-
1
-
-
62249155473
-
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
-
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
-
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
-
4
-
-
0036127307
-
Biotransformation reactions of five-membered aromatic heterocyclic rings
-
Dalvie DK, Kalgutkar AS, Khojasteh-Bakht SC, Obach RS, and O'Donnell JP (2002) Biotransformation reactions of five-membered aromatic heterocyclic rings. Chem Res Toxicol 15:269-299.
-
(2002)
Chem Res Toxicol
, vol.15
, pp. 269-299
-
-
Dalvie, D.K.1
Kalgutkar, A.S.2
Khojasteh-Bakht, S.C.3
Obach, R.S.4
O'Donnell, J.P.5
-
5
-
-
0025133987
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
12
-
-
47949133634
-
Identification of the thiophene ring of methapyrilene as a novel bioactivation-dependent hepatic toxicophore
-
Graham EE, Walsh RJ, Hirst CM, Maggs JL, Martin S, Wild MJ, Wilson ID, Harding JR, Kenna JG, Peter RM, et al. (2008) Identification of the thiophene ring of methapyrilene as a novel bioactivation-dependent hepatic toxicophore. J Pharmacol Exp Ther 326:657-671.
-
(2008)
J Pharmacol Exp Ther
, vol.326
, pp. 657-671
-
-
Graham, E.E.1
Walsh, R.J.2
Hirst, C.M.3
Maggs, J.L.4
Martin, S.5
Wild, M.J.6
Wilson, I.D.7
Harding, J.R.8
Kenna, J.G.9
Peter, R.M.10
-
13
-
-
0021355271
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
|