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solids not characterized in early discovery
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Avdeef. A solution of the compound in the pH range where the compound is soluble is titrated toward the pH region where the compound is insoluble. In the soluble region the normal type of data from a potentiometric titration is collected, namely millivolt versus volume of titrant added. This data range serves to de ne the compound pKa. At and past the compound precipitation point, data corresponding to millivolt versus volume of titrant added continue to be collected. However, the data obtained past the precipitation point de nes not the pKa but the compound solubility product. In favorable cases where the precipitation point occurs about halfway through the titration, it is possible to obtain both compound pKa and compound solubility product from a single titration experiment. The theory is very well worked out for this method for almost every reasonable combination of ionizable groups likely to be present in a drug molecule. The analysis of the change in titration data once precipitation occurs requires very high quality potentiometric titration equipment, requires excellent protection against carbon dioxide uptake and requires very sophisticated curve analysis software. All these are commercially available. The method requires a compound in the low milligrams and works best for very insoluble compounds, which also are the most dif cult to quantitate by other methods. The method is relatively slow, since for best results the titration rate is greatly slowed as the precipitation point is reached. The compound is solubilized at the beginning of the assay, either by pH dissolution of solid or by dissolution of a concentrated DMSO stock solution in aqueous media of appropriate pH.As a result there is no control as to which polymorphic form of the compound corresponds to the solubility product. The method is likely to be particularly useful in the solubility classi cation of compounds according to the FDA bioavailability waiver system because of the extensive validation of the method, its reproducibility, and its particular applicability to compounds with the poorest solubility.
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SOLIDS NOT CHARACTERIZED IN EARLY DISCOVERY
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As previously discussed, the compound s form differs markedly from early discovery to the late discovery and development interface. The early discovery compound is poorly characterized as to crystalline form. It may be non-solid, amorphous, or even crystalline but uncharacterized as to polymorphic form. The late discovery/development interface compound is crystalline as de ned by phase contract microscopy or powder X-ray diffraction and its polymorphic and salt form is frequently characterized. This difference has profound implications for the design of a discovery solubility assay.
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solubility in the design of combinatorial libraries
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The key question is this: Is it better to design an early discovery solubility assay as a separate type of experiment, or is it better to try to automate a traditional thermodynamic solubility assay to handle the very large number of compounds likely to be encountered in early discovery Another way to state this question is: Does it make sense to run a thermodynamic solubility assay on poorly crystalline early discovery compounds This is the type of question about which reasonable people could disagree. However, this author does have a distinct opinion. It is much better to set up a distinctively different solubility assay in early discovery and to maintain a clear distinction between the assay type appropriate in early discovery and the assay type appropriate at the late discovery / development interface. Two issues are relevant to this opinion. One relates to the need for a solubility assay to re ect/predict early discovery stage oral absorption and the other relates to people/chemistry issues. An early discovery solubility assay is most useful to chemists at the stage where oral absorption SAR is not present or poorly de ned. This typically might occur after reasonable in vitro activity has been discovered and attempts are underway in drug metabolism to establish oral absorption or in biology to demonstrate oral activity. The early discovery solubility assay is most likely to predict the early drug metabolism or biology studies when the solubility protocol mimics the manner of dosing in drug metabolism and biology. Typically this means that starting compound is dissolved in DMSO solution, and short read times in the low tens of minutes are used in the solubility assay. These solubility assay conditions mimic the dosing conditions in early drug metabolism and biology. This type of reasoning is a very hard sell for a scientist with a strong development or analytical background because it means setting up a solubility assay that breaks every pharmaceutical sciences textbook rule about the qualities of a proper solubility assay. 16.7.1. Role of Chemistry in Solubility Improvement
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Chemists have the primary responsibility of altering the compound chemical structure so as to improve on a solubility problem. Anything that undermines this primary responsibility of the chemist is harmful to overall research productivity. In my experience, chemists (perhaps unconsciously) are always eager to obtain data that makes their compounds look better. For example, chemists might seek solubility data in simulated intestinal contents in order to obtain better (higher) solubility values. This exercise is of no value if it does not somehow result in compounds with better properties being made. Unfortunately, the search for better appearing solubility
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