메뉴 건너뛰기




Volumn 34, Issue 3, 2006, Pages 369-374

In vitro and in vivo evaluation of the metabolism and bioavailability of ester prodrugs of MGS0039 (3-(3,4-dichlorobenzyloxy)-2-amino-6-fluorobicyclo[3. 1.0]hexane-2,6-dicarboxylic acid), a potent metabotropic glutamate receptor antagonist

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 3 (3,4 DICHLOROBENZYLOXY) 6 FLUOROBICYCLO[3.1.0]HEXANE 2,6 DICARBOXYLIC ACID; ESTER DERIVATIVE; LIVER ENZYME; METABOTROPIC RECEPTOR ANTAGONIST; MGS 0096; MGS 0097; MGS 0103; MGS 0105; MGS 0111; MGS 0112; MGS 0113; MGS 0114; MGS 0115; MGS 0116; MGS 0117; MGS 0144; MGS 0155; MGS 0200; MGS 0201; MGS 0209; MGS 0210; MGS 0211; MGS 0212; MGS 0213; MGS 0215; MGS 0217; PRODRUG; UNCLASSIFIED DRUG;

EID: 33344473087     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: 10.1124/dmd.105.006213     Document Type: Article
Times cited : (15)

References (30)
  • 1
    • 0346958512 scopus 로고    scopus 로고
    • Design of ester prodrugs to enhance oral absorption of poorly permeable compounds: Challenges to the discovery scientist
    • Beaumont K, Webster R, Gardner I, and Dack K (2003) Design of ester prodrugs to enhance oral absorption of poorly permeable compounds: challenges to the discovery scientist. Curr Drug Metab 4:461-485.
    • (2003) Curr Drug Metab , vol.4 , pp. 461-485
    • Beaumont, K.1    Webster, R.2    Gardner, I.3    Dack, K.4
  • 2
    • 0036175724 scopus 로고    scopus 로고
    • Physicochemical aspects of the enzymatic hydrolysis of carboxylic esters
    • Buchwald P and Bodor N (2002) Physicochemical aspects of the enzymatic hydrolysis of carboxylic esters. Pharmazie 57:87-93.
    • (2002) Pharmazie , vol.57 , pp. 87-93
    • Buchwald, P.1    Bodor, N.2
  • 3
    • 0034068655 scopus 로고    scopus 로고
    • Attenuation of specific PCP-evoked behaviors by the potent mGlu2/3 receptor agonist, LY379268 and comparison with the atypical antipsychotic, clozapine
    • Cartmell J, Monn JA, and Schoepp DD (2000) Attenuation of specific PCP-evoked behaviors by the potent mGlu2/3 receptor agonist, LY379268 and comparison with the atypical antipsychotic, clozapine. Psychopharmacology 148:423-429.
    • (2000) Psychopharmacology , vol.148 , pp. 423-429
    • Cartmell, J.1    Monn, J.A.2    Schoepp, D.D.3
  • 5
    • 0030995878 scopus 로고    scopus 로고
    • Pharmacology and functions of metabotropic glutamate receptors
    • Conn PJ and Pin JP (1997) Pharmacology and functions of metabotropic glutamate receptors. Annu Rev Pharmacol Toxicol 37:205-237.
    • (1997) Annu Rev Pharmacol Toxicol , vol.37 , pp. 205-237
    • Conn, P.J.1    Pin, J.P.2
  • 6
    • 0029101703 scopus 로고
    • Species dependent esterase activities for hydrolysis of an anti-HIV prodrug glycovir and bioavailability of active SC-48334
    • Cook CS, Karabatsos PJ, Schoenhard GL, and Karim A (1995) Species dependent esterase activities for hydrolysis of an anti-HIV prodrug glycovir and bioavailability of active SC-48334. Pharm Res (NY) 12:1158-1164.
    • (1995) Pharm Res (NY) , vol.12 , pp. 1158-1164
    • Cook, C.S.1    Karabatsos, P.J.2    Schoenhard, G.L.3    Karim, A.4
  • 8
    • 0041488670 scopus 로고    scopus 로고
    • Anxiolytic effects of a novel group II metabotropic glutamate receptor agonist (LY354740) in the fear-potentiated startle paradigm in humans
    • Grillon C, Cordova J, Levine LR, and Morgan CA 3rd (2003) Anxiolytic effects of a novel group II metabotropic glutamate receptor agonist (LY354740) in the fear-potentiated startle paradigm in humans. Psychopharmacology 168:446-454.
    • (2003) Psychopharmacology , vol.168 , pp. 446-454
    • Grillon, C.1    Cordova, J.2    Levine, L.R.3    Morgan III, C.A.4
  • 9
    • 0031933951 scopus 로고    scopus 로고
    • Anxiolytic and side-effect profile of LY354740: A potent, highly selective, orally active agonist for group II metabotropic glutamate receptors
    • Helton DR, Tizzano JP, Monn JA, Schoepp DD, and Kallman MJ (1998) Anxiolytic and side-effect profile of LY354740: a potent, highly selective, orally active agonist for group II metabotropic glutamate receptors. J Pharmacol Exp Ther 284:651-660.
    • (1998) J Pharmacol Exp Ther , vol.284 , pp. 651-660
    • Helton, D.R.1    Tizzano, J.P.2    Monn, J.A.3    Schoepp, D.D.4    Kallman, M.J.5
  • 10
    • 0018386988 scopus 로고
    • Species difference and characterization of intestinal esterase on the hydrolyzing activity of ester-type drugs
    • Inoue M, Morikawa M, Tsuboi M, and Sugiura M (1979) Species difference and characterization of intestinal esterase on the hydrolyzing activity of ester-type drugs. Jpn J Pharmacol 29:9-16.
    • (1979) Jpn J Pharmacol , vol.29 , pp. 9-16
    • Inoue, M.1    Morikawa, M.2    Tsuboi, M.3    Sugiura, M.4
  • 11
    • 0038017205 scopus 로고    scopus 로고
    • The mGluR2/3 receptor antagonist, LY354740, reduces panic anxiety induced by a CO2 challenge in patients diagnosed with panic disorder
    • Levine L, Gaydos B, Sheehan D, Goddard A, Feighner J, Potter WZ, and Schoepp DD (2002) The mGluR2/3 receptor antagonist, LY354740, reduces panic anxiety induced by a CO2 challenge in patients diagnosed with panic disorder. Neuropharmacology 43:294-295.
    • (2002) Neuropharmacology , vol.43 , pp. 294-295
    • Levine, L.1    Gaydos, B.2    Sheehan, D.3    Goddard, A.4    Feighner, J.5    Potter, W.Z.6    Schoepp, D.D.7
  • 13
    • 0023708137 scopus 로고
    • Species difference in the hydrolysis of meperidine and its inhibition by organophosphate compounds
    • Luttrell WE and Castle MC (1988) Species difference in the hydrolysis of meperidine and its inhibition by organophosphate compounds. Fundam Appl Toxicol 11:323-332.
    • (1988) Fundam Appl Toxicol , vol.11 , pp. 323-332
    • Luttrell, W.E.1    Castle, M.C.2
  • 14
    • 0032575715 scopus 로고    scopus 로고
    • Reversal of phencyclidine effects by a group II metabotropic glutamate receptor agonist in rats
    • Moghaddam B and Adams BW (1998) Reversal of phencyclidine effects by a group II metabotropic glutamate receptor agonist in rats. Science (Wash DC) 281:1349-1352.
    • (1998) Science (Wash DC) , vol.281 , pp. 1349-1352
    • Moghaddam, B.1    Adams, B.W.2
  • 15
    • 15644369847 scopus 로고    scopus 로고
    • Design, synthesis, and pharmacological characterization of (+)-2aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740): A potent, selective and orally active group 2 metabotropic glutamate receptor agonist possessing anticonvulsant and anxiolytic properties
    • Monn JA, Valli MJ, Massey SM, Wright RA, Salhoff CR, Johnson BG, Howe T, Alt CA, Rhodes GA, Robey RL, et al. (1997) Design, synthesis, and pharmacological characterization of (+)-2aminobicyclo[3.1.0]hexane-2,6- dicarboxylic acid (LY354740): a potent, selective and orally active group 2 metabotropic glutamate receptor agonist possessing anticonvulsant and anxiolytic properties. J Med Chem 40:528-537.
    • (1997) J Med Chem , vol.40 , pp. 528-537
    • Monn, J.A.1    Valli, M.J.2    Massey, S.M.3    Wright, R.A.4    Salhoff, C.R.5    Johnson, B.G.6    Howe, T.7    Alt, C.A.8    Rhodes, G.A.9    Robey, R.L.10
  • 16
    • 0016980851 scopus 로고
    • Substrate specificity of carboxylesterase from several animals
    • Morikawa M, Inoue M, and Tsuboi M (1976) Substrate specificity of carboxylesterase from several animals. Chem Pharm Bull 24:1661-1664.
    • (1976) Chem Pharm Bull , vol.24 , pp. 1661-1664
    • Morikawa, M.1    Inoue, M.2    Tsuboi, M.3
  • 17
    • 0034649605 scopus 로고    scopus 로고
    • Synthesis, SARs, and pharmacological characterization of 2-amino-3 or 6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives as potent, selective and orally active group II metabotropic glutamate receptor agonists
    • Nakazato A, Kumagai T, Sakagami K, Yoshikawa R, Suzuki Y, Chaki S, Ito H, Taguchi S, Nakanishi S, and Okuyama S (2000) Synthesis, SARs, and pharmacological characterization of 2-amino-3 or 6-fluorobicyclo[3.1.0]hexane-2, 6-dicarboxylic acid derivatives as potent, selective and orally active group II metabotropic glutamate receptor agonists. J Med Chem 43:4893-4909.
    • (2000) J Med Chem , vol.43 , pp. 4893-4909
    • Nakazato, A.1    Kumagai, T.2    Sakagami, K.3    Yoshikawa, R.4    Suzuki, Y.5    Chaki, S.6    Ito, H.7    Taguchi, S.8    Nakanishi, S.9    Okuyama, S.10
  • 18
    • 4143152743 scopus 로고    scopus 로고
    • Synthesis, in vitro pharmacology, structure-activity relationships and pharmacokinetics of 3-alkoxy-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6- dicarboxylic acid derivatives as potent and selective group II metabotropic glutamate receptor antagonists
    • Nakazato A, Sakagami K, Yasuhara A, Ohta H, Yoshikawa R, Itoh M, Nakamura M, and Chaki S (2004) Synthesis, in vitro pharmacology, structure-activity relationships and pharmacokinetics of 3-alkoxy-2-amino-6-fluorobicyclo[3.1.0] hexane-2,6-dicarboxylic acid derivatives as potent and selective group II metabotropic glutamate receptor antagonists. J Med Chem 47:4570-4587.
    • (2004) J Med Chem , vol.47 , pp. 4570-4587
    • Nakazato, A.1    Sakagami, K.2    Yasuhara, A.3    Ohta, H.4    Yoshikawa, R.5    Itoh, M.6    Nakamura, M.7    Chaki, S.8
  • 19
    • 14444286701 scopus 로고    scopus 로고
    • 2-Substituted (2SR)-2-amino-2-((1SR,2SR)-2-carboxycycloprop-1-yl)glycines as potent and selective antagonists of group II metabotropic glutamate receptors. 2. Effects of aromatic substitution, pharmacological characterization and bioavailability
    • Ornstein PL, Bleisch TJ, Arnold MB, Kennedy JH, Wright RA, Johnson BG, Tizzano JP, Helton DR, Kallman MJ, Schoepp DD, et al. (1998a) 2-Substituted (2SR)-2-amino-2-((1SR,2SR)-2-carboxycycloprop-1-yl)glycines as potent and selective antagonists of group II metabotropic glutamate receptors. 2. Effects of aromatic substitution, pharmacological characterization and bioavailability. J Med Chem 41:358-378.
    • (1998) J Med Chem , vol.41 , pp. 358-378
    • Ornstein, P.L.1    Bleisch, T.J.2    Arnold, M.B.3    Kennedy, J.H.4    Wright, R.A.5    Johnson, B.G.6    Tizzano, J.P.7    Helton, D.R.8    Kallman, M.J.9    Schoepp, D.D.10
  • 20
    • 0032576734 scopus 로고    scopus 로고
    • 2-Substituted (2SR)-2-amino-2-((1SR,2SR)-2-carboxycycloprop-1-yl)glycines as potent and selective antagonists of group II metabotropic glutamate receptors. 1. Effects of alkyl, arylalkyl and diarylalkyl substitution
    • Ornstein PL, Bleisch TJ, Arnold MB, Wright RA, Johnson BG, and Schoepp DD (1998b) 2-Substituted (2SR)-2-amino-2-((1SR,2SR)-2-carboxycycloprop-1-yl) glycines as potent and selective antagonists of group II metabotropic glutamate receptors. 1. Effects of alkyl, arylalkyl and diarylalkyl substitution. J Med Chem 41:346-357.
    • (1998) J Med Chem , vol.41 , pp. 346-357
    • Ornstein, P.L.1    Bleisch, T.J.2    Arnold, M.B.3    Wright, R.A.4    Johnson, B.G.5    Schoepp, D.D.6
  • 21
    • 0032467053 scopus 로고    scopus 로고
    • Glutamate in CNS disorders as a target for drug development: An update
    • Parsons CG, Danysz W, and Quack G (1998) Glutamate in CNS disorders as a target for drug development: an update. Drug News Perspect 11:523-579.
    • (1998) Drug News Perspect , vol.11 , pp. 523-579
    • Parsons, C.G.1    Danysz, W.2    Quack, G.3
  • 22
    • 0026542513 scopus 로고
    • The metabotropic glutamate receptors: Structure and functions
    • Pin JP and Duvoisin R (1992) The metabotropic glutamate receptors: structure and functions. J Nerochem 58:1184-1186.
    • (1992) J Nerochem , vol.58 , pp. 1184-1186
    • Pin, J.P.1    Duvoisin, R.2
  • 24
    • 0029998275 scopus 로고    scopus 로고
    • Comparative studies of drug-metabolizing enzymes in dog, monkey, and human small intestines and in Caco-2 cells
    • Prueksaritanont T, Gorham LM, Hochman JH, Tran LO, and Vyas KP (1996b) Comparative studies of drug-metabolizing enzymes in dog, monkey, and human small intestines and in Caco-2 cells. Drug Metab Dispos 24:634-642.
    • (1996) Drug Metab Dispos , vol.24 , pp. 634-642
    • Prueksaritanont, T.1    Gorham, L.M.2    Hochman, J.H.3    Tran, L.O.4    Vyas, K.P.5
  • 25
    • 0023901668 scopus 로고
    • Species differences in the stereoselective hydrolysis of esmol by blood esterases
    • Quon CY, Mai K, Patil G, and Stampfi HF (1988) Species differences in the stereoselective hydrolysis of esmol by blood esterases. Drug Metab Dispos 16:425-428.
    • (1988) Drug Metab Dispos , vol.16 , pp. 425-428
    • Quon, C.Y.1    Mai, K.2    Patil, G.3    Stampfi, H.F.4
  • 27
    • 0027395275 scopus 로고
    • Metabotropic glutamate receptors in brain function and pathology
    • Schoepp DD and Conn PJ (1993) Metabotropic glutamate receptors in brain function and pathology. Trends Pharmacol Sci 14:13-20.
    • (1993) Trends Pharmacol Sci , vol.14 , pp. 13-20
    • Schoepp, D.D.1    Conn, P.J.2
  • 29
    • 0035996365 scopus 로고    scopus 로고
    • The anxiolytic action of mGlu2/3 receptor agonist, LY354740, in the fear-potentiated startle model in rats is mechanistically distinct from diazepam
    • Tizzano JP, Griffey KI, and Schoepp DD (2002) The anxiolytic action of mGlu2/3 receptor agonist, LY354740, in the fear-potentiated startle model in rats is mechanistically distinct from diazepam. Pharmacol Biochem Behav 73:367-374.
    • (2002) Pharmacol Biochem Behav , vol.73 , pp. 367-374
    • Tizzano, J.P.1    Griffey, K.I.2    Schoepp, D.D.3
  • 30
    • 0026487058 scopus 로고
    • Human P-glycoprotein transports cortisol, aldosterone and dexamethasone, but not progesterone
    • Ueda K, Okamura N, Hirai M, Tanigawara Y, Saeki T, Komano T, and Hori R (1992) Human P-glycoprotein transports cortisol, aldosterone and dexamethasone, but not progesterone. J Biol Chem 267:24248-24252.
    • (1992) J Biol Chem , vol.267 , pp. 24248-24252
    • Ueda, K.1    Okamura, N.2    Hirai, M.3    Tanigawara, Y.4    Saeki, T.5    Komano, T.6    Hori, R.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.