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Shifts in pKa can also be expected if water-soluble aggregates form from the uncharged monomers This may be expected with surface-active molecules or molecules such as piroxicam [500] Consider the case where no DMSO is present, but aggregates form, of the sort mHA ! HA m 6:20
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The working assumption is that the aggregates are water soluble, that they effectively make the compound appear more soluble If ignored, they will lead to erroneous assessment of intrinsic solubility It can be shown that Eq (619) also applies to the case of aggregation
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Compound Compound Aggregation of Charged Weak Bases
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Consider the case of a weak base, where the protonated, positively charged form self-associates to form aggregates, but the uncharged form does not This may be the case with phenazopyridine (Fig 612) Phenazopyridine is a base that consistently shows positive shifts in its apparent pKa , the opposite of what s expected
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CORRECTION FOR THE DMSO EFFECT BY THE D-SHIFT METHOD
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of uncharged compound DMSO or aggregation effects A rationalization of this effect can be based on the formation of partially protonated aggregates (perhaps micelles) Assume that one of the species is (BH )n nBH ! BH n 6:21
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It can be shown that for such a case, the observed solubility pH curve is shifted horizontally, not vertically, as with uncharged-compound DMSO/aggregation effects, and that the apparent intrinsic solubility is not affected by the phenomenon
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Ionizable Compound Binding by Nonionizable Excipients
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It can be postulated that a number of phenomena, similar to those of reactions in Eqs (617), (619), and (620), will shift the apparent pKa in a manner of the discussions above For example, the additives in drug formulations, such as surfactants, bile salts, phospholipids, ion-pair-forming counterions, cyclodextrins, or polymers may make the drug molecule appear more soluble As long as such excipients do not undergo a change of charge state in the pH range of interest (ie, the excipients are effectively non-ionizable), and the drug molecule is ionizable in this app range, the difference between the apparent pKa , pKa , and the true pKa will reveal the true aqueous solubility, as if the excipient were not present Table 62 sumapp marizes some of the relationships developed between solubility, pKa , and pKa
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Results of Aqueous Solubility Determined from D Shifts
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Since the pKa values of the compounds studied are reliably known (Table 61), it was possible to calculate the shifts (Table 62) These shifts were used to calculate the corrected aqueous intrinsic solubilities S0 , also listed in Table 62
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TABLE 62 True Aqueous Solubility Determined from pKa Shifts of Monoprotic Compounds Ionizable Compound Type Acid
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APP pKa pKa
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True Aqueous log S0 log SAPP 0 log SAPP 0 log SAPP 0 log SAPP 0
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Examples Diclofenac, furosemide, indomethacin, probenecid, naphthoic acid Prostaglandin F2a [485] Phenazopyridine Amitriptyline, chlorpromazine, miconazole, terfenadine
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Acid Base Base
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0 !0 <0
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SOLUBILITY
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Table 63 Solubility Constants of Drug Molecules, Measured by the Dissolution Template Titration Methoda Compound Acyclovir Amiloride Amiodarone Amitriptyline Amoxicilin Ampicillin Atenolol Atropine Benzoic acid Benzydamine Bromocriptine Cephalexin Chlorpromazine Cimetidine Cipro oxacin Clozapine Desipramine Diclofenac Diltiazem Doxycycline Enalapril Erythromycin Ethinyl estradiol Famotidine Flurbiprofen Furosemide Hydrochlorothiazide Ibuprofen Indomethacin Ketoprofen Labetolol Lasinavir Methotrexate Metoprolol Miconazole Metolazone Nadolol Nalidixic acid 2-Naphthoic acid Naproxen Nor oxacin Nortriptyline log S0 (log mol L 1 ) 224 336 810 519 217 169 130 161 159 383 470 158 527 143 373 370 381 559 295 235 136 314 395 248 436 475 263 362 520 333 345 400 429 120 585 410 157 426 393 421 278 418 Ref 506 506 pION 506, b 506 pION 473 506 474 472 509 pION 506, b 474 506 509 506 473 474 506 474 506 506 473 473 473 473 473 506, b 473 473 509 506 474 25 509 474 pION 25 473 pION pION
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log S0 GOLD STANDARD FOR DRUG MOLECULES
Table 63 Compound
(Continued) log S0 (log mol L 1 ) 424 413 370 548 277 568 439 501 362 282 350 755 669 138 453 420 467 474 116 Ref 506, b 473 pION pION 506 25 506 474 473 474 509 506 474 506 474 509 506 506 506
Phenazopyradine Phenytoin Pindolol Piroxicam Primaquine Probenecid Promethazine Propoxyphene Propranolol Quinine Ru namide Tamoxifen Terfenadine Theophylline Trova oxacin Valsartan Verapamil Warfarin Zidovudine
Temperature 25 C, 015 M ionic strength (KCl) M A Strafford, A Avdeef, P Artursson, C A S Johansson, K Luthman, C R Brownell, and R Lyon, Am Assoc Pharm Sci Ann Mtng 2000, poster presentation