Stereoselective and regiospecific hydroxylation of ketamine and norketamine

Xenobiotica

Volumn 42, Issue 11, 2012, Pages 1076-1087

  Desta, Zeruesenay ^a   Moaddel, Ruin ^b   Ogburn, Evan T ^a   Xu, Cong ^a   Ramamoorthy, Anuradha ^b   Venkata, Swarajya Lakshmi Vattem ^b   Sanghvi, Mitesh ^b   Goldberg, Michael E ^c   Torjman, Marc C ^c   Wainer, Irving W ^b  

^a INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b NATIONAL INSTITUTE ON AGING   (United States)

^c Cooper Medical School of Rowan University ^*  (United States)

Author keywords

Complex regional pain syndrome; Cytochrome; Dehydronorketamine; Depression; Hydroxyketamine; Hydroxynorketamine; Ketamine; P450s

Indexed keywords

CYTOCHROME P450 2A6; CYTOCHROME P450 2B6; CYTOCHROME P450 2C19; CYTOCHROME P450 2C8; CYTOCHROME P450 2C9; CYTOCHROME P450 3A; CYTOCHROME P450 3A4; CYTOCHROME P450 3A5; KETAMINE; N DEMETHYLASE;

ARTICLE; CONTROLLED STUDY; DRUG CLEARANCE; DRUG HYDROXYLATION; DRUG METABOLISM; ENANTIOSELECTIVITY; HUMAN; HUMAN CELL; IN VITRO STUDY; METABOLIC CLEARANCE RATE; OXIDATION; PHARMACOGENETICS; STEREOCHEMISTRY;

ANESTHETICS, DISSOCIATIVE; COMPLEX REGIONAL PAIN SYNDROMES; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; HYDROXYLATION; KETAMINE;

EID: 84867184164     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.3109/00498254.2012.685777     Document Type: Article

References (36)

1. Adams JD Jr, Baillie TA, Trevor AJ, Castagnoli N Jr. (1981). Studies on the biotransformation of ketamine. 1-Identification of metabolites produced in vitro from rat liver microsomal preparations. Biomed Mass Spectrom 8:527-538. (Pubitemid 12169796)
2. Angst MS, Clark JD. (2010). Ketamine for managing perioperative pain in opioid-dependent patients with chronic pain: a unique indication? Anesthesiology 113:514-515.
3. Bolze S, Boulieu R. (1998). HPLC determination of ketamine, norketamine, and dehydronorketamine in plasma with a highpurity reversed-phase sorbent. Clin Chem 44:560-564. (Pubitemid 28141352)
4. Chan WH, Sun WZ, Ueng TH. (2005). Induction of rat hepatic cytochrome P-450 by ketamine and its toxicological implications. J Toxicol Environ Health Part A 68:1581-1597.
5. Chen JT, Chen RM. (2010). Mechanisms of ketamine-involved regulation of cytochrome P450 gene expression. Expert Opin Drug Metab Toxicol 6:273-281.
6. Diazgranados N, Ibrahim L, Brutsche NE, Newberg A, Kronstein P, Khalife S, Kammerer WA, Quezado Z, Luckenbaugh DA, Salvadore G, Machado-Vieira R, Manji HK, Zarate CA Jr. (2010). A randomized add-on trial of an N-methyl-D-aspartate antagonist in treatment-resistant bipolar depression. Arch Gen Psychiatry 67:793-802.
7. Domino EF. (2010). Taming the ketamine tiger. 1965. Anesthesiology 113:678-684.
8. Goldberg ME, Torjman MC, Schwartzman RJ, Mager DE, Wainer IW. (2010). Pharmacodynamic profiles of ketamine ®- and (S)- with 5-day inpatient infusion for the treatment of complex regional pain syndrome. Pain Physician 13:379-387.
9. Goldberg ME, Torjman MC, Schwartzman RJ, Mager DE, Wainer IW. (2011). Enantioselective pharmacokinetics of ®- and (S)-ketamine after a 5-day infusion in patients with complex regional pain syndrome. Chirality 23:138-143.
10. Hijazi Y, Boulieu R. (2002). Contribution of CYP3A4, CYP2B6, and CYP2C9 isoforms to N-demethylation of ketamine in human liver microsomes. Drug Metab Dispos 30:853-858. (Pubitemid 34671099)
11. Kharasch ED, Labroo R. (1992). Metabolism of ketamine stereoisomers by human liver microsomes. Anesthesiology 77:1201-1207. (Pubitemid 23001132)
12. Kharasch ED, Herrmann S, Labroo R. (1992). Ketamine as a probe for medetomidine stereoisomer inhibition of human liver microsomal drug metabolism. Anesthesiology 77:1208-1214. (Pubitemid 23001133)
13. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. (2011). DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Nucleic Acids Res 39:D1035-D1041.
14. Lester L, Braude DA, Niles C, Crandall CS. (2010). Low-dose ketamine for analgesia in the ED: a retrospective case series. Am J Emerg Med 28:820-827.
15. Leung LY, Baillie TA. (1986). Comparative pharmacology in the rat of ketamine and its two principal metabolites, norketamine and (Z)-6- hydroxynorketamine. J Med Chem 29:2396-2399. (Pubitemid 17182325)
16. Lester L, Braude DA, Niles C, Crandall CS. (2010). Low-dose ketamine for analgesia in the ED: a retrospective case series. Am J Emerg Med 28:820-827.
17. Loftus RW, Yeager MP, Clark JA, Brown JR, Abdu WA, Sengupta DK, Beach ML. (2010). Intraoperative ketamine reduces perioperative opiate consumption in opiate-dependent patients with chronic back pain undergoing back surgery. Anesthesiology 113:639-646.
18. Matzke GR, Frye RF, Early JJ, Straka RJ, Carson SW. (2000). Evaluation of the influence of diabetes mellitus on antipyrine metabolism and CYP1A2 and CYP2D6 activity. Pharmacotherapy 20:182-190. (Pubitemid 30073838)
19. Moaddel R, Venkata SL, Tanga MJ, Bupp JE, Green CE, Iyer L, Furimsky A, Goldberg ME, Torjman MC, Wainer IW. (2010). A parallel chiralachiral liquid chromatographic method for the determination of the stereoisomers of ketamine and ketamine metabolites in the plasma and urine of patients with complex regional pain syndrome. Talanta 82:1892-1904.
20. Nama S, Meenan DR, Fritz WT. (2010). The use of sub-anesthetic intravenous ketamine and adjuvant dexmedetomidine when treating acute pain from CRPS. Pain Physician 13:365-368.
21. Noppers I, Olofsen E, Niesters M, Aarts L, Mooren R, Dahan A, Kharasch E, Sarton E. (2011). Effect of rifampicin on S-ketamine and S-norketamine plasma concentrations in healthy volunteers after intravenous S-ketamine administration. Anesthesiology 114:1435-1445.
22. O'Neil WM, Gilfix BM, DiGirolamo A, Tsoukas CM, Wainer IW. (1997). N-acetylation among HIV-positive patients and patients with AIDS: when is fast, fast and slow, slow? Clin Pharmacol Ther 62:261-271. (Pubitemid 27417791)
23. Portmann S, Kwan HY, Theurillat R, Schmitz A, Mevissen M, Thormann W. (2010). Enantioselective capillary electrophoresis for identification and characterization of human cytochrome P450 enzymes which metabolize ketamine and norketamine in vitro. J Chromatogr A 1217:7942-7948.
24. Renton KW. (2005). Regulation of drug metabolism and disposition during inflammation and infection. Expert Opin Drug Metab Toxicol 1:629-640.
25. Sabia M, Hirsh RA, Torjman MC, Wainer IW, Cooper N, Domsky R, Goldberg ME. (2011). Advances in translational neuropathic research: example of enantioselective pharmacokineticpharmacodynamic modeling of ketamine-induced pain relief in complex regional pain syndrome. Curr Pain Headache Rep 15:207-214.
26. Seripa D, Pilotto A, Panza F, Matera MG, Pilotto A. (2010). Pharmacogenetics of cytochrome P450 (CYP) in the elderly. Ageing Res Rev 9:457-474.
27. Sigtermans M, Dahan A, Mooren R, Bauer M, Kest B, Sarton E, Olofsen E. (2009). S(+)-ketamine effect on experimental pain and cardiac output: a population pharmacokinetic-pharmacodynamic modeling study in healthy volunteers. Anesthesiology 111:892-903.
28. Tanaka E. (1998). In vivo age-related changes in hepatic drug-oxidizing capacity in humans. J Clin Pharm Ther 23:247-255. (Pubitemid 28532449)
29. Trevor AJ, Woolf TF, Baillie TA, Adams JD, Castagnoli N. (1983). Stereoselective metabolism of ketamine enantiomers. In: Kamenka JM, Domino EF, Geneste P, ed. Phencyclidine and Related Arylcyclohexylamines, Present and Future Applications. Ann Arbor, MI: NPP Books, 279-289.
30. Turfus SC, Parkin MC, Cowan DA, Halket JM, Smith NW, Braithwaite RA, Elliot SP, Steventon GB, Kicman AT. (2009). Use of human microsomes and deuterated substrates: an alternative approach for the identification of novel metabolites of ketamine by mass spectrometry. Drug Metab Dispos 37: 1769-1778.
31. Wang Z, Hall SD, Maya JF, Li L, Asghar A, Gorski JC. (2003). Diabetes mellitus increases the in vivo activity of cytochrome P450 2E1 in humans. Br J Clin Pharmacol 55:77-85. (Pubitemid 36110842)
32. Williams ML, Wainer IW. (2002). Genotype/phenotype comparisons: a probe for the effect of disease progression on drug metabolism. Curr Opin Drug Discov Devel 5:144-149. (Pubitemid 34453252)
33. Williams ML, Mager DE, Parenteau H, Gudi G, Tracy TS, Mulheran M, Wainer IW. (2004). Effects of protein calorie malnutrition on the pharmacokinetics of ketamine in rats. Drug Metab Dispos 32:786-793. (Pubitemid 38955606)
34. Woolf TF, Adams JD. (1987). Biotransformation of ketamine, (Z)-6- hydroxyketamine, and (E)-6-hydroxyketamine by rat, rabbit, and human liver microsomal preparations. Xenobiotica 17: 839-847. (Pubitemid 17105580)
35. Zhao X, Venkata SLV, Moaddel R, Luckenbaugh DA, Brutsche NE, Ibrahim L, Zarate CA Jr., Mager DE, Wainer IW. (2012). Simultaneous population pharmacokinetic modeling of ketamine and three major metabolites in patients with treatmentresistant bipolar depression. Br J Clin Pharmacol. DOI: 10.1111/j.1365-2125.2012.04198.x.
36. Zarate CA Jr, Brutsche N, Laje G, Luckenbaugh DA, Venkata SLV, Ramamoorthy A, Moaddel R, Wainer IW. (2012). Relationship of ketamine's plasma metabolites with response, diagnosis, and side effects in major depression. Biol Psychiatry, http://dx.doi.org/10.1016/j.biopsych.2012.03.004.