메뉴 건너뛰기




Volumn 311, Issue 1, 2004, Pages 315-323

XP13512 [(±)-1-([(α-isobutanoyloxyethoxy)carbonyl] aminomethyl)-1-cyclohexane acetic acid], a novel gabapentin prodrug: I. Design, synthesis, enzymatic conversion to gabapentin, and transport by intestinal solute transporters

Author keywords

[No Author keywords available]

Indexed keywords

1 [[(ALPHA ISOBUTANOYLOXYETHOXY)CARBONYL]AMINOMETHYL] 1 CYCLOHEXANE ACETIC ACID; ACETIC ACID DERIVATIVE; CARBON 14; CYTOCHROME P450; GABAPENTIN; ISOPROTEIN; LACTIC ACID; PRODRUG; UNCLASSIFIED DRUG; XP 13512; 1 (((ALPHA ISOBUTANOYLOXYETHOXY)CARBONYL)AMINOMETHYL) 1 CYCLOHEXANEACETIC ACID; 1-(((ALPHA-ISOBUTANOYLOXYETHOXY)CARBONYL)AMINOMETHYL)-1-CYCLOHEXANEACETIC ACID; 4 AMINOBUTYRIC ACID; AMINE; AMINO ACID TRANSPORTER; BIOTIN TRANSPORTER; CARBAMIC ACID DERIVATIVE; COTRANSPORTER; CYCLOHEXANECARBOXYLIC ACID DERIVATIVE; DRUG DERIVATIVE; MONOCARBOXYLATE TRANSPORTER;

EID: 4644328982     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: 10.1124/jpet.104.067934     Document Type: Article
Times cited : (149)

References (41)
  • 1
    • 0000658454 scopus 로고
    • (Acyloxy)alkyl carbamates as novel bioreversible prodrugs for amines: Increased permeation through biological membranes
    • Alexander J, Cargill R, Michelson SR, and Schwam H (1988) (Acyloxy)alkyl carbamates as novel bioreversible prodrugs for amines: increased permeation through biological membranes. J Med Chem 31:318-322.
    • (1988) J Med Chem , vol.31 , pp. 318-322
    • Alexander, J.1    Cargill, R.2    Michelson, S.R.3    Schwam, H.4
  • 2
    • 0032477294 scopus 로고    scopus 로고
    • Gabapentin for the symptomatic treatment of painful neuropathy in patients with diabetes mellitus: A randomized controlled trial
    • Backonja M, Beydoun A, Edwards KR, Schwartz SL, Fonseca V, Hes M, LaMoreaux L, and Garofalo E (1998) Gabapentin for the symptomatic treatment of painful neuropathy in patients with diabetes mellitus: a randomized controlled trial. J Am Med Assoc 280:1831-1836.
    • (1998) J Am Med Assoc , vol.280 , pp. 1831-1836
    • Backonja, M.1    Beydoun, A.2    Edwards, K.R.3    Schwartz, S.L.4    Fonseca, V.5    Hes, M.6    LaMoreaux, L.7    Garofalo, E.8
  • 5
    • 0032958091 scopus 로고    scopus 로고
    • Effects of age and gender on single-dose pharmacokinetics of gabapentin
    • Boyd RA, Turck D, Abel RB, Sedman AJ, and Bockbrader HN (1999) Effects of age and gender on single-dose pharmacokinetics of gabapentin. Epilepsia 40:474-479.
    • (1999) Epilepsia , vol.40 , pp. 474-479
    • Boyd, R.A.1    Turck, D.2    Abel, R.B.3    Sedman, A.J.4    Bockbrader, H.N.5
  • 6
    • 0022357922 scopus 로고
    • Measurement of rat-intestinal cefuroxime axetil esterase activity: Comparison of an HPLC and coupled-enzyme assay
    • Campbell CJ and Langley C (1985) Measurement of rat-intestinal cefuroxime axetil esterase activity: comparison of an HPLC and coupled-enzyme assay. Xenobiotica 15:1011-1019.
    • (1985) Xenobiotica , vol.15 , pp. 1011-1019
    • Campbell, C.J.1    Langley, C.2
  • 7
    • 4644251930 scopus 로고    scopus 로고
    • XP13512 [(±)-1-([(α-isobutanoyloxyethoxy)carbonyl] aminomethyl)-1-cyclohexane acetic acid], a novel gabapentin prodrug: II. Improved oral bioavailability, dose proportionality, and colonic absorption compared with gabapentin in rats and monkeys
    • Cundy KC, Annamalai T, Bu L, De Vera J, Estrela J, Luo W, Shirsat P, Torneros A, Yao F, Zou J, et al. (2004) XP13512 [(±)-1-([(α- isobutanoyloxyethoxy)carbonyl]aminomethyl)-1-cyclohexane acetic acid], a novel gabapentin prodrug: II. improved oral bioavailability, dose proportionality, and colonic absorption compared with gabapentin in rats and monkeys. J Pharmacol Exp Ther 311:324-333.
    • (2004) J Pharmacol Exp Ther , vol.311 , pp. 324-333
    • Cundy, K.C.1    Annamalai, T.2    Bu, L.3    De Vera, J.4    Estrela, J.5    Luo, W.6    Shirsat, P.7    Torneros, A.8    Yao, F.9    Zou, J.10
  • 9
    • 0043212093 scopus 로고    scopus 로고
    • Molecular features, regulation and function of monocarboxylate transporters: Implications for drug delivery
    • Enerson BE and Drewes LR (2003) Molecular features, regulation and function of monocarboxylate transporters: implications for drug delivery. J Pharm Sci 92: 1531-1544.
    • (2003) J Pharm Sci , vol.92 , pp. 1531-1544
    • Enerson, B.E.1    Drewes, L.R.2
  • 13
    • 0036168946 scopus 로고    scopus 로고
    • Clinical pharmacokinetics of candesartan
    • Gleiter CH and Morike KE (2002) Clinical pharmacokinetics of candesartan. Clin Pharmacokinet 41:7-17.
    • (2002) Clin Pharmacokinet , vol.41 , pp. 7-17
    • Gleiter, C.H.1    Morike, K.E.2
  • 14
    • 0037311026 scopus 로고    scopus 로고
    • Gabapentin's effects on hot flashes in postmenopausal women: A randomized controlled trial
    • Guttuso T Jr, Kurlan R, McDermott MP, and Kieburtz K (2003) Gabapentin's effects on hot flashes in postmenopausal women: a randomized controlled trial. Obstet Gynecol 101:337-345.
    • (2003) Obstet Gynecol , vol.101 , pp. 337-345
    • Guttuso Jr., T.1    Kurlan, R.2    McDermott, M.P.3    Kieburtz, K.4
  • 15
    • 0033569442 scopus 로고    scopus 로고
    • The proton-linked monocarboxylate transporter (MCT) familiy: Structure, function and regulation
    • Halestrap AP and Price NT (1999) The proton-linked monocarboxylate transporter (MCT) familiy: structure, function and regulation. Biochem J 343:281-299.
    • (1999) Biochem J , vol.343 , pp. 281-299
    • Halestrap, A.P.1    Price, N.T.2
  • 19
    • 0032819783 scopus 로고    scopus 로고
    • Gabapentin in the management of convulsive disorders
    • McLean MJ (1999) Gabapentin in the management of convulsive disorders. Epilepsia 40 (Suppl 6):S39-S50.
    • (1999) Epilepsia , vol.40 , Issue.SUPPL. 6
    • McLean, M.J.1
  • 20
    • 0029057902 scopus 로고
    • Gabapentin
    • McLean MJ (1995) Gabapentin. Epilepsia 36 (Suppl 2):S73-S86.
    • (1995) Epilepsia , vol.36 , Issue.SUPPL. 2
    • McLean, M.J.1
  • 21
    • 0031802463 scopus 로고    scopus 로고
    • Gabapentin as a potential treatment for anxiety disorders
    • Pollack MH, Matthews J, and Scott EL (1998) Gabapentin as a potential treatment for anxiety disorders. Am J Psychiatry 155:992-993.
    • (1998) Am J Psychiatry , vol.155 , pp. 992-993
    • Pollack, M.H.1    Matthews, J.2    Scott, E.L.3
  • 22
    • 0033957622 scopus 로고    scopus 로고
    • Gabapentin-lactam, a close analogue of the anticonvulsant gabapentin, exerts convulsant activity in amygdala kindled rats
    • Potschka H, Feuerstein TJ, and Loscher W (2000) Gabapentin-lactam, a close analogue of the anticonvulsant gabapentin, exerts convulsant activity in amygdala kindled rats. Naunyn Schmiedebergs Arch Pharmacol 361:200-205.
    • (2000) Naunyn Schmiedebergs Arch Pharmacol , vol.361 , pp. 200-205
    • Potschka, H.1    Feuerstein, T.J.2    Loscher, W.3
  • 26
    • 0031951397 scopus 로고    scopus 로고
    • Metabolism and pharmacokinetics of sucrose acetate isobutyrate (SAIB) and sucrose octa-isobutyrate (SOIB) in rats, dogs, monkeys or humans: A review
    • Reynolds RC (1998) Metabolism and pharmacokinetics of sucrose acetate isobutyrate (SAIB) and sucrose octa-isobutyrate (SOIB) in rats, dogs, monkeys or humans: a review. Food Chem Toxicol 36:95-99.
    • (1998) Food Chem Toxicol , vol.36 , pp. 95-99
    • Reynolds, R.C.1
  • 27
    • 0034750718 scopus 로고    scopus 로고
    • Gabapentin in postherpetic neuralgia: A randomised, double blind, placebo controlled study
    • Rice AS and Maton S; Postherpetic Neuralgia Study Group (2001) Gabapentin in postherpetic neuralgia: a randomised, double blind, placebo controlled study. Pain 94:215-224.
    • (2001) Pain , vol.94 , pp. 215-224
    • Rice, A.S.1    Maton, S.2
  • 28
    • 0041384468 scopus 로고    scopus 로고
    • The impact of reducing dose frequency on health outcomes
    • Richter A, Anton SE, Koch P, and Dennett SL (2003) The impact of reducing dose frequency on health outcomes. Clin Ther 25:2307-2335.
    • (2003) Clin Ther , vol.25 , pp. 2307-2335
    • Richter, A.1    Anton, S.E.2    Koch, P.3    Dennett, S.L.4
  • 29
    • 0032477305 scopus 로고    scopus 로고
    • Gabapentin for the treatment of postherpetic neuralgia: A randomized controlled trial
    • Rowbotham M, Harden N, Stacey B, Bernstein P, and Magnus-Miller L (1998) Gabapentin for the treatment of postherpetic neuralgia: a randomized controlled trial. J Am Med Assoc 280:1837-1842.
    • (1998) J Am Med Assoc , vol.280 , pp. 1837-1842
    • Rowbotham, M.1    Harden, N.2    Stacey, B.3    Bernstein, P.4    Magnus-Miller, L.5
  • 30
    • 0031790299 scopus 로고    scopus 로고
    • Biotin uptake by human colonic epithelial NCM460 cells: A carrier-mediated process shared with pantothenic acid
    • Said HM, Ortiz A, McCloud E, Dyer D, Moyer MP, and Rubin S (1998) Biotin uptake by human colonic epithelial NCM460 cells: a carrier-mediated process shared with pantothenic acid. Am J Physiol 275:C1365-C1371.
    • (1998) Am J Physiol , vol.275
    • Said, H.M.1    Ortiz, A.2    McCloud, E.3    Dyer, D.4    Moyer, M.P.5    Rubin, S.6
  • 32
    • 0036146331 scopus 로고    scopus 로고
    • Tissue distribution and renal developmental changes in rat organic cation transporter mRNA levels
    • Slitt AL, Cherrington NJ, Hartley DP, Leazer TM, and Klaassen CD (2002) Tissue distribution and renal developmental changes in rat organic cation transporter mRNA levels. Drug Metab Dispos 30:212-219.
    • (2002) Drug Metab Dispos , vol.30 , pp. 212-219
    • Slitt, A.L.1    Cherrington, N.J.2    Hartley, D.P.3    Leazer, T.M.4    Klaassen, C.D.5
  • 34
    • 0033948189 scopus 로고    scopus 로고
    • Short-chain fatty acid (SCFA) uptake into Caco-2 cells by a pH-dependent and carrier mediated transport mechanism
    • Stein J, Zores M, and Schroder O (2000) Short-chain fatty acid (SCFA) uptake into Caco-2 cells by a pH-dependent and carrier mediated transport mechanism. Eur J Nutr 39:121-125.
    • (2000) Eur J Nutr , vol.39 , pp. 121-125
    • Stein, J.1    Zores, M.2    Schroder, O.3
  • 36
    • 0027402753 scopus 로고
    • A saturable transport mechanism in the intestinal absorption of gabapentin is the underlying cause of the lack of proportionality between increasing dose and drug levels in plasma
    • Stewart BH, Kugler AR, Thompson PR, and Bockbrader HN (1993) A saturable transport mechanism in the intestinal absorption of gabapentin is the underlying cause of the lack of proportionality between increasing dose and drug levels in plasma. Pharm Res (NY) 10:276-281.
    • (1993) Pharm Res (NY) , vol.10 , pp. 276-281
    • Stewart, B.H.1    Kugler, A.R.2    Thompson, P.R.3    Bockbrader, H.N.4
  • 37
    • 0035834179 scopus 로고    scopus 로고
    • Optimized conditions of bio-mimetic artificial membrane permeation assay
    • Sugano K, Hamada H, Machida M, Ushio H, Saitoh K, and Terada K (2001) Optimized conditions of bio-mimetic artificial membrane permeation assay. Int J Pharm 228:181-188.
    • (2001) Int J Pharm , vol.228 , pp. 181-188
    • Sugano, K.1    Hamada, H.2    Machida, M.3    Ushio, H.4    Saitoh, K.5    Terada, K.6
  • 38
    • 0032493741 scopus 로고    scopus 로고
    • Molecular and functional identification of sodium ion-dependent, high affinity human carnitine transporter OCTN2
    • Tamai I, Ohashi R, Nezu J, Yabuuchi H, Oku A, Shimane M, Sai Y, and Tsuji A (1998) Molecular and functional identification of sodium ion-dependent, high affinity human carnitine transporter OCTN2. J Biol Chem 273:20378-20382.
    • (1998) J Biol Chem , vol.273 , pp. 20378-20382
    • Tamai, I.1    Ohashi, R.2    Nezu, J.3    Yabuuchi, H.4    Oku, A.5    Shimane, M.6    Sai, Y.7    Tsuji, A.8
  • 40
    • 0036208155 scopus 로고    scopus 로고
    • Transport of amino acid-related compounds mediated by L-type amino acid transporter 1 (LAT1): Insights into the mechanisms of substrate recognition
    • Uchino H, Kanai Y, Kim do K, Wempe MF, Chairoungdua A, Morimoto E, Anders MW, and Endou H (2002) Transport of amino acid-related compounds mediated by L-type amino acid transporter 1 (LAT1): insights into the mechanisms of substrate recognition. Mol Pharmacol 61:729-737.
    • (2002) Mol Pharmacol , vol.61 , pp. 729-737
    • Uchino, H.1    Kanai, Y.2    Kim Do, K.3    Wempe, M.F.4    Chairoungdua, A.5    Morimoto, E.6    Anders, M.W.7    Endou, H.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.