메뉴 건너뛰기




Volumn 38, Issue 9, 2010, Pages 1522-1531

Novel metabolic bioactivation mechanism for a series of anti-inflammatory agents (2,5-diaminothiophene derivatives) mediated by cytochrome P450 enzymes

Author keywords

[No Author keywords available]

Indexed keywords

(2,4 DIAMINOTHIOPHENE,1 [2 CARBAMOYL 5 (QUINOLINE 4 CARBOXAMIDO)THIOPHEN 3 YL]UREA; (2,5 DIAMINOTHIOPHENE), 1 [3 CARBAMOYL 5 (2,3,5 TRICHLOROBENZAMIDO)THIOPHEN 2 YL]UREA; 1 [3 CARBAMOYL 5 [(3 CHLOROPHENYL)CARBAMOYL]THIOPHEN 2 YL]UREA; 2,5 DIAMINOTHIOPHENE; 2,5 DIAMINOTHIOPHENE DERIVATIVE; 2,5 DIIMINE THIOPHENE; ACETYLCYSTEINE; ANTIINFLAMMATORY AGENT; CYTOCHROME P450; CYTOCHROME P450 1A2; CYTOCHROME P450 2C; CYTOCHROME P450 2D6; CYTOCHROME P450 3A4; GLUTATHIONE; THIOPHENE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 77955987697     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.110.032581     Document Type: Article
Times cited : (16)

References (38)
  • 1
    • 62249155473 scopus 로고    scopus 로고
    • Can in vitro metabolism-dependent covalent binding data distinguish hepatotoxic from non-hepatotoxic drugs? An analysis using human hepatocytes and liver S-9 fraction
    • Bauman JN, Kelly JM, Tripathy S, Zhao SX, Lam WW, Kalgutkar AS, and Obach RS (2009) Can in vitro metabolism-dependent covalent binding data distinguish hepatotoxic from non-hepatotoxic drugs? An analysis using human hepatocytes and liver S-9 fraction. Chem Res Toxicol 22:332-340.
    • (2009) Chem Res Toxicol , vol.22 , pp. 332-340
    • Bauman, J.N.1    Kelly, J.M.2    Tripathy, S.3    Zhao, S.X.4    Lam, W.W.5    Kalgutkar, A.S.6    Obach, R.S.7
  • 2
    • 0242668517 scopus 로고
    • Human anti-endoplasmic reticulum autoantibodies appearing in a drug-induced hepatitis are directed against a human liver cytochrome P-450 that hydroxylates the drug
    • Beaune P, Dansette PM, Mansuy D, Kiffel L, Finck M, Amar C, Leroux JP, and Homberg JC (1987) Human anti-endoplasmic reticulum autoantibodies appearing in a drug-induced hepatitis are directed against a human liver cytochrome P-450 that hydroxylates the drug. Proc Natl Acad Sci USA 84:551-555.
    • (1987) Proc Natl Acad Sci USA , vol.84 , pp. 551-555
    • Beaune, P.1    Dansette, P.M.2    Mansuy, D.3    Kiffel, L.4    Finck, M.5    Amar, C.6    Leroux, J.P.7    Homberg, J.C.8
  • 3
    • 0032978204 scopus 로고    scopus 로고
    • Opposite behaviors of reactive metabolites of tienilic acid and its isomer toward liver proteins: Use of specific anti-tienilic acid-protein adduct antibodies and the possible relationship with different hepatotoxic effects of the two compounds
    • Bonierbale E, Valadon P, Pons C, Desfosses B, Dansette PM, and Mansuy D (1999) Opposite behaviors of reactive metabolites of tienilic acid and its isomer toward liver proteins: use of specific anti-tienilic acid-protein adduct antibodies and the possible relationship with different hepatotoxic effects of the two compounds. Chem Res Toxicol 12:286-296.
    • (1999) Chem Res Toxicol , vol.12 , pp. 286-296
    • Bonierbale, E.1    Valadon, P.2    Pons, C.3    Desfosses, B.4    Dansette, P.M.5    Mansuy, D.6
  • 5
    • 0025133987 scopus 로고
    • Oxidative activation of the thiophene ring by hepatic enzymes. Hydroxylation and formation of electrophilic metabolites during metabolism of tienilic acid and its isomer by rat liver microsomes
    • DOI 10.1016/0006-2952(90)90207-2
    • Dansette PM, Amar C, Smith C, Pons C, and Mansuy D (1990) Oxidative activation of the thiophene ring by hepatic enzymes. Hydroxylation and formation of electrophilic metabolites during metabolism of tienilic acid and its isomer by rat liver microsomes. Biochem Pharmacol 39:911-918. (Pubitemid 20060688)
    • (1990) Biochemical Pharmacology , vol.39 , Issue.5 , pp. 911-918
    • Dansette, P.M.1    Amar, C.2    Smith, C.3    Pons, C.4    Mansuy, D.5
  • 6
    • 0025968699 scopus 로고
    • Hydroxylation and formation of electrophilic metabolites of tienilic acid and its isomer by human liver microsomes. Catalysis by a cytochrome P450 IIC different from that responsible for mephenytoin hydroxylation
    • Dansette PM, Amar C, Valadon P, Pons C, Beaune PH, and Mansuy D (1991) Hydroxylation and formation of electrophilic metabolites of tienilic acid and its isomer by human liver microsomes. Catalysis by a cytochrome P450 IIC different from that responsible for mephenytoin hydroxylation. Biochem Pharmacol 41:553-560.
    • (1991) Biochem Pharmacol , vol.41 , pp. 553-560
    • Dansette, P.M.1    Amar, C.2    Valadon, P.3    Pons, C.4    Beaune, P.H.5    Mansuy, D.6
  • 7
    • 27544482086 scopus 로고    scopus 로고
    • First evidence that cytochrome P450 may catalyze both S-oxidation and epoxidation of thiophene derivatives
    • Dansette PM, Bertho G, and Mansuy D (2005) First evidence that cytochrome P450 may catalyze both S-oxidation and epoxidation of thiophene derivatives. Biochem Biophys Res Commun 338:450-455.
    • (2005) Biochem Biophys Res Commun , vol.338 , pp. 450-455
    • Dansette, P.M.1    Bertho, G.2    Mansuy, D.3
  • 8
    • 62249112083 scopus 로고    scopus 로고
    • Metabolic oxidative cleavage of thioesters: Evidence for the formation of sulfenic acid intermediates in the bioactivation of the antithrombotic prodrugs ticlopidine and clopidogrel
    • Dansette PM, Libraire J, Bertho G, and Mansuy D (2009) Metabolic oxidative cleavage of thioesters: evidence for the formation of sulfenic acid intermediates in the bioactivation of the antithrombotic prodrugs ticlopidine and clopidogrel. Chem Res Toxicol 22:369-373.
    • (2009) Chem Res Toxicol , vol.22 , pp. 369-373
    • Dansette, P.M.1    Libraire, J.2    Bertho, G.3    Mansuy, D.4
  • 9
    • 0026989166 scopus 로고
    • Evidence for thiophene-S-oxide as a primary reactive metabolite of thiophene in vivo: Formation of a dihydrothiophene sulfoxide mercapturic acid
    • Dansette PM, Thang DC, el Amri H, and Mansuy D (1992) Evidence for thiophene-S-oxide as a primary reactive metabolite of thiophene in vivo: formation of a dihydrothiophene sulfoxide mercapturic acid. Biochem Biophys Res Commun 186:1624-1630.
    • (1992) Biochem Biophys Res Commun , vol.186 , pp. 1624-1630
    • Dansette, P.M.1    Thang, D.C.2    El Amri, H.3    Mansuy, D.4
  • 10
    • 1642281756 scopus 로고    scopus 로고
    • Drug-protein adducts: An industry perspective on minimizing the potential for drug bioactivation in drug discovery and development
    • Evans DC, Watt AP, Nicoll-Griffith DA, and Baillie TA (2004) Drug-protein adducts: an industry perspective on minimizing the potential for drug bioactivation in drug discovery and development. Chem Res Toxicol 17:3-16.
    • (2004) Chem Res Toxicol , vol.17 , pp. 3-16
    • Evans, D.C.1    Watt, A.P.2    Nicoll-Griffith, D.A.3    Baillie, T.A.4
  • 11
    • 66149104042 scopus 로고    scopus 로고
    • In vitro screening of 50 highly prescribed drugs for thiol adduct formation - Comparison of potential for drug-induced toxicity and extent of adduct formation
    • Gan J, Ruan Q, He B, Zhu M, Shyu WC, and Humphreys WG (2009) In vitro screening of 50 highly prescribed drugs for thiol adduct formation - comparison of potential for drug-induced toxicity and extent of adduct formation. Chem Res Toxicol 22:690-698.
    • (2009) Chem Res Toxicol , vol.22 , pp. 690-698
    • Gan, J.1    Ruan, Q.2    He, B.3    Zhu, M.4    Shyu, W.C.5    Humphreys, W.G.6
  • 13
    • 0021355271 scopus 로고
    • A new anti-liver-kidney microsome antibody (anti-LKM2) in tienilic acid-induced hepatitis
    • Homberg JC, Andre C, and Abuaf N (1984) A new anti-liver-kidney microsome antibody (anti-LKM2) in tienilic acid-induced hepatitis. Clin Exp Immunol 55:561-570.
    • (1984) Clin Exp Immunol , vol.55 , pp. 561-570
    • Homberg, J.C.1    Andre, C.2    Abuaf, N.3
  • 14
    • 58149463629 scopus 로고    scopus 로고
    • Mechanism-based inactivation of cytochrome P450 2C9 by tienilic acid and (+/-)-suprofen: A comparison of kinetics and probe substrate selection
    • Hutzler JM, Balogh LM, Zientek M, Kumar V, and Tracy TS (2009) Mechanism-based inactivation of cytochrome P450 2C9 by tienilic acid and (+/-)-suprofen: a comparison of kinetics and probe substrate selection. Drug Metab Dispos 37:59-65.
    • (2009) Drug Metab Dispos , vol.37 , pp. 59-65
    • Hutzler, J.M.1    Balogh, L.M.2    Zientek, M.3    Kumar, V.4    Tracy, T.S.5
  • 15
    • 0029910243 scopus 로고    scopus 로고
    • Oxidation of tienilic acid by human yeast-expressed cytochromes P-450 2C8, 2C9, 2C18 and 2C19. Evidence that this drug is a mechanism-based inhibitor specific for cytochrome P-450 2C9
    • Jean P, Lopez-Garcia P, Dansette P, Mansuy D, and Goldstein JL (1996) Oxidation of tienilic acid by human yeast-expressed cytochromes P-450 2C8, 2C9, 2C18 and 2C19. Evidence that this drug is a mechanism-based inhibitor specific for cytochrome P-450 2C9. Eur J Biochem 241:797-804.
    • (1996) Eur J Biochem , vol.241 , pp. 797-804
    • Jean, P.1    Lopez-Garcia, P.2    Dansette, P.3    Mansuy, D.4    Goldstein, J.L.5
  • 16
    • 45249088967 scopus 로고    scopus 로고
    • Many drugs and phytochemicals can be activated to biological reactive intermediates
    • Johnson WW (2008) Many drugs and phytochemicals can be activated to biological reactive intermediates. Curr Drug Metab 9:344-351.
    • (2008) Curr Drug Metab , vol.9 , pp. 344-351
    • Johnson, W.W.1
  • 17
    • 0035996570 scopus 로고    scopus 로고
    • Mechanism of idiosyncratic drug reactions: Reactive metabolites formation, protein binding and the regulation of the immune system
    • DOI 10.2174/1389200023337333
    • Ju C and Uetrecht JP (2002) Mechanism of idiosyncratic drug reactions: reactive metabolite formation, protein binding and the regulation of the immune system. Curr Drug Metab 3:367-377. (Pubitemid 34778003)
    • (2002) Current Drug Metabolism , vol.3 , Issue.4 , pp. 367-377
    • Ju, C.1    Uetrecht, J.P.2
  • 18
    • 70350273017 scopus 로고    scopus 로고
    • Structural alerts, reactive metabolites, and protein covalent binding: How reliable are these attributes as predictors of drug toxicity?
    • Kalgutkar AS and Didiuk MT (2009) Structural alerts, reactive metabolites, and protein covalent binding: how reliable are these attributes as predictors of drug toxicity? Chem Biodivers 6:2115-2137.
    • (2009) Chem Biodivers , vol.6 , pp. 2115-2137
    • Kalgutkar, A.S.1    Didiuk, M.T.2
  • 19
    • 0029790276 scopus 로고    scopus 로고
    • Tienilic acid-induced autoimmune hepatitis: Anti-liver and-kidney microsomal type 2 autoantibodies recognize a three-site conformational epitope on cytochrome P4502C9
    • Lecoeur S, André C, and Beaune PH (1996) Tienilic acid-induced autoimmune hepatitis: anti-liver and-kidney microsomal type 2 autoantibodies recognize a three-site conformational epitope on cytochrome P4502C9. Mol Pharmacol 50:326-333.
    • (1996) Mol Pharmacol , vol.50 , pp. 326-333
    • Lecoeur, S.1    André, C.2    Beaune, P.H.3
  • 20
    • 0033941434 scopus 로고    scopus 로고
    • Metabolism of ticlopidine by activated neutrophils: Implications for ticlopidine-induced agranulocytosis
    • Liu ZC and Uetrecht JP (2000) Metabolism of ticlopidine by activated neutrophils: implications for ticlopidine-induced agranulocytosis. Drug Metab Dispos 28:726-730.
    • (2000) Drug Metab Dispos , vol.28 , pp. 726-730
    • Liu, Z.C.1    Uetrecht, J.P.2
  • 21
    • 0028078626 scopus 로고
    • Thiophene derivatives as new mechanism-based inhibitors of cytochromes P-450: Inactivation of yeast-expressed human liver cytochrome P-450 2C9 by tienilic acid
    • López-Garcia MP, Dansette PM, and Mansuy D (1994) Thiophene derivatives as new mechanism-based inhibitors of cytochromes P-450: inactivation of yeast-expressed human liver cytochrome P-450 2C9 by tienilic acid. Biochemistry 33:166-175.
    • (1994) Biochemistry , vol.33 , pp. 166-175
    • López-Garcia, M.P.1    Dansette, P.M.2    Mansuy, D.3
  • 22
    • 0027468338 scopus 로고
    • Human-liver cytochromes P-450 expressed in yeast as tools for reactive-metabolite formation studies. Oxidative activation of tienilic acid by cytochromes P-450 2C9 and 2C10
    • Lopez Garcia MP, Dansette PM, Valadon P, Amar C, Beaune PH, Guengerich FP, and Mansuy D (1993) Human-liver cytochromes P-450 expressed in yeast as tools for reactive-metabolite formation studies. Oxidative activation of tienilic acid by cytochromes P-450 2C9 and 2C10. Eur J Biochem 213:223-232.
    • (1993) Eur J Biochem , vol.213 , pp. 223-232
    • Lopez Garcia, M.P.1    Dansette, P.M.2    Valadon, P.3    Amar, C.4    Beaune, P.H.5    Guengerich, F.P.6    Mansuy, D.7
  • 23
    • 0030911121 scopus 로고    scopus 로고
    • Molecular structure and hepatotoxicity: Compared data about two closely related thiophene compounds
    • Mansuy D (1997) Molecular structure and hepatotoxicity: compared data about two closely related thiophene compounds. J Hepatol 26 (Suppl 2):22-25. (Pubitemid 27229586)
    • (1997) Journal of Hepatology, Supplement , vol.26 , Issue.2 , pp. 22-25
    • Mansuy, D.1
  • 24
    • 34447124577 scopus 로고    scopus 로고
    • Toxicological significance of mechanism-based inactivation of cytochrome p450 enzymes by drugs
    • Masubuchi Y and Horie T (2007) Toxicological significance of mechanism-based inactivation of cytochrome p450 enzymes by drugs. Crit Rev Toxicol 37:389-412.
    • (2007) Crit Rev Toxicol , vol.37 , pp. 389-412
    • Masubuchi, Y.1    Horie, T.2
  • 25
    • 51449109566 scopus 로고    scopus 로고
    • Cytochrome P450 oxidation of the thiophene-containing anticancer drug 3-[(quinolin-4-ylmethyl)-amino]-thiophene-2-carboxylic acid (4-trifluoromethoxy- phenyl)-amide to an electrophilic intermediate
    • Medower C, Wen L, and Johnson WW (2008) Cytochrome P450 oxidation of the thiophene-containing anticancer drug 3-[(quinolin-4-ylmethyl)-amino]-thiophene- 2-carboxylic acid (4-trifluoromethoxy-phenyl)-amide to an electrophilic intermediate. Chem Res Toxicol 21:1570-1577.
    • (2008) Chem Res Toxicol , vol.21 , pp. 1570-1577
    • Medower, C.1    Wen, L.2    Johnson, W.W.3
  • 26
    • 0035996571 scopus 로고    scopus 로고
    • The metabolism and toxicity of quinones, quinonimines, quinone methides, and quinone-thioethers
    • Monks TJ and Jones DC (2002) The metabolism and toxicity of quinones, quinonimines, quinone methides, and quinone-thioethers. Curr Drug Metab 3:425-438.
    • (2002) Curr Drug Metab , vol.3 , pp. 425-438
    • Monks, T.J.1    Jones, D.C.2
  • 27
    • 70349103856 scopus 로고    scopus 로고
    • A zone classification system for risk assessment of idiosyncratic drug toxicity using daily dose and covalent binding
    • Nakayama S, Atsumi R, Takakusa H, Kobayashi Y, Kurihara A, Nagai Y, Nakai D, and Okazaki O (2009) A zone classification system for risk assessment of idiosyncratic drug toxicity using daily dose and covalent binding. Drug Metab Dispos 37:1970-1977.
    • (2009) Drug Metab Dispos , vol.37 , pp. 1970-1977
    • Nakayama, S.1    Atsumi, R.2    Takakusa, H.3    Kobayashi, Y.4    Kurihara, A.5    Nagai, Y.6    Nakai, D.7    Okazaki, O.8
  • 28
    • 0035701966 scopus 로고    scopus 로고
    • Structure toxicity relationships - How useful are they in predicting toxicities of new drugs?
    • Nelson SD (2001) Structure toxicity relationships - how useful are they in predicting toxicities of new drugs? Adv Exp Med Biol 500:33-43.
    • (2001) Adv Exp Med Biol , vol.500 , pp. 33-43
    • Nelson, S.D.1
  • 29
    • 53549100467 scopus 로고    scopus 로고
    • Can in vitro metabolism-dependent covalent binding data in liver microsomes distinguish hepatotoxic from nonhepatotoxic drugs? An analysis of 18 drugs with consideration of intrinsic clearance and daily dose
    • Obach RS, Kalgutkar AS, Soglia JR, and Zhao SX (2008) Can in vitro metabolism-dependent covalent binding data in liver microsomes distinguish hepatotoxic from nonhepatotoxic drugs? An analysis of 18 drugs with consideration of intrinsic clearance and daily dose. Chem Res Toxicol 21:1814-1822.
    • (2008) Chem Res Toxicol , vol.21 , pp. 1814-1822
    • Obach, R.S.1    Kalgutkar, A.S.2    Soglia, J.R.3    Zhao, S.X.4
  • 30
    • 0142150012 scopus 로고    scopus 로고
    • Mechanism-based inactivation of human recombinant P450 2C9 by the nonsteroidal anti-inflammatory drug suprofen
    • O'Donnell JP, Dalvie DK, Kalgutkar AS, and Obach RS (2003) Mechanism-based inactivation of human recombinant P450 2C9 by the nonsteroidal anti-inflammatory drug suprofen. Drug Metab Dispos 31:1369-1377.
    • (2003) Drug Metab Dispos , vol.31 , pp. 1369-1377
    • O'Donnell, J.P.1    Dalvie, D.K.2    Kalgutkar, A.S.3    Obach, R.S.4
  • 31
    • 77956009124 scopus 로고    scopus 로고
    • SAR of thiophene amide derivatives for interaction with intestinal and hepatobiliary transporters associated with in vivo bioavailability and clearance
    • American Association of Pharmaceutical Scientist, Arlington, VA
    • Sampson K, Lai Y, Li N, Heyde BR, and Hu Y (2008) SAR of thiophene amide derivatives for interaction with intestinal and hepatobiliary transporters associated with in vivo bioavailability and clearance. AAPS Annual Meeting and Exposition; 2008 Nov 16-20, 2008; Atlanta, GA. American Association of Pharmaceutical Scientist, Arlington, VA.
    • (2008) AAPS Annual Meeting and Exposition; 2008 Nov 16-20, 2008; Atlanta, GA
    • Sampson, K.1    Lai, Y.2    Li, N.3    Heyde, B.R.4    Hu, Y.5
  • 33
    • 33845409838 scopus 로고    scopus 로고
    • Evaluation of which reactive metabolite, if any, is responsible for a specific idiosyncratic reaction
    • Uetrecht J (2006) Evaluation of which reactive metabolite, if any, is responsible for a specific idiosyncratic reaction. Drug Metab Rev 38:745-753.
    • (2006) Drug Metab Rev , vol.38 , pp. 745-753
    • Uetrecht, J.1
  • 34
    • 38949104743 scopus 로고    scopus 로고
    • Idiosyncratic drug reactions: Past, present, and future
    • Uetrecht J (2008) Idiosyncratic drug reactions: past, present, and future. Chem Res Toxicol 21:84-92.
    • (2008) Chem Res Toxicol , vol.21 , pp. 84-92
    • Uetrecht, J.1
  • 35
    • 0029852501 scopus 로고    scopus 로고
    • Thiophene sulfoxides as reactive metabolites: Formation upon microsomal oxidation of a 3-aroylthiophene and fate in the presence of nucleophiles in vitro and in vivo
    • DOI 10.1021/tx9601622
    • Valadon P, Dansette PM, Girault JP, Amar C, and Mansuy D (1996) Thiophene sulfoxides as reactive metabolites: formation upon microsomal oxidation of a 3-aroylthiophene and fate in the presence of nucleophiles in vitro and in vivo. Chem Res Toxicol 9:1403-1413. (Pubitemid 26403849)
    • (1996) Chemical Research in Toxicology , vol.9 , Issue.8 , pp. 1403-1413
    • Valadon, P.1    Dansette, P.M.2    Girault, J.-P.3    Amar, C.4    Mansuy, D.5
  • 36
    • 16444377083 scopus 로고    scopus 로고
    • Mechanism-based inhibition of cytochrome P450 3A4 by therapeutic drugs
    • DOI 10.2165/00003088-200544030-00005
    • Zhou S, Yung Chan S, Cher Goh B, Chan E, Duan W, Huang M, and McLeod HL (2005) Mechanism-based inhibition of cytochrome P450 3A4 by therapeutic drugs. Clin Pharmacokinet 44:279-304. (Pubitemid 40477790)
    • (2005) Clinical Pharmacokinetics , vol.44 , Issue.3 , pp. 279-304
    • Zhou, S.1    Chan, S.Y.2    Goh, B.C.3    Chan, E.4    Duan, W.5    Huang, M.6    McLeod, H.L.7
  • 37
    • 45249121177 scopus 로고    scopus 로고
    • Drugs behave as substrates, inhibitors and inducers of human cytochrome P450 3A4
    • Zhou SF (2008) Drugs behave as substrates, inhibitors and inducers of human cytochrome P450 3A4. Curr Drug Metab 9:310-322.
    • (2008) Curr Drug Metab , vol.9 , pp. 310-322
    • Zhou, S.F.1
  • 38
    • 0021234189 scopus 로고
    • Ticrynafen-associated hepatic injury: Analysis of 340 cases
    • Zimmerman HJ, Lewis JH, Ishak KG, and Maddrey WC (1984) Ticrynafen-associated hepatic injury: analysis of 340 cases. Hepatology 4:315-323. (Pubitemid 14131442)
    • (1984) Hepatology , vol.4 , Issue.2 , pp. 315-323
    • Zimmerman, H.J.1    Lewis, J.H.2    Ishak, K.G.3    Maddrey, W.C.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.