메뉴 건너뛰기




Volumn 92, Issue 4, 2004, Pages 797-802

Paracetamol (acetaminophen) warfarin interaction: NAPQI, the toxic metabolite of paracetamol, is an inhibitor of enzymes in the vitamin K cycle

Author keywords

Drug interaction; Oral anticoagulation; Paracetamol; Vitamin K dependent factors

Indexed keywords

ACENOCOUMAROL; AMINO ACID; ANALGESIC AGENT; ANTICOAGULANT AGENT; CARBOXYLASE; DRUG METABOLITE; ENZYME INHIBITOR; GLUTATHIONE; HYDROQUINONE; MENADIONE EPOXIDE; N ACETYL 1,4 BENZOQUINONE IMINE; OXIDOREDUCTASE; PARACETAMOL; VITAMIN K GROUP; WARFARIN;

EID: 6344230026     PISSN: 03406245     EISSN: None     Source Type: Journal    
DOI: 10.1160/TH04-02-0109     Document Type: Article
Times cited : (81)

References (29)
  • 1
    • 0035128503 scopus 로고    scopus 로고
    • Oral anticoagulants: Mechanism of action, clinical effectiveness, and optimal therapeutic range
    • Hirsh J, Dalen JE, Anderson DR, et al. Oral anticoagulants: mechanism of action, clinical effectiveness, and optimal therapeutic range. Chest 2001; 119: 8S-21S.
    • (2001) Chest , vol.119
    • Hirsh, J.1    Dalen, J.E.2    Anderson, D.R.3
  • 2
    • 0020033168 scopus 로고
    • Interaction between paracetamol and coumarin anticogulants
    • Boeijinga JJ, Boerstra EE, Ris P, et al. Interaction between paracetamol and coumarin anticogulants. Lancet 1982; I: 506.
    • (1982) Lancet , vol.1 , pp. 506
    • Boeijinga, J.J.1    Boerstra, E.E.2    Ris, P.3
  • 3
    • 0032481644 scopus 로고    scopus 로고
    • Acetaminophen and other risk factors for excessive warfarin anticoagulation
    • Hylek EM, Heiman H, Skates SJ, et al. Acetaminophen and other risk factors for excessive warfarin anticoagulation. JAMA 1998; 279: 657-62.
    • (1998) JAMA , vol.279 , pp. 657-662
    • Hylek, E.M.1    Heiman, H.2    Skates, S.J.3
  • 4
    • 0036145889 scopus 로고    scopus 로고
    • Retroperitoneal haematoma after paracetamol increased anticoagulation
    • Andrews FJ. Retroperitoneal haematoma after paracetamol increased anticoagulation. Emerg Med J 2002; 19: 84-5.
    • (2002) Emerg. Med. J. , vol.19 , pp. 84-85
    • Andrews, F.J.1
  • 6
    • 0032881464 scopus 로고    scopus 로고
    • Warfarin-acetaminophen drug interaction revisisted
    • Shek KLA, Chan L-N, Nutescu E. Warfarin-acetaminophen drug interaction revisisted. Pharmacotherapy 1999; 19: 1153-8.
    • (1999) Pharmacotherapy , vol.19 , pp. 1153-1158
    • Shek, K.L.A.1    Chan, L.-N.2    Nutescu, E.3
  • 7
    • 0035720240 scopus 로고    scopus 로고
    • No clinically relevant drug interaction between paracetamol and phenprocoumon based on a pharmacoepidemiological cohort study in medical patients
    • Fattinger K, Frisullo R, Masche U, et al. No clinically relevant drug interaction between paracetamol and phenprocoumon based on a pharmacoepidemiological cohort study in medical patients. Eur J Clin Pharmacol 2002; 57: 863-7.
    • (2002) Eur. J. Clin. Pharmacol. , vol.57 , pp. 863-867
    • Fattinger, K.1    Frisullo, R.2    Masche, U.3
  • 8
    • 0032945551 scopus 로고    scopus 로고
    • The effects of acetaminophen on pharmacokinetics and pharmacodynamics of warfarin
    • Kwan D, Bartle WR, Walker SE. The effects of acetaminophen on pharmacokinetics and pharmacodynamics of warfarin. J Clin Pharmacol 1999; 39: 68-75.
    • (1999) J. Clin. Pharmacol. , vol.39 , pp. 68-75
    • Kwan, D.1    Bartle, W.R.2    Walker, S.E.3
  • 9
    • 0033653694 scopus 로고    scopus 로고
    • Acetaminophen causes an increased international normalized ratio by reducing functional factor VII
    • Whyte IM, Buckley NA, Reith DM, et al. Acetaminophen causes an increased international normalized ratio by reducing functional factor VII. Therap Drug Monitor 2000; 22: 742-8.
    • (2000) Therap. Drug Monitor , vol.22 , pp. 742-748
    • Whyte, I.M.1    Buckley, N.A.2    Reith, D.M.3
  • 10
    • 85047692812 scopus 로고
    • Vitamin K and vitamin K dependent proteins
    • Shearer MJ. Vitamin K and vitamin K dependent proteins. Br J Haematol 1990; 75: 156-62.
    • (1990) Br. J. Haematol. , vol.75 , pp. 156-162
    • Shearer, M.J.1
  • 12
    • 0033546393 scopus 로고    scopus 로고
    • The propeptides of the vitamin K-dependent proteins possess different affinities for the vitamin K-dependent carboxylase
    • Stanley TB, Jin, D, Lin, PJ, et al. The propeptides of the vitamin K-dependent proteins possess different affinities for the vitamin K-dependent carboxylase. J Biol Chem 1999; 274: 16940-4.
    • (1999) J. Biol. Chem. , vol.274 , pp. 16940-16944
    • Stanley, T.B.1    Jin, D.2    Lin, P.J.3
  • 13
    • 0030804175 scopus 로고    scopus 로고
    • Assay of vitamin K-dependent carboxylase activity in hepatic and extrahepatic tissues
    • Houben RJ, Soute BA, Vermeer C. Assay of vitamin K-dependent carboxylase activity in hepatic and extrahepatic tissues. Meth Enzymol 1997; 282: 358-68.
    • (1997) Meth. Enzymol. , vol.282 , pp. 358-368
    • Houben, R.J.1    Soute, B.A.2    Vermeer, C.3
  • 14
    • 0023276260 scopus 로고
    • Warfarin resistance. Vitamin K epoxide reductase of Scottish resistance genes is not irreversible blocked by warfarin
    • Thijssen HH. Warfarin resistance. Vitamin K epoxide reductase of Scottish resistance genes is not irreversible blocked by warfarin. Biochem Pharmacol 1987; 36: 2753-7.
    • (1987) Biochem. Pharmacol. , vol.36 , pp. 2753-2757
    • Thijssen, H.H.1
  • 15
    • 0020427899 scopus 로고
    • Synthesis, decomposition kinetics, and preliminary toxicological studies of pure N-acetyl-p-benzoquinone imine, a proposed toxic metabolite of acetaminophen
    • Dahlin DC, Nelson SD. Synthesis, decomposition kinetics, and preliminary toxicological studies of pure N-acetyl-p-benzoquinone imine, a proposed toxic metabolite of acetaminophen. J Med Chem 1982; 25: 885-6.
    • (1982) J. Med. Chem. , vol.25 , pp. 885-886
    • Dahlin, D.C.1    Nelson, S.D.2
  • 16
    • 0035132183 scopus 로고    scopus 로고
    • Paracetamol-induced toxicity. Molecular and biochemical mechanisms, analogues and protective approaches
    • Bessems JGM, Vermeulen NPE. Paracetamol-induced toxicity. Molecular and biochemical mechanisms, analogues and protective approaches. Crit Rev Toxicol 2001; 31: 55-138.
    • (2001) Crit. Rev. Toxicol. , vol.31 , pp. 55-138
    • Bessems, J.G.M.1    Vermeulen, N.P.E.2
  • 17
    • 0029124853 scopus 로고
    • Paracetamol (acetaminophen) poisoning
    • Vale JA, Proudfoot AT. Paracetamol (acetaminophen) poisoning. The Lancet. 1995; 346: 547-52.
    • (1995) The Lancet , vol.346 , pp. 547-552
    • Vale, J.A.1    Proudfoot, A.T.2
  • 18
    • 0025272062 scopus 로고
    • In vitro gamma-carboxylation of a 59-residue recombinant peptide including the propeptide and the gamma-carboxyglutamic acid domain of coagulation factor IX. Effect of mutations near the propeptide cleavage site
    • Wu SM, Soute BA, Vermeer C, et al. In vitro gamma-carboxylation of a 59-residue recombinant peptide including the propeptide and the gamma-carboxyglutamic acid domain of coagulation factor IX. Effect of mutations near the propeptide cleavage site. J Biol Chem 1990; 265: 13124-9.
    • (1990) J. Biol. Chem. , vol.265 , pp. 13124-13129
    • Wu, S.M.1    Soute, B.A.2    Vermeer, C.3
  • 19
    • 0142197163 scopus 로고    scopus 로고
    • Sustained intake of paracetamol (acetaminophen) during oral anticoagulant therapy with coumarins does not cause clinically important INR changes: A randomized double-blind clinical trial
    • Gadisseur AP, Van der Meer FJ, Rosendaal FR. Sustained intake of paracetamol (acetaminophen) during oral anticoagulant therapy with coumarins does not cause clinically important INR changes: a randomized double-blind clinical trial. J Thromb Haemost 2003; 1: 714-7.
    • (2003) J. Thromb. Haemost. , vol.1 , pp. 714-717
    • Gadisseur, A.P.1    Van der Meer, F.J.2    Rosendaal, F.R.3
  • 20
    • 0030583721 scopus 로고    scopus 로고
    • Natural prenylquinones inhibit the enzymes of the vitamin K cycle in vitro
    • Ronden JE, Soute BAM, Thijssen HHW, et al. Natural prenylquinones inhibit the enzymes of the vitamin K cycle in vitro. Biochim Biophys Acta 1996; 1298: 87-94.
    • (1996) Biochim. Biophys. Acta , vol.1298 , pp. 87-94
    • Ronden, J.E.1    Soute, B.A.M.2    Thijssen, H.H.W.3
  • 21
    • 0034700163 scopus 로고    scopus 로고
    • Identification of the vitamin K-dependent carboxylase active site: Cys-99 and Cys-450 are required for both epoxidation and carboxylation
    • Pudota BN, Miyagi M, Hallgren KW, et al. Identification of the vitamin K-dependent carboxylase active site: Cys-99 and Cys-450 are required for both epoxidation and carboxylation. Proc Natl Acad Sci USA 2000; 97: 13033-8.
    • (2000) Proc. Natl. Acad. Sci. USA , vol.97 , pp. 13033-13038
    • Pudota, B.N.1    Miyagi, M.2    Hallgren, K.W.3
  • 22
    • 0242580898 scopus 로고    scopus 로고
    • Determination of disulfide bond assignment of human vitamin K-dependent γ-glutamyl carboxylase by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry
    • Tie J-K, Mutucumarena VP, Straight DL, et al. Determination of disulfide bond assignment of human vitamin K-dependent γ -glutamyl carboxylase by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. J Biol Chem 2003; 278: 45468-75.
    • (2003) J. Biol. Chem. , vol.278 , pp. 45468-45475
    • Tie, J.-K.1    Mutucumarena, V.P.2    Straight, D.L.3
  • 23
    • 0021242408 scopus 로고
    • Metabolism of vitamin K and vitamin K 2,3-epoxide via interaction with a common disulfide
    • Lee JJ, Fasco MJ. Metabolism of vitamin K and vitamin K 2,3-epoxide via interaction with a common disulfide. Biochem 1984; 23: 2246-52.
    • (1984) Biochem. , vol.23 , pp. 2246-2252
    • Lee, J.J.1    Fasco, M.J.2
  • 24
    • 0033587479 scopus 로고    scopus 로고
    • Glutamyl substrate-induced exposure of a free cysteine residue in the vitamin K-dependent γ-glutamyl carboxylase is critical for vitamin K epoxidation
    • Bouchard BA, Furie B, Furie BC. Glutamyl substrate-induced exposure of a free cysteine residue in the vitamin K-dependent γ-glutamyl carboxylase is critical for vitamin K epoxidation. Biochem 1999; 38: 9517-23.
    • (1999) Biochem. , vol.38 , pp. 9517-9523
    • Bouchard, B.A.1    Furie, B.2    Furie, B.C.3
  • 25
    • 0029081222 scopus 로고
    • On the mechanism of the anticlotting action of vitamin E quinone
    • Dowd P, Zheng ZB. On the mechanism of the anticlotting action of vitamin E quinone. Proc Natl Acad Sci USA 1995; 92: 8171-5.
    • (1995) Proc. Natl. Acad. Sci. USA , vol.92 , pp. 8171-8175
    • Dowd, P.1    Zheng, Z.B.2
  • 26
    • 0029917723 scopus 로고    scopus 로고
    • Effect of liver cirrhosis and age on the glutathione concentration in the plasma, erythrocytes, and gastric mucosa of man
    • Loguerco C, Taranto D, Vitale LM, et al. Effect of liver cirrhosis and age on the glutathione concentration in the plasma, erythrocytes, and gastric mucosa of man. Free Rad Biol Med 1996; 20: 483-8.
    • (1996) Free Rad. Biol. Med. , vol.20 , pp. 483-488
    • Loguerco, C.1    Taranto, D.2    Vitale, L.M.3
  • 27
    • 0035153227 scopus 로고    scopus 로고
    • High sensitivity of Nrf2 knockout mice to acetaminophen hepatotoxicity associated with decreased expression of ARE-regulated drug metabolizing enzymes and antioxidant genes
    • Enomoto A, Itoh K, Nagayoshi E, et al. High sensitivity of Nrf2 knockout mice to acetaminophen hepatotoxicity associated with decreased expression of ARE-regulated drug metabolizing enzymes and antioxidant genes. Toxicol Sci 2001; 59: 169-77.
    • (2001) Toxicol. Sci. , vol.59 , pp. 169-177
    • Enomoto, A.1    Itoh, K.2    Nagayoshi, E.3
  • 28
    • 0037068944 scopus 로고    scopus 로고
    • Effect of acetylcysteine on prothrombin index in paracetamol poisoning without hepatocellular injury
    • Schmidt LE, Knudsen TT, Dalhoff K, et al. Effect of acetylcysteine on prothrombin index in paracetamol poisoning without hepatocellular injury. Lancet 2002; 360: 1151-2.
    • (2002) Lancet , vol.360 , pp. 1151-1152
    • Schmidt, L.E.1    Knudsen, T.T.2    Dalhoff, K.3
  • 29
    • 0024380927 scopus 로고
    • The disposition and kinetics of intravenous N-acetylcysteine in patients with paracetamol overdosage
    • Prescott LF, Donovan JW, Jarvie DR, et al. The disposition and kinetics of intravenous N-acetylcysteine in patients with paracetamol overdosage. Eur J Clin Pharmacol 1989; 37: 501-6.
    • (1989) Eur. J. Clin. Pharmacol. , vol.37 , pp. 501-506
    • Prescott, L.F.1    Donovan, J.W.2    Jarvie, D.R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.