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1

STINSON, STEPHEN C. "CHIRAL DRUGS." Chemical & Engineering News 70, no. 39 (September 28, 1992): 46–79. http://dx.doi.org/10.1021/cen-v070n039.p046.

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2

STINSON, STEPHEN C. "CHIRAL DRUGS." Chemical & Engineering News 78, no. 43 (October 23, 2000): 55–78. http://dx.doi.org/10.1021/cen-v078n043.p055.

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3

STINSON, STEPHEN C. "CHIRAL DRUGS." Chemical & Engineering News 71, no. 39 (September 27, 1993): 38–65. http://dx.doi.org/10.1021/cen-v071n039.p038.

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4

STINSON, STEPHEN C. "Chiral Drugs." Chemical & Engineering News 72, no. 38 (September 19, 1994): 38–50. http://dx.doi.org/10.1021/cen-v072n038.p038.

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5

STINSON, STEPHEN C. "CHIRAL DRUGS." Chemical & Engineering News 73, no. 41 (October 9, 1995): 44–546274. http://dx.doi.org/10.1021/cen-v073n041.p044.

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6

Caner, Hava, and Israel Agranat. "Chiral Drugs." Enantiomer 7, no. 6 (November 1, 2002): 405–6. http://dx.doi.org/10.1080/10242430215704.

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7

Aboul-Enein, Hassan Y. "Chiral drugs." Chirality 15, no. 8 (2003): 730. http://dx.doi.org/10.1002/chir.10286.

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8

Brossi, Arnold. "Chiral drugs: Synopsis." Medicinal Research Reviews 14, no. 6 (November 1994): 665–91. http://dx.doi.org/10.1002/med.2610140604.

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9

Ranade, Vasant V., and John C. Somberg. "Chiral Cardiovascular Drugs." American Journal of Therapeutics 12, no. 5 (September 2005): 439–59. http://dx.doi.org/10.1097/01.mjt.0000167429.37357.0c.

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10

Mehvar, Reza, and Fakhreddin Jamali. "Bioequivalence of Chiral Drugs." Clinical Pharmacokinetics 33, no. 2 (August 1997): 122–41. http://dx.doi.org/10.2165/00003088-199733020-00004.

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11

STINSON, STEPHEN C. "COUNTING ON CHIRAL DRUGS." Chemical & Engineering News 76, no. 38 (September 21, 1998): 83–104. http://dx.doi.org/10.1021/cen-v076n038.p083.

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12

Porter, W. H. "Resolution of chiral drugs." Pure and Applied Chemistry 63, no. 8 (January 1, 1991): 1119–22. http://dx.doi.org/10.1351/pac199163081119.

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13

JACOBY, MITCH. "FAST SEPARATIONS FOR CHIRAL DRUGS." Chemical & Engineering News 79, no. 21 (May 21, 2001): 68–69. http://dx.doi.org/10.1021/cen-v079n021.p068.

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14

Gross, Michael, Anthony Cartwright, Bruce Campbell, Roger Bolton, Keith Holmes, Karin Kirkland, Tomas Salmonson, and Jean-Louis Robert. "Regulatory Requirements for Chiral Drugs." Drug Information Journal 27, no. 2 (April 1993): 453–57. http://dx.doi.org/10.1177/009286159302700232.

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15

Dorey, Emma. "Chiral drugs viable, despite failure." Nature Biotechnology 18, no. 12 (December 2000): 1239–40. http://dx.doi.org/10.1038/82335.

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16

Chen, Fuxin, Qiaoxiu Bai, Qingfeng Wang, Suying Chen, Xiaoxian Ma, Changlong Cai, Danni Wang, Ahsan Waqas, and Pin Gong. "Stereoselective Pharmacokinetics and Chiral Inversions of Some Chiral Hydroxy Group Drugs." Current Pharmaceutical Biotechnology 21, no. 15 (December 23, 2020): 1632–44. http://dx.doi.org/10.2174/1389201021666200727144053.

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Background: Chiral safety, especially chiral drug inversion in vivo, is the top priority of current scientific research. Medicine researchers and pharmacists often ignore that one enantiomer will be converted or partially converted to another enantiomer when it is ingested in vivo. So that, in the context that more than 50% of the listed drugs are chiral drugs, it is necessary and important to pay attention to the inversion of chiral drugs. Methods: The metabolic and stereoselective pharmacokinetic characteristics of seven chiral drugs with one chiral center in the hydroxy group were reviewed in vivo and in vitro including the possible chiral inversion of each drug enantiomer. These seven drugs include (S)-Mandelic acid, RS-8359, Tramadol, Venlafaxine, Carvedilol, Fluoxetine and Metoprolol. Results: The differences in stereoselective pharmacokinetics could be found for all the seven chiral drugs, since R and S isomers often exhibit different PK and PD properties. However, not every drug has shown the properties of one direction or two direction chiral inversion. For chiral hydroxyl group drugs, the redox enzyme system may be one of the key factors for chiral inversion in vivo. Conclusion: In vitro and in vivo chiral inversion is a very complex problem and may occur during every process of ADME. Nowadays, research on chiral metabolism in the liver has the most attention, while neglecting the chiral transformation of other processes. Our review may provide the basis for the drug R&D and the safety of drugs in clinical therapy.
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17

Benedetti, Michele, Jaroslav Malina, Jana Kasparkova, Viktor Brabec, and Giovanni Natile. "Chiral discrimination in platinum anticancer drugs." Environmental Health Perspectives 110, suppl 5 (October 2002): 779–82. http://dx.doi.org/10.1289/ehp.02110s5779.

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18

Kostyanovsky, Remir G., Gul’nara K. Kadorkina, Konstantin A. Lyssenko, Vladimir Yu Torbeev, Angelina N. Kravchenko, Oleg V. Lebedev, Gennadii V. Grintselev-Knyazev, and Vasily R. Kostyanovsky. "Chiral drugs via the spontaneous resolution." Mendeleev Communications 12, no. 1 (January 2002): 6–8. http://dx.doi.org/10.1070/mc2002v012n01abeh001521.

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19

Nitchuk, Wayne M. "Regulatory Requirements for Generic Chiral Drugs." Journal of Clinical Pharmacology 32, no. 10 (October 1992): 953–54. http://dx.doi.org/10.1002/j.1552-4604.1992.tb04644.x.

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20

You, Qi-Dong. "ChemInform Abstract: Resolution of Chiral Drugs." ChemInform 43, no. 17 (March 29, 2012): no. http://dx.doi.org/10.1002/chin.201217255.

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21

Qiu, Xiao-Long, Xuyi Yue, and Feng-Ling Qing. "ChemInform Abstract: Fluorine-Containing Chiral Drugs." ChemInform 43, no. 24 (May 21, 2012): no. http://dx.doi.org/10.1002/chin.201224226.

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22

PORTER, W. H. "ChemInform Abstract: Resolution of Chiral Drugs." ChemInform 22, no. 48 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199148350.

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23

Millership, Jeffrey S., and Anne Fitzpatrick. "Commonly used chiral drugs: A survey." Chirality 5, no. 8 (1993): 573–76. http://dx.doi.org/10.1002/chir.530050802.

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24

Ariëns, E. J. "Nonchiral, homochiral and composite chiral drugs." Trends in Pharmacological Sciences 14, no. 2 (February 1993): 68–75. http://dx.doi.org/10.1016/0165-6147(93)90033-g.

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25

Witte, Dirk T., Kees Ensing, Jan-Piet Franke, and Rokus A. Zeeuw. "Development and registration of chiral drugs." Pharmacy World & Science 15, S1 (January 1993): 10–16. http://dx.doi.org/10.1007/bf02116164.

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26

Wozniak, Timothy J., Ronald J. Bopp, and Eric C. Jensen. "Chiral drugs: An industrial analytical perspective." Journal of Pharmaceutical and Biomedical Analysis 9, no. 5 (January 1991): 363–82. http://dx.doi.org/10.1016/0731-7085(91)80160-b.

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27

Capon, Rob. "Chiral Drugs and Chiral Intermediates (Ed. Cynthia A. Challenger)." Australian Journal of Chemistry 56, no. 11 (2003): 1174. http://dx.doi.org/10.1071/ch00312_br.

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28

Saganuwan, Saganuwan Alhaji. "Chirality of Central Nervous System (CNS) Acting Drugs: A Formidable Therapeutic Hurdle Against CNS Diseases." Central Nervous System Agents in Medicinal Chemistry 19, no. 3 (October 31, 2019): 171–79. http://dx.doi.org/10.2174/1871524919666190624150214.

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Background: Over fifty percent of drugs being used clinically are chiral and 90% of them are racemates. Unfortunately, they have both adverse and beneficial effects on body systems. Methods: Because of the erratic effects of chiral compounds on body functional systems, literature search was carried out with a view to identify CNS chiral drugs, their clinical advantages and disadvantages, unique physicochemical properties and structural modifications into safer drugs. Results: Findings have shown that majority of CNS and non-CNS acting drugs have chiral functional groups that may occur as either dextrorotatory (clockwise) or levorotatory (anticlockwise) or racemates which are inert. Sometimes, the enantiomers (optical isomers) could undergo keto-enol tautomerism, appearing in either acidic or basic or inert form. Chiral CNS acting drugs have agonistic and antagonistic effects, clinical advantages, disadvantages, and special clinical applications, possible modifications for better therapeutic effects and possible synthesis of more potent drugs from racemates. Clockwise chirality may be more effective and safer than the drugs with anticlockwise chirality. When chiral drugs are in racemate state they become inert and may be safer than when they are single. Also, diastereoisomers may be more dangerous than stereoisomers. Conclusion: Therefore, chiral compounds should be adequately studied in lab rodents and primates, and their mechanisms of actions should be comprehensively understood before being used in clinical setting. Since many of them are toxic, their use should be based on principle of individualized medicine. Their molecular weights, functional groups, metabolites, polymers and stereoisomers could be valuable tools for their modifications.
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29

Chmielewska, Aleksandra, and Tomasz Bączek. "Comparative Analysis of Chiral Drugs in View of Chemometrics." Journal of AOAC INTERNATIONAL 95, no. 3 (May 1, 2012): 624–35. http://dx.doi.org/10.5740/jaoacint.sge_chmielewska.

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Abstract With the development of methods for obtaining chiral compounds as potential drugs, there is also need to develop analytical methods for the separation of both enantiomers. Keeping in mind that the physical and chemical properties of both enantiomers are identical, their different nature will only be revealed in a chiral environment that is appropriately designed. Physicochemical systems can be used to predict the differences in biological activity of both enantiomers. The complexity of the problem requires the use of additional tools, which are various chemometric methods. This paper reviews the application of chemometry in the analysis of chiral drugs and discusses the effects of a combination of chromatographic, electrophoretic, and spectroscopic analysis (UV-Vis absorption spectroscopy, and near-IR spectroscopy aided by cyclodextrin inclusion complexes) with chemometrics for improving the methods of enantioseparation (experimental design), explaining the mechanisms of behavior and chiral recognition (quantitative structure-enantioselective retention relationships) and indicating chiral purity (enantiomeric excess).
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30

Wsol, V., L. Skalova, and B. Szotakova. "Chiral Inversion of Drugs: Coincidence or Principle?" Current Drug Metabolism 5, no. 6 (December 1, 2004): 517–33. http://dx.doi.org/10.2174/1389200043335360.

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31

BORMAN, STU. "FDA issues flexible policy on chiral drugs." Chemical & Engineering News 70, no. 24 (June 15, 1992): 5. http://dx.doi.org/10.1021/cen-v070n024.p005.

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32

Caner, Hava, Efrat Groner, Liron Levy, and Israel Agranat. "Trends in the development of chiral drugs." Drug Discovery Today 9, no. 3 (February 2004): 105–10. http://dx.doi.org/10.1016/s1359-6446(03)02904-0.

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33

Boussouar, Imene, Qianjin Chen, Xue Chen, Yulun Zhang, Fan Zhang, Demei Tian, Henry S. White, and Haibing Li. "Single Nanochannel Platform for Detecting Chiral Drugs." Analytical Chemistry 89, no. 2 (December 22, 2016): 1110–16. http://dx.doi.org/10.1021/acs.analchem.6b02682.

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34

Lin, Guo-Qiang, and Xing-Wen Sun. "ChemInform Abstract: Chiral Drugs Through Asymmetric Synthesis." ChemInform 43, no. 21 (April 26, 2012): no. http://dx.doi.org/10.1002/chin.201221233.

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35

韩, 建冬. "Application Potential of Chiral Drugs in Diagnostics." Medical Diagnosis 09, no. 01 (2019): 29–33. http://dx.doi.org/10.12677/md.2019.91006.

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36

Bertin, Sophie, Kyari Yates, and Bruce Petrie. "Enantiospecific behaviour of chiral drugs in soil." Environmental Pollution 262 (July 2020): 114364. http://dx.doi.org/10.1016/j.envpol.2020.114364.

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37

Margolin, Alexey L. "Enzymes in the synthesis of chiral drugs." Enzyme and Microbial Technology 15, no. 4 (April 1993): 266–80. http://dx.doi.org/10.1016/0141-0229(93)90149-v.

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38

Wang, Yi, Huaiyi Huang, Qianling Zhang, and Pingyu Zhang. "Chirality in metal-based anticancer agents." Dalton Transactions 47, no. 12 (2018): 4017–26. http://dx.doi.org/10.1039/c8dt00089a.

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Chiral metal-based drugs are currently an interesting and rapidly growing field in anticancer research. Here the different chiral metal-based anticancer agents and the extent to which the chiral resolution affects their biological properties are discussed. This review will aid the design of new potent and efficient chiral metal-based anticancer drugs that exploit the unique properties combined with their potential selectivity toward targeted chiral biomolecules.
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39

Xiong, Fei, Bei-Bei Yang, Jie Zhang, and Li Li. "Enantioseparation, Stereochemical Assignment and Chiral Recognition Mechanism of Sulfoxide-Containing Drugs." Molecules 23, no. 10 (October 18, 2018): 2680. http://dx.doi.org/10.3390/molecules23102680.

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The distinct pharmacodynamic and pharmacokinetic properties of enantiopure sulfoxide drugs have stimulated us to systematically investigate their chiral separation, stereochemical assignment, and chiral recognition mechanism. Herein, four clinically widely-used sulfoxide drugs were chosen and optically resolved on various chiral stationary phases (CSPs). Theoretical simulations including electronic circular dichroism (ECD) calculation and molecular docking were adopted to assign the stereochemistry and reveal the underlying chiral recognition mechanism. Our results showed that the sequence of calculated mean binding energies between each pair of enantiomers and CSP matched exactly with experimentally observed enantiomeric elution order (EEO). It was also found that the length of hydrogen bond might contribute dominantly the interaction between two enantiomers and CSP. We hope our study could provide a fresh perspective to explore the stereochemistry and chiral recognition mechanism of chiral drugs.
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40

Vakily, Majid, Reza Mehvar, and Dion Brocks. "Stereoselective Pharmacokinetics and Pharmacodynamics of Anti-Asthma Agents." Annals of Pharmacotherapy 36, no. 4 (April 2002): 693–701. http://dx.doi.org/10.1345/aph.1a248.

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OBJECTIVE: To review the previously published studies on pharmacokinetics and pharmacodynamics of chiral drugs used in the treatment of asthma. DATA SOURCES: Primary and review articles were identified with a MEDLINE search (1980–May 2001) and through secondary sources. STUDY SELECTION AND DATA EXTRACTION: All English-language studies and reviews obtained from the MEDLINE search pertaining to stereoselective pharmacokinetics and pharmacodynamics of chiral anti-asthma drugs were assessed. DATA SYNTHESIS: Several anti-asthma drugs (e.g., β2-adrenergic agonists, leukotriene modifiers) are chiral and marketed as racemates, which consist of equal proportions of 2 enantiomers. Significant stereoselectivity has also been reported in pharmacodynamics and pharmacokinetics of the β2-agonists. The enantiomers of β2-agonists in the R configuration are primarily responsible for the bronchodilating effects of the racemate. The plasma concentrations of the enantiomers of anti-asthma drugs may differ as a reflection of stereoselectivity in clearance, volume of distribution, and route of administration. CONCLUSIONS: Stereoselectivity in the pharmacokinetics of anti-asthma drugs may complicate the relationship between dose and/or plasma concentration of racemic drug versus effect relationship. An appreciation of the stereoselective pharmacokinetics and pharmacodynamics of chiral anti-asthma drugs may optimize the use of these agents in asthmatic patients.
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41

Gandhi, Karan, Umang Shah, and Sandip Patel. "Drug Stereochemistry: A Prodigy For Pharmacology and Drug Development." Current Drug Discovery Technologies 17, no. 5 (December 23, 2020): 565–73. http://dx.doi.org/10.2174/1570163816666190502101803.

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Stereochemistry has evinced the importance of many chiral drugs with respect to drug designing and development. A literature review was conducted for several chiral drugs involving pharmacokinetic and pharmacodynamic parameters of their enantiomers along with their uses in certain diseased conditions. This article mainly includes the pharmacological profile review of some chiral drugs and the aspects due to which the single enantiomer is of importance as compared to the racemic mixture of the drug. This was achieved by moderating the side effects or toxic effects; or by the potentiated activity of the single enantiomer. Resolution deals with the separation of racemic compounds which shows up the credibility to obtain the desired enantiomeric properties. As isomers vary in their pharmacokinetic and pharmacodynamic profiles, chiral drugs have showcased considerable importance in the drug development process. Both the enantiomers have a different pharmacological profile in the treatment of a disease, which differentiates them from drug racemates.
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42

Xu, Ronghua, He Yang, and Wenjun Tang. "Efficient Synthesis of Chiral Drugs Facilated by P-Chiral Phosphorus Ligands." Chinese Journal of Organic Chemistry 40, no. 6 (2020): 1409. http://dx.doi.org/10.6023/cjoc202003015.

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43

Fouad, Ali, Adel A. Marzouk, Montaser Sh A. Shaykoon, Samy M. Ibrahim, Sobhy M. El-Adl, and Ashraf Ghanem. "Daptomycin: A Novel Macrocyclic Antibiotic as a Chiral Selector in an Organic Polymer Monolithic Capillary for the Enantioselective Analysis of a Set of Pharmaceuticals." Molecules 26, no. 12 (June 9, 2021): 3527. http://dx.doi.org/10.3390/molecules26123527.

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Daptomycin, a macrocyclic antibiotic, is here used as a new chiral selector in preparation of chiral stationary phase (CSP) in a recently prepared polymer monolithic capillary. The latter is prepared using the copolymerization of the monomers glycidyl methacrylate (GMA) and ethylene glycol dimethacrylate (EGDMA) in the presence of daptomycin in water. Under reversed phase conditions (RP), the prepared capillaries were tested for the enantioselective nanoliquid chromatographic separation of fifty of the racemic drugs of different pharmacological groups, such as adrenergic blockers, H1-blockers, NSAIDs, antifungal drugs, and others. Baseline separation was attained for many drugs under RP-HPLC. Daptomycin expands the horizon of chiral selectors in HPLC.
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44

Matsuyama, Midori, Eri Kamiya, Nobuko Yoshida, Yoshiko Nagata, and Hideko Kanazawa. "Stereospecific analysis of chiral drugs by metabolic enzyme." Journal of Life Support Engineering 16, Supplement (2004): 135–36. http://dx.doi.org/10.5136/lifesupport.16.supplement_135.

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45

Sui, Jianjun, Jianhua Zhang, Chi Bun Ching, and Wei Ning Chen. "Expanding proteomics into the analysis of chiral drugs." Molecular BioSystems 5, no. 6 (2009): 603. http://dx.doi.org/10.1039/b903858b.

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46

Blaschke, Gottfried, and Bezhan Chankvetadze. "ChemInform Abstract: Resolution of Enantiomers of Chiral Drugs." ChemInform 32, no. 2 (January 9, 2001): no. http://dx.doi.org/10.1002/chin.200102260.

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47

Mehvar, Reza. "Stereochemical Considerations in Pharmacodynamic Modeling of Chiral Drugs." Journal of Pharmaceutical Sciences 81, no. 2 (February 1992): 199–200. http://dx.doi.org/10.1002/jps.2600810220.

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48

Shen, Qi, Lu Wang, Hui Zhou, Hui-di Jiang, Lu-shan Yu, and Su Zeng. "Stereoselective binding of chiral drugs to plasma proteins." Acta Pharmacologica Sinica 34, no. 8 (July 15, 2013): 998–1006. http://dx.doi.org/10.1038/aps.2013.78.

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49

Muller, N., E. Payan, F. Lapicque, B. Bannwarth, and P. Netter. "Pharmacological aspects of chiral nonsteroidal anti-inflammatory drugs." Fundamental & Clinical Pharmacology 4, no. 6 (November 12, 1990): 617–34. http://dx.doi.org/10.1111/j.1472-8206.1990.tb00042.x.

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50

Coutts, Ronald T., and Glen B. Baker. "Metabolic implications of chiral centres in psychotropic drugs." Progress in Neuro-Psychopharmacology and Biological Psychiatry 13, no. 3-4 (January 1989): 405–17. http://dx.doi.org/10.1016/0278-5846(89)90129-2.

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