Types of stereoselectivity in drug metabolism: a heuristic approach

References

• Äbelö A, Andersson TB, Antonsson M, et al. (2000). Stereoselective metabolism of omeprazole by human cytochrome P450 enzymes. Drug Metab Dispos 28:966–972
   PubMed Web of Science ®Google Scholar
• Aberg G, Ciofalo VB, Pendleton RG, et al. (1995). Inversion of (R)- to (S)-ketoprofen in eight animal species. Chirality 7:383–387
   PubMed Web of Science ®Google Scholar
• Ariëns EJ, Soudijn W, Timmermans PBM, eds. (1983). Stereochemistry and biological activity of drugs. Oxford, UK: Blackwell, 194 p
   Google Scholar
• Aso Y, Yoshioka S, Shibazaki T, Uchiyama M. (1988). The kinetics of the racemization of oxazepam in aqueous solution. Chem Pharm Bull 36:1834–1840
   PubMed Web of Science ®Google Scholar
• Baumann P, Prelog V. (1958). The stereospecific reduction of stereoisomeric decalindiones-(1,4) [in German]. Helv Chim Acta 41:2362–2379
   Google Scholar
• Brugger R, Garcia Alia B, Reichel C, et al. (1996). Isolation and characterization of rat liver microsomal R-ibuprofenoyl-CoA synthetase. Biochem Pharmacol 52:1007–1013
   PubMed Web of Science ®Google Scholar
• Brugger R, Reichel C, Garcia Alia B, et al. (2001). Expression of rat liver long-chain acyl-CoA synthetase and characterization of its role in the metabolism of R-ibuprofen and other fatty acid-like xenobiotics. Biochem Pharmacol 61:651–656
   PubMed Web of Science ®Google Scholar
• Cahn RS, Ingold C, Prelog V. (1966). Specification of molecular chirality. Angew Chem, Int Ed 5:385–415, 511
   Web of Science ®Google Scholar
• Caldwell J. (1995). Stereochemical determinants of the nature and consequences of drug metabolism. J Chromatogr A 694:39–48
   PubMed Web of Science ®Google Scholar
• Carroll FI, Brine GA, Boldt KG, et al. (1981). Phencyclidine metabolism: Resolution, structure, and biological activity of the isomers of the hydroxy metabolite, 4-phenyl-4-(1-piperidinyl)cyclohexanol. J Med Chem 24:1047–1051
   PubMed Web of Science ®Google Scholar
• Cashman JR. (1998). Stereoselectivity in S- and N-oxygenation by the mammalian flavin-containing and cytochrome P-450 monooxygenases. Drug Metab Rev 30:675–707
   PubMed Web of Science ®Google Scholar
• Casy AF. (1993). The steric factor in medicinal chemistry – Dissymmetric probes of pharmacological receptors. New York: Plenum Press, 570
   Google Scholar
• Damani LA, Pool WF, Crooks PA, et al. (1988). Stereoselectivity in the N′-oxidation of nicotine isomers by flavin-containing monooxygenase. Mol Pharmacol 33:702–705
   PubMed Web of Science ®Google Scholar
• Ding G, Liu Y, Sun J, et al. (2007). Effect of absorption rate on pharmacokinetics of ibuprofen in relation to chiral inversion in humans. J Pharm Pharmacol 59:1509–1513
   PubMed Web of Science ®Google Scholar
• Dow J, Berg C. (1995). Stereoselectivity of the carbonyl reduction of dolasetron in rats, dogs and humans. Chirality 7:342–348
   PubMed Web of Science ®Google Scholar
• Draffan AG, Evans GR, Henshilwood JA. (2003). Chirality and biological activity. In: Abraham DJ, ed. Burger’s medicinal chemistry & drug discovery, 6th ed. Hoboken, NJ, USA: Wiley, 781–826
   Google Scholar
• Eichelbaum M, Testa B, Somogyi A, eds. (2003). Stereochemical aspects of drug action and disposition. Berlin, Germany: Springer-Verlag, 442 p
   Google Scholar
• Ferdinandusse S, Rusch H, van Lint AE, et al. (2002). Stereochemistry of the peroxisomal branched-chain fatty acid alpha- and beta-oxidation systems in patients suffering from different peroxisomal disorders. J Lipid Res 43:438–444
   PubMed Web of Science ®Google Scholar
• Francotte E, Lindner W, eds. (2006). Chirality in drug research. Weinheim, Germany: Wiley-VCH, 351 p
   Google Scholar
• Gal J. (2013). Molecular chirality in chemistry and biology: Historical milestones. Helv Chim Acta 96:1617–1657
   Web of Science ®Google Scholar
• Garton KJ, Yuen P, Meinwald J, et al. (1995). Stereoselective metabolism of enflurane by human liver cytochrome P450 2E1. Drug Metab Dispos 23:1426–1430
   PubMed Web of Science ®Google Scholar
• Guo J, Nikolic D, Chadwick LR, et al. (2006). Identification of human hepatic cytochrome P450 enzymes involved in the metabolism of 8-prenylnaringenin and isoxanthohumol from hops (Humulus lupulus L.). Drug Metab Dispos 34:1152–1159
   PubMed Web of Science ®Google Scholar
• Hao H, Wang G, Sun J. (2005). Enantioselective pharmacokinetics of ibuprofen and involved mechanisms. Drug Metab Rev 37:215–234
   PubMed Web of Science ®Google Scholar
• Hermans JJR, Thijssen HHW. (1992). Stereoselective acetonyl side chain reduction of warfarin and analogs. Drug Metab Dispos 20:268–274
   PubMed Web of Science ®Google Scholar
• Holsztynska EJ, Domino EF. (1985–1986). Biotransformation of phencyclidine. Drug Metab Rev 16:285–320
   PubMed Web of Science ®Google Scholar
• Hu Y, Krausz K, Gelboin HV, Kupfer D. (2004). CYP2C subfamily, primarily CYP2C9, catalyses the enantioselective demethylation of the endocrine disruptor pesticide methoxychlor in human liver microsomes: Use of inhibitory monoclonal antibodies in P450 identification. Xenobiotica 34:117–132
   PubMed Web of Science ®Google Scholar
• IUBMB (International Union of Biochemistry and Molecular Biology). (2014). Enzyme Nomenclature. Available from: http://www.chem.qmul.ac.uk/iubmb/enzyme/ [last accessed Sep 2014]
   Google Scholar
• IUPAC (International Union of Pure and Applied Chemistry). (1996). Recommendations 1996 – Basic terminology of stereochemistry. Pure Appl Chem 68:2193–2222. Available from: http://www.chem.qmul.ac.uk/iupac/stereo/ [last accessed Sep 2014]
   Web of Science ®Google Scholar
• Jenner P, Testa B. (1973). The influence of stereochemical factors on drug disposition. Drug Metab Rev 2:117–184
   PubMed Web of Science ®Google Scholar
• Kantoci D, Wechter WJ. (1996). Calculation of inversion half-lives of arylpropionic acid class nonsteroidal antiinflammatory drugs. J Clin Pharmacol 36:500–504
   PubMed Web of Science ®Google Scholar
• Koyama E, Chiba K, Tani M, Ishizaki T. (1996). Identification of human cytochrome P450 isoforms involved in the stereoselective metabolism of mianserin enantiomers. J Pharmacol Exp Ther 279:21–30
   Google Scholar
• Kuks PF, Weekers LE, Goldhoorn PB. (1990). Decomposition of pilocarpine eye drops assessed by a highly efficient high pressure liquid chromatographic method. Pharm Weekbl Sci 12:196–199
   PubMedGoogle Scholar
• Laurenzana EM, Owens SM. (1997). Metabolism of phencyclidine by human liver microsomes. Drug Metab Dispos 25:557–563
   PubMed Web of Science ®Google Scholar
• Lawrence RF, Rettie AE, Eddy AC, Trager WF. (1990). Chemical synthesis, absolute configuration, and stereochemistry of formation of 10-hydroxywarfarin. Chirality 2:96–105
   PubMed Web of Science ®Google Scholar
• Lloyd MD, Darley DJ, Wierzbicki AS, Threadgill MD. (2008). Alpha-methylacyl-CoA racemase – An “obscure” metabolic enzyme takes centre stage. FEBS J 275:1089–1102
   PubMed Web of Science ®Google Scholar
• Martin HJ, Breyer-Pfaff U, Wsol V, et al. (2006). Purification and characterization of AKR1B10 from human liver: Role in carbonyl reduction of xenobiotics. Drug Metab Dispos 34:464–470
   PubMed Web of Science ®Google Scholar
• Mayer JM, Testa B. (1997). Pharmacodynamics, pharmacokinetics and toxicity of ibuprofen enantiomers. Drugs Future 22:1347–1366
   Google Scholar
• Mesecar AD, Koshland Jr DE. (2000). A new model for protein stereospecificity. Nature 403:614–615
   PubMed Web of Science ®Google Scholar
• Mey B, Paulus H, Lamparter E, Blaschke G. (1998). Kinetics of racemization of (+)- and (−)-diethylpropion: Studies in aqueous solution, with and without the addition of cyclodextrins, in organic solvents and in human plasma. Chirality 10:307–315
   PubMed Web of Science ®Google Scholar
• Ngui JS, Chen Q, Shou M, et al. (2001). In vitro stimulation of warfarin metabolism by quinidine: Increases in the formation of 4′-and 10-hydroxywarfarin. Drug Metab Dispos 29:877–886
   PubMed Web of Science ®Google Scholar
• Nobel Prize. (1975). Available from: http://www.nobelprize.org/nobel_prizes/chemistry/laureates/1975/prelog-facts.html [last accessed Sep 2014]
   Google Scholar
• Nunes MA, Brochmann-Hanssen E. (1974). Hydrolysis and epimerization kinetics of pilocarpine in aqueous solution. J Pharm Sci 63:716–721
   PubMed Web of Science ®Google Scholar
• Porst H, Kny L. (1985). On the stability of pilocarpine hydrochloride in eye drops. Pharmazie 40:23–29
   PubMed Web of Science ®Google Scholar
• Portoghese PS. (1970). Relationships between stereostructure and pharmacological activities. Ann Rev Pharmacol 10:51–76
   PubMedGoogle Scholar
• Prelog V. (1962). On the stereospecificity of the enzymatic reduction of carbonyl groups [in German]. Ind Chim Belge 27:1309
   Google Scholar
• Reist M, Christiansen LH, Christoffersen P, et al. (1995a). Low configurational stability of amfepramone and cathinone: Mechanism and kinetics of chiral inversion. Chirality 7:469–473
   Web of Science ®Google Scholar
• Reist M, Testa B, Carrupt PA, et al. (1995b). Racemization, enantiomerization, diastereomerization, and epimerization: Their meaning and pharmacological significance. Chirality 7:396–400
   Web of Science ®Google Scholar
• Reist M, Testa B, Carrupt PA. (2003). Drug racemization and its significance in pharmaceutical research. In: Eichelbaum M, Testa B, Somogyi A, eds. Stereochemical aspects of drug action and disposition. Berlin, Germany: Springer Verlag, 91–112
   Google Scholar
• Rettie AE, Korzekwa KR, Kunze KL, et al. (1992). Hydroxylation of warfarin by cDNA-expressed cytochromes P450: A role for P4502C9 in the etiology of (S)-warfarin-drug interactions. Chem Res Toxicol 5:54–59
   PubMed Web of Science ®Google Scholar
• Roiban GD, Agudo R, Reetz MT. (2014). Cytochrome P450 catalyzed oxidative hydroxylation of achiral organic compounds with simultaneous creation of two chirality centers in a single C–H activation step. Angew Chem, Int Ed 53:8659–8663
   PubMed Web of Science ®Google Scholar
• Schoetz G, Trapp O, Schurig V. (2000). Determination of the enantiomerization barrier of oxazepam by dynamic micellar electrokinetic chromatography – Comparison of experiment and simulation with ChromWin 99. Enantiomer 5:391–396
   PubMedGoogle Scholar
• Shah RR. (2003). Improving clinical risk/benefit through stereochemistry. In: Eichelbaum M, Testa B, Somogyi A, eds. Stereochemical aspects of drug action and disposition. Berlin, Germany: Springer Verlag, 401–432
   Google Scholar
• Shebley M, Jushchyshyn MI, Hollenberg PF. (2006). Selective pathways for the metabolism of phencyclidine by cytochrome P450 2b enzymes: Identification of electrophilic metabolites, glutathione, and N-acetylcysteine adducts. Drug Metab Dispos 34:375–383
   PubMed Web of Science ®Google Scholar
• Singh J, Hagen TJ. (2010). Chirality and biological activity. In: Abraham DJ, Rotella DP, eds. Burger’s medicinal chemistry, drug discovery, and development, 7th ed. Hoboken, NJ: Wiley, 127–166
   Google Scholar
• Soudijn W, van Wijngaarden I, Ijzerman AP. (2003). Enantioselectivity in drug-receptor interactions. In: Eichelbaum M, Testa B, Somogyi A, eds. Stereochemical aspects of drug action and disposition. Berlin, Germany: Springer-Verlag, 161–182
   Google Scholar
• Sten T, Qvisen S, Uutela P, et al. (2006). Prominent but reverse stereoselectivity in propranolol glucuronidation by human UDP-glucuronosyltransferases 1A9 and 1A10. Drug Metab Dispos 34:1488–1494
   PubMed Web of Science ®Google Scholar
• Sugiyama K, Trager WF. (1986). Prochiral selectivity and intramolecular isotope effects in the cytochrome P450 catalyzed ω-hydroxylation of cumene. Biochemistry 25:7336–7343
   PubMed Web of Science ®Google Scholar
• Tan SC, Patel BK, Jackson SH, et al. (2002). Stereoselectivity of ibuprofen metabolism and pharmacokinetics following the administration of the racemate to healthy volunteers. Xenobiotica 32:683–697
   PubMed Web of Science ®Google Scholar
• Tegeder I, Williams K, Geisslinger G. (2003). Metabolic chiral inversion of 2-arylpropionic acids. In: Eichelbaum M, Testa B, Somogyi A, eds. Stereochemical aspects of drug action and disposition. Berlin, Germany: Springer-Verlag, 341–354
   Google Scholar
• Tenmizu D, Noguchi K, Kamimura H. (2006). Elucidation of the effects of the CYP1A2 deficiency polymorphism in the metabolism of 4-cyclohexyl-1-ethyl-7-methylpyrido[2,3-d]pyrimidine-2-(1h)-one (YM-64227), a phosphodiesterase type 4 inhibitor, and its metabolites in dogs. Drug Metab Dispos 34:1811–1816
   PubMed Web of Science ®Google Scholar
• Testa B. (1988). Substrate and product stereoselectivity in monooxygenase-mediated drug activation and inactivation. Biochem Pharmacol 37:85–92
   PubMed Web of Science ®Google Scholar
• Testa B. (2013a). Organic stereochemistry. Part 7. The concept of substrate stereoselectivity in biochemistry and xenobiotic metabolism. Helv Chim Acta 96:1203–1234
   Web of Science ®Google Scholar
• Testa B. (2013b). Organic stereochemistry. Part 8. Prostereoisomerism and the concept of product stereoselectivity in biochemistry and xenobiotic metabolism. Helv Chim Acta 96:1409–1451
   Web of Science ®Google Scholar
• Testa B. (2013c). Organic stereochemistry. Part 2. Stereoisomerism resulting from one or several stereogenic centers. Helv Chim Acta 96:159–188
   Web of Science ®Google Scholar
• Testa B, Caldwell J, Kisakürek MV, eds. (2014). Organic stereochemistry – Guiding principles and biomedicinal relevance. Weinheim, Germany: Wiley-VCH
   Google Scholar
• Testa B, Carrupt PA, Gal J. (1993). The so-called “interconversion” of stereoisomeric drugs: An attempt at clarification. Chirality 5:105–111
   PubMed Web of Science ®Google Scholar
• Testa B, Krämer SD. (2010). The biochemistry of drug metabolism, Vol. 2: Conjugations, consequences of metabolism, influencing factors. Weinheim, Germany: Wiley-VCH, 1–165
   Google Scholar
• Testa B, Vistoli G, Pedretti A, Caldwell J. (2013). Organic stereochemistry. Part 5. Stereoselectivity in molecular and clinical pharmacology. Helv Chim Acta 96:747–798
   Web of Science ®Google Scholar
• Trager WF, Testa B. (1985). Stereoselective drug disposition. In: Wilkinson GR, Rawlins MD, eds. Drug metabolism and disposition: Considerations in clinical pharmacology. Lancaster, GB: MTP Press, 35–61
   Google Scholar
• Triggle DJ. (1996). Ion channels as pharmacologic receptors: The chirality of drug interactions. Chirality 8:35–38
   PubMed Web of Science ®Google Scholar
• Valenzuela C. (2003). Stereoselective drug-channel interactions. In: Eichelbaum M, Testa B, Somogyi A, eds. Stereochemical aspects of drug action and disposition. Berlin, Germany: Springer Verlag, 199–228
   Google Scholar
• Wermuth CG. (2008). Optical isomerism in drugs. In: Wermuth CG, ed. The practice of medicinal chemistry, 3rd ed. London, UK: Academic Press, 533–548
   Google Scholar
• Wistuba D, Träger O, Schurig V. (1992). Enantio- and regioselectivity in the epoxide-hydrolase-catalyzed ring opening of simple aliphatic oxiranes. Part II: Dialkyl- and trialkylsubstituted oxiranes. Chirality 4:185–192
   PubMed Web of Science ®Google Scholar
• Wistuba D, Schurig V. (1992). Enantio- and regioselectivity in the epoxide-hydrolase-catalyzed ring opening of simple aliphatic oxiranes. Part I: Monoalkylsubstituted oxiranes. Chirality 4:178–184
   PubMed Web of Science ®Google Scholar
• Woodworth JR, Mayersohn M, Owens SM. (1986). Disposition kinetics of the monohydroxy metabolites of phencyclidine in the dog. J Pharmacol Exp Ther 238:900–904
   PubMed Web of Science ®Google Scholar
• Yang SK, Liu KL. (1992). Resolution and stability of oxazepam enantiomers. Chirality 4:443–446
   Web of Science ®Google Scholar
• Zhang Z, Fasco MJ, Huang Z, et al. (1995). Human cytochromes P4501A1 and P4501A2: R-Warfarin metabolism as a probe. Drug Metab Dispos 23:1339–1345
   PubMed Web of Science ®Google Scholar