Gene/Protein Disease Symptom Drug Enzyme Compound
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Query: CAS:34834-67-8 (trans-3'-hydroxycotinine)
 135 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

Trans-3'-hydroxycotinine was found to be a main metabolite of nicotine in smokers. It is the most abundant among all nicotine metabolites, if the total urine is collected over 7 consecutive days of smoking and 5 following days without smoking. Its steady-state blood plasma concentration on the 6th day of smoking is second only to cotinine. In the experiments nine habitual smokers smoked 19 cigarettes per day on 7 days of smoking. Three runs were carried out with three types of cigarettes which differed in mainstream nicotine. After oral administration of 30 mg trans-3'-hydroxycotinine, the cumulative excretion rates of two subjects were 81% and 93% of the unchanged compound, respectively.
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PMID:Trans-3'-hydroxycotinine--a main metabolite in smokers. 318 75

Polyclonal rabbit anticotinine antiserum, which can be used for biomonitoring nicotine uptake by the determination of cotinine in body fluids, was checked by a competitive ELISA for its cross-reactivity with nine nicotine metabolites. The highest percentage of relative cross-reactivity (about 30%) was observed with trans-3'-hydroxycotinine, a metabolite which is known to be excreted in 3-fold higher amounts than cotinine in the urine of human smokers. Therefore, it is possible that cotinine determinations performed by immunochemical methods--especially in urine--may yield overestimated cotinine concentrations.
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PMID:Cotinine determination by immunoassays may be influenced by other nicotine metabolites. 324 51

1. High performance liquid radiochromatographic systems have been developed for the identification and quantification of 7 urinary metabolites of both S-(-)-[3H-N'-CH3]nicotine and R-(+)-[3H-N'-CH3] nicotine in guinea pig, hamster, rat and rabbit. 2. 3'-Hydroxycotinine was a major urinary metabolite of both S-(-)-nicotine and R-(+)-nicotine in guinea pig, hamster and rabbit. Cotinine was not generally a significant urinary metabolite of either nicotine enantiomer, except in rat, where it constituted 14.6 and 10.4%, respectively, of the total radiolabel in the urine after administration of [3H]-S-(-)-nicotine or [3H]-R-(+)-nicotine. Nicotine N'-oxide was an important urinary metabolite of both nicotine isomers in guinea pig and rat, but in both cases, was not observable in hamster and rabbit. No N-methylated urinary metabolite of S-(-)-nicotine could be detected in any of the species examined. In R-(+)-nicotine experiments, only guinea pig afforded N-methylated metabolites. Significant amounts of 2 unidentified polar, non-basic urinary metabolites of both S-(-)- and R-(+)-nicotine-treated animals were observed. 3. Analysis of the comparative metabolism of the nicotine enantiomers in the four animals species studied, showed that stereoselective differences in the formation of oxidative metabolites existed, particularly in the formation of 3'-hydroxycotinine and nicotine-N'-oxide. A clear stereospecificity was observed in the guinea pig, in that only the R-(+)-nicotine enantiomer was N-methylated in this species. 4. Sex differences appear to exist in the metabolism of nicotine enantiomers in the rat. Female rats excreted more of the unidentified polar metabolite B than male rats, whereas the converse was true for nicotine-N'-oxide. In experiments with R-(+)-nicotine, urinary levels of 3'-hydroxycotinine and R-(+)-nicotine in female rats were higher than in male rats. Conversely, higher amounts of nicotine-N'-oxide were observed in the urine of male rats compared to those in female rats.
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PMID:Species variation and stereoselectivity in the metabolism of nicotine enantiomers. 324 30

Nine male smokers smoked three types of cigarettes that differed in mainstream nicotine. The experiment was carried out in three runs, each consisting of 7 d when smoking was allowed and 5 d when it was not allowed. Urine fractions were collected throughout the whole period of the experiments. As assumed, nicotine and four of its known metabolites, i.e., cotinine, nicotine-N'-oxide, nornicotine, and N-methyl-nicotinum ions were found in the urine. In addition, trans-3'-hydroxycotinine was determined. The amount of this metabolite was well in excess of those of nicotine and cotinine in the urine. The serum concentration trans-3'-hydroxycotinine was found to be second to serum cotinine.
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PMID:Trans-3'-hydroxycotinine as a main metabolite in urine of smokers. 355 28

1. The metabolism of [3H]-S-(-)-cotinine in vivo has been investigated in the guinea pig. The quantitive determination of urinary metabolites has been carried out using a high-performance liquid radiochromagraphic procedure. Metabolite analysis of C- and N-oxidation products, and N-methylcotininium ion, were carried out on two chromatographic systems: (a) Partisil-10 SCX cation-exchange chromatography, and (b) Partisil-10 ODS reverse-phase chromatography. 2. 3-Hydroxycotinine was the major urinary metabolite of cotinine in the guinea pig, accounting for 57% of the total radioactivity in the urine. Cotinine-N-oxide constituted 18% of total metabolites in the urine, whereas neither nicotine nor the N-methylcotininium ion were detected as urinary metabolites of [3H]-S-(-)cotinine. S-(-)-Cotinine was extensively metabolized in the guinea pig; total recovery of radioactivity in 24 h urine was very high (greater than 95%) and very little cotinine was detected (less than 1%) in the urine. 3. Two unidentified metabolites of [3H]-S-(-)-cotinine were detected which collectively constituted approximately 20% of total urinary tritium.
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PMID:Biotransformation of primary nicotine metabolites. II. Metabolism of [3H]-S-(-)-cotinine in the guinea pig: determination of in vivo urinary metabolites by high-performance liquid-radiochromatography. 366 Aug 48

The effects of smoking cessation with and without nicotine substitution on prostaglandin E2, leukotriene B4, leukotriene E4, and thromboxane B2 synthesis ex vivo in man were investigated. Blood samples were obtained from 20 healthy non-smoking controls and from 30 healthy smoking volunteers before and 3, 7 and 14 days after smoking cessation. Half of the smokers used nicotine chewing gum as a substitution therapy. Urinary cotinine and trans-3'-hydroxycotinine as well as thiocyanate excretions were used as indicators for the use of nicotine chewing gum and smoking, respectively. Prostaglandin E2, leukotriene E4, and thromboxane B2 were measured from whole blood after calcium ionophore A23187 stimulation by direct radioimmunoassay and leukotriene B4 by RP-HPLC. Prostaglandin E2 and thromboxane B2 syntheses were about three times and leukotriene B4 and E4 syntheses four times higher in smokers than in controls. Three days after smoking cessation without nicotine substitution, levels were lowered significantly to about 70%, 80%, 45% and 60% of the initial values; and after 14 days to 55%, 80%, 45% and 50%, respectively. In the nicotine substitution group no significant decreases were seen during the two-week follow-up. The increased level of eicosanoid synthesis detected in smokers in this ex vivo study may contribute to the harmful cardiovascular effects of smoking. Long-term nicotine substitution might diminish the beneficial effects of smoking cessation due to the possible stimulatory effects of nicotine and cotinine on eicosanoid synthesis even in vivo.
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PMID:Smoking cessation and nicotine substitution modulate eicosanoid synthesis ex vivo in man. 747 18

Nicotine is a naturally occurring alkaloid found primarily in members of the solanaceous plant family, which includes tobacco. Nicotine is rapidly absorbed by humans and then metabolized, primarily by cytochrome P450's. Studies on the genotoxic potential of these metabolites are limited. Nicotine and four of its major metabolites: cotinine, nicotine-N'-oxide, cotinine-N-oxide, and trans-3'-hydroxycotinine were evaluated for genotoxic potential in the Salmonella mutagenicity assay (strains TA98, TA100, TA1535, TA1537, and TA1538) at concentrations ranging from 0 to 1000 micrograms/plate and in the Chinese hamster ovary sister-chromatid exchange (SCE) assay at concentrations ranging from 0 to 1000 micrograms/ml. All assays were conducted with and without S9 metabolic activation. None of the five compounds increased the frequency of mutations or the frequency of SCEs. These results indicate that nicotine and its major metabolites are not genotoxic in the assays conducted.
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PMID:The genotoxic potential of nicotine and its major metabolites. 749 Nov 33

A solid-phase extraction, using Extrelut-1 glass columns, has been applied to urine samples of both passive and active smokers for high-performance liquid chromatographic determination of nicotine and its metabolites cotinine and trans-3'-hydroxycotinine. Chromatography was performed using a reversed-phase LC8DB column and a mobile phase consisting of water-acetonitrile (80:9, v/v) containing 5 ml triethylamine, 670 mg/l sodium heptanesulphonate, and 0.034 M each of K2HPO4 and citric acid (pH 4.4), at a flow-rate of 1.6 ml/min. The results obtained indicate that solid-phase extraction is a reliable and quick procedure which can be applied also to other nicotine metabolites.
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PMID:Solid-phase extraction of nicotine and its metabolites for high-performance liquid chromatographic determination in urine. 755 Sep 77

We measured nicotine metabolites (cotinine and trans-3'-hydroxycotinine) in meconium of infants of passive or active smokers as a direct marker of fetal exposure to tobacco smoke. Meconium was collected from 55 infants whose mothers were nonsmokers, passive smokers, or light or heavy active smokers. Nicotine metabolite concentration (NMC) in meconium was analyzed by radioimmunoassay and gas chromatography-mass spectrometry. Radioimmunoassay showed the following mean meconium NMCs (in nanograms per milliliter); nonsmoker, 10.9; passive smoker, 31.6; light active smoker; 34.7, and heavy active smoker, 54.6. Analysis of available samples by gas chromatography-mass spectrometry confirmed the presence of cotinine. Correlation between meconium NMC and the degree of maternal smoking was 0.54 (p < 0.001). Meconium NMCs in infants of passive and active smokers were significantly higher than in those of nonsmokers (p < 0.05). Meconium NMC in passive smokers was not significantly different from that in light active smokers (p > 0.05). Thus exposure of the fetus to tobacco smoke is substantial, even by passive maternal smoking. Meconium analysis for nicotine metabolites may be useful for clinical and research purposes.
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PMID:Meconium analysis to assess fetal exposure to nicotine by active and passive maternal smoking. 812 Jul 24

A thermospray liquid chromatographic/mass spectrometric method has been developed for direct determination of cotinine-N-glucuronide in the urine of smokers. Quantification was performed using methyl-d3-cotinine-N-glucuronide as internal standard and monitoring the protonated aglycons. Using a simple preparation, urine samples from four smokers were analyzed and the results compared favorably with those from a previously reported method that quantifies aglycon release following beta-glucuronidase treatment. Amounts of cotinine-N-glucuronide found in urine from smokers ranged from less than 0.7 to 21 nmol ml-1, indicating wide inter-individual variability in the metabolic production of this metabolite. Cotinine-N-glucuronide was found to be the second most abundant urinary nicotine metabolite. A similar method was developed for trans-3'-hydroxycotinine-N-glucuronide but this compound was not detected in smokers' urine.
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PMID:Direct determination of cotinine-N-glucuronide in urine using thermospray liquid chromatography/mass spectrometry. 812 88


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