Nevirapine significantly reduces the levels of racemic methadone and (R)-methadone in human immunodeficiency virus-infected patients

Antimicrobial Agents and Chemotherapy

Volumn 48, Issue 11, 2004, Pages 4148-4153

  Stocker, Hartmut ^a,b   Kruse, Guido ^a   Kreckel, Peter ^a   Herzmann, Christian ^a   Arastéh, Keikawus ^a,b   Claus, Jörg ^a   Jessen, Heiko ^a   Cordes, Christiane ^a   Hintsche, Bettina ^a   Schlote, Frank ^a   Schneider, Lothar ^a   Kurowski, Michael ^a,b  

^a Vivantes Auguste Viktoria Klinikum   (Germany)

^b Kompetenznetz HIV/AIDS   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 ETHYLIDENE 1,5 DIMETHYL 3,3 DIPHENYLPYRROLIDINE; DRUG METABOLITE; METHADONE; NEVIRAPINE; PYRROLIDINE DERIVATIVE; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG;

ADULT; AREA UNDER THE CURVE; ARTICLE; CLINICAL ARTICLE; CLINICAL TRIAL; CONTROLLED CLINICAL TRIAL; CONTROLLED STUDY; CROSSOVER PROCEDURE; DOSE CALCULATION; DOSE RESPONSE; DRUG BLOOD LEVEL; DRUG EFFECT; DRUG METABOLISM; FEMALE; GERMANY; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; LIQUID CHROMATOGRAPHY; MALE; PRIORITY JOURNAL; PROSPECTIVE STUDY; RACEMIC MIXTURE; TANDEM MASS SPECTROMETRY; TREATMENT PLANNING; WITHDRAWAL SYNDROME;

ADULT; AGED; ANALGESICS, OPIOID; ANTI-HIV AGENTS; AREA UNDER CURVE; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG INTERACTIONS; FEMALE; HEROIN DEPENDENCE; HIV INFECTIONS; HUMANS; MALE; METHADONE; MIDDLE AGED; NEVIRAPINE; STEREOISOMERISM;

EID: 7244226310     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.48.11.4148-4153.2004     Document Type: Article

References (35)

1. Altice, F. L., G. H. Friedland, and E. L. Cooney. 1999. Nevirapine induced opiate withdrawal among injection drug users with HIV infection receiving methadone. AIDS 13:957-962.
2. Bachiller Luque, P., A. M. Flores, M. de Hoyos Llorente, and C. Navarro Canadas. 2000. Methadone withdrawal syndrome induced by nevirapine. Med. Clin. (Barcelona) 114:399. (In Spanish.)
3. Bano Rodrigo, M. D., M. Agujetas Rodriguez, M. L. Lopez Garcia, and J. L. Guillen Llera. 2000. Nevirapine induces abstinence symptoms in patients on a methadone maintenance program with HIV infection. Rev. Clin. Esp. 200:12-14. (In Spanish.)
4. Beckett, A. H., J. F. Taylor, A. F. Casy, and M. M. Hassan. 1968. The biotransformation of methadone in man: synthesis and identification of a major metabolite. J. Pharm. Pharmacol. 20:754-762.
5. Boehringer Ingelheim. 2004. Viramune Produktmonographie. Boehringer Ingelheim, Ingelheim, Germany.
6. Brown, L. S., R. C. Sawyer, R. Li, et al. 1996. Lack of a pharmacologic interaction between rifabutin and methadone in HIV-infected former injecting drug users. Drug Alcohol Depend. 43:71-77.
7. Brunelle, E., M. Rotily, J. R. Caplehorn, and O. H. Drummer. 2002. A cluster of nine overdoses (one fatal) related to methadone in the north of France: a lesson for drug policy in frontier regions. Addiction 97:1221-1223.
8. Cantilena, L., J. McCrea, D. Blazes, et al. 1999. Lack of a pharmacokinetic interaction between indinavir and methadone. Clin. Pharmacol. Ther. 65:135 (abstr. PI-74).
9. Caplehorn, J. R., and O. H. Drummer. 1999. Mortality associated with New South Wales methadone programs in 1994: lives lost and saved. Med J. Aust. 170:104-109.
10. Clarke, S., F. Mulcahy, C. Bergin, H. Reynolds, N. Boyle, M. Barry, and D. J. Back. 2002. Absence of opioid withdrawal symptoms in patients receiving methadone and the protease inhibitor lopinavir-ritonavir. Clin. Infect. Dis. 34:1143-1145.
11. Clarke, S. M., F. M. Mulcahy, J. Tjia, H. E. Reynolds, S. E. Gibbons, M. G. Barry, and D. J. Back. 2001. Pharmacokinetic interactions of nevirapine and methadone and guidelines for use of nevirapine to treat injection drug users. Clin. Infect. Dis. 33:1595-1597.
12. Clarke, S. M., F. M. Mulcahy, J. Tjia, H. E. Reynolds, S. E. Gibbons, M. G. Barry, and D. J. Back. 2001. The pharmacokinetics of methadone in HIV-positive patients receiving the non-nucleoside reverse transcriptase inhibitor efavirenz. Br. J. Clin. Pharmacol. 51:213-217.
13. Eap, C. B., T. Finkbeiner, M. Gastpar, N. Scherbaum, K. Powell, and P. Baumann. 1996. Replacement of (R)-methadone by a double dose of (R,S)-methadone in addicts: interindividual variability of the (R)/(S) ratios and evidence of adaptive changes in methadone pharmacokinetics. Eur. J. Clin. Pharmacol. 50:385-389.
14. Erickson, D. A., G. Mather, W. F. Trager, R. H. Levy, and J. J. Keirns. 1999. Characterization of the in vitro biotransformation of the HIV-1 reverse transcriptase inhibitor nevirapine by human hepatic cytochromes P-450. Drug Metab. Dispos. 27:1488-1495.
15. Foster, D. J., A. A. Somogyi, K. R. Dyer, J. M. White, and F. Bochner. 2000. Steady-state pharmacokinetics of (R)- and (S)-methadone in methadone maintenance patients. Br. J. Clin. Pharmacol. 50:427-440.
16. Gerber, J. G., R. J. Rhodes, and J. Gal. 2004. Stereoselective metabolism of methadone N-demethylation by cytochrome P4502B6 and 2C19. Chirality 16:36-44.
17. Gerber, J. G., S. Rosenkranz, Y. Segal, J. Aberg, R. D'Amico, D. Mildvan, R. Gulick. V. Hughes, C. Flexner, F. Aweeka, A. Hsu, and J. Gal. 2001. Effect of ritonavir/saquinavir on stereoselective pharmacokinetics of methadone: results of AIDS Clinical Trials Group (ACTG) 401. J. Acquir. Immune Defic. Syndr. 27:153-160.
18. Heelon, M. W., and L. B. Meade. 1999. Methadone withdrawal when starting an antiretroviral regimen including nevirapine. Pharmacotherapy 19:471-472.
19. Hendrix, C., J. Wakeford, M. Wire, et al. 2000. Pharmacokinetic and pharmacodynamic evaluation of methadone enantiomers following co-administration with amprenavir in opioid-dependent subjects, abstr. 1649. In Abstracts of the 40th Interscience Conference on Antimicrobial Agents and Chemotherapy. American Society for Microbiology, Washington, D.C.
20. Hsyu, P. H., J. H. Lillibridge, et al. 2000. Pharmacokinetic (PK) and pharmacodynamic (PD) interactions between nelfinavir and methadone. In Abstracts of the Seventh Conference on Retroviruses and Opportunistic Infections, abstr. 87.
21. Iribarne, C., F. Berthou, S. Baird, Y. Dreano, D. Picart, J. P. Bail, P. Beaune, and J. F. Menez. 1996. Involvement of cytochrome P450 3A4 enzyme in the N-demethylation of methadone in human liver microsomes. Chem. Res. Toxicol. 9:365-373.
22. Kristensen, K., T. Blemmer, H. R. Angelo, L. L. Christrup, N. E. Drenck, S. N. Rasmussen, and P. Sjogren. 1996. Stereoselective pharmacokinetics of methadone in chronic pain patients. Ther. Drug Monit. 18:221-227.
23. Lamson, M., T. MacGregor, and P. Riska. 1999. Nevirapine induces both CYP3A4 and CYP2B6 metabolic pathways. Clin. Pharmacol. Ther. 65:137.
24. Lanz, M., and W. Thormann. 1996. Characterization of the Stereoselective metabolism of methadone and its primary metabolite via cyclodextrin capillary electrophoretic determination of their urinary enantiomers. Electrophoresis 17:1945-1949.
25. McCance-Katz, E. F., P. M. Rainey, G. Friedland, and P. Jatlow. 2003. The protease inhibitor lopinavir-ritonavir may produce opiate withdrawal in methadone-maintained patients. Clin. Infect. Dis. 37:476-482.
26. Moody, D. E., M. E. Alburges, R. J. Parker, J. M. Collins, and J. M. Strong. 1997. The involvement of cytochrome P450 3A4 in the N-demethylation of L-alpha-acetylmethadol (LAAM), norLAAM, and methadone. Drug Metab. Dispos. 25:1347-1353.
27. Moya, J., L. Aranzabal, J. L. Casado, S. Diz, C. Quereda, A. Moreno, L. Moreno, M. J. Perez-Elias, A. Antela, A. Marin, and S. Moreno. 2004. HAART-associated hepatotoxicity in HIV/HCV co-infected patients: correlation with liver histologic stage. In Abstracts of the Eleventh Conference on Retroviruses and Opportunistic Infections, abstr. 747.
28. Otero, M. J., A. Fuertes, R. Sanchez, and G. Luna. 1999. Nevirapine-induced withdrawal symptoms in HIV patients on methadone maintenance programme: an alert. AIDS 13:1004-1005.
29. Pinzani, V., V. Faucherre, H. Peyriere, and J. P. Blayac. 2000. Methadone withdrawal symptoms with nevirapine and efavirenz. Ann. Pharmacother. 34:405-407.
30. Pohland, A., H. E. Boaz, and H. R. Sullivan. 1971. Synthesis and identification of metabolites resulting from the biotransformation of DL-methadone in man and in the rat. J. Med. Chem. 14:194-197.
31. Prost, F., and W. Thormann. 2003. Capillary electrophoresis to assess drug metabolism induced in vitro using single CYP450 enzymes (Supersomes): application to the chiral metabolism of mephenytoin and methadone. Electrophoresis 24:2577-2587.
32. Riska, P., M. Lamson, T. MacGregor, J. Sabo, S. Hattox, J. Pav, and J. Keirns. 1999. Disposition and biotransformation of the antiretroviral drug nevirapine in humans. Drug Metab. Dispos. 27:895-901.
33. van Heeswijk, R. P., A. I. Veldkamp, J. W. Mulder, P. L. Meenhorst, F. W. Wit, J. M. Lange, S. A. Danner, N. A. Foudraine, M. O. Kwakkelstein, P. Reiss, J. H. Bcijnen. and R. M. Hoetelmans. 2000. The steady-state pharmacokinetics of nevirapine during once daily and twice daily dosing in HIV-1-infected individuals. AIDS 14:F77-F82.
34. von Moltke, L. L., D. J. Greenblatt, B. W. Granda, G. M. Giancarlo, S. X. Duan, J. P. Daily, J. S. Harmatz, and R. I. Shader. 2001. Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors. J. Clin. Pharmacol. 41:85-91.
35. Wang, J. S., and C. L. DeVane. 2003. Involvement of CYP3A4, CYP2C8, and CYP2D6 in the metabolism of (R)- and (S)-methadone in vitro. Drug Metab. Dispos. 31:742-747.