Characterization of differential cocaine metabolism in mouse and rat through metabolomics-guided metabolite profiling

Drug Metabolism and Disposition

Volumn 41, Issue 1, 2013, Pages 79-88

  Yao, Dan ^a   Shi, Xiaolei ^a   Wang, Lei ^a   Gosnell, Blake A ^a   Chen, Chi ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE AMINOTRANSFERASE; ALPHA GLUCOSIDASE; BENZOYLECGONINE; COCAINE; CYTOCHROME P450; ECGONINE; KETOCONAZOLE; N HYDROXYBENZOYLNORECGONINE; NORCOCAINE; ORPHENADRINE; UNCLASSIFIED DRUG;

AEROBIC METABOLISM; ALANINE AMINOTRANSFERASE BLOOD LEVEL; ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CONJUGATION; CONTROLLED STUDY; DEALKYLATION; DEMETHYLATION; ENZYME MECHANISM; GLUCURONIDATION; HISTOPATHOLOGY; HUMAN; HUMAN CELL; HYDROLYSIS; HYDROXYLATION; IN VITRO STUDY; ISOTOPE TRACING; LIQUID CHROMATOGRAPHY; LIVER METABOLISM; LIVER NECROSIS; MALE; METABOLITE; METABOLOMICS; METHYLATION; MOUSE; NONHUMAN; OXIDATION; PRIORITY JOURNAL; RAT; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY; TOXICITY TESTING; URINALYSIS;

ANIMALS; COCAINE; METABOLOMICS; MICE; RATS;

ANIMALIA; MUS; RATTUS; RODENTIA;

EID: 84871598157     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.112.048678     Document Type: Article

References (52)

1. Aoki K, Takimoto M, Ota H, and Yoshida T (2000) Participation of CYP2A in cocaine-induced hepatotoxicity in female mice. Pharmacol Toxicol 87:26-32. (Pubitemid 30644596)
2. Boelsterli UA and Göldlin C (1991) Biomechanisms of cocaine-induced hepatocyte injury mediated by the formation of reactive metabolites. Arch Toxicol 65:351-360.
3. Boelsterli UA, Lanzotti A, Göldlin C, and Oertle M (1992) Identification of cytochrome P-450IIB1 as a cocaine-bioactivating isoform in rat hepatic microsomes and in cultured rat hepatocytes. Drug Metab Dispos 20:96-101.
4. Boyer CS, Ross D, and Petersen DR (1988) Sex and strain differences in the hepatotoxic response to acute cocaine administration in the mouse. J Biochem Toxicol 3:295-307.
5. Chen C, Gonzalez FJ, and Idle JR (2007a) LC-MS-based metabolomics in drug metabolism. Drug Metab Rev 39:581-597. (Pubitemid 47355739)
6. Chen C, Ma X, Malfatti MA, Krausz KW, Kimura S, Felton JS, Idle JR, and Gonzalez FJ (2007b) A comprehensive investigation of 2-amino-1-methyl-6- phenylimidazo[4,5-b]pyridine (PhIP) metabolism in the mouse using a multivariate data analysis approach. Chem Res Toxicol 20:531-542. (Pubitemid 46548699)
7. Chen C, Meng L, Ma X, Krausz KW, Pommier Y, Idle JR, and Gonzalez FJ (2006) Urinary metabolite profiling reveals CYP1A2-mediated metabolism of NSC686288 (aminoflavone). J Pharmacol Exp Ther 318:1330-1342. (Pubitemid 44268343)
8. Evans MA (1983) Role of protein binding in cocaine-induced hepatic necrosis. J Pharmacol Exp Ther 224:73-79. (Pubitemid 13171033)
9. Evans MA and Harbison RD (1978) Cocaine-induced hepatotoxicity in mice. Toxicol Appl Pharmacol 45:739-754. (Pubitemid 9095778)
10. Gottfried MR, Kloss MW, Graham D, Rauckman EJ, and Rosen GM (1986) Ultrastructure of experimental cocaine hepatotoxicity. Hepatology 6:299-304. (Pubitemid 16144883)
11. Harbison RD, James RC, and Roberts SM (1992) Cocaine-induced hepatotoxicity, in Cocaine: Pharmacology, Physiology, and Clinical Strategies (Lakoski JM, Galloway, and White FJ, eds) pp 15-34, CRC Press, Boca Raton.
12. Idle JR and Gonzalez FJ (2007) Metabolomics. Cell Metab 6:348-351. (Pubitemid 350012005)
13. Jindal SP and Lutz T (1986) Ion cluster techniques in drug metabolism: use of a mixture of labeled and unlabeled cocaine to facilitate metabolite identification. J Anal Toxicol 10:150-155. (Pubitemid 17100550)
14. Johnson CH, Patterson AD, Idle JR, and Gonzalez FJ (2012) Xenobiotic metabolomics: major impact on the metabolome. Annu Rev Pharmacol Toxicol 52:37-56.
15. Kamimura H, Kawai R, and Kudo H (1988) Metabolic fate of indeloxazine hydrochloride: alpha-glucoside formation in rats. Xenobiotica 18:141-149. (Pubitemid 18071741)
16. Kanel GC, Cassidy W, Shuster L, and Reynolds TB (1990) Cocaine-induced liver cell injury: comparison of morphological features in man and in experimental models. Hepatology 11:646-651. (Pubitemid 20151743)
17. Kloss MW, Cavagnaro J, Rosen GM, and Rauckman EJ (1982) Involvement of FAD-containing monooxygenase in cocaine-induced hepatotoxicity. Toxicol Appl Pharmacol 64:88-93. (Pubitemid 12085517)
18. Kloss MW, Rosen GM, and Rauckman EJ (1983) N-demethylation of cocaine to norcocaine. Evidence for participation by cytochrome P-450 and FAD-containing monooxygenase. Mol Pharmacol 23:482-485. (Pubitemid 13116874)
19. Kloss MW, Rosen GM, and Rauckman EJ (1984) Cocaine-mediated hepatotoxicity. A critical review. Biochem Pharmacol 33:169-173. (Pubitemid 14191041)
20. Knuepfer MM (2003) Cardiovascular disorders associated with cocaine use: myths and truths. Pharmacol Ther 97:181-222.
21. Lakoski JM, Galloway MP, and White FJ (1992) Cocaine: Pharmacology, Physiology, and Clinical Strategies, CRC Press, Boca Raton.
22. Lasoń W (2001) Neurochemical and pharmacological aspects of cocaine-induced seizures. Pol J Pharmacol 53:57-60.
23. Lewis DF and Lake BG (1997) Molecular modelling of mammalian CYP2B isoforms and their interaction with substrates, inhibitors and redox partners. Xenobiotica 27:443-478. (Pubitemid 27220178)
24. Lloyd RV, Shuster L, and Mason RP (1993) Reexamination of the microsomal transformation of N-hydroxynorcocaine to norcocaine nitroxide. Mol Pharmacol 43:645-648. (Pubitemid 23112742)
25. Marks V and Chapple PA (1967) Hepatic dysfunction in heroin and cocaine users. Br J Addict Alcohol Other Drugs 62:189-195.
26. Martignoni M, Groothuis GM, and de Kanter R (2006) Species differences between mouse, rat, dog, monkey and human CYP-mediated drug metabolism, inhibition and induction. Expert Opin Drug Metab Toxicol 2:875-894. (Pubitemid 44911538)
27. Masini A, Gallesi D, Giovannini F, Trenti T, and Ceccarelli D (1997) Membrane potential of hepatic mitochondria after acute cocaine administration in rats - the role of mitochondrial reduced glutathione. Hepatology 25:385-390. (Pubitemid 27069059)
28. Mehanny SZ and Abdel-Rahman MS (1991) Cocaine hepatotoxicity in mice: histologic and enzymatic studies. Toxicol Pathol 19:24-29.
29. Misra AL, Pontani RB, and Vadlamani NL (1979) Metabolism of norcocaine, N-hydroxy norcocaine and cocaine-N-oxide in the rat. Xenobiotica 9:189-199. (Pubitemid 9188076)
30. Ndikum-Moffor FM, Schoeb TR, and Roberts SM (1998) Liver toxicity from norcocaine nitroxide, an N-oxidative metabolite of cocaine. J Pharmacol Exp Ther 284:413-419. (Pubitemid 28109573)
31. Nicholson JK, Connelly J, Lindon JC, and Holmes E (2002) Metabonomics: a platform for studying drug toxicity and gene function. Nat Rev Drug Discov 1:153-161. (Pubitemid 41646523)
32. Nicholson JK and Wilson ID (2003) Opinion: understanding 'global' systems biology: metabonomics and the continuum of metabolism. Nat Rev Drug Discov 2:668-676. (Pubitemid 37361770)
33. Nutt D, King LA, Saulsbury W, and Blakemore C (2007) Development of a rational scale to assess the harm of drugs of potential misuse. Lancet 369:1047-1053. (Pubitemid 46436128)
34. Patkar AA, Rozen S, Mannelli P, Matson W, Pae CU, Krishnan KR, and Kaddurah-Daouk R (2009) Alterations in tryptophan and purine metabolism in cocaine addiction: a metabolomic study. Psychopharmacology (Berl) 206:479-489.
35. Pellinen P, Honkakoski P, Stenbäck F, Niemitz M, Alhava E, Pelkonen O, Lang MA, and Pasanen M (1994) Cocaine N-demethylation and the metabolism-related hepatotoxicity can be prevented by cytochrome P450 3A inhibitors. Eur J Pharmacol 270:35-43.
36. Pellinen P, Kulmala L, Konttila J, Auriola S, Pasanen M, and Juvonen R (2000) Kinetic characteristics of norcocaine N-hydroxylation in mouse and human liver microsomes: involvement of CYP enzymes. Arch Toxicol 74:511-520.
37. Perino LE, Warren GH, and Levine JS (1987) Cocaine-induced hepatotoxicity in humans. Gastroenterology 93:176-180. (Pubitemid 17084111)
38. Powers JF, Alroy J, and Shuster L (1992) Hepatic morphologic and biochemical changes induced by subacute cocaine administration in mice. Toxicol Pathol 20:61-70.
39. Shi X, Yao D, Gosnell BA, and Chen C (2012) Lipidomic profiling reveals protective function of fatty acid oxidation in cocaine-induced hepatotoxicity. J Lipid Res 53:2318-2330.
40. Shuster L(1992) Pharmacokinetics, metabolism, and disposition of cocaine, in Cocaine: Pharmacology, Physiology, and Clinical Strategies (Lakoski JM, Galloway MP, and White FJ, eds) pp 1-14. CRC Press, Boca Raton.
41. Shuster L, Casey E, and Welankiwar SS (1983) Metabolism of cocaine and norcocaine to N-hydroxynorcocaine. Biochem Pharmacol 32:3045-3051. (Pubitemid 14227004)
42. Shuster L, Garhart CA, Powers J, Grunfeld Y, and Kanel G (1988) Hepatotoxicity of cocaine. NIDA Res Monogr 88:250-275. (Pubitemid 20097846)
43. Smith RM (1984) Arylhydroxy metabolites of cocaine in the urine of cocaine users. J Anal Toxicol 8:35-37.
44. Smith RM, Poquette MA, and Smith PJ (1984) Hydroxymethoxybenzoylmethylecgonines: new metabolites of cocaine from human urine. J Anal Toxicol 8:29-34. (Pubitemid 14152603)
45. Tang BK (1990) Drug glucosidation. Pharmacol Ther 46:53-56.
46. Thompson ML, Shuster L, Casey E, and Kanel GC (1984) Sex and strain differences in response to cocaine. Biochem Pharmacol 33:1299-1307. (Pubitemid 14131883)
47. Thompson ML, Shuster L, and Shaw K (1979) Cocaine-induced hepatic necrosis in mice - the role of cocaine metabolism. Biochem Pharmacol 28:2389-2395. (Pubitemid 9253330)
48. Toennes SW, Thiel M, Walther M, and Kauert GF (2003) Studies on metabolic pathways of cocaine and its metabolites using microsome preparations from rat organs. Chem Res Toxicol 16:375-381. (Pubitemid 36373702)
49. Wanless IR, Dore S, Gopinath N, Tan J, Cameron R, Heathcote EJ, Blendis LM, and Levy G (1990) Histopathology of cocaine hepatotoxicity. Report of four patients. Gastroenterology 98:497-501. (Pubitemid 20037937)
50. Watanabe K, Hida Y, Matsunaga T, Yamamoto I, and Yoshimura H (1993) Formation of p-hydroxycocaine from cocaine by hepatic microsomes of animals and its pharmacological effects in mice. Biol Pharm Bull 16:1041-1043. (Pubitemid 23352141)
51. Wiener HL and Reith ME (1990) Differential effects of daily administration of cocaine on hepatic and cerebral glutathione in mice. Biochem Pharmacol 40:1763-1768. (Pubitemid 20337955)
52. Zhang JY and Foltz RL (1990) Cocaine metabolism in man: identification of four previously unreported cocaine metabolites in human urine. J Anal Toxicol 14:201-205. (Pubitemid 20230988)