Optimizing solubility and permeability of a biopharmaceutics classification system (BCS) class 4 antibiotic drug using lipophilic fragments disturbing the crystal lattice

Journal of Medicinal Chemistry

Volumn 56, Issue 6, 2013, Pages 2690-2694

  Tehler, Ulrika ^a,b   Fagerberg, Jonas H ^a   Svensson, Richard ^a   Larhed, Mats ^a   Artursson, Per ^a   Bergström, Christel A S ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CIPROFLOXACIN;

ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG PENETRATION; DRUG SOLUBILITY; DRUG STRUCTURE; ESTERIFICATION; HUMAN; HUMAN CELL; INTESTINE MUCOSA PERMEABILITY; LIPOPHILICITY; MELTING POINT; PROCESS OPTIMIZATION; SOLID STATE;

ANTI-BACTERIAL AGENTS; CACO-2 CELLS; CRYSTALLOGRAPHY, X-RAY; DRUG DISCOVERY; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; PERMEABILITY; SOLUBILITY;

EID: 84875739359     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301721e     Document Type: Article

References (20)

1. Rane, S. S.; Anderson, B. D. What determines drug solubility in lipid vehicles: Is it predictable? Adv. Drug Delivery Rev. 2008, 60 (6) 638-656
2. Bergström, C. A. S.; Wassvik, C. M.; Johansson, K.; Hubatsch, I. Poorly soluble marketed drugs display solvation limited solubility J. Med. Chem. 2007, 50 (23) 5858-5862
3. Fagerberg, J. H.; Tsinman, O.; Sun, N.; Tsinman, K.; Avdeef, A.; Bergström, C. A. S. Dissolution rate and apparent solubility of poorly soluble drugs in biorelevant dissolution media Mol. Pharmaceutics 2010, 7 (5) 1419-1430
4. Wassvik, C. M.; Holmen, A. G.; Draheim, R.; Artursson, P.; Bergström, C. A. S. Molecular characteristics for solid-state limited solubility J. Med. Chem. 2008, 51 (10) 3035-3039
5. Zaki, N. M.; Artursson, P.; Bergström, C. A. S. A modified physiological BCS for prediction of intestinal absorption in drug discovery Mol. Pharmaceutics 2010, 7 (5) 1478-1487
6. Amidon, G. L.; Lennernas, H.; Shah, V. P.; Crison, J. R. A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability Pharm. Res. 1995, 12 (3) 413-420
7. Bergström, C. A. S.; Strafford, M.; Lazorova, L.; Avdeef, A.; Luthman, K.; Artursson, P. Absorption classification of oral drugs based on molecular surface properties J. Med. Chem. 2003, 46 (4) 558-570
8. Neuhoff, S.; Ungell, A. L.; Zamora, I.; Artursson, P. pH-dependent bidirectional transport of weakly basic drugs across Caco-2 monolayers: implications for drug-drug interactions Pharm. Res. 2003, 20 (8) 1141-1148
9. Stella, V. J.; Martodihardjo, S.; Terada, K.; Rao, V. M. Some relationships between the physical properties of various 3-acyloxymethyl prodrugs of phenytoin to structure: potential in vivo performance implications J. Pharm. Sci. 1998, 87 (10) 1235-1241
10. Yamaoka, Y.; Roberts, R. D.; Stella, V. J. Low-melting phenytoin prodrugs as alternative oral delivery modes for phenytoin: a model for other high-melting sparingly water-soluble drugs J. Pharm. Sci. 1983, 72 (4) 400-405
11. Varia, S. A.; Schuller, S.; Sloan, K. B.; Stella, V. J. Phenytoin prodrugs III: water-soluble prodrugs for oral and/or parenteral use J. Pharm. Sci. 1984, 73 (8) 1068-1073
12. Press, N. J.; Taylor, R. J.; Fullerton, J. D.; Tranter, P.; McCarthy, C.; Keller, T. H.; Arnold, N.; Beer, D.; Brown, L.; Cheung, R.; Christie, J.; Denholm, A.; Haberthuer, S.; Hatto, J. D.; Keenan, M.; Mercer, M. K.; Oakman, H.; Sahri, H.; Tuffnell, A. R.; Tweed, M.; Tyler, J. W.; Wagner, T.; Fozard, J. R.; Trifilieff, A. Solubility-driven optimization of phosphodiesterase-4 inhibitors leading to a clinical candidate J. Med. Chem. 2012, 55 (17) 7472-7479
13. Mahaptra, S.; Venugopala, K. N.; Guru, T. N. A device to crystallize organic solids: structure of ciprofloxacin, midazolam, and ofloxacin as targets Cryst. Growth Des. 2010, 10 (4) 1866-1870
14. Bergström, C. A. S.; Norinder, U.; Luthman, K.; Artursson, P. Experimental and computational screening models for prediction of aqueous drug solubility Pharm. Res. 2002, 19 (2) 182-188
15. United States Pharmacopeia and National Formulary (USP 32-NF 27); United States Pharmacopeia Convention: Rockville, MD, 2009; Vol. 1.
16. Galia, E.; Nicolaides, E.; Horter, D.; Lobenberg, R.; Reppas, C.; Dressman, J. B. Evaluation of various dissolution media for predicting in vivo performance of class I and II drugs Pharm. Res. 1998, 15 (5) 698-705
17. Hubatsch, I.; Ragnarsson, E. G.; Artursson, P. Determination of drug permeability and prediction of drug absorption in Caco-2 monolayers Nat. Protoc. 2007, 2 (9) 2111-2119
18. de Bruin, M.; Miyake, K.; Litman, T.; Robey, R.; Bates, S. E. Reversal of resistance by GF120918 in cell lines expressing the ABC half-transporter, MXR Cancer Lett. 1999, 146 (2) 117-126
19. Taipalensuu, J.; Tavelin, S.; Lazorova, L.; Svensson, A. C.; Artursson, P. Exploring the quantitative relationship between the level of MDR1 transcript, protein and function using digoxin as a marker of MDR1-dependent drug efflux activity Eur. J. Pharm. Sci. 2004, 21 (1) 69-75
20. LeCluyse, E. L..; Alexandre, E. Isolation and culture of primary hepatocytes from resected human liver tissue Methods Mol. Biol. 2010, 640, 57-82