메뉴 건너뛰기




Volumn 42, Issue 14, 1999, Pages 2542-2560

Chemical stability and fate of the cytostatic drug ifosfamide and its N- dechloroethylated metabolites in acidic aqueous solutions

Author keywords

[No Author keywords available]

Indexed keywords

DRUG METABOLITE; IFOSFAMIDE;

EID: 0033566213     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980587g     Document Type: Article
Times cited : (60)

References (49)
  • 1
    • 0015968586 scopus 로고
    • Some studies of the active intermediates formed in the microsomal metabolism of cyclophosphamide and isophosphamide
    • Connors, T. A.; Cox, P. J.; Farmer, P. B.; Foster, A. B.; Jarman, M. Some studies of the active intermediates formed in the microsomal metabolism of cyclophosphamide and isophosphamide. Biochem. Pharmacol. 1974, 23, 115-129.
    • (1974) Biochem. Pharmacol. , vol.23 , pp. 115-129
    • Connors, T.A.1    Cox, P.J.2    Farmer, P.B.3    Foster, A.B.4    Jarman, M.5
  • 2
    • 0023945947 scopus 로고
    • Metabolism of oxazaphosphorines
    • Sladek, N. E. Metabolism of oxazaphosphorines. Pharmacol. Ther. 1988, 37, 301-355.
    • (1988) Pharmacol. Ther. , vol.37 , pp. 301-355
    • Sladek, N.E.1
  • 3
    • 0027787745 scopus 로고
    • Pharmacokinetics of alkylating agents
    • Lind, M. J.; Ardiet, C. Pharmacokinetics of alkylating agents. Cancer Surveys 1993, 17, 157-188.
    • (1993) Cancer Surveys , vol.17 , pp. 157-188
    • Lind, M.J.1    Ardiet, C.2
  • 4
    • 0001908456 scopus 로고
    • Metabolism and pharmacokinetics behavior of cyclophosphamide and related oxazaphosphorines
    • Powis, G., Ed.; Pergamon Press: Oxford
    • Sladek, N. E. Metabolism and pharmacokinetics behavior of cyclophosphamide and related oxazaphosphorines. In Anticancer Drugs: Reactive metabolism and drug interactions; Powis, G., Ed.; Pergamon Press: Oxford, 1994; pp 79-156.
    • (1994) Anticancer Drugs: Reactive Metabolism and Drug Interactions , pp. 79-156
    • Sladek, N.E.1
  • 6
    • 0028183382 scopus 로고
    • Ifosfamide clinical pharmacokinetics
    • Wagner, T. Ifosfamide clinical pharmacokinetics. Clin. Pharmacokinet. 1994, 26, 439-456.
    • (1994) Clin. Pharmacokinet. , vol.26 , pp. 439-456
    • Wagner, T.1
  • 7
    • 0017097821 scopus 로고
    • Studies on the metabolism of isophosphamide in man
    • Norpoth, K. Studies on the metabolism of isophosphamide in man. Cancer Treat. Rep. 1978, 60, 437-443.
    • (1978) Cancer Treat. Rep. , vol.60 , pp. 437-443
    • Norpoth, K.1
  • 9
    • 0027394560 scopus 로고
    • Determination of the urinary excretion of ifosfamide and its phosphorated metabolites by phosphorus-31 nuclear magnetic resonance spectroscopy
    • Gilard, V.; Malet-Martino, M. C.; de Forni, M.; Niemeyer, U.; Ader, J. C.; Martino, R: Determination of the urinary excretion of ifosfamide and its phosphorated metabolites by phosphorus-31 nuclear magnetic resonance spectroscopy. Cancer Chemother. Pharmacol. 1993, 31, 387-394.
    • (1993) Cancer Chemother. Pharmacol. , vol.31 , pp. 387-394
    • Gilard, V.1    Malet-Martino, M.C.2    De Forni, M.3    Niemeyer, U.4    Ader, J.C.5    Martino, R.6
  • 10
    • 0029012073 scopus 로고
    • Identification of new metabolites of ifosfamide in rat urine using ion cluster technique
    • Wang, J. J. H.; Chan, K. K. Identification of new metabolites of ifosfamide in rat urine using ion cluster technique. J. Mass Spectrom. 1995, 30, 675-683.
    • (1995) J. Mass Spectrom. , vol.30 , pp. 675-683
    • Wang, J.J.H.1    Chan, K.K.2
  • 11
    • 0023035082 scopus 로고
    • Dechloroethylation of ifosfamide and neurotoxicity
    • Goren, M. P.; Wright, R. K.; Pratt, C. B.; Pell, F. E. Dechloroethylation of ifosfamide and neurotoxicity. Lancet II 1986, 1219.
    • (1986) Lancet II , vol.2 , pp. 1219
    • Goren, M.P.1    Wright, R.K.2    Pratt, C.B.3    Pell, F.E.4
  • 12
    • 0024383898 scopus 로고
    • Chloroacetaldehyde and its contribution to urotoxicity during treatment with cyclophosphamide or ifosfamide
    • Pohl, J.; Stekar, J.; Hilgard, P. Chloroacetaldehyde and its contribution to urotoxicity during treatment with cyclophosphamide or ifosfamide. Arzneim. Forsch. 1989, 39, 704-705.
    • (1989) Arzneim. Forsch. , vol.39 , pp. 704-705
    • Pohl, J.1    Stekar, J.2    Hilgard, P.3
  • 13
    • 0002510291 scopus 로고    scopus 로고
    • 13C-chloroacetaldehyde, a metabolite of ifosfamide and cyclophosphamide, in the isolated perfused rabbit heart model. Initial observations on its cardiotoxicity and cardiac metabolism
    • 13C-chloroacetaldehyde, a metabolite of ifosfamide and cyclophosphamide, in the isolated perfused rabbit heart model. Initial observations on its cardiotoxicity and cardiac metabolism. Cell. Mol. Biol. 1997, 43, 773-782.
    • (1997) Cell. Mol. Biol. , vol.43 , pp. 773-782
    • Joqueviel, C.1    Malet-Martino, M.2    Martino, R.3
  • 14
    • 0027359027 scopus 로고
    • Comparative pharmacokinetics of ifosfamide, 4-hydroxyifosfamide, chloroacetaldehyde, and 2- and 3-dechloroethylifosfamide in patients on fractionated intravenous ifosfamide therapy
    • Kurowski, V.; Wagner, T. Comparative pharmacokinetics of ifosfamide, 4-hydroxyifosfamide, Chloroacetaldehyde, and 2- and 3-dechloroethylifosfamide in patients on fractionated intravenous ifosfamide therapy. Cancer Chemother. Pharmacol. 1993, 33, 36-42.
    • (1993) Cancer Chemother. Pharmacol. , vol.33 , pp. 36-42
    • Kurowski, V.1    Wagner, T.2
  • 17
    • 84988057754 scopus 로고
    • Determination of iphosphamide and seven metabolites in blood plasma, as stable trifluoroacetyl derivatives, by electron capture chemical ionization GC-MS
    • Momerency, G.; Van Cauwenberghe, K.; de Bruijn, E. A.; Van Oosterom, A. T.; Highley, M. S.; Harper, P. G. Determination of iphosphamide and seven metabolites in blood plasma, as stable trifluoroacetyl derivatives, by electron capture chemical ionization GC-MS. J. High Resolut. Chromatogr. 1994, 17, 655-661.
    • (1994) J. High Resolut. Chromatogr. , vol.17 , pp. 655-661
    • Momerency, G.1    Van Cauwenberghe, K.2    De Bruijn, E.A.3    Van Oosterom, A.T.4    Highley, M.S.5    Harper, P.G.6
  • 18
    • 0344669544 scopus 로고    scopus 로고
    • Chemical stability of cyclophosphamide, trofosfamide, and 2- and 3-dechloroethylifosfamide in aqueous solutions
    • Kaijser, G. P.; Aalbers, T.; Beijnen, J. H.; Bult, A.; Underberg, W. J. M. Chemical stability of cyclophosphamide, trofosfamide, and 2- and 3-dechloroethylifosfamide in aqueous solutions. J. Oncol. Pharm. Pract. 1996, 2, 15-21.
    • (1996) J. Oncol. Pharm. Pract. , vol.2 , pp. 15-21
    • Kaijser, G.P.1    Aalbers, T.2    Beijnen, J.H.3    Bult, A.4    Underberg, W.J.M.5
  • 19
    • 0017671322 scopus 로고
    • High-resolution nuclear magnetic resonance investigations of the chemical stability of cyclophosphamide and related phosphoramidic compounds
    • Zon, G.; Ludeman, S. M.; Egan, W. High-resolution nuclear magnetic resonance investigations of the chemical stability of cyclophosphamide and related phosphoramidic compounds. J. Am. Chem. Soc. 1977, 99, 5785-5795.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 5785-5795
    • Zon, G.1    Ludeman, S.M.2    Egan, W.3
  • 21
    • 0025282739 scopus 로고
    • The stability of ifosfamide in aqueous solution and its suitability for continuous 7-day infusion by ambulatory pump
    • Radford, J. A.; Margison, J. M.; Swindell, R.; Lind, M. J.; Wilkinson, P. M.; Thatcher, N. The stability of ifosfamide in aqueous solution and its suitability for continuous 7-day infusion by ambulatory pump. Cancer Chemother. Pharmacol. 1990, 26, 144-146.
    • (1990) Cancer Chemother. Pharmacol. , vol.26 , pp. 144-146
    • Radford, J.A.1    Margison, J.M.2    Swindell, R.3    Lind, M.J.4    Wilkinson, P.M.5    Thatcher, N.6
  • 23
    • 0026503430 scopus 로고
    • Stability of ifosfamide in 0.9% sodium chloride solution or water for injection in a portable i.v. pump cassette
    • Muñoz, M.; Girona, V.; Pujol, M.; Durán, S.; Vicente, P.; Solé, L. A. Stability of ifosfamide in 0.9% sodium chloride solution or water for injection in a portable i.v. pump cassette. Am. J. Hosp. Pharm. 1992, 49, 1137-1139.
    • (1992) Am. J. Hosp. Pharm. , vol.49 , pp. 1137-1139
    • Muñoz, M.1    Girona, V.2    Pujol, M.3    Durán, S.4    Vicente, P.5    Solé, L.A.6
  • 27
    • 0010514135 scopus 로고    scopus 로고
    • Separation of ifosfamide and its degradation products using micellar electrokinetic chromatography
    • Hill, S.; Aexiou, J.; Kavanagh, P. E.; Livingstone, P. C.; Shalliker, R. A.; Soscic, J. Separation of ifosfamide and its degradation products using micellar electrokinetic chromatography. Anal. Commun. 1996, 33, 235-237.
    • (1996) Anal. Commun. , vol.33 , pp. 235-237
    • Hill, S.1    Aexiou, J.2    Kavanagh, P.E.3    Livingstone, P.C.4    Shalliker, R.A.5    Soscic, J.6
  • 30
    • 0345531795 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra.
  • 31
    • 0345100331 scopus 로고
    • Solvent effects in NMR spectroscopy. II. A repulsive interaction between the benzene solvent molecule and the nitrogen lone-pair, and the effects induced by the addition of protic substances
    • Yonezawa, T.; Morishima, I.; Fukuta, K. Solvent effects in NMR spectroscopy. II. A repulsive interaction between the benzene solvent molecule and the nitrogen lone-pair, and the effects induced by the addition of protic substances. Bull. Chem. Soc. Jpn. 1968, 41, 2297-2305.
    • (1968) Bull. Chem. Soc. Jpn. , vol.41 , pp. 2297-2305
    • Yonezawa, T.1    Morishima, I.2    Fukuta, K.3
  • 34
    • 0011865804 scopus 로고
    • Phosphoramidate solvolysis
    • Öney, I.; Caplow, M. Phosphoramidate Solvolysis. J. Am. Chem. Soc. 1967, 89, 6972-6980.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 6972-6980
    • Öney, I.1    Caplow, M.2
  • 36
    • 0011774535 scopus 로고
    • Acid-catalyzed and alkaline hydrolyses of phosphinamides. The lability of phosphorus - Nitrogen bonds in acid and the mechanisms of reaction
    • Koizumi, T.; Haake, P. Acid-catalyzed and alkaline hydrolyses of phosphinamides. The lability of phosphorus - nitrogen bonds in acid and the mechanisms of reaction. J. Am. Chem. Soc. 1973, 95, 8073-8079.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 8073-8079
    • Koizumi, T.1    Haake, P.2
  • 37
    • 0001430026 scopus 로고
    • Reactivity and mechanism of hydrolysis of phosphonamides
    • Rahil, J.; Haake, P. Reactivity and mechanism of hydrolysis of phosphonamides. J. Am. Chem. Soc. 1981, 103, 1723-1734.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 1723-1734
    • Rahil, J.1    Haake, P.2
  • 38
    • 0001095357 scopus 로고
    • Phosphoric amides. 3. Acidic cleavage of the phosphorus - Nitrogen bond in acyclic and cyclic phosphoramidates
    • Modro, T. A.; Graham, D. H. Phosphoric Amides. 3. Acidic cleavage of the phosphorus - nitrogen bond in acyclic and cyclic phosphoramidates. J. Org. Chem. 1981, 46, 1923-1925.
    • (1981) J. Org. Chem. , vol.46 , pp. 1923-1925
    • Modro, T.A.1    Graham, D.H.2
  • 40
    • 0030738712 scopus 로고    scopus 로고
    • Stability of commercial formulations and aqueous solutions of ifosfamide
    • Guard, V.; Martino, R.; Malet-Martino, M.; Niemeyer, U. Stability of commercial formulations and aqueous solutions of ifosfamide (a reply). Drug Metab. Dispos. 1997, 25, 927-931.
    • (1997) Drug Metab. Dispos. , vol.25 , pp. 927-931
    • Guard, V.1    Martino, R.2    Malet-Martino, M.3    Niemeyer, U.4
  • 41
    • 0000523042 scopus 로고
    • Decomposition of N-phosphorylated nitrogen mustards: A mechanistic investigation
    • Le Roux, C.; Modro, A. M.; Modro, T. A. Decomposition of N-phosphorylated nitrogen mustards: a mechanistic investigation. J. Org. Chem. 1995, 60, 3832-3839.
    • (1995) J. Org. Chem. , vol.60 , pp. 3832-3839
    • Le Roux, C.1    Modro, A.M.2    Modro, T.A.3
  • 42
    • 21344451821 scopus 로고    scopus 로고
    • Chemistry of N-phosphorylated nitrogen mustards: The effect of a second nitrogen substituent at phosphorus on the stability of the system
    • Wan, H.; Modro, T. A. Chemistry of N-phosphorylated nitrogen mustards: the effect of a second nitrogen substituent at phosphorus on the stability of the system. Phosphorus, Sulfur Silicon 1996, 108, 155-168.
    • (1996) Phosphorus, Sulfur Silicon , vol.108 , pp. 155-168
    • Wan, H.1    Modro, T.A.2
  • 44
    • 0031950583 scopus 로고    scopus 로고
    • Urinary excretion of cyclophosphamide in humans, determined by phosphorus-31 nuclear magnetic resonance spectroscopy
    • Joqueviel, C.; Martino, R.; Guard, V.; Malet-Martino, M.; Canal, P.; Niemeyer, U. Urinary excretion of cyclophosphamide in humans, determined by phosphorus-31 nuclear magnetic resonance spectroscopy. Drug Metab. Dispos. 1998, 26, 418-428.
    • (1998) Drug Metab. Dispos. , vol.26 , pp. 418-428
    • Joqueviel, C.1    Martino, R.2    Guard, V.3    Malet-Martino, M.4    Canal, P.5    Niemeyer, U.6
  • 45
    • 4243710644 scopus 로고
    • Preparation of ifosfamide
    • Spanish Pat. ES 526194, 1985
    • Sociedad Espanola Especialidades Farmaco-Therapeuticas SA. Preparation of ifosfamide. Spanish Pat. ES 526194, 1985; Chem. Abstr. 1987, 107, 7385r.
    • (1987) Chem. Abstr. , vol.107
  • 46
    • 0030806421 scopus 로고    scopus 로고
    • Urinary stability of carboxycyclophosphamide and carboxyifosfamide, two major metabolites of the anticancer drugs cyclophosphamide and ifosfamide
    • Joqueviel, C.; Guard, V.; Martino, R.; Malet-Martino, M.; Niemeyer, U. Urinary stability of carboxycyclophosphamide and carboxyifosfamide, two major metabolites of the anticancer drugs cyclophosphamide and ifosfamide. Cancer Chemother. Pharmacol. 1997, 40, 391-399.
    • (1997) Cancer Chemother. Pharmacol. , vol.40 , pp. 391-399
    • Joqueviel, C.1    Guard, V.2    Martino, R.3    Malet-Martino, M.4    Niemeyer, U.5
  • 48
    • 84986773599 scopus 로고
    • 31P nuclear magnetic resonance titrations. Simultaneous evaluation of all pH-dependent resonance signals
    • 31P nuclear magnetic resonance titrations. Simultaneous evaluation of all pH-dependent resonance signals. Org. Magn. Reson. 1984, 22, 101-105.
    • (1984) Org. Magn. Reson. , vol.22 , pp. 101-105
    • Lachmann, H.1    Schnackerz, K.D.2
  • 49
    • 0017718628 scopus 로고
    • Primary bioassay of human myeloma stem cells
    • Hamburger, A. W.; Salmon, S. E. Primary bioassay of human myeloma stem cells. J. Clin. Invest. 1977, 60, 846-854.
    • (1977) J. Clin. Invest. , vol.60 , pp. 846-854
    • Hamburger, A.W.1    Salmon, S.E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.