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Volumn 98, Issue 2, 2009, Pages 583-594

Transdermal delivery of bupropion and its active metabolite, hydroxybupropion: A prodrug strategy as an alternative approach

Author keywords

Bupropion; Guinea pig skin; Human skin; Hydroxybupropion; LC MS; Pharmacokinetics; Prodrug; Transdermal drug delivery

Indexed keywords

AMFEBUTAMONE; DRUG METABOLITE; PRODRUG; RADAFAXINE; CARBAMIC ACID DERIVATIVE; DOPAMINE UPTAKE INHIBITOR; DRUG DERIVATIVE;

EID: 59849117388     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.21463     Document Type: Article
Times cited : (23)

References (36)
  • 2
    • 0032934644 scopus 로고    scopus 로고
    • Noncompetitive functional inhibition at diverse, human nicotinic acetylcholine receptor subtypes by bupropion, phencyclidine, and ibogaine
    • Fryer JD, Lukas RJ. 1999. Noncompetitive functional inhibition at diverse, human nicotinic acetylcholine receptor subtypes by bupropion, phencyclidine, and ibogaine. J Pharmacol Exp Ther 288:88-92.
    • (1999) J Pharmacol Exp Ther , vol.288 , pp. 88-92
    • Fryer, J.D.1    Lukas, R.J.2
  • 3
    • 0036721522 scopus 로고    scopus 로고
    • Bupropion inhibits nicotine-evoked [(3)H]overflow from rat striatal slices preloaded with [(3)H]dopamine and from rat hippocampal slices preloaded with [(3)H]norepinephrine
    • Miller DK, Sumithran SP, Dwoskin LP. 2002. Bupropion inhibits nicotine-evoked [(3)H]overflow from rat striatal slices preloaded with [(3)H]dopamine and from rat hippocampal slices preloaded with [(3)H]norepinephrine. J Pharmacol Exp Ther 302:1113-1122.
    • (2002) J Pharmacol Exp Ther , vol.302 , pp. 1113-1122
    • Miller, D.K.1    Sumithran, S.P.2    Dwoskin, L.P.3
  • 5
    • 0030065670 scopus 로고    scopus 로고
    • 2S,3S,5R)-2-(3,5-difluorophenyl)-3,5-dimethyl-2-morpholinol: A novel antidepressant agent and selective inhibitor of norepinephrine uptake
    • Kelley JL, Musso DL, Boswell GE, Soroko FE, Cooper BR. 1996. (2S,3S,5R)-2-(3,5-difluorophenyl)-3,5-dimethyl-2-morpholinol: A novel antidepressant agent and selective inhibitor of norepinephrine uptake. J Med Chem 39:347-349.
    • (1996) J Med Chem , vol.39 , pp. 347-349
    • Kelley, J.L.1    Musso, D.L.2    Boswell, G.E.3    Soroko, F.E.4    Cooper, B.R.5
  • 7
    • 0025485293 scopus 로고
    • Bupropion dose, seizures, women, and age
    • Goldberg JP. 1990. Bupropion dose, seizures, women, and age. J Clin Psychiatry 51:388-389.
    • (1990) J Clin Psychiatry , vol.51 , pp. 388-389
    • Goldberg, J.P.1
  • 8
    • 60549084129 scopus 로고    scopus 로고
    • Patch and method for transdermal delivery of bupropion base. PAT
    • US Patent No 6, 312, 716
    • Midha KK, Junginger HE, Hirsh M. 2001. Patch and method for transdermal delivery of bupropion base. PAT US Patent No 6, 312, 716.
    • (2001)
    • Midha, K.K.1    Junginger, H.E.2    Hirsh, M.3
  • 9
    • 18744393390 scopus 로고    scopus 로고
    • Exposure measures applied to the bioequivalence of two sustained release formulations of bupropion
    • Midha KK, Rawson MJ, McKay G, Hubbard JW. 2005. Exposure measures applied to the bioequivalence of two sustained release formulations of bupropion. Int J Clin Pharmacol Ther 43:244-254.
    • (2005) Int J Clin Pharmacol Ther , vol.43 , pp. 244-254
    • Midha, K.K.1    Rawson, M.J.2    McKay, G.3    Hubbard, J.W.4
  • 10
    • 60549088463 scopus 로고    scopus 로고
    • Cyclodextrin stabilized pharmaceutical compositions of bupropion hydrochloride
    • US Patent No 6, 462, 237
    • Gidwani SK, Singnurkar P, Tewari PK. 2002. Cyclodextrin stabilized pharmaceutical compositions of bupropion hydrochloride. US Patent No 6, 462, 237.
    • (2002)
    • Gidwani, S.K.1    Singnurkar, P.2    Tewari, P.K.3
  • 11
    • 0033049626 scopus 로고    scopus 로고
    • Metabolism of some "second"-and "fourth"-generation antidepressants: Iprindole, viloxazine, bupropion, mianserin, maprotiline, trazodone, nefazodone, and venlafaxine
    • Rotzinger S, Bourin M, Akimoto Y, Coutts RT, Baker GB. 1999. Metabolism of some "second"-and "fourth"-generation antidepressants: Iprindole, viloxazine, bupropion, mianserin, maprotiline, trazodone, nefazodone, and venlafaxine. Cell Mol Neurobiol 19:427-442.
    • (1999) Cell Mol Neurobiol , vol.19 , pp. 427-442
    • Rotzinger, S.1    Bourin, M.2    Akimoto, Y.3    Coutts, R.T.4    Baker, G.B.5
  • 12
    • 0020608139 scopus 로고
    • Clinical pharmacokinetics of bupropion: A review
    • Lai AA, Schroeder DH. 1983. Clinical pharmacokinetics of bupropion: A review. J Clin Psychiatry 44:82-84.
    • (1983) J Clin Psychiatry , vol.44 , pp. 82-84
    • Lai, A.A.1    Schroeder, D.H.2
  • 17
    • 0022526926 scopus 로고
    • The effect of experimentally-induced renal failure on accumulation of bupropion and its major basic metabolites in plasma and brain of guinea pigs
    • DeVane CL, Laizure SC, Cameron DF. 1986. The effect of experimentally-induced renal failure on accumulation of bupropion and its major basic metabolites in plasma and brain of guinea pigs. Psychopharmacology (Berl) 89:404-408.
    • (1986) Psychopharmacology (Berl) , vol.89 , pp. 404-408
    • DeVane, C.L.1    Laizure, S.C.2    Cameron, D.F.3
  • 18
    • 0030913764 scopus 로고    scopus 로고
    • Enantiomeric determination of the phenylmorpholinol metabolite of bupropion in human plasma using coupled achiral-chiral liquid chromatography
    • Suckow RF, Zhang MF, Cooper TB. 1997. Enantiomeric determination of the phenylmorpholinol metabolite of bupropion in human plasma using coupled achiral-chiral liquid chromatography. Biomed Chromatogr 11:174-179.
    • (1997) Biomed Chromatogr , vol.11 , pp. 174-179
    • Suckow, R.F.1    Zhang, M.F.2    Cooper, T.B.3
  • 19
    • 0021200888 scopus 로고
    • Determination of bupropion and its major basic metabolites in plasma by liquid chromatography with dual-wavelength ultraviolet detection
    • Cooper TB, Suckow RF, Glassman A. 1984. Determination of bupropion and its major basic metabolites in plasma by liquid chromatography with dual-wavelength ultraviolet detection. J Pharm Sci 73:1104-1107.
    • (1984) J Pharm Sci , vol.73 , pp. 1104-1107
    • Cooper, T.B.1    Suckow, R.F.2    Glassman, A.3
  • 20
    • 0028877064 scopus 로고
    • Cyclization-activated prodrugs: N-(substituted 2-hydroxyphenyl and 2-hydroxypropyl)carbamates based on ring-opened derivatives of active benzoxazolones and oxazolidinones as mutual prodrugs of acetaminophen
    • Vigroux A, Bergon M, Zedde C. 1995. Cyclization-activated prodrugs: N-(substituted 2-hydroxyphenyl and 2-hydroxypropyl)carbamates based on ring-opened derivatives of active benzoxazolones and oxazolidinones as mutual prodrugs of acetaminophen. J Med Chem 38:3983-3994.
    • (1995) J Med Chem , vol.38 , pp. 3983-3994
    • Vigroux, A.1    Bergon, M.2    Zedde, C.3
  • 21
    • 0035974621 scopus 로고    scopus 로고
    • New 3′-azido-3′-deoxythymidin-5′-yl O-(4-hydroxyalkyl or -alkenyl or -alkylepoxide) carbonate prodrugs: Synthesis and anti-HIV evaluation
    • Vlieghe P, Clerc T, Pannecouque C, Witvrouw M, De Clercq E, Salles JP, Kraus JL. 2001. New 3′-azido-3′-deoxythymidin-5′-yl O-(4-hydroxyalkyl or -alkenyl or -alkylepoxide) carbonate prodrugs: Synthesis and anti-HIV evaluation. J Med Chem 44:3014-3021.
    • (2001) J Med Chem , vol.44 , pp. 3014-3021
    • Vlieghe, P.1    Clerc, T.2    Pannecouque, C.3    Witvrouw, M.4    De Clercq, E.5    Salles, J.P.6    Kraus, J.L.7
  • 22
    • 33748108652 scopus 로고    scopus 로고
    • Synthesis and hydrolytic behavior of two novel tripartate codrugs of naltrexone and 6beta-naltrexol with hydroxybupropion as potential alcohol abuse and smoking cessation agents
    • Hamad MO, Kiptoo PK, Stinchcomb AL, Crooks PA. 2006. Synthesis and hydrolytic behavior of two novel tripartate codrugs of naltrexone and 6beta-naltrexol with hydroxybupropion as potential alcohol abuse and smoking cessation agents. Bioorg Med Chem 14:7051-7061.
    • (2006) Bioorg Med Chem , vol.14 , pp. 7051-7061
    • Hamad, M.O.1    Kiptoo, P.K.2    Stinchcomb, A.L.3    Crooks, P.A.4
  • 23
    • 33745278513 scopus 로고    scopus 로고
    • Enhancement of transdermal delivery of 6-beta-naltrexol via a codrug linked to hydroxybupropion
    • Kiptoo PK, Hamad MO, Crooks PA, Stinchcomb AL. 2006. Enhancement of transdermal delivery of 6-beta-naltrexol via a codrug linked to hydroxybupropion. J Control Release 113:137-145.
    • (2006) J Control Release , vol.113 , pp. 137-145
    • Kiptoo, P.K.1    Hamad, M.O.2    Crooks, P.A.3    Stinchcomb, A.L.4
  • 25
    • 0033761878 scopus 로고    scopus 로고
    • Normalization of stratum corneum barrier function and transepidermal water loss in vivo
    • Kalia YN, Alberti I, Sekkat N, Curdy C, Naik A, Guy RH. 2000. Normalization of stratum corneum barrier function and transepidermal water loss in vivo. Pharm Res 17:1148-1150.
    • (2000) Pharm Res , vol.17 , pp. 1148-1150
    • Kalia, Y.N.1    Alberti, I.2    Sekkat, N.3    Curdy, C.4    Naik, A.5    Guy, R.H.6
  • 26
    • 3242700655 scopus 로고    scopus 로고
    • Physicochemical evaluation, in vitro human skin diffusion, and concurrent biotransformation of 3-O-alkyl carbonate prodrugs of naltrexone
    • Pillai O, Hamad MO, Crooks PA, Stinchcomb AL. 2004. Physicochemical evaluation, in vitro human skin diffusion, and concurrent biotransformation of 3-O-alkyl carbonate prodrugs of naltrexone. Pharm Res 21:1146-1152.
    • (2004) Pharm Res , vol.21 , pp. 1146-1152
    • Pillai, O.1    Hamad, M.O.2    Crooks, P.A.3    Stinchcomb, A.L.4
  • 28
    • 0026606514 scopus 로고
    • Predicting skin permeability
    • Potts RO, Guy RH. 1992. Predicting skin permeability. Pharm Res 9:663-669.
    • (1992) Pharm Res , vol.9 , pp. 663-669
    • Potts, R.O.1    Guy, R.H.2
  • 29
    • 0032897090 scopus 로고    scopus 로고
    • Correlation of aqueous and lipid solubilities with flux for prodrugs of 5-fluorouracil, theophylline, and 6-mercaptopurine: A Potts-Guy approach
    • Roberts WJ, Sloan KB. 1999. Correlation of aqueous and lipid solubilities with flux for prodrugs of 5-fluorouracil, theophylline, and 6-mercaptopurine: A Potts-Guy approach. J Pharm Sci 88:515-522.
    • (1999) J Pharm Sci , vol.88 , pp. 515-522
    • Roberts, W.J.1    Sloan, K.B.2
  • 30
    • 0029950564 scopus 로고    scopus 로고
    • Epidermal permeability: Penetrant structure relationships. 2. The effect of h-bonding groups in penetrants on their diffusion through the stratum corneum
    • Roberts MS, Pugh WJ, Hadgraft J. 1996. Epidermal permeability: Penetrant structure relationships. 2. The effect of h-bonding groups in penetrants on their diffusion through the stratum corneum. Int J Pharm 132:23-32.
    • (1996) Int J Pharm , vol.132 , pp. 23-32
    • Roberts, M.S.1    Pugh, W.J.2    Hadgraft, J.3
  • 31
    • 0033995212 scopus 로고    scopus 로고
    • Epidermal permeability-penetrant structure relationships: 4, QSAR of permeant diffusion across human stratum corneum in terms of molecular weight, H- bonding and electronic charge
    • Pugh WJ, Degim IT, Hadgraft J. 2000. Epidermal permeability-penetrant structure relationships: 4, QSAR of permeant diffusion across human stratum corneum in terms of molecular weight, H- bonding and electronic charge. Int J Pharm 197:203-211.
    • (2000) Int J Pharm , vol.197 , pp. 203-211
    • Pugh, W.J.1    Degim, I.T.2    Hadgraft, J.3
  • 32
    • 0041825159 scopus 로고    scopus 로고
    • HPLC determination and pharmacokinetics of sustained-release bupropion tablets in dogs
    • Zhang D, Yuan B, Qiao M, Li F. 2003. HPLC determination and pharmacokinetics of sustained-release bupropion tablets in dogs. J Pharm Biomed Anal 33:287-293.
    • (2003) J Pharm Biomed Anal , vol.33 , pp. 287-293
    • Zhang, D.1    Yuan, B.2    Qiao, M.3    Li, F.4
  • 35
    • 0028967706 scopus 로고
    • A high-performance liquid chromatographic method for quantitating bupropion in human plasma or serum
    • Jennison TA, Brown P, Crossett J, Urry FM. 1995. A high-performance liquid chromatographic method for quantitating bupropion in human plasma or serum. J Anal Toxicol 19:69-72.
    • (1995) J Anal Toxicol , vol.19 , pp. 69-72
    • Jennison, T.A.1    Brown, P.2    Crossett, J.3    Urry, F.M.4
  • 36
    • 4043171420 scopus 로고    scopus 로고
    • Pharmacokinetics of bupropion and its metabolites in haemodialysis patients who smoke. A. single dose study
    • Worrall SP, Almond MK, Dhillon S. 2004. Pharmacokinetics of bupropion and its metabolites in haemodialysis patients who smoke. A. single dose study. Nephron Clin Pract 97:c83-c89.
    • (2004) Nephron Clin Pract , vol.97
    • Worrall, S.P.1    Almond, M.K.2    Dhillon, S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.