Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “Cyclohexanones”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 19 recordsLinked to original sources
PubMed1986

Chronic toxicity study of cyclohexanone in rats and mice.

A 2-year chronic toxicity assay of cyclohexanone (CAS: 108-94-1) was conducted in F344 rats and (C57BL/6 X C3H)F1 mice by administering a solution of cyclohexanone in drinking water. Two concentrations were given to rats, 6,500 and 3,300 ppm (wt/vol). Male mice received 13,000 and 6,500 ppm, while female mice were given three concentrations, 25,000, 13,000, and 6,500 ppm. Each treatment group consisted of 50 or 52 male and 50 or 52 female rats or mice, except 47 male mice treated with the highest dose and 41 female mice treated with the highest dose, and there was a group of untreated controls of each species. Survival and weight gain were similar to those of controls at the lowest cyclohexanone dose in both sexes of both species, but weight gain was depressed at all of the higher doses. Survival was good (greater than 80% at 90 wk) in all groups except in female mice at the 2 highest doses; at 25,000 ppm of cyclohexanone, only 50% of mice lived beyond 1 year. Most of the neoplasms in the treated groups did not differ significantly in number from those in the controls. Male rats receiving 3,300 ppm cyclohexanone had a 13% incidence of adrenal cortex adenomas (7 animals) compared with an incidence of 2% in controls; the incidence of this neoplasm did not increase in the male rats receiving 6,500 ppm or in the female rats given either dose. The mice had a statistically significant increase in incidence of lymphomas-leukemias among the females given 6,500 ppm, but not among the groups given higher doses of cyclohexanone. Male mice given 6,500 ppm cyclohexanone showed an increased incidence of hepatocellular adenomas and carcinomas, 50% versus 32.5% in controls, but the incidence of these neoplasms was only 37% in the male mice given 13,000 ppm cyclohexanone. The incidence of lymphomas in male mice and of hepatocellular neoplasms in female mice given cyclohexanone did not differ from that in the controls. The evidence for carcinogenic activity of cyclohexanone is marginal and the effect, if any, is weak.

Adenoma↗
PubMed1990

Convulsant and anticonvulsant cyclopentanones and cyclohexanones.

The convulsant and/or anticonvulsant activity of unsubstituted and mono-alkyl-substituted cyclopentanones and cyclohexanones were examined by testing the ability of these compounds to produce seizures or to inhibit seizures induced by pentylenetetrazol and maximal electroshock in CF-1 mice. In addition, these compounds were tested for their ability to bind to the picrotoxin receptor. The unsubstituted compounds, cyclopentanone and cyclohexanone, prevented both pentylnetetrazol- and maximal electroshock-induced seizures. Cyclopentanones and cyclohexanones with small (less than 3 carbon atoms) alkyl substituents in the 2-position were also anticonvulsant; all of these compounds, except 2-ethylcyclohexanone, blocked both pentylenetrazol- and maximal electroshock-induced seizures. 2-Ethylcyclohexanone was very effective against pentylenetetrazol seizures but did not prevent maximal electroshock seizures. Cyclohexanones with larger alkyl substituents in the 2-position, 2-propylcyclohexanone and 2-t-butylcyclohexanone, caused clonic seizures following injection into mice. Of the cyclopentanones and cyclohexanones with alkyl substitutions in the 3-position that were studied, one was an anticonvulsant (3-methylcyclopentanone), one was a mixed convulsant/anticonvulsant (3-ethylcyclohexanone), and the other two (3-ethylcyclopentanone and 3-t-butylcyclohexanone) were convulsants. Finally, two cyclohexanones with alkyl substituents in the 4-position were studied. Both 4-ethylcyclohexanone and 4-t-butylcyclohexanone produced convulsions when injected into mice. All the neuroactive cyclopentanones and cyclohexanones competitively displaced [35S]t-butylbicyclophosphorothionate, a ligand specific for the picrotoxin receptor, from rat brain membranes. The convulsant compounds were generally more potent than the anticonvulsants. The cyclohexanones were more potent than their corresponding cyclopentanones and the binding potency of both increased as the size of the alkyl substituent increased. These results suggest that cyclopentanone, cyclohexanone, and their alkyl-substituted derivatives act at the picrotoxin receptor to increase or decrease neuronal activity. Thus, they appear to have sites and mechanisms of action similar to those of the neuroactive gamma-butyrolactones and gamma-thiobutyrolactones.

Animals↗
PubMed1991

Monitoring of exposure to cyclohexanone through the analysis of breath and urine.

Occupational exposure to cyclohexanone was studied for 59 workers through the analysis of environmental air, alveolar air, and urinary cyclohexanol. Environmental cyclohexanone exposure was measured by personal sampling with a carbon-felt passive dosimeter. Cyclohexanone in alveolar air and cyclohexanol in urine were determined with gas chromatography with a flame ionization detector. The end-of-shift urinary cyclohexanol levels correlated well with the time-weighted average environmental cyclohexanone values (r = 0.66). Urinary cyclohexanol corrected for creatinine correlated best with cyclohexanone in air (r = 0.77); when corrected for specific gravity, it gave a similar correlation coefficient (r = 0.73). When the time-weighted average of the exposure was 25 ppm, the corresponding calculated concentration for urinary cyclohexanol was 54.5 mg/1, 23.3 mg/g of creatinine, or 43.5 mg/l at a specific gravity of 1.018. The relationship between cyclohexanone exposure and its concentration in exhaled breath was found to be poorer than that for cyclohexanone exposure and the urinary metabolite (r = 0.51).

Adolescent↗
PubMed1989

Disposition of acetone, methyl ethyl ketone and cyclohexanone in acute poisoning.

A case of coma due to the drinking of a liquid cement for polyvinyl chloride resin, containing acetone, methyl ethyl ketone, cyclohexanone and polyvinyl chloride is described. The patient also simultaneously ingested the alcoholic beverage, sake. After gastric lavage, plasma exchanges and direct hemoperfusions, the patient recovered. The concentrations of these chemicals in plasma and urine were analyzed at various time intervals to estimate the clearance. The elimination half lives for acetone and methyl ethyl ketone were 18 hours and 10 hours, respectively. Although cyclohexanone made up the largest component in the solvents, the blood level was extremely low and a large amount of cyclohexanol, a metabolite of cyclohexanone was detected in the blood and urine. The glucuronide metabolite of cyclohexanol was also estimated after the hydrolysis with beta-glucuronidase. Since the conversion of cyclohexanone to cyclohexanol is known to be catalyzed by alcohol dehydrogenase, possible interactions between sake ingestion and cyclohexanone metabolism is proposed.

Acetone↗
PubMed1989

Characterization of an FMN-containing cyclohexanone monooxygenase from a cyclohexane-grown Xanthobacter sp.

A soluble cyclohexanone monooxygenase was purified 16.1-fold to homogeneity from a Xanthobacter sp. grown upon cyclohexane as sole source of carbon and energy. The native enzyme is a 50-kDa single polypeptide chain associated with FMN rather than FAD as flavin prosthetic group in a 1:1 stoichiometric relationship. The monooxygenase catalyses the transformation of cyclohexanone to the lactone 1-oxa-2-oxocycloheptane in an oxygen ring insertion reaction. Only related cycloalkanone substrates are accepted for oxygenation, no activity is shown towards straight-chain alkanones. Enzyme activity is strongly inhibited by sulphydryl-reactive agents, but is relatively insensitive to metal chelators, electron transport inhibitors and the metal ions Fe3+ and Cu2+. Cyclohexanone monooxygenase has Km values for cyclohexanone and NADPH of less than 0.5 microM and 12.5 microM respectively. Kinetic investigations under steady-state conditions demonstrate that the flavoprotein prosthetic group, FMN, is involved in the monooxygenase catalytic mechanism. The systematic name for the enzyme is cyclohexanone, NADPH:oxygen oxidoreductase (6-hydroxylating, 1,2-lactonizing) (EC 1.14.13.22).

Chromatography↗
PubMed1986

Synthesis of alpha-methyl-benzamido-alpha'-substituted styryl cyclohexanone thiosemicarbazones as potential antifertility agents.

Cyclohexanone was condensed with N-hydroxymethyl benzamide in conc. sulphuric acid to give alpha-methyl-benzamido-cyclohexanone (I). The reaction of (I) with thiosemicarbazide in ethanol resulted in alpha-methyl-benzamido-cyclohexanone thiosemicarbazone (II). Condensation of (II) with various aromatic aldehydes in the presence of ethanol afforded alpha-methyl-benzamido-alpha'-substituted-styryl-cyclohexanone thiosemicarbazones (III) in yields ranging from 40 to 50 percent. The compounds exhibited pronounced antiimplantation activity in female albino rats.

Animals↗
PubMedDate not supplied

Determination of cyclohexanol in urine and its use in environmental monitoring of cyclohexanone exposure.

A simple and sensitive method for determining urinary cyclohexanol, the main metabolite of cyclohexanone, by hydrolysis and gas chromatography (GC) with a flame ionization detector was developed. A 2-mL urine sample was hydrolyzed with 0.4 mL of concentrated HCl and followed by extracting twice with diethylether. Two microL of the filtrate was injected into the GC with a methyl silicone column. The detection limit is estimated to be 0.4 mg/L. The coefficient of variation for the procedure is 8% and 10% for the range of concentration 5 and 50 mg/L, respectively. The within-run variation was 5.4% and between-day variation was 9.67%. The method was verified with urine samples collected from workers exposed to cyclohexanone. An excellent correlation (r = 0.88) was observed between environmental cyclohexanone exposure and cyclohexanol in urine. The procedure is relatively simple and reproducible and it can be applied for occupational health measurement of cyclohexanone exposure.

Calibration↗
PubMedDate not supplied

Capillary gas chromatographic determination of cyclohexanone and 2-ethyl-1-hexanol leached from solution administration sets.

A capillary gas chromatographic method is described for the determination of cyclohexanone and 2-ethyl-1-hexanol leached from solution administration sets. A preliminary study was made of compounds leached from solution administration sets by 5% sodium bicarbonate solution (pH 8.1), 0.9% sodium chloride solution (pH 6.8), and water. Water was selected as the leaching solvent because similar quantities of the compounds were leached into water and into both types of parenteral solutions. The correlation coefficients were 0.99977 for cyclohexanone and 0.99974 for 2-ethyl-1-hexanol, and recoveries were good (93-94%). Five administration sets from each of 2 manufacturers were analyzed by this method. The amounts of cyclohexanone that were leached from the individual sets varied considerably; however, similar quantities were leached from sets of both manufacturers. 2-Ethyl-1-hexanol was also found in extracts from each of the sets analyzed.

Chromatography, Gas↗
PubMed1987

Studies on the resistance of activated sludge bacteria to high concentrations of methanol, butanol, glycol, cyclohexanone and cyclohexylamine.

The resistance of bacterial strains isolated from activated sludge purifying petrochemical wastewaters to high concentrations of methanol, butanol, glycol, cyclohexanone and cyclohexylamine was examined. The strains were found to be resistant to up to 5000 mg/l of methanol, butanol and glycol. Cyclohexylamine in concentration 1500 mg/l completely inhibited the growth of all examined strains whereas cyclohexanone even at concentration 4500 mg/l eliminated only about half of the isolated strains. The highest resistance to cyclohexane derivatives was shown by bacteria belonging to Pseudomonas III. None of the studied strains was, however, able to utilize cyclohexanone and cyclohexylamine as a source of barbon and energy.

Alcohols↗
PubMed1989

Effect of cyclohexanone derivatives on in vitro percutaneous absorption of indomethacin.

We have previously shown that cyclohexanone derivatives exert a promoting effect on the in vivo percutaneous absorption of indomethacin (IMC), and now describe in vitro permeation studies to gain understanding of the mechanism of action. The results of the in vitro experiment were consistent with those of the previous in vivo experiments. 2-tert-Butylcyclohexanone was the most effective of six enhancers examined. The partition coefficient of IMC was determined in a buffer-octanol system containing the cyclohexanone derivatives, and the lipophilicities of these derivatives are discussed using a lipophilic index. We conclude that the cyclohexanone derivatives penetrate into the stratum corneum and alter the skin permeability of IMC by fluidizing or modifying the hard hydrophobic barrier of the corneum.

Animals↗
PubMed1976

Multiple forms of cyclohexanone oxygenase from Nocardia globerula CL1.

The cyclohexanone 1,2-monooxygenase of Nocardia globerula CL1 exists as two electrophoretically distinct forms. These are present in crude cell extracts and are not artifacts of enzyme purification or electrophoresis. They have been separated in mg amounts by preparative polyacrylamide gel electrophoresis and shown to have essentially identical kinetic, spectral and physical characteristics. They do differ in pH-activity profile and temperature stability. Whether or not they are conformational isoenzymes or arise by gene duplication and divergent evolution has not been established. Cyclohexanone oxygenase constitutes 8% of the soluble protein of induced cells. This high level would correlate well with the presence of duplicate genes. It is proposed that the presence of a large amount of cyclohexanone oxygenase may confer an ecological advantage on the organism.

Drug Stability↗
PubMedDate not supplied

Metabolism and disposition of cyclohexanone oxime in male F-344 rats.

Cyclohexanone oxime (CHOX), an intermediate used in the synthesis of Polycaprolactam/Nylon, was found to be rapidly absorbed and cleared from the body within 24 hours after a single oral administration of 1, 10 and 30 mg/kg of [14C]-CHOX to the adult male Fischer rats. The majority of the CHOX derived radioactivity (65-90% of the dose) was excreted in the urine. Elimination in the feces accounted for 5-10% of the dose and very low levels of radioactivity (2-3%) were retained in the tissues 24 hours after exposure. After iv administration of 1 mg/kg of [14C]-CHOX, the oxime was rapidly cleared from plasma with half-lives of 1.6 (alpha phase) and 18.2 min (beta phase). However, when CHOX was applied dermally (30 mg/kg), only about 4-5% of the dose was recovered in urine, feces and the tissues. The majority of the dose volatilized from the skin surface. However, the absorbed oxime was readily distributed and excreted, and its metabolic fate was no different than observed after oral administrations. HPLC analysis of urine showed that the majority of the radioactivity excreted was in the form of three metabolites, cyclohexylglucuronide and the monoglucuronides of cis- and trans-cyclohexane-1,2-diol. In vitro studies showed that these metabolites arise primarily by hydrolysis of the oxime to cyclohexanone which is then reduced to cyclohexanol and eliminated as the glucuronide conjugate. The cyclohexanol, in turn could be metabolized to cis- and trans-cyclohexane-1,2-diols, which excreted as their monoglucuronides.

Administration, Oral↗
PubMed1990

Urinary excretion of cyclohexanediol, a metabolite of the solvent cyclohexanone, by infants in a special care unit.

Using gas chromatography-mass spectrometry, we investigated the urinary excretion of organic acids of 278 newborn babies in a special care unit to obtain reference data and monitor metabolism. In 101 of 584 urine samples analyzed, we found isomers of cyclohexanediol. trans-1,2-Cyclohexanediol was always most abundant, with small amounts of 1,3- and 1,4-cyclohexanediol and, sometimes, traces of cis-1,2-cyclohexanediol. Glucuronide conjugates were not detected. The probable source was the solvent cyclohexanone, which was found as a contaminant of intravenous dextrose and the parenteral feeding solution, and was also leached into the infusion fluids from the administration set. We recovered 0.89 mg (range 0.74-0.98 mg, n = 5) of cyclohexanone from 150 mL of dextrose pumped through the infusion apparatus over 24 h, the normal rate for a 1-kg premature baby. Although this is well below toxic doses reported for mature animals, more data are needed for the newborn, particularly preterm infants who have a decreased capacity for glucuronide conjugation.

Cyclohexanes↗
PubMed1988

Effect of cyclohexanone derivatives on percutaneous absorption of ketoprofen and indomethacin.

The promoting effect of cyclohexanone derivatives on the percutaneous absorption of ketoprofen and indomethacin from gel ointments was investigated in rats. Drug absorption was markedly enhanced by the addition of 2-tert-butylcyclohexanone. Promoting activities of 2,6-dimethyl and 4-tert-butylcyclohexanone were also observed, but their effects were significantly lower than that of the 2-tert-butyl derivative. The effect of side chain length at the 2-position of the cyclohexanone ring on the percutaneous absorption of these drugs was determined similarly using a series of 2-n-alkylcyclohexanones. Pronounced effects were observed in the case of 2-n-octylcyclohexanone, suggesting that a chain length of eight carbons is an important factor for absorption enhancement in this series. The extent of absorption enhancement was found to be an almost linear function of 2-n-octycyclohexanone concentrations in the range from 0 to 10%.

Administration, Cutaneous↗
PubMed1976

Evaluation of 2-benzylidenecyclohexanones and 2,6-bis(benzylidene)cyclohexanones for antitumor and cytotoxic activity and as inhibitors of mitochondrial function in yeast: metabolism studies of (E)-2-benzylidenecyclohexanone.

Some 2-benzylidenecyclohexanones, 2,6-bis(benzylidene)cyclohexanones, and related compounds were evaluated for antitumor and cytotoxic activities; (E)-2-benzylidenecyclohexanone (Ia) was shown to have significant cytotoxic properties and a potent inhibitory effect on yeast mitochondria. After intraperitoneal injection of Ia, unchanged drug and a metabolite, tentatively identified as 2-(p-hydroxybenzyl)cyclohexanol, were found in the urine. No metabolites were found in the feces. Oral administration of Ia afforded three unidentified metabolites in the urine and three unidentified metabolites in the feces.

Animals↗
PubMed1992

Synthesis and cytotoxic evaluation of some 6-arylidene-2-(alpha-hydroxyamino-alpha-arylmethyl)cyclohexanone oximes and related compounds.

Reaction of 2,6-bis-(phenylmethylene)cyclohexanone (1) with a 4-molar excess of hydroxylamine hydrochloride and sodium acetate to produce the corresponding oxime 2 gave rise to 2-(alpha-hydroxyamino-alpha-phenylmethyl)-6-phenylmethylenecyclohexan one oxime (5a), whose structure was deduced from high-resolution proton nuclear magnetic resonance spectroscopy and confirmed by X-ray analysis. Compound 2 was eventually prepared from 1 with hydroxylamine per se and not with a mixture of hydroxylamine hydrochloride and sodium acetate. Ten analogues of 5a, namely 5b-5k, were prepared and evaluated for cytotoxicity. Six of the 11 compounds in series 5, as well as 1, showed activity in the 240-950 microM range against murine mammary EMT6 cells. Series 5 was also examined for cytotoxicity in an in vitro screen conducted by the National Cancer Institute with approximately 54 cell lines, and four compounds demonstrated selective toxicity toward various groups of tumors.

Animals↗
PubMed1985

Effects of (1,6-di(O-carbamoyl)cyclohexanone oxime)hexane (RHC 80267) on prostaglandin biosynthesis and accumulation of diacylglycerol and arachidonic acid in rabbit iris.

The effects of RHC 80267, (1-6-di(O-carbamoyl)cyclohexanone oxime)hexane, a diacylglycerol (DG) lipase inhibitor, on the DG lipase pathway and on arachidonic acid (AA) metabolism were investigated in the iris muscle. Incubation of the iris for 30 min at 37 degrees resulted in a loss of AA from phosphatidylinositol, phosphatidylcholine, and phosphatidylethanolamine of 40, 25, and 32% respectively. It was found that the drug inhibited the activity of DG lipase in the iris microsomal fraction and it increased the accumulation of DG, AA and other glycerolipids in iris muscle prelabeled with [14C]AA, presumably by inhibiting this enzyme. Under the same experimental conditions, the drug increased the accumulation of DG and AA in the tissue in a dose- and time-dependent manner, and it inhibited the synthesis of prostaglandin E2 (PGE2) and PGF2 alpha by iris and iris microsomes in a dose-dependent manner. The data presented indicate that RHC 80267 has nonspecific effects on glycerolipid and AA metabolism in this tissue. We conclude that, while the drug does inhibit DG lipase in the intact iris, the present findings that it increased the accumulation of glycerolipids and AA and that it inhibited the biosynthesis of PGs in this tissue throw some doubt on its use in studies on the mechanism of AA release from membrane phosphoinositides for PG synthesis.

Animals↗