Metabolism of cocaine and heroin is catalyzed by the same human liver carboxylesterases

Journal of Pharmacology and Experimental Therapeutics

Volumn 279, Issue 2, 1996, Pages 713-717

  Kamendulis, Lisa M ^a   Brzezinski, Monica R ^a   Pindel, Evgenia V ^a   Bosron, William F ^a,c   Dean, Robert A ^a,b  

^a INDIANA UNIVERSITY   (United States)

^b ELI LILLY AND COMPANY   (United States)

^c INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLESTERASE; CHOLINESTERASE; COCAINE; DIAMORPHINE; LIVER ENZYME; MORPHINE; MORPHINE 6 ACETATE;

ARTICLE; CATALYSIS; COMPETITIVE INHIBITION; CONTROLLED STUDY; DEACETYLATION; DRUG HYDROLYSIS; DRUG METABOLISM; HUMAN; HUMAN TISSUE; PRIORITY JOURNAL;

CARBOXYLIC ESTER HYDROLASES; COCAINE; HEROIN; HUMANS; HYDROLYSIS; LIVER; MORPHINE DERIVATIVES; NARCOTICS; PSEUDOCHOLINESTERASE;

EID: 0030441048     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

1. BARNETT, G., HAWKS, R. AND RESNICK, R.: Cocaine pharmacokinetics in humans. J. Ethnopharmacol. 3: 353-366, 1981.
2. BARRETT, D. A., DYSSEGAARD, A. L. AND SHAW, P. N.: The effect of temperature and pH on the deacetylation of diamorphine in aqueous solution and in human plasma. J. Pharm. Pharmacol. 44: 606-608, 1992.
3. BOERNER, U., ABBOTT, S. AND ROE, R. L.: The metabolism of morphine and heroin in man. Drug Metab. Rev. 4: 39-73, 1975.
4. BRZEZINSKI, M. R., ABRAHAM, T. L., STONE, C. L., DEAN, R. A. AND BOSRON, W. F.: Purification and characterization of a human liver cocaine carboxylesterase that catalyzes the production of benzoylecgonine and the formation of cocaethylene from alcohol and cocaine. Biochem. Pharmacol. 48: 1747-1755, 1994.
5. COHEN, S. D.: Mechanisms of toxicological interactions involving organophosphate insecticides. Fundam. Appl. Toxicol. 4: 315-324, 1984.
6. COHN, G. L., CRAMER, J. A. AND KLEBER, H. D.: Heroin metabolism in the rat. Proc. Soc. Exp. Biol. Med. 144: 351-355, 1973.
7. DAS, G.: Cocaine abuse in North America: A milestone in history. J. Clin. Pharmacol. 33: 296-310, 1993.
8. DEAN, R. A., CHRISTIAN, C. D., SAMPLE, R. H. B. AND BOSRON, W. F.: Human liver cocaine eaterases: Ethanol-mediated formation of ethylcocaine. FASEB J. 5: 2735-2739, 1994.
9. ELLIOTT, H. W., PARKER, K. D., CRIM, M., WRIGHT, J. A. AND NOMOF, N.: Actions and metabolism of heroin administered by continuous intravenous infusion to man. Clin. Pharmacol. Ther. 12: 806-814, 1971.
10. GIANUTSOS, G., COHEN, S. D., CARLSON, G., HEYMAN, R., SALVA, P., MORROW, G. AND HITE, G. J.: Alteration of in vivo and in vitro effects of heroin by esterase inhibition. Toxicol. Appl. Pharmacol. 82: 14-18, 1986.
11. INTURRISI, C. E., MAX, M. B., FOLEY, K. M., SCHULTZ, M., SHIN, S.-U. AND HOUDE, R. W.: The pharmacokinetics of heroin in patients with chronic pain. N. Engl. J. Med. 310: 1213-1217, 1984.
12. KAMENDULIS, L. M., BRZEZINSKI, M. R., PINDEL, E. V., BOSRON, W. F. AND DEAN, R. A.: Metabolism of cocaine and heroin is regulated by the same human liver carboxylesterases. Toxicologist 16: 37, 1996.
13. KREEK, M. J., ORATZ, M. AND ROTHSCHILD, M. A.: Hepatic extraction of long- and short-acting narcotics in the isolated perfused rabbit liver. Gastroenterology 75: 88-94, 1978.
14. LAEMMLI, U. K.: Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature (Lond.) 227: 680-685, 1970.
15. LOCKRIDCE, O., MOTTERSHAW-JACKSON, N., ECKERSON, H. W. AND LADU, B. N.: Hydrolysis of diacetylmorphine (heroin) by human serum cholinesterase. J. Pharmacol. Exp. Ther. 215: 1-8, 1980.
16. NAKAMURA, G. R. AND UKITA, T.: Paper chromatography study of in vitro and in vivo hydrolysis of heroin in blood. J. Pharm. Sci. 56: 29994-29995, 1967.
17. NATIONAL INSTITUTE ON DRUG ABUSE: Annual Emergency Room Data, 1990: Data from the Drug Abuse Warning Network (DAWN): Statistical Series I, No. 10-A [United States Department of Health and Human Services Publication (ADM) 91-1839]. United States Government Printing Office, Washington, D.C., 1991.
18. NATIONAL INSTITUTE ON DRUG ABUSE, DIVISION OF EPIDEMIOLOGY AND STATISTICAL ANALYSIS: National Household Survey on Drug Abuse: Main Findings, 1992 [United States Department of Health and Human Services Publication (SMA) 94-3012]. United States Department of Health and Human Services, United States Public Health Service, Alcohol, Drug Abuse and Mental Health Administration, Rockville, MD, 1994.
19. OFFICE OF NATIONAL DRUG CONTROL POLICY, EXECUTIVE OFFICE OF THE PRESIDENT: National Drug Control Strategy. United States Government Printing Office, Washington, D.C., 1994.
20. OWEN, J. A. AND NAKATSU, K.: Diacetylmorphine (heroin) hydrolases in human blood. Can. J. Physiol. Pharmacol. 61: 870-875, 1983.
21. OZOLS, J.: Isolation, properties, and the complete amino acid sequence of a second form of 60-kDa glycoprotein esterase. J. Biol. Chem. 264: 12533-12545, 1989.
22. PICKETT, R. D. AND GRAHAM, J. D. P.: Acute toxicity of heroin, alone and in combination with cocaine or quinine. Br. J. Pharmacol. 40: 145P-146P, 1970.
23. SIEGAL, H. A., CARLSON, R. G., WANG, J., FALCK, R. S, STEPHENS, R. C. AND NELSON, E. D.: Injection drug users in the Midwest: An epidemiologic comparison of drug use patterns in four Ohio cities. J. Psychoactive Drugs 26: 265-275, 1994.
24. SMITH, D. A. AND COLE, W. J.: Identification of an arylesterase as the enzyme hydrolyzing diacetylmorphine (heroin) in human plasma. Biochem. Pharmacol. 25: 367-370, 1976.
25. STEWART, D. J., INABA, T., TANG, B. K. AND KALOW, W.: Hydrolysis of cocaine in human plasma by cholinesterase. Life Sci. 20: 1557-1563, 1977.
26. UNITED STATES DEPARTMENT OF HEALTH AND HUMAN SERVICES: Press release from Secretary Louis W. Sullivan, M.D., on the 1988 National Household Survey on Drug Abuse. United States Department of Health and Human Services, Washington, D.C., July 31, 1989.
27. WAY, E. L., KEMP, J. W., YOUNG, J. M. AND GRASSETTI, D. R.: The pharmacologic effects of heroin in relationship to its rate of biotransformation. J. Pharmacol. Exp. Ther. 129: 144-154, 1960.
28. WAY, E. L., YOUNG, J. M. AND KEMP, J. W.: Metabolism of heroin and its pharmacological implications. Bull. Narc. 17: 25-33, 1965.