An interesting relationship between drug absorption and melting point

International Journal of Pharmaceutics

Volumn 373, Issue 1-2, 2009, Pages 24-40

  Chu, Katherine A ^a   Yalkowsky, Samuel H ^a  

^a UNIVERSITY OF ARIZONA   (United States)

Author keywords

Absorption; Absorption potential; Bioavailability; Dose; Fraction absorbed; Melting point; Partition coefficient; Passive absorption; Solubility; Suspension

Indexed keywords

ACICLOVIR; ALLOPURINOL; ALPRENOLOL; AMFEBUTAMONE; CAMAZEPAM; CEFAMANDOLE NAFATE; CEFAZOLIN; CEFMETAZOLE; CEFOPERAZONE; CEFOXITIN; CEFTAZIDIME; CEFTIZOXIME; CHLORAMPHENICOL; CHLOROTHIAZIDE; CHLORPROMAZINE; CISAPRIDE; CLOFIBRATE; CLOMIPRAMINE; CLOZAPINE; DIAZEPAM; DICLOFENAC; DICLOXACILLIN; DILTIAZEM; DISULFIRAM; ETHINYLESTRADIOL; ETOPOSIDE; FELODIPINE; FENCLOFENAC; FLECAINIDE; UNINDEXED DRUG;

ARTICLE; DRUG ABSORPTION; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG TRANSPORT; INTESTINE ABSORPTION; MATHEMATICAL MODEL; MELTING POINT; PARTITION COEFFICIENT; PASSIVE TRANSPORT; PKA; PREDICTOR VARIABLE; PRIORITY JOURNAL;

ALGORITHMS; BIOLOGICAL AVAILABILITY; HUMANS; INTESTINAL ABSORPTION; MODELS, BIOLOGICAL; MOLECULAR STRUCTURE; PHARMACEUTICAL PREPARATIONS; PHARMACOKINETICS; SOLUBILITY; TRANSITION TEMPERATURE;

EID: 67349254634     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2009.01.026     Document Type: Article

References (36)

1. Ajay, Walters W.P., and Murcko M.A. Can we learn to distinguish between "drug-like" and "nondrug-like" molecules?. J. Med. Chem. 41 (1998) 3314-3324
2. American Chemical Society. SciFinder Scholar, 2006.
3. Amidon G.L., Lennernas H., Shah V.P., and Crison J.R. A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailabilty. Pharm. Res. 12 (1995) 413-420
4. Balon K., Riebesehl B.U., and Muller B.W. Drug liposome partitioning as a tool for the prediction of human passive intestinal absorption. Pharm. Res. 16 (1999) 882-888
5. Biobyte Corp. 1995-1999. ClogP for Windows. 4.0.
6. Biswas D., Roy S., and Sen S. A simple approach for indexing the oral druglikeness of a compound: discriminating druglike compounds from nondruglike ones. J. Chem. Inf. Model 46 (2006) 1394-1401
7. Branchu, et al. A decision-support tool for the formulation of orally active, poorly soluble compounds. Eur. J. Pharm. Sci. 32 (2007) 128-139
8. Curatolo W. Physical chemical properties of oral drug candidates in the discovery and exploratory development settings. Res. Focus 1 (1998) 387-393
9. Dressman J.B., Amidon G.L., and Fleisher D. Absorption potential: estimating the fraction absorbed for orally administered compounds. J. Pharm. Sci. 74 (1985) 588-589
10. Flynn G.L., and Yalkowsky S.H. Correlation and prediction of mass transport across membranes I: influence of alkyl chain length on flux-determining properties of barrier and diffusant. J. Pharm. Sci. 61 (1972) 838-852
11. Herper, M. 2007. Drug Drought, Forbes.com.
12. Hou T., Wang J., Zhang W., and Xu X. ADME evaluation in drug discovery, 7. Prediction of oral absorption by correlation and classification. J. Chem. Inf. Model 47 (2007) 208-218
13. Jain N., and Yalkowsky S.H. Estimation of the aqueous solubility I: application to organic nonelectrolytes. J. Pharm. Sci. 90 (2001) 234-252
14. Johnson K.C., and Swindell A.C. Guidance in the setting of drug particle size specifications to minimize variability in absorption. Pharm. Res. 13 (1996) 1795-1798
15. Kohda-Shimizu R., Li Y., Shitara Y., Ito K., Tsuda Y., Yamada H., and Itoh T. Oral absorption of cephalosporins is quantitatively predicted from in vitro uptake into intestinal brush border membrane vesicles. Int. J. Pharm. 220 (2001) 119-128
16. Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 23 (1997) 3-25
17. Macheras P.E., and Symillides M.Y. Toward a quantitative approach for the prediction of the fraction of dose absorbed using the absorption potential concept. Biopharm. Drug Dispos. 10 (1989) 43-53
18. MayoClinic.com, 2008, Jan. 1, 2008-last update, Cephalosporin (Oral Route, Injection Route, Intravenous Route, Intramuscular Route). Available: http://www.mayoclinic.com/health/drug-information/DR600239.
19. Merck Research Laboratories (Ed.) 2001, The Merck Index, 13th edn, Whitehouse Station, NJ.
20. Ni N., Sanghvi T., and Yalkowsky S.H. Independence of the product of solubility and distribution coefficient of pH. Pharm. Res. 19 (2002) 1862-1866
21. Obata K., Sugano K., Saitoh R., Higashida A., Nabuchi Y., Machida M., and Aso Y. Prediction of oral drug absorption in humans by theoretical passive absorption model. Int. J. Pharm. 293 (2005) 183-192
22. Oprea T.I. Current trends in lead discovery: are we looking for the appropriate properties. J. Comput. Aid. Mol. Des. 16 (2002) 325-334
23. Oprea T.I., Davis A.M., Teague S.J., and Leeson P.D. Is there a difference between leads and drugs? A historical perspective. J. Chem. Inf. Comput. Sci. 41 (2001) 1308-1315
24. Physicians' Desk Reference, 2002. 56th ed. Medical Economics Company, Inc., Montvale.
25. Sadowski J., and Kubinyi H. A scoring scheme for discriminating between drugs and nondrugs. J. Med. Chem. 41 (1998) 3325-3329
26. Sanghvi T., Ni N., Mayersohn M., and Yalkowsky S.H. Predicting passive intestinal absorption using a single parameter. QSAR Comb. Sci. 22 (2003) 247-257
27. Sanghvi T., Ni N., and Yalkowsky S.H. A simple modified absorption potential. Pharm. Res. 18 (2001) 1794-1796
28. Stehle R.G., and Higuchi W.I. In vitro model for transport of solutes in three-phase system I: theoretical principles. J. Pharm. Sci. 61 (1972) 1922-1930
29. Stehle R.G., and Higuchi W.I. In vitro model for transport of solutes in three-phase system II: experimental considerations. J. Pharm. Sci. 61 (1972) 1931-1935
30. United States Environmental Protection Agency, 2000-2007. Estimation Programs Interface (EPI) Suite. 3.20.
31. Wessel M.D., Jurs P.C., Tolan J.W., and Muskal S.M. Prediction of human intestinal absorption of drug compounds from molecular structure. J. Chem. Inf. Comput. Sci. 38 (1998) 726-735
32. Willmann S., Schmitt W., Keldenich J., Lippert J., and Dressman J.B. A physiological model for the estimation of the fraction dose absorbed in humans. J. Med. Chem. 47 (2004) 4022-4031
33. Yalkowsky S.H., Johnson J.L.H., Sanghvi T., and Machatha S.G. A 'Rule of Unity' for human intestinal absorption. Pharm. Res. 23 (2006) 2475-2481
34. Yalkowsky, S. H. (Ed.). 1999. AQUASOL dATAbASE of aqueous solubility.
35. Yalkowsky S.H., Carpenter 0.S., Flynn G.L., and Slunick T.G. Drug absorption kinetics in goldfish. J. Pharm. Sci. 62 (1973) 1949-1954
36. Zhao Y.H., Le J., Abraham M.H., Hersey A., Eddersshaw P.J., Luscombe C.N., Boutina D., Beck G., Sherborne B., and Cooper I. Evaluation of human intestinal absorption data and subsequent derivation of a quantitative structure-activity relationship (QSAR) with the Abraham descriptors. J. Pharm. Sci. 90 (2001) 749-784