Metabolism of prazosin in rat and characterization of metabolites in plasma, urine, faeces, brain and bile using liquid chromatography/mass spectrometry (LC/MS)

Xenobiotica

Volumn 38, Issue 5, 2008, Pages 540-558

  Erve, J C L ^a   Vashishtha, S C ^a   Ojewoye, O ^b   Adedoyin, A ^a   Espina, R ^a   DeMaio, W ^a   Talaat, R E ^a  

^a PFIZER INC   (United States)

^b UNIVERSITY OF MARYLAND BALTIMORE COUNTY   (United States)

Author keywords

Bioactivation; Biotransformation; Furan metabolism; Mass spectrometry; Nuclear magnetic resonance; Prazosin

Indexed keywords

5 [4 (4 AMINO 6,7 DIMETHOXYQUINAZOLIN 2 YL)PIPERAZIN 1 YL] 4,5 DIOXOPENTANOIC ACID; DRUG METABOLITE; PRAZOSIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; CRYOPRESERVATION; DRUG BILE LEVEL; DRUG BLOOD LEVEL; DRUG BRAIN LEVEL; DRUG CONJUGATION; DRUG DETERMINATION; DRUG FECES LEVEL; DRUG ISOLATION; DRUG METABOLISM; DRUG URINE LEVEL; ELECTROSPRAY MASS SPECTROMETRY; IN VIVO STUDY; LIQUID CHROMATOGRAPHY; LIVER CELL CULTURE; LIVER METABOLISM; LIVER MICROSOME METABOLISM; MALE; NANOFLOW ELECTROSPRAY IONIZATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAT; RING OPENING; TIME OF FLIGHT MASS SPECTROMETRY; ULTRAPERFORMANCE LIQUID CHROMATOGRAPHY;

ANIMALS; ANTIHYPERTENSIVE AGENTS; BILE; BRAIN; CHROMATOGRAPHY, LIQUID; FECES; MAGNETIC RESONANCE SPECTROSCOPY; MALE; PRAZOSIN; RATS; RATS, SPRAGUE-DAWLEY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

RATTUS;

EID: 42249105209     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.1080/00498250802001826     Document Type: Article

References (32)

1. Althuis TH, Hess HJ. 1977. Synthesis and identification of the major metabolites of prazosin formed in dog and rat. Journal of Medicine and Chemistry 20(1):146-149.
2. Bawaskar HS, Bawaskar PH. 1986. Prazosin in management of cardiovascular manifestations of scorpion sting. Lancet 1(8479):510-511.
3. Bawaskar HS, Bawaskar PH. 2007. Utility of scorpion antivenin vs. prazosin in the management of severe Mesobuthus tamulus (Indian red scorpion) envenoming at rural setting. Journal of the Association of Physicians of India 55:14-21.
4. Constantine J. 1974. Analysis of the hypotensive action of prazosin. In: Cotton D, editor. Prazosin - Evaluation of a new antihypertensive agent. Geneva: Excerpta Medica. pp 16-36.
5. Daly Christine M, Doyle Michael E, Radkind M, Raskind E, Daniels C. 2005. Clinical case series: the use of prazosin for combat-related recurrent nightmares among Operation Iraqi Freedom combat veterans. Military Medicine 170:513-515.
6. Dick RA, Kwak MK, Sutter TR, Kensler TW. 2001. Antioxidative function and substrate specificity of NAD(P)H-dependent alkenal/one oxidoreductase. A new role for leukotriene B4 12-hydroxydehydrogenase/ 15-oxoprostaglandin 13-reductase. Journal of Biology and Chemistry 276(44):40803-40810.
7. Dierks MR, Jordan JK, Sheehan AH. 2007. Prazosin treatment of nightmares related to posttraumatic stress disorder. Annals of Pharmacotherapy 41(6):1013-1017.
8. Erve JCL, Vashishtha SC, DeMaio W, Talaat RE. 2007. Metabolism of prazosin in rat, dog, and human liver microsomes and cryopreserved rat and human hepatocytes and characterization of metabolites by liquid chromatography/tandem mass spectrometry. Drug Metabolism and Disposition 35(6):908-916.
9. Hieble JP, Ruffolo Jr. RR. 1996. The use of alpha-adrenoceptor antagonists in the pharmacological management of benign prostatic hypertrophy: an overview. Pharmacology Research 33(3):145-160.
10. Kalgutkar AS, Soglia JR. 2005. Minimising the potential for metabolic activation in drug discovery. Expert Opinion on Drug Metabolism and Toxicology 1(1):91-142.
11. Kirkman SK, Zhang M-Y, Horwatt PM, Scatina J. 1998. Isolation and identification of bromfenac glucoside from rat bile. Drug Metabolism and Disposition 26(7):720-723.
12. Kobayashi T, Sugihara J, Harigaya S. 1987. Mechanism of metabolic cleavage of a furan ring. Drug Metabolism and Disposition 15(6):877-881.
13. Le Fur JM, Labaune JP. 1985. Metabolic pathway by cleavage of a furan ring. Xenobiotica 15(7):567-577.
14. Lefkowitz RJ, Hoffman BB. 1996. Catecholamines, sympathomimetic drugs, and andrenergic receptor antagonists. In: Hardman JG, Limbird LE, Milinoff PB, Ruddon RW, editors. Goodman and Gilman's: The Pharmacological Basis of Therapeutics. New York, NY: McGraw-Hill. pp 199-248.
15. Lindstrom TD, Whitaker GW. 1984. Saturation of an a,b-unsaturated ketone: a novel xenobiotic biotransformation in mammals. Xenobiotica 14(7):503-508.
16. Menkes DB, Baraban JM, Aghajanian GK. 1981. Prazosin selectively antagonizes neuronal responses mediated by alpha1-adrenoceptors in brain. Naunyn Schmiedebergs Archives in Pharmacology 317(3):273-275.
17. Nassar A-EF, Talaat RE, Kamel AM. 2006. The impact of recent innovations in the use of liquid chromatographymass spectrometry in support of drug metabolism studies: Are we all the way there yet? Current Opinion in Drug Discovery and Development 9(1):61-74.
18. Neighbors SM, Soine WH. 1995. Identification of phenobarbital N-glucuronides as urinary metabolites of phenobarbital in mice. Drug Metabolism and Disposition 23(5):548-552.
19. Plumb R, Castro-Perez J, Granger J, Beattie I, Joncour K, Wright A. 2004. Ultra-performance liquid chromatography coupled to quadrupole-orthogonal time-of-flight mass spectrometry. Rapid Communications in Mass Spectrometry 18(19):2331-2337.
20. Raskind MA, Peskind ER, Hoff DJ, Hart KL, Holmes HA, Warren D, Shofer J, O'Connell J, Taylor F, Gross C, et al. 2007. A parallel group placebo controlled study of prazosin for trauma nightmares and sleep disturbance in combat veterans with post-traumatic stress disorder. Biological Psychiatry 61(8):928-934.
21. Sayre LM, Engelhart DA, Nadkarni DV, Manoj Babu MK, Flammang AM, McCoy GD. 1997. The role of iminium-enamine species in the toxication and detoxication of cyclic tertiary amines. NIDA Research Monograph 173(Pharmacokinetics, Metabolism, and Pharmaceutics of Drugs of Abuse):106-127.
22. Staack RF, Varesio E, Hopfgartner G. 2005. The combination of liquid chromatography/tandem mass spectrometry and chip-based infusion for improved screening and characterization of drug metabolites. Rapid Communications in Mass Spectrometry 19(5):618-626.
23. Stanaszek WF, Kellerman D, Brogden RN, Romankiewicz JA. 1983. Prazosin update. A review of its pharmacological properties and therapeutic use in hypertension and congestive heart failure. Drugs 25(4):339-384.
24. Stierlin H, Faigle JW, Sallmann A, Kung W, Richter WJ, Kriemler HP, Alt KO, Winkler T. 1979. Biotransformation of diclofenac sodium (Voltaren) in animals and in man. I. Isolation and identification of principal metabolites. Xenobiotica 9(10):601-610.
25. Tang W, Stearns RA, Miller RR, Ngui JS, Mathvink RJ, Weber AE, Kwei GY, Strauss JR, Keohane CA, Doss GA, et al. 2002. Metabolism of a thiazole benzenesulfonamide derivative, a potent and selective agonist of the human b3-adrenergic receptor, in rats: identification of a novel isethionic acid conjugate. Drug Metabolism and Disposition 30(7):778-787.
26. Taskinen J, Wikberg T, Ottoila P, Kanner L, Lotta T, Pippuri A, Backstrom R. 1991. Identification of major metabolites of the catechol -O-methyltransferase-inhibitor nitecapone in human urine. Drug Metabolism and Disposition: The Biological Fate of Chemicals 19(1):178-183.
27. Taylor F, Raskind MA. 2002. The a1-adrenergic antagonist prazosin improves sleep and nightmares in civilian trauma posttraumatic stress disorder. Journal of Clinical Psychopharmacology 22(1):82-85.
28. Taylor JA, Twomey TM, Schach Von Wittenau M. 1977. The metabolic fate of prazosin. Xenobiotica 7(6):357-364.
29. Uetrecht J. 2003. Screening for potential of a drug candidate to cause idiosyncratic drug reactions. Drug Discovery Today 8(18):832-837.
30. Watt AP, Mortishire-Smith RJ, Gerhard U, Thomas SR. 2003. Metabolite identification in drug discovery. Current Opinion in Drug Discovery and Development 6(1):57-65.
31. Williams DP, Park BK. 2003. Idiosyncratic toxicity: The role of toxicophores and bioactivation. Drug Discovery Today 8(22):1044-1050.
32. Wilson ID, Wade KE, Nicholson JK. 1989. Analysis of biological fluids by high-field nuclear magnetic resonance spectroscopy. TrAC, Trends in Analytical Chemistry 8(10):368-374.