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Chirality Clinical Pharmacokinetic and Pharmacodynamic Considerations

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References

  • Aberg G, Toxicological and local anaesthetic effects of optically active isomers of two local anaesthetic compounds. Acta Pharmacologica el Toxicologica 31: 255–266, 1972

    Article  CAS  Google Scholar 

  • Ames MM, Frank SK. Stereochemical aspects of para-chloramphetamine metabolism. Biochemical Pharmacology 31: 5–9, 1982

    Article  PubMed  CAS  Google Scholar 

  • Ariens EJ, Stereochemistry, a basis for sophisticated nonsense in pharmacokinelics and clinical pharmacology. European Journal of Clinical Pharmacology 26: 663–668, 1984

    Article  PubMed  CAS  Google Scholar 

  • Ariens EJ, Wuis EW. Bias in pharmacokinetics and clinical pharmacology. Clinical Pharmacology and Therapeutics 424: 361–363, 1987

    Google Scholar 

  • Armstrong DW, Optical isomer separation by liquid chromatography. Analytical Chemistry 592: 84A–91A, 1987

    Google Scholar 

  • Bai SA, Walle UK, Wilson MJ, Walle T. Stereoselective binding of the (−)-enantiomer of Propranolol to plasma and extravascular binding sites in the dog. Drug Metabolism and Disposition 11: 394–395, 1983

    PubMed  CAS  Google Scholar 

  • Borgstrom L, Nyberg L, Jonsson S, Lindberg C, Paulson J, Pharmacokinetic evaluation in man of terbutaline given as separate enantiomers and as the racemate. British Journal of Clinical Pharmacology 27: 49–56, 1989

    Article  PubMed  CAS  Google Scholar 

  • Boyd RA, Chin SK, Don-Pedro O, Williams RL, Giacomini KM, The pharmacokinetics of the enantiomers of atenolol. Clinical Pharmacology and Therapeutics 454: 403–410, 1989

    Google Scholar 

  • Cahn RS, Ingold CK, Prelog V. The specification of asymmetric configuration in organic chemistry Experientia 12: 81–124, 1956

    CAS  Google Scholar 

  • Cowan A, Geller EB, Adler MW, Classification of Opioids on the basis of change in seizure threshold in rats. Science 206: 465–467, 1979

    Article  PubMed  CAS  Google Scholar 

  • Day RO, Williams KM, Graham GG, Lee EJD, Knihinicki RD, et al. Stereoselective disposition of ibuprofen enantiomers in synovial fluid. Clinical Pharmacology and Therapeutics 435: 480–487, 1989

    Google Scholar 

  • Drayer DE, On the use of drugs administered as racemates. Clinical Pharmacology and Therapeutics 42: 364, 1987

    Article  PubMed  CAS  Google Scholar 

  • Evans AM, Nation RL, Sansom LN, Bochner F, Somogyi AA, Stereoselectne drug disposition: potential for misinterpretation of drug disposition data. British Journal of Clinical Pharmacology 26: 771–780, 1988

    Article  PubMed  CAS  Google Scholar 

  • Evans AM, Nation RL, Sansom LN, Bochner F, Somogyi AA, Stereoselective plasma protein binding of ibuprofen enantiomers. European Journal of Clinical Pharmacology 36: 283–290, 1989

    Article  PubMed  CAS  Google Scholar 

  • Fitos I, Tegyey Z, Simonyi M, Sjoholm I, Larsson T, Lagercrantz C, Stereoselective binding of 3-acetoxy-. and 3-hydrox-1.4-benzodiazepine-2-ones to human serum albumin. Selective allosteric interaction with warfarin enantiomers. Biochemical Pharmacology 352: 263–269, 1986

    Article  Google Scholar 

  • Gal J, Stereoisomerism and drug nomenclature. Clinical Pharmacology and Therapeutics 443: 251–253, 1988

    Google Scholar 

  • Giacomini KM, Nelson WL, Pershe RA, Valdivieso L, Turner-Tamiyasu K, et al. In vivo interaction of the enanliomers of disopyramide in human subjects. Journal of Pharmacokinetics and Biopharmaceutics 14: 335–356, 1986

    PubMed  CAS  Google Scholar 

  • Greig ME, Griffin RL. Antagonism of slow reacting substance in anaphylaxis SRS-A and other spasmogens on the guinea pig tracheal chain by hydratropic acids and their effects on anaphylaxis. Journal of Medicinal Chemistry 18: 112–116, 1975

    Article  PubMed  CAS  Google Scholar 

  • Hendel J, Brodthagen H. Entero-hepatic cycling of methotrexate estimated by the use of the D-isomer as a reference marker. European Journal of Clinical Pharmacology 26: 103–107, 1984

    Article  PubMed  CAS  Google Scholar 

  • Hsyu P-H, Giacomini KM. Stereoselective renal clearance of pindolol in humans. Journal of Clinical Investigation 76: 1720–1726, 1985

    Article  PubMed  CAS  Google Scholar 

  • Karnes TH, Sarkar MA. Enantiomeric resolution of drug compounds by liquid chromatography. Pharmaceutical Research 44: 285–292, 1987

    Article  Google Scholar 

  • Kawashima K, Levy A, Speclor S. Stereospecific radioimmunoassay for Propranolol isomers. Journal of Pharmacology and Experimental Therapeutics 196: 517–523, 1976

    PubMed  CAS  Google Scholar 

  • Lee EJD, Williams KM, Graham GG, Day RO, Champion GD, Stereoselective disposition of ibuprofen enantiomers in man. British Journal of Clinical Pharmacology 19: 669–674, 1985

    Article  PubMed  CAS  Google Scholar 

  • Lennard MS, Tucker GT, Silas JH, Freestone S, Ramsay LE, et al. Differential stereoselective metabolism of metoprolol in extensive and poor debrisoquine metabolisers. Clinical Pharmacology and Therapeutics 34: 732–737, 1983

    Article  PubMed  CAS  Google Scholar 

  • Lima JJ, Boudoulas H, Shields B. Stereoselective pharmacokinetics of disopyramide enantiomes in man. Drug Metabolism and Disposition 13: 572–577, 1985

    PubMed  CAS  Google Scholar 

  • Ofori-Adjei D, Ericsson O, Lindstrom B, Hermansson J, Adjepon-Yamoah, et al. Enantioselective analysis of chloroquine and desethylchloroquine after oral administration of racemic chloroquine. Therapeutic Drug Monitoring 8: 457–461, 1986

    Article  PubMed  CAS  Google Scholar 

  • Pike MC, Snyderman R, Augmentation of human monocyte chemotactic response by levamisole. Nature 261: 136–137, 1976

    Article  PubMed  CAS  Google Scholar 

  • Richards R, Tattersfield AE, Bronchial beta-adrenoeeptor blockade following eyedrops of timolol and its isomer L-714,465 in normal subjects. British Journal of Clinical Pharmacology 20: 459–462, 1985

    Article  PubMed  CAS  Google Scholar 

  • Schilsky RL, Choi KE, Vokes EE, Guaspari A, Guanieri C, et al. Clinical pharmacology of the stereoisomers of leucovorin during repeated oral dosing. Cancer 63(Suppl. 6): 1018–1021, 1989

    Article  PubMed  CAS  Google Scholar 

  • Simonyi M, Gal J, Testa B, Signs of the times: the need for a stereochemically informative generic name system. Trends in Pharmacological Sciences 10: 349–354, 1989

    Article  PubMed  CAS  Google Scholar 

  • Testa B, Mechanisms of chiral recognition in xenobiotic metabolism and drug-receptor interactions. Chirality 1: 7–9, 1989

    Article  PubMed  CAS  Google Scholar 

  • Testa B, Mayer JM. Stereoselective drug metabolism in its significance in drug research. Progress in Drug Research 32: 249–303, 1988

    PubMed  CAS  Google Scholar 

  • Tocco DJ, Hooke KF, Deluna FA, Duncan AEW. Stereospecific binding of timolol, a bela-adrenergic blocking agent. Drug Metabolism and Disposition 4: 323–329, 1976

    PubMed  CAS  Google Scholar 

  • Wade DN, Mearrick PT, Morris J. Active transport of L-dopa in the intestine. Nature 242: 463–465, 1973

    Article  PubMed  CAS  Google Scholar 

  • Webb JG, Street JA, Bagwell EE, Walle T, Gaffney TE. Stereoselective secretion of atenolol from PC12 cells. Journal of Pharmacology and Experimental Therapeutics 2473: 958–964, 1988

    Google Scholar 

  • White PF, Ham J, Way WL, Trevor AJ. Pharmacology of ketamine isomers in surgical patients. Anesthesiology 523: 231–239, 1980

    Article  Google Scholar 

  • Williams KM, Day R, Knihinicki R, Duffield A. The stereoselective uptake of ibuprofen enantiomers into adipose tissue. Biochemical Pharmacology 35: 3403–3405, 1986

    Article  PubMed  CAS  Google Scholar 

  • Williams KM, Lee EJD. Importance of drug enantiomers in clinical pharmacology. Drugs 30: 333–354, 1985

    Article  PubMed  CAS  Google Scholar 

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Lee, E.J.D., Williams, K.M. Chirality Clinical Pharmacokinetic and Pharmacodynamic Considerations. Clin Pharmacokinet 18, 339–345 (1990). https://doi.org/10.2165/00003088-199018050-00001

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