Improved pharmacokinetics of AMG 517 through co-crystallization part 1: Comparison of two acids with corresponding amide co-crystals

Journal of Pharmaceutical Sciences

Volumn 99, Issue 9, 2010, Pages 3769-3778

  Stanton, Mary K ^a   Kelly, Ron C ^a   Colletti, Adria ^a   Kiang, Y H ^a   Langley, Meghan ^a   Munson, Eric J ^b   Peterson, Matthew L ^a   Roberts, John ^a   Wells, Mary ^a  

^a AMGEN INC   (United States)

^b UNIVERSITY OF KANSAS   (United States)

Author keywords

Co crystals; Dissolution; Pharmacokinetics

Indexed keywords

AMIDE; BENZAMIDE; BENZOIC ACID; CINNAMAMIDE; CINNAMIC ACID; N [4 [6 [4 (TRIFLUOROMETHYL)PHENYL] 4 PYRIMIDINYLOXY]BENZOTHIAZOL 2 YL]ACETAMIDE; POVIDONE; UNCLASSIFIED DRUG; WATER;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; CRYSTALLIZATION; DISSOLUTION; HYDROGEN BOND; INTESTINE FLUID; MALE; NONHUMAN; POWDER; RAT;

EID: 77956387616     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22181     Document Type: Article

References (28)

1. Engel GL, Farid NA, Faul MM, Richardson LA, Winneroski LL. 2000. Salt form selection and characterization of LY333531 mesylate monohydrate. Int J Pharm 198:239-247.
2. Hirsch CA, Messenger RJ, Brannon JL. 1978. Fenoprofen: Drug form selection and preformulation stability studies. J Pharm Sci 67:231-236.
3. Bowker MJ. 2002. A procedure for salt selection and optimization. In: Stahl HP, Wermuth CG, editors. Handbook of pharmaceutical salts properties, selection, and use. 1st edition. Zürich: Verlag Helvetica Chimica Acta. pp. 161-189.
4. Saxena V, Panicucci R, Joshi Y, Garad S. 2009. Developability assessment in pharmaceutical industry: An integrated group approach for selecting developable candidates. J Pharm Sci 98:1962-1979.
5. Morris KR, Fakes MG, Thakur AB, Newman AW, Singh AK, Venit JJ, Spagnuolo CJ, Serajuddin ATM. 1994. An integrated approach to the selection of optimal salt form for a new drug candidate. Int J Pharm 105:209-217. (Pubitemid 124013771)
6. Serajuddin ATM, Pudipeddi M. 2002. Salt selection strategies. In: Stahl HP, Wermuth CG, editors. Handbook of pharmaceutical salts properties, selection, and use. 1st edition. Zürich: Verlag Helvetica Chimica Acta. pp. 135-160.
7. Guzmán HR, Tawa M, Zhang Z, Ratanabanangkoon P, Shaw P, Gardner CR, Chen H, Moreau J-P, Almarsson Ö, Remenar JF. 2007. Combined use of crystalline salt forms and precipitation inhibitors to improve oral absorption of celecoxib from solid oral formulations. J Pharm Sci 96:2686-2700.
8. Sandburg A, Abrahamsson B, Sjögren J. 1991. Influence of dissolution rate on the extent and rate of bioavailability of metoprolol. Int J Pharm 68:167-177.
9. Meyer MC, Straughn AB, Mhatre RM, Shah VP, Williams RL, Lesko LJ. 1998. The relative bioavailability and in vivo-in vitro correlations for four marketed carbamazepine tablets. Pharm Res 15:1787-1791.
10. Dressman JB, Amidon GL, Reppas C, Shah VP. 1998. Dissolution testing as a prognostic tool for oral drug absorption: Immediate release dosage forms. Pharm Res 15:11-22.
11. Hörter D, Dressman JB. 2001. Influence of physicochemical properties on dissolution of drugs in the gastrointestinal tract. Adv Drug Delivery Rev 46:75-87. (Pubitemid 33653415)
12. Peterson ML, Hickey MB, Zaworotko MJ, Almarsson Ö. 2006. Expanding the scope of crystal form evaluation in pharmaceutical science. J Pharm Sci 9:317-326. (Pubitemid 46620646)
13. Chen AM, Ellison ME, Peresypkin A, Wenslow RM, Variankaval N, Savarin CG, Natishan TK, Mathre DJ, Dormer PG, Euler DH, Ball RG, Ye Z, Wanga Y, Santos I. 2007. Development of a pharmaceutical cocrystal of a monophosphate salt with phosphoric acid. Chem Commun 419-421.
14. Schultheiss N, Newman A. 2009. Pharmaceutical cocrystals and their physicochemical properties. Cryst Growth Des 9:2950-2967.
15. Meanwell NA. 2008. The emerging utility of co-crystals in drug discovery and development. In: Macor JE, editor. Annu Rep Med Chem. 43rd edition. Elsevier Inc. pp. 373-404.
16. Bettis JW, Lach JL, Hood J. 1973. Effect of complexation with phenobarbital on the biologic availability of theophylline from three tablet formulations. Amer J Hosp Pharm 30:240-243.
17. McNamara DP, Childs SL, Giordano J, Iarriccio A, Cassidy J, Shet MS, Mannion R, O'Donnell E, Park A. 2006. Use of a glutaric acid cocrystal to improve oral bioavailability of a low solubility API. Pharm Res 23:1888-1897.
18. Hickey MB, Peterson ML, Scoppettuolo LA, Morrisette SL, Vetter A, Guzmán HR, Remenar JF, Zhang Z, Tawa MD, Haley S, Zaworotko MJ, Almarsson Ö. 2007. Performance comparison of a co-crystal of carbamazepine with marketed product. Eur J Pharm Biopharm 67:112-119.
19. Variankaval N, Wenslow R, Murry J, Hartman R, Helmy R, Kwong E, Clas S-D, Dalton C, Santos I. 2006. Preparation and solid-state characterization of nonstoichiometric cocrystals of a phosphodiesterase-IV inhibitor and L-tartaric acid. Cryst Growth Des 6:690-700. (Pubitemid 43475360)
20. Cheney ML, Shan N, Healey ER, Hanna M, Wojtas L, Zaworotko MJ, Sava V, Song S, Sanchez-Ramos JR. 2010. Effects of crystal form on solubility and pharmacokinetics: A crystal engineering case study of lamotrigine. Cryst Growth Des 10:394-405.
21. Stanton MK, Bak A. 2008. Physicochemical properties of pharmaceutical co-crystals: A case study of ten AMG 517 co-crystals. Cryst Growth Des 8:3856-3862.
22. Stanton MK, Tufekcic S, Morgan C, Bak A. 2009. Drug substance and former structure property relationships in 15 diverse pharmaceutical co-crystals. Cryst Growth Des 9:1344-1352.
23. Bak A, Gore A, Yanez E, Stanton M, Tufekcic S, Syed R, Akrami A, Rose M, Surapaneni S, Bostick T, King A, Neervannan S, Ostovic D, Koparkar A. 2008. The co-crystal approach to improve the exposure of a water-insoluble compound: AMG 517 sorbic acid co-crystal characterization and pharmacokinetics. J Pharm Sci 97:3942-3956.
24. Doherty EM, Fotsch C, Bannon AW, Bo Y, Chen N, Dominguez C, Falsey J, Gavva NR, Katon J, Nixey T, Ognyanov VI, Pettus L, Rzasa R, Stec M, Surapaneni S, Tamir R, Zhu J, Treanor JJS, Norman MH. 2007. Novel vanilloid receptor-1 antagonists: 2. Structure-activity relationships of 4-oxopyrimidines leading to the selection of a clinical candidate. J Med Chem 50:3515-3527.
25. Galia E, Nicolaides E, Hörter D, Löbenberg R, Reppas C, Dressman JB. 1998. Evaluation of various dissolution media for predicting in vivo performance of class I and II drugs. Pharm Res 15:698-705.
26. Merck & Co., Inc., The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals. 4th edition. Whitehouse Station, NJ: Merck & Co., Inc. 2006.
27. Cotterill J, Nadian AK, Cowan DP. 2004. Improving the persistence of a formulation of the avian repellent cinnamamide, for the protection of autumn-sown oilseed rape. Pest Manag Sci 60:1019-1024. (Pubitemid 39265793)
28. Davies B, Morris T. 1993. Physiological parameters in laboratory animals and humans. Pharm Res 10:1093-1095.