Evidence for the biosynthesis of a glucuronide conjugate of (S)-(-)- nicotine, but not (S)-(-)-cotinine or (±)-trans-3'-hydroxycotinine by marmoset hepatic microsomes

Drug Metabolism and Drug Interactions

Volumn 15, Issue 4, 1999, Pages 223-237

  Tsai, Mui Chiung ^a   Gorrod, John W ^a  

^a UNIVERSITY OF ESSEX   (United Kingdom)

Author keywords

(S) ( ) nicotine N+ 1 glucuronide; Hydrolysis; Marmoset

Indexed keywords

3' HYDROXYCOTININE; BETA GLUCURONIDASE; COTININE; NICOTINE; NICOTINE N' 1BETA GLUCURONIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; CHEMICAL STRUCTURE; DRUG GLUCURONIDATION; DRUG HYDROLYSIS; DRUG METABOLISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIVER MICROSOME; MARMOSET; NONHUMAN; RABBIT; REVIEW; SYNTHESIS;

ANIMALS; CALLITHRIX; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COTININE; GLUCURONATES; GUINEA PIGS; MALE; MICROSOMES, LIVER; NICOTINE; OCTOXYNOL; RABBITS; RATS; RATS, WISTAR; URIDINE DIPHOSPHATE GLUCURONIC ACID;

EID: 0032701917     PISSN: 07925077     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (14)

1. Curvall M, Vala EK, Englund G. Conjugation pathways in nicotine metabolism; In: Adlkofer F, Thurau K, eds. Effects of Nicotine on Biological Systems. Birkhauser: Advances in Pharmacological Sciences, 1991; 69-75.
2. Byrd GD, Chang K-M, Greene JM, deBethizy JD. Evidence for urinary excretion of glucuronide conjugates of nicotine, cotinine, and trans-3′-hydroxycotinine in smokers. Drug Metab Dispos 1992, 20: 192-197.
3. Schepers G, Demetriou D, Rustemeier K, Voncken P, Diehl B. Nicotine phase 2 metabolites in human urine - structure of metabolically formed trans-3′-hydroxycotinine glucuronide. Med Sci Res 1992; 20: 863-865,
4. Seaton MJ, Vesell ES, Luo H, Hawes EM. Identification of S-(-)-nicotine N-glucuronide and direct separation of nicotine-derived conjugates using high-performance liquid chromatography. J Chromatogr 1993; 621: 49-53.
5. Crooks PA, Bhatti BS, Ravard A, Riggs RM, Caldwell WS. Synthesis of N-glucuronic acid conjugates of cotinine, cis-3-hydroxycotinine and trans-3-hydroxycotinine. Med Sci Res 1992; 20: 881-883.
6. Dagne E, Castagnoli N. Structure of hydroxycotinine, a nicotine metabolite. J Med Chem 1972; 15: 356-360.
7. Gorrod JW, Temple DJ, Beckett AH. The metabolism of N-ethyl-N-methylaniline by rabbit liver microsomes: The measurement of metabolites by gas-liquid chromatography. Xenobiotica 1975; 5: 453-463.
8. Burchell B, Coughtrie MWH. UDP-Glucuronosyltransferases. Pharmac Therap 1989; 43: 261-289.
9. Bock KW, Burchell B, Dutton GJ, Hanninen O, Mulder GJ, Owens IS, Siest G, Tephly TR. UDP-glucuronosyltransferase activities: Guidelines for consistent interim terminology and assay conditions. Biochem Pharmacol 1983; 32: 953-955.
10. Caldwell WS, Greene JM, Byrd GD, Chang K-M, Uhrig MS, deBethizy JD, Crooks PA, Bhatti BS, Riggs RM. Characterization of the glucuronide conjugate of cotinine: A previously unidentified major metabolite of nicotine in smokers' urine. Chem Res Toxicol 1992; 5: 280-285.
11. Lehman JP, Fenselau C. Synthesis of quaternary ammonium-linked glucuronides by rabbit hepatic microsomal UDP-glucuronyltransferase and analysis by fast-atom bombardment mass spectrometry. Drug Metab Dispos 1982; 10: 446-449.
12. Le Bigot JF, Begue JM, Kiechel JR, Guillouzo A. Species differences in metabolism of ketotifen in rat, rabbit and man: Demonstration of similar pathways in vivo and in cultured hepatocytes. Life Sci 1987; 40: 883-890.
13. Remmel RP, Sinz MW. A quaternary ammonium glucuronide is the major metabolite of lamotrigine in guinea pigs. Drug Metab Dispos 1991; 19: 630-636.
14. Burchell B, Brierley CH, Rance D. Specificity of human UDP-glucuronosyltransferases and xenobiotic glucuronidation. Life Sci 1995; 57: 1819-1831.