredient initially registered before November 1, 1984. List A consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA had issued Registration Standards prior to the effective date of FIFRA 88. List: A; Case: Cycloheximide; Case No.: 0038; Pesticide type: Fungicide; Registration Standard Date: 6/1/83; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active Ingredient: cycloheximide; AI Status: The active ingredient is no longer contained in any registered products ... "cancelled."

Reactivity ProfileCYCLOHEXIMIDE is an imide. This chemical is incompatible with strong oxidizing agents, acid chlorides and acid anhydrides. It decomposes rapidly in alkali at room temperature. (NTP, 1992)
Chemical DangersDecomposes on heating. This produces toxic and corrosive fumes including nitrogen oxides.
Packaging and LabellingUnbreakable packaging. Put breakable packaging into closed unbreakable container. Do not transport with food and feedstuffs.

安全と保護具

Fire Fighting · 2 件

(Non-Specific -- Fungicides, Poison B Solid) Avoid breathing dusts and fumes from burning material. Keep upwind. Wear self-contained breathing apparatus. Avoid bodily contact with the material. Wear full protective clothing.;(Non-Specific -- Fungicides, Poison B Solid) Use agent suitable for surrounding fire. Use alcohol foam, carbon dioxide, or dry chemical. Use water in flooding quantities as fog. (EPA, 1998)

In case of fire in the surroundings, use appropriate extinguishing media.

First Aid Measures · 4 件

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Rest.

First Aid · 1 件

Warning: Effects may be delayed for 6 to 24 hours. Caution is advised.;Signs and Symptoms of Acute Cycloheximide Exposure: Signs and symptoms of acute exposure to cycloheximide may include increased salivation, nausea, vomiting, diarrhea, and dark, bloodstained stools. Dermal effects may range from erythema (redness) to sloughing. Central nervous system excitement, including tremor, may be noted. Liver and kidney damage, coma, and cardiovascular collapse are also possible.;Emergency Life-Support Procedures: Acute exposure to cycloheximide may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination.;Inhalation Exposure:;1. Move victims to fresh air. Emergency personnel should avoid self-exposure to cycloheximide.;2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support.;3. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures.;4. Transport to a health care facility.;Dermal/Eye Exposure:;1. Remove victims from exposure. Emergency personnel should avoid self- exposure to cycloheximide.;2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support.;3. Remove contaminated clothing as soon as possible.;4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes.;5. Wash exposed skin areas THOROUGHLY with soap and water.;6. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures.;7. Transport to a health care facility.;Ingestion Exposure:;1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support.;2. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures.;3. Vomiting may be induced with syrup of Ipecac. If elapsed time since ingestion of cycloheximide is unknown or suspected to be greater than 30 minutes, do not induce vomiting and proceed to Step

Safe StorageSeparated from food and feedstuffs. Well closed. Keep in a well-ventilated room.
Cleanup Methods · 2 件

In situ amelioration: Seek professional environmental engineering assistance through EPA's Environmental Response Team (ERT), Edison, NJ, 24-hour phone number (201) 321-6660. Contain and isolate spill to limit spread. Construct clay/bentonite swale to divert uncontaminated portion of the watershed around contaminated portion. Isolation procedures include construction of bentonite, polyethylene-lined dams, interceptor trenches, or impoundments. ... Conduct bench-scale and pilot-scale tests prior to decontamination program implementation. Solids must be removed in settling basins. Treatment alternatives for diluted contaminated waters include powdered activated carbon sorption, granular activated carbon filtration, and impoundment in a lined pit with leachate collection system and domed cover.

Treatment alternatives for contaminated soils include well point collection and treatment of leachates as for contaminated waters; bentonite/cement ground injection to immobilize spill, physical removal of immobilized residues, and placement in alined pit with leachate collection system and domed cover.

Nonfire Spill Response(Non-Specific -- Fungicides, Poison B Solid) Avoid breathing dusts. Keep upwind. Avoid bodily contact with the material. Material is rapidly inactivated at room temperature by dilute alkali. (EPA, 1998)
Disposal Methods · 1 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Spillage Disposal · 1 件

Evacuate danger area! Consult an expert! Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT wash away into sewer. Sweep spilled substance into covered sealable containers. Carefully collect remainder. Then store and dispose of according to local regulations.

Isolation and Evacuation · 1 件

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:;IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.;SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.;FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

Eye PreventionWear safety spectacles.
Inhalation RiskEvaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly.
Skin PreventionProtective gloves.

毒性情報

Interactions · 2 件

CHLORDANE IS REPORTED TO CAUSE RAPID LOSS OF ACTIVITY /OF CYCLOHEXIMIDE/.

Pretreatment of rats with ... spironolactone & ethylestrenol ... protected against the fungicide cycloheximide.

Ecotoxicity Values · 2 件

LD50 Mallard duck oral 82.5 mg/kg (95% confidence limit 54.3-126 mg/kg), 3-4-mo old males /sample purity 88.7%/

LD50 Pheasant oral 9.38 mg/kg (95% confidence limit 6.91-12.7 mg/kg), 4-mo old females /sample purity 88.7%/

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 47(SRC), determined from a log Kow of 0.55(2) and a regression-derived equation(3), indicates that cycloheximide is expected to have very high mobility in soil(SRC). Volatilization of cycloheximide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.8X10-18 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Cycloheximide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.5X10-13 mm Hg(SRC), determined from a fragment constant method(5). Cycloheximide, present at 100 mg/l, reached 1% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/l and the Japanese MITI test(6), suggesting slow biodegradation in soil(SRC). Cycloheximide is stable in neutral and acid conditions, but is rapidly decomposed by alkali at room temperature to form 2,4-dimethylcyclohexanone(7).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 47(SRC), determined from a log Kow of 0.55(2) and a regression-derived equation(3), indicates that cycloheximide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.5X10-15 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). At a concentration of 50 ug/l, cycloheximide had a BCF of <0.3 while at 5 ug/l it had a BCF of <2.8 in orange-red killi fish(5). According to a classification scheme(6), these BCF values suggest bioconcentration in aquatic organisms is low(SRC). Cycloheximide, present at 100 mg/l, reached 1% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/l and the Japanese MITI test(5), suggesting slow biodegradation in water(SRC). Cycloheximide is stable in neutral and acid solutions, but is rapidly decomposed under alkaline conditions(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cycloheximide, which has an estimated vapor pressure of 4.5X10-13 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase cycloheximide may be removed from the air by wet and dry deposition(SRC).

Adverse Effects · 1 件

Neurotoxin - Other CNS neurotoxin;Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.;Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.

Exposure RoutesThe substance can be absorbed into the body by inhalation and by ingestion.
Signs and Symptoms · 3 件

Redness. Pain.

Redness. Pain.

Diarrhoea. Unconsciousness.

ICSC Environmental DataThis substance does enter the environment under normal use. Great care, however, should be taken to avoid any additional release, for example through inappropriate disposal.
Soil Adsorption/Mobility · 1 件

The Koc of cycloheximide is estimated as 47(SRC), using a log Kow of 0.55(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that cycloheximide is expected to have very high mobility in soil. Cycloheximide was classified as a relatively mobile compound in soil based upon a measured Rf value of 0.89 as determined by soil thin-layer chromatography (TLC) in Hagerstown silty clay loam soil(4).

Natural Pollution Sources · 2 件

Produced by Streptomyces griseus ...

Cycloheximide is produced in cultures of the streptomycin-producing strains of Streptomyces griseus(1).

Human Toxicity Excerpts · 3 件

Hyaluronic acid synthesis was studied in cultured skin fibroblasts derived from normal subjects. ... Treatment of cells with cycloheximide under conditions in which protein synthesis is inhibited by greater than or equal to 90% had no effect on hyaluronic acid synthesis. ...

No human poisonings have been reported.

CYCLOHEXIMIDE @ 10-4 MOLAR INHIBITED LEUCINE INCORPORATION IN SLICES OF HUMAN LUNG TUMORS, REGENERATING RAT LIVER & HEPATOMAS.

Artificial Pollution Sources · 1 件

Cycloheximide's production and use as a fungicide(1) may have resulted in its direct release to the environment through various waste streams(SRC). Cycloheximide is produced as a byproduct during the production of streptomycen(1); therefore, waste releases from streptomycen production may release cycloheximide to the environment(SRC).

Environmental BiodegradationCycloheximide, present at 100 mg/l, reached 1% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/l and the Japanese MITI test(1).

法規制情報

Regulatory Information · 4 件

Chemical: 2,6-Piperidinedione, 4-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]-, [1S-[1.alpha.(S*),3.alpha.,5.beta.]]-

Hazard Traits - Developmental Toxicity; Reproductive Toxicity;Authoritative List - EC Annex VI CMRs - Cat. 1B; Prop 65;Report - regardless of intended function of ingredient in the product

Cycloheximide: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

FIFRA Requirements · 1 件

In 1988, Congress amended FIFRA to strengthen and accelerate EPA's reregistration program. The nine-year reregistration scheme mandated by "FIFRA 88" applies to each registered pesticide product containing an active ingredient initially registered before November 1, 1984. List A consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA had issued Registration Standards prior to the effective date of FIFRA 88. List: A; Case: Cycloheximide; Case No.: 0038; Pesticide type: Fungicide; Registration Standard Date: 6/1/83; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active Ingredient: cycloheximide; AI Status: The active ingredient is no longer contained in any registered products ... "cancelled."

CERCLA Reportable Quantities · 1 件

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Cycloheximide is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... .

安全データ

wgk
3
rtecs
MA4375000
ridadr
UN 2811 6.1/PG 1
毒性
LD50 i.v. in mice: 150 mg/kg (Leach)
hs_code
29419000
risk_code
22-68-61-51/53-28-38-52/53
化審法
一般化学物質
hazard_code
Xn,T,N,T+
safety_code
53-45-61-36/37-28
hazard_class
6.1(a)
packing_group
II
毒劇物取締法
I
Hazard Classifications
Acute Tox. 3 OralAquatic Chronic 3Muta. 2Repr. 1B
ストレージクラス
6.1C - Combustible, acute toxic Cat.3toxic compounds or compounds which causing chronic effects
有毒物質データの
66-81-9(Hazardous Substances Data)

Farming (Pesticides) [Category: Industry]

For Cycloheximide (USEPA/OPP Pesticide Code: 043401) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

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.

Methods of Manufacturing · 1 件

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).

Formulations/Preparations · 5 件

USEPA/OPP Pesticide Code 043401; Trade Names: Acti-dione; Acti-aid; ENT-15541; Acti-dione BR; Acti-dione PM; Actispray; Hizarocin; Kaken; Naramycin A; NSC-185; U 4527.

Discontinued names: Acti-Aid, Acti-dione, ... Actispray, Hizarocin

7.7% WETTABLE POWDER; ACTI-DIONE FERRATED (UPJOHN) 4% WT/WT CYCLOHEXIMIDE, 96% EXSICCATED FERROUS SULFATE USED FOR TREATMENT OF TURF. ACTI-DIONE THIRAM (0.75%, 75.00% & 24.25% INERT INGREDIENTS) TURF FUNGICIDE; ACTI-DIONE PM (0.027%) POWDERY MILDEW CONTROL ON ORNAMENTALS. ACTI-AID CITRUS ABSCISSION AGENT (COMPONENT A 4.22% WT/WT WATER SOL FORMULATION AND A SEPARATE COMPONENT B- SURFACTANT).

This ... compound is ... formulated as an oily soln ... & water-sol tablets.

For more Formulations/Preparations (Complete) data for CYCLOHEXIMIDE (21 total), please visit the HSDB record page.

General Manufacturing Information... /Cycloheximide/ is recovered as a byproduct during streptomycin manufacturing through fermentation.
応用分野 · 5 件

解説シクロヘキシミド.タンパク質合成の阻害剤.放射菌の一種Streptomyces griseusによって生産される抗生物質.白色の結晶.融点119.5~121 ℃.[α]D20-3.38°(メタノール).有機溶媒に可溶,水に微溶.真核生物の60Sリボソームに結合し,tRNAの遊離を抑制し,ペプチド鎖の伸長を抑える.殺菌剤,果樹の摘果剤として使用される.LD50 150 mg/kg(マウス,静脈).

説明Cycloheximide is a glutarimide-type antibiotic produced by Streptomyces griseus. Colorless crystals, C15H23NO4 (281.4), melting point: 115.5–117 C, weak acidic substance (pKa 11.2), Soluble in chloroform, isopropanol and methanol; water > 21 g/L (2 C). Stable in pH 3–5, but rapidly destroyed in alkaline solutions.

使用Cycloheximide is an antibiotic substance isolated from the beers of streptomycin-producing strains of Streptomyces griseus. Cycloheximide is used as fungicide.

一般的な説明Colorless crystals. Used as a fungicide and as a anticancer drug.

使用用途1. タンパク質合成阻害剤 シクロヘキシミドは、真核生物細胞におけるタンパク質合成を阻害する目的で、生化学研究分野において広く用いられています。ただし、その毒性の強さから、一般には試験管内の実験飲みに使われ、臨床では使用されていません。 リボソームに結合する2つのtRNA分子とmRNAの移動を防ぐことにより、タンパク質の翻訳を阻害します。シクロヘキシミドの作用は迅速で、培地から取り除くことで効果を除去できる便利な薬剤です。 また、ミトコンドリアのタンパク質合成は、シクロヘキシミドによる阻害に抵抗性があります。したがって、ミトコンドリアで翻訳されるタンパク質と細胞質で翻訳されるタンパク質を区別するためにも用いられていました。 2. 農薬・殺鼠剤 シクロヘキシミドは、エチレン産生を刺激するため植物の成長調節剤や、殺鼠剤などの動物用駆除剤として使用されます。また、ビール発酵における不要な細菌を検出するための培地にも有用です。 農業分野では、抗真菌剤としても使用されていました。しかしながら、DNA損傷や催奇性をはじめとする生殖への影響などの強い毒性を有することから、シクロヘキシミドの使用が減少しています。現在は、ネギべと病、カラマツ先枯病などの限られた植物病にのみ使用されている状況です。

調製方法

純化方法It crystallises from H2O /MeOH (4:1), amyl acetate, isopropyl acetate/isopropyl ether or H2O. [Beilstein 21/13 V 434.]

上流・下流製品情報

上流原料

trans-2,4-dimethylcyclohexanone, (2S)4-Pentenoic acid, 4-methyl-