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PubMed1987

Effect of buffers on testing of Candida species susceptibility to flucytosine.

Synthetic amino acid medium for fungi (SAAMF) is a totally defined, nutritionally adequate, macromolecule-free culture medium for fungi that is buffered with an organic weak acid-weak base pair: 2-(N-morpholino)-propanesulfonic acid (MOPS) and 2-amino-2-(hydroxymethyl)-1,3-propanediol (Tris). In 1984, it was reported that MOPS-Tris in SAAMF antagonized the activity of flucytosine against Candida albicans (D. L. Calhoun and J. N. Galgiani, Antimicrob. Agents Chemother. 26:364-367, 1984). Accordingly, we evaluated the buffering capacity of seven synthetic organic buffers and monobasic potassium phosphate, both singly and in pairs, over the pH range 7.4 to 6.0. Of these buffers, MOPS, BES [N,N-bis(2-hydroxyethyl)-2-aminomethanesulfonic acid], a BES-MOPS combination, and KH2PO4 provided the best buffering. Growth of C. albicans, in unbuffered SAAMF was equivalent overall to that in SAAMF containing buffers, singly or in pairs. Twelve strains of C. albicans and five strains of Candida lusitaniae were tested for susceptibility to flucytosine in SAAMF, with and without buffers. In the presence of Tris, the geometric mean MICs were 6.5- and 3.6-fold higher, respectively, for C. albicans and C. lusitaniae. We recommend replacing Tris with the nonantagonistic MOPS.

Buffers↗
PubMed2001

Experimental exposure to propylene glycol mist in aviation emergency training: acute ocular and respiratory effects.

OBJECTIVES: Propylene glycol (PG) (1-2 propanediol; CAS No 57-55-6) is a low toxicity compound widely used as a food additive, in pharmaceutical preparations, in cosmetics, and in the workplace-for example, water based paints, de-icing fluids, and cooling liquids. Exposure to PG mist may occur from smoke generators in discotheques, theatres, and aviation emergency training. Propylene glycol may cause contact allergy, but there is sparse information on health effects from occupational exposure to PG. METHODS: Non-asthmatic volunteers (n=27) were exposed in an aircraft simulator to PG mist over 1 minute, during realistic training conditions. Geometric mean concentration of PG was 309 mg/m3 (range 176-851 mg/m3), with the highest concentrations in the afternoon. The medical investigation was performed both before and after the exposure (within 15 minutes). It included an estimate of tear film stability break up time, nasal patency by acoustic rhinometry, dynamic spirometry, and a doctor's administered questionnaire on symptoms. RESULTS: After exposure to PG mist for 1 minute tear film stability decreased, ocular and throat symptoms increased, forced expiratory volume in 1 second/forced vital capacity (FEV1/FVC) was slightly reduced, and self rated severity of dyspnoea was slightly increased. No effect was found for nasal patency, vital capacity (VC), FVC, nasal symptoms, dermal symptoms, smell of solvent, or any systemic symptoms. Those exposed to the higher concentrations in the afternoon had a more pronounced increase of throat symptoms, and a more pronounced decrease of tear film stability. In four subjects who reported development of irritative cough during exposure to PG, FEV1 was decreased by 5%, but FEV1 was unchanged among those who did not develop a cough. Those who developed a cough also had an increased perception of mild dyspnoea. CONCLUSION: Short exposure to PG mist from artificial smoke generators may cause acute ocular and upper airway irritation in non-asthmatic subjects. A few may also react with cough and slight airway obstruction.

Adult↗
PubMed1980

Enzymatic detection of Neisseria gonorrhoeae.

In a study using a non-serological enzymatic approach for the detection of Neisseria gonorrhoeae in cervical and urethral swabs, the technique was shown to be technically feasible. The enzyme, 1, 2-propanediol oxidoreductase, was used as a presumptive diagnostic marker for N gonorrhoeae. Enzymatic activity was measured with a fluorometer. Two assay procedures were performed: (a) enzyme detection (two-tube and three-tube assays) requiring 60 minutes; and (b) enzyme inhibition (EI) (90-minute and modified 20-minute assays). Sensitivities of the two-tube, three-tube, and the 90-minute EI assays with male urethral specimens from a high-prevalence population were 80%, 84%, and 91% respectively. The specificities of these assays in a low-prevalence male population were not determined. Sensitivity of the 90-minute EI assay in a high-prevalence female group was 77% and specificity in a low-prevalence female group was 75%. The modified EI assay was tested only in a low-prevalence female group and had 87% specificity. Although the specificity of the assays needs improvement, several advantages--including early case detection, rapid availability of results, detection of current active infections, and the possibility of automation--are intrinsic in this enzymatic approach.

Alcohol Oxidoreductases↗
PubMed1981

The effects of cofactor and species differences on the in vitro metabolism of propiophenone and phenylacetone.

In vitro metabolism of the aromatic ketone propiophenone and its nonaromatic isomer phenylacetone was studied using fortified 12 000 X g supernatants of liver homogenates from rat and rabbit. Reduction to the corresponding alcohols was the major metabolic route observed, although aliphatic C-hydroxylation and alcohol dehydrogenation also occurred. Marked differences were observed in the amounts of carbonyl reduction of the substrates, which was dependent on the species as well as the cofactor employed. Using rat liver preparation, phenylacetone was reduced to 1-phenyl-2-propanol much more efficiently with an NADH-fortified system than when NADPH was used whereas in rabbit, extensive reduction occurred in the presence of either cofactor. Reduction of propiophenone to 1-phenyl-1-propanol by rat liver preparation was slightly greater in the presence of NADH than with NADPH; the converse was observed in rabbit. Aliphatic hydroxylation of propiophenone to 2-hydroxy-1-phenyl-1-propanone was also a significant metabolic pathway in both species, with NADPH being the more efficient cofactor, but C-1 hydroxylation of phenylacetone to 1-hydroxy-1-phenyl-2-propanone occurred only to a minor extent. Small amounts of 1-phenyl-1,2-propanedione, as well as both erythro and threo isomers of 1-phenyl-1,2-propanediol, were also identified as metabolites in both species. Similar metabolic studies were carried out on the alcohols 1-phenyl-1-propanol and 1-phenyl-2-propanol and again the nature and quantities of metabolites isolated showed both species and cofactor dependencies.

Acetone↗
PubMed1997

Testosterone receptor blockade after trauma-hemorrhage improves cardiac and hepatic functions in males.

Although studies have shown that testosterone receptor blockade with flutamide after hemorrhage restores the depressed immune function, it remains unknown whether administration of flutamide following trauma and hemorrhage and resuscitation has any salutary effects on the depressed cardiovascular and hepatocellular functions. To study this, male rats underwent a laparotomy (representing trauma) and were then bled and maintained at a mean arterial pressure (MAP) of 40 mmHg until the animals could not maintain this pressure. Ringer lactate was given to maintain a MAP of 40 mmHg until 40% of the maximal shed blood volume was returned in the form of Ringer lactate. The rats were then resuscitated with four times the shed blood volume in the form of Ringer lactate over 60 min. Flutamide (25 mg/kg) or an equal volume of the vehicle propanediol was injected subcutaneously 15 min before the end of resuscitation. Various in vivo heart performance parameters (e.g., maximal rate of the pressure increase or decrease), cardiac output, and hepatocellular function (i.e., the maximum velocity and the overall efficiency of indocyanine green clearance) were determined at 20 h after resuscitation. Additionally, hepatic microvascular blood flow (HMBF) was determined using a laser Doppler flowmeter. The results indicate that left ventricular performance, cardiac output, HMBF, and hepatocellular function decreased significantly at 20 h after the completion of trauma, hemorrhage, and resuscitation. Administration of the testosterone receptor blocker flutamide, however, significantly improved cardiac performance, HMBF, and hepatocellular function. Thus flutamide appears to be a novel and useful adjunct for improving cardiovascular and hepatocellular functions in males following trauma and hemorrhagic shock.

Androgen Antagonists↗
PubMed1976

Permeability of dog lung endothelium to sodium, diols, amides, and water.

Bolus injection of T-1824-albumin, test indicator, and tritiated water into a jugular vein of the anesthetized dog and sequential sampling of blood from a carotid artery yielded multiple-indicator outflow patterns for the lung. Permeability-surface products of the test indicator for the lung endothelial barrier were obtained by comparison of test indicator with T-1824-albumin on the upslope of the test-indicator curve and correction for backdiffusion. The derived endothelial permeability coefficients, based on surface area/wet lung weight-500 cm2/g (mean +/- 2 SE, 10(-5) cm s(-1)), were: sodium ion, 2.9 +/- 0.8; ethylene glycol, 7.3 +/- 1.5; 1, 3-propranediol, 7.9 +/- 3.2; 1, 2-propanediol, 10 +/- 4; 1, 4-butanediol, 14 +/- 8; 1, 5-pentanediol, 21 +/- 6; 1, 6-hexanediol, 41 +/- 11; formamide, 16 +/- 9; acetamide, 13 +/- 4; propionamide, 31 +/- 12; butyramide, 42 +/- 24; valeramide, 79 +/- 12; tritiated water, 150 +/- 50. The backdiffusion correction varies from 8% for sodium to 75% for valeramide. A parallel-pathway model of blood-tissue passive exchange of small nonelectrolyte solutes is compatible with these results, with a lipid pathway through endothelial cells and an aqueous pathway possibly through interendothelial clefts.

Acetamides↗
PubMed1994

Pulmonary vascular resistance distribution and recruitment of microvascular surface area.

To test the hypothesis that the distribution of hemodynamic resistance is involved in the control of pulmonary capillary surface area, we measured permeability-surface area product (PS) and longitudinal resistance distribution (LRD) as functions of perfusion rate in isolated rabbit lungs under zone II conditions (n = 10) and through the zone II-III transition (n = 4). PS, considered to be indicative of functioning capillary surface area, was measured with the aid of the diffusion-limited tracer [14C]propanediol, whereas LRD was determined using a viscous bolus technique. LRD was seen to change character with increasing flow and increasing PS/surface area, becoming bimodal with low central resistance as full capillary recruitment was approached in zone III. Effects of hypoxic ventilation were studied in zone II in five lungs; it was found that hypoxia altered the LRD and eradicated the normoxic dependence of PS/surface area on perfusion rate. It was concluded that LRD is involved in the determination of functioning capillary surface area.

Animals↗
PubMed2003

Metagenomes of complex microbial consortia derived from different soils as sources for novel genes conferring formation of carbonyls from short-chain polyols on Escherichia coli.

Metagenomic DNA libraries from three different soil samples (meadow, sugar beet field, cropland) were constructed. The three unamplified libraries comprised approximately 1267000 independent clones and harbored approximately 4.05 Gbp of environmental DNA. Approximately 300000 recombinant Escherichia coli strains of each library per test substrate were screened for the production of carbonyls from short-chain (C2 to C4) polyols such as 1,2-ethanediol, 2,3-butanediol, and a mixture of glycerol and 1,2-propanediol on indicator agar. Twenty-four positive E. COLI clones were obtained during the initial screen. Fifteen of them contained recombinant plasmids, designated pAK201-215, which conferred a stable carbonyl-forming phenotype on E. coli Sequencing revealed that the inserts of pAK201-215 encoded 26 complete and 14 incomplete predicted protein-encoding genes. Most of these genes were similar to genes with unknown functions from other microorganisms or unrelated to any other known gene. The further analysis was focused on the 7 plasmids (pAK204, pAK206, pAK208, and pAK210-213) recovered from the positive clones, which exhibited an NAD(H)-dependent alcohol oxidoreductase activity with polyols or the correlating carbonyls as substrates in crude extracts. Three genes (ORF6, ORF24, and ORF25) conferring this activity were identified during subcloning of the inserts of pAK204, pAK211, and pAK212. The sequences of the three deduced gene products revealed no significant similarities to known alcohol oxidoreductases, but contained putative glycine-rich regions, which are characteristic for binding of nicotinamide cofactors.

Alcohol Oxidoreductases↗
PubMed2004

Insights into the genome of the enteric bacterium Escherichia blattae: cobalamin (B12) biosynthesis, B12-dependent reactions, and inactivation of the gene region encoding B12-dependent glycerol dehydratase by a new mu-like prophage.

The enteric bacterium Escherichia blattae has been analyzed for the presence of cobalamin (B12) biosynthesis and B12-dependent pathways. Biochemical studies revealed that E. blattae synthesizes B12 de novo aerobically and anaerobically. Genes exhibiting high similarity to all genes of Salmonella enterica serovar Typhimurium, which are involved in the oxygen-independent route of B12 biosynthesis, were present in the genome of E. blattae DSM 4481. The dha regulon encodes the key enzymes for the anaerobic conversion of glycerol to 1,3-propanediol, including coenzyme B12-dependent glycerol dehydratase. E. blattae DSM 4481 lacked glycerol dehydratase activity and showed no anaerobic growth with glycerol, but the genome of E. blattae DSM 4481 contained a dha regulon. The E. blattaedha regulon is unusual, since it harbors genes for two types of dihydroxyacetone kinases. The major difference to dha regulons of other enteric bacteria is the inactivation of the dehydratase-encoding gene region by insertion of a 33,339-bp prophage (MuEb). Sequence analysis revealed that MuEb belongs to the Mu family of bacteriophages. The E. blattae strains ATCC 33429 and ATCC 33430 did not contain MuEb. Accordingly, both strains harbored an intact dehydratase-encoding gene region and fermented glycerol. The properties of the glycerol dehydratases and the correlating genes (dhaBCE) of both strains were similar to other B12-dependent glycerol and diol dehydratases, but both dehydratases exhibited the highest affinity for glycerol of all B12-dependent dehydratases characterized so far. In addition to the non-functional genes encoding B12-dependent glycerol dehydratase, the genome of E. blattae DSM 4481 contained the genes for only one other B12-dependent enzyme, the methylcobalamin-dependent methionine synthase.

Amino Acid Sequence↗
PubMed1984

Benzodiazepine and nonbenzodiazepine anxiolytics.

A review of anxiolytic drugs is presented, including ethyl alcohol, barbiturates, diphenylmethane derivatives, glycerol and propanediol derivatives, antipsychotics, and antidepressants. Focus on the benzodiazepines and their metabolism and method of action follows. The newest two groups are then reviewed: triazolobenzodiazepines and azaspirodecanediones. The first member of this latter group, buspirone, is then reviewed in detail including the author's personal studies of the drug. The fact that it appears nonaddicting, nonsynergistic with alcohol, lacks impairment of driving-related skills, and is very effective in treating anxiety, may represent a breakthrough.

Adrenergic beta-Antagonists↗
PubMed1977

Relationship between bile flow and Na+, K+-adenosinetriphosphatase in liver plasma membranes enriched in bile canaliculi.

The relationship between bile flow and Na+,K+-ATPase activity in liver plasma membranes enriched in bile canaliculi was studied in rats treated with ethinyl estradiol, phenobarbital, or 20-methyl cholanthrene. In comparison with controls (1.49+/-0.12 microliter/min per g liver), bile flow was significantly diminished by ethinyl estradiol, increased by phenobarbital, and unchanged by 20-methyl cholanthrene or the solvent, propanediol (0.92+/-0.31, 2.50+/-0.21, 1.62+/-0.18, and 1.64+/-0.30 microliter/min per g liver, respectively). The corresponding values for canalicular Na+,K+-ATPase activity were 80.7+/-19.2, 50.0+/-18.4, 231.7+/-42.6, 82.7+/-30.7, and 143.6+/-55.3 micronmol Pi/h per g liver. Canalicular Na+,K+-ATPase activity was significantly correlated (r=0.785, n=31) with bile flow. These findings support the hypothesis that a fraction of bile flow is related to Na+,K+-ATPase activity and canalicular Na+ transport.

Adenosine Triphosphatases↗
PubMedDate not supplied

Cytotoxicity of amino alcohols to rat hepatoma-derived Fa32 cells.

Amino alcohols are used as emulsifying agents in dry-cleaning soaps, wax removers, cosmetics, paints and insecticides. The cytotoxicities of 12 amino alcohols, which differed in chain length, position of the amino and alcohol groups, and the presence of an additional phenyl group, were determined by the neutral red uptake inhibition assay with normally cultured, glutathione-depleted or antioxidant-enriched Fa32 rat hepatoma-derived cells. Glutathione depletion and antioxidant enrichment were achieved by including 50(M L-buthionine-S,R-sulphoximine (BSO) or 100(M (-tocopherol acetate (vitamin E) in the culture medium for 24 hours before and during the assay. The cytotoxicity of the amino alcohols observed after treatment for 24 hours was expressed as the concentration of compound needed to induce a 50% reduction in neutral red uptake (NI50). The observed NI50 values ranged from 3mM to 30mM. The individual stereoisomers and a racemic mixture of 1-amino-2-propanol exhibited similar cytotoxicities (with normally cultured Fa32 cells, and vitamin E- and BSO-treated cultures). Similar NI50 values for D-(+)-2-amino-1-propanol, 3-amino-1-propanol and the L-, D- or DL- forms of 1-amino-2-propanol, indicated that the position of the amino group had little influence on the cytotoxicities of the amino alcohols. In contrast, the position of the hydroxyl group appeared to play an important role for the toxicity of the compound, as indicated by the significantly different NI50 values for 4-amino-1-butanol and 4-amino-2-butanol. An additional phenyl group greatly increased the cytotoxicity of 2-amino-1,3-propanediol. For most of the compounds, cytotoxicity increased when GSH was depleted, and decreased when the cells were enriched with vitamin E. This indicated that most of the tested chemicals interact with GSH, either directly or indirectly, by processes which generate oxygen free-radicals. Decreased toxicity was found for most of the chemicals administered to vitamin E-enriched cells, indicating that reactive oxygen species could be involved in the toxicity of the amino alcohols.

Amino Alcohols↗
PubMedDate not supplied

Penetration of human spermatozoa through the zona pellucida of nonviable human oocytes.

OBJECTIVE: The purpose of this study was to evaluate the penetrating capacity of human sperm through the intact zonae of nonviable human oocytes and the influence of oocyte storage conditions and gamete coincubation times on penetration rates. METHODS: Immature oocytes were obtained from surgically removed ovarian tissue and from in vitro fertilization (IVF) and subjected to four storage conditions: 1) storage at 4 degrees C for up to 48 hours in culture medium (refrigeration, n = 53), 2) cryopreservation in 1.5 mol/L propanediol with storage at -196 degrees C (PrOH; n = 49), 3) cryopreservation in 2.0 mol/L dimethylsulfoxide with storage at -70 degrees C (DMSO; n = 20), and 4) storage in a hypertonic salt solution at 4 degrees C (salt; n = 30). Semen was obtained from fertile donors (n = 7) and after a wash and swim-up, samples were adjusted to 500,000 motile sperm/mL. Zonae and sperm were coincubated in 100-microL drops under oil, and penetration was assessed at 5 and 20 hours. Penetration was evidenced by visualization of at least one sperm head in the perivitelline space at 200x magnification. RESULTS: Zona penetration rates were 50.9, 32.7, 23.3, and 10.0% for refrigeration, PrOH, salt, and DMSO storage, respectively (P < .004). There was a significantly higher number of sperm in the perivitelline space after 20 hours' coincubation (3.8 +/- 0.2) compared to 5 hours (0.8 +/- 0.1) (P < .0006). This represented an increase in the penetration rate from 31.2% (34 of 109) at 5 hours to 37.6% (41 of 109) at 20 hours, although the difference was not significant. CONCLUSIONS: These results demonstrate that the zona pellucida of nonviable human oocytes can be used in a zona penetration assay and that refrigerated and PrOH-frozen intact zonae have the highest rates of penetration. The decrease in penetrability seen in DMSO and salt-stored oocytes may be due to alterations occurring in the zona pellucida.

Cell Survival↗
PubMed1981

Effect of continuous thyroxine administration on thyrotropin secretion in thyroidectomized rats.

We have studied the effect of T4 itself (i.e. without extrapituitary conversion to T3) on the feedback regulation of pituitary TSH secretion in thyroidectomized rats receiving continuous T4 or T3 replacement. Continuous sc infusion of 1.0 or 2.0 microgram T4/100 g . day in 0.01 N NaOH, 20% 1,2-propanediol vehicle failed to maintain the plasma T4 concentration in thyroidectomized rats for more than 48 h, despite the verification of T4 delivery. Continuous sc infusion of 1.0 or 2.0 microgram T4/100 g . day in 0.01 N NaOH, 5% rat serum resulted in a dose-dependent elevation in the plasma T4 concentration and inhibition of the postthyroidectomy rise in plasma TSH, in the presence of low plasma T3 concentrations. Mimicking the low plasma T3 concentrations that resulted from T4 infusion by continuous replacement of 280 ng T3/100 g . day failed to inhibit the postthyroidectomy rise in plasma TSH. The pituitary responsiveness to TRH (250 ng/100 g, iv) after 96 h of thyroid hormone infusion was significantly (P less than 0.05) inhibited only in the group receiving 2.0 microgram T4/100 g . day. These results indicate that the plasma T4, concentration in addition to that of plasma T3, conveys feedback information to the pituitary. With regard to pituitary TSH secretion, T4 acts as both a prohormone giving rise to a protion of the plasma T3 by peripheral monodeiodination and as a hormone conveying feedback information via the blood to the pituitary.

Animals↗
PubMed2001

Azo-containing urethane analogues for colonic drug delivery: synthesis, characterization and in-vitro evaluation.

A urethane-based analogue containing an azo aromatic linkage in the backbone was synthesized for use in colon-specific delivery systems by reacting toluene-2,6-diisocyanate with a mixture of an aromatic azo diol, (bis-4-hydroxyphenyl)-4,4'-diazobiphenyl, poly(ethylene glycol) (Mn = 4000; number-average molecular weight) and 1,2-propanediol (propylene glycol). The resultant compounds (UR-1 and UR-2) were characterized by IR spectroscopy, 1H NMR spectroscopy, DSC studies, X-ray diffraction studies and molecular weight determination by gel permeation chromatography. The compounds exhibited low molecular weight, lacked film-forming properties and crystallinity in the structure. An in-vitro bacterial degradation test to demonstrate the susceptibility of azo bond to bacterial enzymes was performed using media inoculated with lactobacillus culture. The results indicated degradation of films by azoreductase. In-vitro permeation of 5-aminosalicylic acid was studied in control and lactobacilli-treated films. The permeability of the lactobacilli treated films was significantly increased suggesting the potential of these compounds for application in colonic targeting.

Antineoplastic Agents↗
PubMed1999

Effect of pretreatment with FTY720 and cyclosporin on ischaemia-reperfusion injury of the liver in rats.

The effect of pretreatment with FTY720 (2-amino-2-[2-(4-octylphenyl)ethyl]-1,3-propanediol hydrochloride) or cyclosporin, or both, on neutrophil-mediated injury has been examined by use of a rat model of transient clamping of hepatic flow. Pretreatment with FTY720 alone or with cyclosporin induced a marked reduction of circulatory lymphocytes, whereas the use of these drugs in combination was very effective at suppressing the elevation of the number of peripheral polymorphonuclear neutrophils (PMN) after reperfusion. Pretreatment with cyclosporin, with or without FTY720, significantly reduced hepatic damage, whereas FTY720 alone tended to prolong hepatic damage. Pretreatment of cyclosporin alone, but not in combination with FTY720, significantly reduced the accumulation of PMN and led to lower myeloperoxidase levels in the damaged liver. In conclusion, pretreatment with cyclosporin, with or without FTY720, reduced hepatic damage after warm ischaemia-reperfusion, whereas pretreatment with FTY720 alone tended to prolong this damage.

Animals↗
PubMed1991

Felbamate for partial seizures: results of a controlled clinical trial.

Felbamate (2-phenyl-1,3-propanediol dicarbamate) has a favorable preclinical profile in animal models of epilepsy. We present the results of a double-blind, randomized, placebo-controlled clinical trial in patients with partial seizures. Criteria for entry included a requirement for four or more partial seizures per month despite concomitant therapeutic blood levels of phenytoin and carbamazepine. Fifty-six patients (mean age, 31.4 years; 32 men, 24 women) completed the trial. The mean seizure frequencies for the 8-week periods analyzed were felbamate = 34.9, placebo = 40.2. Felbamate was statistically superior to placebo in seizure reduction, percent seizure reduction, and truncated percent seizure reduction. The mean felbamate dosage was 2,300 mg/d. Plasma felbamate concentrations ranged from 18.4 to 51.9 mg/l, mean = 32.5 mg/l. Adverse experiences during felbamate therapy were minor and consisted primarily of nausea and CNS effects. This trial indicates that felbamate is safe and effective in the treatment of comedicated patients with severely refractory epilepsy.

Adult↗
PubMed1994

The enantioselective metabolism of 4-isopropenyltoluene in rabbits.

4-Isopropenyltoluene (8) was administered orally to rabbits and the following four optically active metabolites, 2-(p-tolyl)propanoic acid (10), p-(1-carboxyethyl)benzoic acid (11), 2-hydroxy-2-(p-tolyl)propanoic acid (12), and 2-(p-tolyl)-1,2-propanediol (13) were isolated from urine in addition to an optically inactive metabolite, 4-isopropenylbenzoic acid (9). The enantiomeric ratios of the metabolites 10 and 11 were respectively R/S = 33:67 and 39:61 (S predominance), whereas those of the metabolites 12 and 13 possessing a tertiary hydroxyl group were R/S = 77:23 and 84:16 respectively (R predominance). The presumed metabolic pathways of 8 in rabbits leading to these metabolites are discussed.

Animals↗