Stereoselective pharmacokinetics and metabolism of the enantiomers of cyclophosphamide

Holm, Karsten A.; Kindberg, Carl G.; Stobaugh, John F.; Slavik, Milan; Riley, Christopher M.

doi:10.1016/0006-2952(90)90015-d

Cited by 25 publications

(17 citation statements)

References 17 publications

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“…This is in agreement with Holm et al, who have reported a lack of stereoselectivity in the disposition of CP enantiomers following intravenous administration of the racemate to humans. 24 PK parameter values obtained for the separate enantiomers of CP and DCE-CP may be compared to those of others for racemic CP. For example, using non-compartmental techniques, Tasso et al found a steady-state volume of distribution (Vss) of 0.5 L/kg in a group of pediatric patients.…”

mentioning

confidence: 99%

Pharmacokinetics of (R)- and (S)-cyclophosphamide and their dechloroethylated metabolites in cancer patients

et al. 1999

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confidence: 99%

Pharmacokinetics of (R)- and (S)-cyclophosphamide and their dechloroethylated metabolites in cancer patients

et al. 1999

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“…1,8,9 The authors reported no differences in pharmacokinetic parameters between (1)-(R)-CPA and (2)-(S)-CPA. Figure 3 shows the plasma concentration of (1)-(R)-CPA and (2)-(S)-CPA vs. time and Table 4 presents the pharmacokinetic parameters observed during the investigation of a patient with lupus nephritis and a patient with breast cancer treated with 1 g and 900 mg racemic CPA infused over 2 and 1 h, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…188, 8 (158,8-218,9) 174, 8* 168,1 (139-197,3) 0,0001 5,6 (4,6-6,6) 5,7* 6,4 (5,(1)(2)(3)(4)(5)(6)(7)8) A análise enantiosseletiva da CPA em plasma é descrita por poucos autores empregando colunas quirais ou agentes de derivatização quirais e utilizando HPLC com detecção UV ou GC-MS (REID; STOBAUGH; LIU et al, 2004; A farmacocinética dos enantiômeros da CPA foi reportada em poucos estudos, todos com pacientes portadores de câncer JARMAN et al, 1989;BRAMWELL et al, 1979). Os autores não observaram diferenças nos parâmetros farmacocinéticos entre os enantiômeros (R)- As meias-vidas de eliminação obtidas nesse estudo diferiram entre os enantiômeros (Tabela 11), o que não foi observado nos estudos existentes na literatura (JARMAN et al, 1979;BRAMWELL et al, 1979;.…”

Section: Figura 9 Concentração Plasmática Dos Enantiômeros (R)-(+)-cunclassified

“…1,8,9 The authors showed no differences in pharmacokinetic parameters between (1)-(R)-CPA and (2)-(S)-CPA.…”

Section: Anexosmentioning

confidence: 99%

“…selectivity in the kinetic disposition and metabolism of CPA. 1,[5][6][7][8][9] It has been suggested that (1)- (R) and (2)-(S)-CPA may differ in their therapeutic and toxic effects, but the clinical consequences of these differences have not been adequately determined. 1 Many chromatography-based analytical techniques have been used to measure CPA as enantiomeric mixture in human plasma, including high-performance liquid chromatography with ultraviolet detection (HPLC-UV), gas chromatography-nitrogen phosphorus detection (GC-NPD), gas chromatography-mass spectrometry (GC-MS), liquid chromatography-mass spectrometry (LC-MS), and thinlayer chromatography (TLC)-photography densitometry.…”

Section: Anexosmentioning

confidence: 99%

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Farmacocinética enantiosseletiva da ciclofosfamida em pacientes com câncer de mama

Fernandes¹

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Chirality and Biological Activity

Singh¹,

Hagen²

2010

Burger's Medicinal Chemistry and Drug Discovery

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The relationship between chirality and biological activity has been of increasing importance to the pharmaceutical and biopharmaceutical areas as evidenced by a growing number of chiral drugs that have been developed within the last two decades. This chapter covers several areas of importance in the design and synthesis of novel small molecule chiral drugs for medicinal chemists. The focus of this chapter is to provide an overview of the impact of chirality in medicinal chemistry and pharmaceutical sciences, and this should not be considered an exhaustive review of the topic. Several examples reported in the recent literature have been used to highlight the impact of chirality on development of therapeutics for various molecular targets. Chirality, as used in this chapter, also includes examples of atropisomers. The effects of chirality on pharmacological activities, absorption, distribution, metabolism, and excretion and toxicity are exemplified. In addition to chirality at carbon, examples of chiral compounds involving chirality at noncarbon atoms are included. A section on chirality in drug design provides several examples from recent literature covering diverse target classes. Regulatory considerations that apply to chiral drugs are addressed briefly. Section 10 covers recent drug development and marketed single enantiomers. Multiple synthetic approaches to produce chiral compounds with high enantiomeric purity, including chromatographic separation and enantioselective syntheses, were covered adequately in the 6th edition, and thus these areas and general definitions of chirality are not repeated in this chapter.

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Stereoselective pharmacokinetics and metabolism of the enantiomers of cyclophosphamide

Cited by 25 publications

References 17 publications

Pharmacokinetics of (R)- and (S)-cyclophosphamide and their dechloroethylated metabolites in cancer patients

Pharmacokinetics of (R)- and (S)-cyclophosphamide and their dechloroethylated metabolites in cancer patients

Farmacocinética enantiosseletiva da ciclofosfamida em pacientes com câncer de mama

Chirality and Biological Activity

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