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PubMed1996

Effects of cytochrome P450 2E1 modulators on the pharmacokinetics of chlorzoxazone and 6-hydroxychlorzoxazone in rats.

A previously observed correlation between the rate of 6-hydroxylation of chlorzoxazone (CZX), a potent skeletal muscle relaxant, and cytochrome P450 2E1 activity in vitro led to the postulation that this drug may be used as a non-invasive probe for P450 2E1 activity in vivo. In this study, comparative pharmacokinetics of CZX and 6-hydroxychlorzoxazone (OH-CZX) were conducted in rats pretreated with an inhibitor or inducer of P450 2E1. After administration of CZX (150 mumol/kg, i.v.) to rats, blood samples were taken at different time points and the plasma concentrations of CZX and OH-CZX were determined by HPLC. The concentrations for CZX and OH-CZX over time were simultaneously fitted to a model of first-order elimination of CZX and first-order formation and elimination of OH-CZX using the computer program PCNONLIN to give pharmacokinetic parameters. Diallyl sulfide, a P450 2E1 inhibitor, at an oral dose of 50 or 200 mg/kg 12 hr prior to the CZX dose markedly inhibited the hydroxylation of CZX. Pretreatment with ethanol (15% in the drinking water for six days), a condition known to induce P450 2E1, slightly enhanced the formation of OH-CZX. To observe possible involvement of enzymes other than P450 2E1 in CZX metabolism, dexamethasone and phenobarbital were also used. Pretreatment with dexamethasone (50 mg/kg, i.p. daily for four days) did not cause changes in CZX and OH-CZX pharmacokinetics. Pretreatment with phenobarbital (75 mg/kg, i.p. daily for three days) enhanced CZX metabolism slightly. Our results suggest that P450 2E1 plays a major role in CZX hydroxylation in rats, but other factors may also be involved in the metabolism in vivo.

Allyl Compounds↗
PubMed1983

Conditioned aversions to an intravascular odorant.

The odorant allyl sulfide (essence of garlic) dissolved in a corn oil vehicle was injected into rats to induce a conditioned aversion. In subsequent two-choice drinking tests, rats injected with odorant and lithium chloride, and rats injected with odorant and saline avoided drinking from a water bottle paired with the odorant. Because allyl sulfide and saline injections produced symptoms of malaise, we suspect that the odorant served as its own unconditioned stimulus. Rats injected with vehicle and saline showed no differential behavior. In a second experiment, gas chromatography indicated that allyl sulfide was present on the rat's breath within 3 minutes of injection, and was detectable for up to 5 hours post-injection. We conclude that conditioned aversions can be obtained to an intravascular odorant and that one route by which such odorants reach the nose is the breath.

Adaptation, Physiological↗
PubMed1983

Bile acids. LXVIII. Allylic and benzylic photo-chemical oxidation of steroids.

To provide 7-oxocholesterol derivatives in yields superior to those obtained by chemical oxidation, the preparation of steroidal allylic or benzylic ketones was studied. Air-induced oxidation was investigated with a highly selective low energy UV lamp in the presence of mercuric bromide. With this procedure cholesterol acetate, 5-cholestene-3 beta, 27-diol diacetate, 24(R)-24-methyl-5-cholesten-2 beta-yl acetate, 24(R)-24-ethyl-5-cholesten-28-yl acetate and 24(R)-24-ethyl-(22E)-cholesta-5,22-dien-3 beta-yl acetate were oxidized to the allylic keto-derivative in good yields; estradiol-17 beta diacetate was similarly converted to the 6-oxo-product in improved yield. This method can be very useful in the synthesis of 7-oxocholesteryl acetate and its analogs and 6-oxo-estratrienes.

Allyl Compounds↗
PubMed1985

Disposition and metabolism of 2,3-[14C]dichloropropene in rats after inhalation.

2,3-Dichloropropene (2,3-DCP) is a constituent of some commercially available preplant soil fumigants for the control of plant parasitic nematodes. Human exposure potential exists during manufacture of the chemicals or during bulk handling activities. The purpose of this investigation was to determine the disposition and metabolism of 2,3-[14C]DCP in rats after inhalation. Male Fischer-344 rats were exposed nose-only to a vapor concentration of 250 nmol 2,3-[14C]DCP/liter air (7.5 ppm; 25 degrees C, 620 Torr) for 6 hr. Blood samples were taken during exposure, and urine, feces, expired air, and tissues were collected for up to 65 hr after exposure. Urinary excretion was the major route of elimination of 14C (55% of estimated absorbed 2,3-DCP). Half-time for elimination of 14C in urine was 9.8 +/- 0.05 hr (means +/- SE). Half-time for elimination of 14C feces (17% of absorbed 2,3-DCP) was 12.9 +/- 0.14 hr (means +/- SE). Approximately 1 and 3% of the estimated absorbed 2,3-[14C]DCP were exhaled as either 2,3-[14C]DCP or 14CO2, respectively. Concentrations of 14C in blood increased during 240 min of exposure, after which no further increases in blood concentration of 14C were seen. 14C was widely distributed in tissues analyzed after a 6-hr exposure of rats to 2,3-[14C]DCP. Urinary bladder (150 nmol/g), nasal turbinates (125 nmol/g), kidneys (84 nmol/g), small intestine (61 nmol/g), and liver (35 nmol/g) were tissues with the highest concentrations of 14C immediately after exposure. Over 90% of the 14C in tissues analyzed was 2,3-DCP metabolites. Half-times for elimination of 14C from tissues examined ranged from 3 to 11 hr. The data from this study indicate that after inhalation 2,3-DCP is metabolized in tissues and readily excreted.

Allyl Compounds↗
PubMed1986

Inhalation pharmacokinetics of technical grade 1,3-dichloropropene in rats.

Kinetic data on the uptake of vapors of technical grade 1,3-dichloropropene (DCP) and resultant cis- and trans-DCP blood concentrations were obtained in rats exposed to 30, 90, 300, or 900 ppm DCP for 3 hr. The uptake of DCP did not increase proportionately with increasing exposure concentration due to an exposure level-related decrease in the respiratory ventilatory frequency of rats exposed to greater than or equal to 90 ppm DCP and the saturation of metabolism of DCP by rats exposed to greater than or equal to 300 ppm DCP. Absorption of inhaled DCP occurred primarily in the lower respiratory tract, although a small amount of the chemical was absorbed via the nasal mucosa, a known target tissue of inhaled DCP in rats. Following absorption, both isomers of DCP were, at less than or equal to 300 ppm exposure levels, rapidly eliminated from the bloodstream (3-6 min half-life). In addition, data obtained in rats exposed to 300 ppm DCP revealed that this rapid elimination phase was followed by a slower elimination phase having a 33-43 min half-life. Rats exposed to 900 ppm vapors also eliminated DCP in a biphasic manner; however, in this case the blood half-life of DCP during the initial phase of excretion was 14 to 27 min. Exposure to 90 ppm DCP also produced a significant decrease in renal (31%) and hepatic (41%), but not pulmonary, nonprotein sulfhydryl content. Overall, these data demonstrated that a combination of saturable metabolism and chemically induced changes in respiration control DCP uptake and body burden in rats.

Allyl Compounds↗
PubMed1979

Potential halogenated industrial carcinogenic and mutagenic chemicals. I. Halogenated unsaturated hydrocarbons.

The halogenated aliphatic hydrocarbons represent one of the most important categories of industrial chemicals from a consideration of use categories, production volume, environmental and toxicological considerations, and hence most importantly, potential population risk. The major unsaturated hydrocarbons reviewed, primarily in terms of their synthesis, utility, stability, distribution and levels of exposure as well as their reactivity, carcinogenicity, mutagenicity and metabolism, include: vinyl chloride, vinylidene chloride, trichloroethylene, perchloroethylene, chloroprene, trans-1,4-dichlorobutene, hexachlorobutadiene and allyl chloride.

Adult↗
PubMed1981

Carcinogenicity and mutagenicity of solvents. I. Glycidyl ethers, dioxane, nitroalkanes, dimethylformamide and allyl derivatives.

The carcinogenicity and/or mutagenicity as well as structural features and relationships of the glycidylethers (principally phenyl-, butyl-, allyl-, and isopropyl-), dioxane, nitroalkanes (nitro methane, ethane and propane), dimethylformamide and allyl derivatives (chloride, alcohol and amine) were examined. Additionally, considerations of the production, use patterns, estimated populations at risk, TLV's and metabolism of the above agents were discussed.

Allyl Compounds↗
PubMed1992

Mathematical descriptions of accelerated transformation of 1,3-dichloropropene in soil; a microbiological assessment.

The rate of transformation of the soil fumigant (Z)-and (E)-1,3-dichloropropene in moist soil layers was measured at incubation temperatures of 5 degrees C, 10 degrees C and 20 degrees C. 'DD95' was added to four characterized soil layers, in amounts corresponding to realistic field contents after fumigation. Rapid transformation immediately after application was observed in layers with low initial contents (30-300 micrograms/kg dm) and could well be described with a first-order rate model. Incubation at higher doses (5-15 mg/kg dm respectively) showed distinctly different transformation pathways. Degradation curves could well be computed using a microbiological interspective competition (MIC) model for moist soil. The transformation rate is inversely correlated to microorganism population size and growth. Transformation curves described by MIC are characterized by a lag-time, a period of accelerated transformation and a period of decreasing transformation rates. At low temperatures, DT50 values of more than 20 days could be observed. First-order rate computations did not exceed 8 days. The use of different mathematical discriptions for various soil layers and soil temperatures permits simulation of DD95-transformation by microorganisms in the soil profile throughout the growing season.

Allyl Compounds↗
PubMed1993

Surface characterization and platelet adhesion studies of plasma-sulphonated polyethylene.

Canine platelet adhesion on sulphur dioxide and allyl phenyl sulphone plasma-treated low density polyethylene (LDPE) was studied. Both 5 W plasma excitation energy-treated surfaces showed the highest S:C atomic ratio by ESCA analysis. Surface hydrophilicity increased drastically after plasma treatment. However, surface hydrophilicity decreased with time. This might be due to the diffusion of the hydrophilic functional groups into the bulk of the material and/or the migration of low molecular weight hydrocarbon species into the surface region. The allyl phenyl sulphone plasma-treated LDPE was less platelet-activating in terms of platelet adhesion and spreading and was independent of the different plasma excitation energy levels used. Sulphur dioxide plasma-treated LDPE showed a higher level platelet activation than the untreated LDPE. Among the sulphur dioxide plasma-treated LDPE samples, the sample prepared using the 5 W excitation energy was less platelet-activating than the samples treated by higher plasma excitation energies.

Allyl Compounds↗