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Figure 747 Examples of three bases that appear to violate the pH partition hypothesis in 2% DOPC/dodecane PAMPA models: (a) verapamil (pKa 907); (b) propranolol; (c) guinine (pKa 855, 424)
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PAMPA: 50 MODEL LIPID SYSTEMS
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Figure 747 (Continued)
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log Pe
pH 74 (Acceptor)
-8 3 4 5 6 7 8 9 10
pH (Donor)
Figure 748 Negatively charged PAMPA models showing no evidence for violation of the pH partition hypothesis
Seiler [250] proposed a way of estimating the extent of hydrogen bonding in solute partitioning between water and a lipid phase by measuring the so-called log P parameter The latter parameter is usually de ned as the difference between the partition coef cient of a solute measured in the octanol water system and that measured in an inert alkane water suspension: log P log Kp; oct log Kp; alk Young et al [599] demonstrated the usefulness of the log P parameter in the prediction of brain penetration of a series of H2-receptor histamine antagonists Neither log Kp; oct nor log Kp; alk was found to correlate with brain penetration, log BB (where BB is de ned as the ratio of the compound concentration in the brain and the compound concentration in plasma) However, the difference between the two partition coef cients correlated well, as shown in Fig 749 When the difference is large, so is the H bonding expressed by the solute, and less brain penetration is expected It was suggested that the log P parameter accounts for H-bonding ability and re ects two distinct processes alkane encodes the partitioning into nonpolar regions of the brain and octanol encodes protein binding in the peripheral blood El Tayar et al [255] elaborated that the parameter contains information on the capacity of a solute to donate H bonds; the rate-limiting step in brain penetration was proposed to be the donation of H bonds of solute to hydrophilic parts of lipids in the blood brain barrier (BBB) Van de Waterbeemd and Kansy [251] reexamined Young et al [599] data with solvatochromic equations for identifying physicochemical properties governing solubility and partitioning They suggested that the combination of calculated molar volumes and just the log log Kp;alk could
PAMPA: 50 MODEL LIPID SYSTEMS
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substitute for two-lipid partition measurements, thus reducing the amount of measurement needed Also, they introduced the use of polar surface areas as an interesting alternative to the use of log P Abraham et al [257] analyzed the log P parameter in terms of the Abraham descriptors to broaden the understanding of the concept Von Geldern et al [252] used the log P parameter to optimize structural modi cations to a series of endothelin A-receptor antagonists to improve gut absorption A urea fragment in their series of molecules had NH residues systematically replaced with NCH3, O, and CH2, and correlations between log P and antagonist selectivity effectively guided the optimization procedure Avdeef et al [556] measured the PAMPA permeabilities of a series of drug molecules and natural products using both dodecane- and (dodecane 2%DOPC)-coated lters It was proposed that a new H-bonding scale could be explored, based not on partition coef cients but on permeabilities log Pe log P2%DOPC log Pdodecane e e 7:61
Figure 750 shows log Pe (difference permeability) versus log Pe (dodecanetreated lters) for a series of common drugs and research compounds at pH 74 Some of the differences are positive, and some are negative For example, phenazopyridine is attenuated by the presence of DOPC in the dodecane, but diltiazem is accelerated by the DOPC [556] The effects are most pronounced where the permeability in pure dodecane is less than about 3 10 6 cm=s That is, molecules that are very permeable in dodecane are unaffected by the presence of DOPC, as