Preparation and physicochemical characterization of a novel water-soluble prodrug of carbamazepine

Journal of Pharmaceutical Sciences

Volumn 99, Issue 4, 2010, Pages 1810-1825

  Hemenway, Jeffrey N ^a,b   Jarho, Pekka ^a,c   Henri, John T ^a,d   Nair, Sajiv K ^a,e   Vandervelde, David ^a,f   Georg, Gunda I ^a,g   Stella, Valentino J ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b BRISTOL MYERS SQUIBB   (United States)

^c UNIVERSITY OF EASTERN FINLAND   (Finland)

^d Pfizer Global R and D ^*  (United States)

^e PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

^f California Institute of Technology   (United States)

^g UNIVERSITY OF MINNESOTA   (United States)

Author keywords

Carbamazepine; Glycine; pH rate profile; Prodrug; Solubility; Stability

Indexed keywords

CARBAMAZEPINE; N ACETYL CARBAMAZEPINE; N GLYCYL CARBAMAZEPINE; PRODRUG; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; COMPLEX FORMATION; DRUG DEGRADATION; DRUG ISOLATION; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; MICELLIZATION; PH; PHYSICAL CHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 77949864238     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.21952     Document Type: Article

References (50)

1. Levy RH, Mattson RH, Meldrum BS. 1995. Antiepileptic drugs, 4th edition. New York: Raven Press. 1120. p.
2. Loiseau P, Duche B, Pedespan JM. 1985. Absence epilepsies. Epilepsia 36:1182-1186.
3. Bazil CW, Pedley TA. 1998. Advances in the medical treatment of epilepsy. Annu Rev Med 49:135-162.
4. Birkhimer LJ, Curtis JL, Jann MW. 1985. Use of carbamazepine in psychiatric disorders. Clin Pharm 4:425-434.
5. Williams Robin SB, Cheng L, Mudge Anne W, Harwood Adrian J. 2002. A common mechanism of action for three mood-stabilizing drugs. Nature 417:292-295.
6. Brewster ME, Anderson WR, Estes KS, Bodor N. 1991. Development of aqueous parenteral formulations for carbamazepine through the use of modified cyclodextrins. J Pharm Sci 80:380-383.
7. McMahon LE, Timmins P, Williams AC, York P. 1996. Characterization of dihydrates prepared from carbamazepine polymorphs. J Pharm Sci 85:1064-1069.
8. Kobayashi Y, Ito S, Itai S, Yamamoto K. 2000. Physicochemical properties and bioavailability of carbamazepine polymorphs and dihydrate. Int J Pharm 193:137-146.
9. Kaneniwa N, Ichikawa J, Yamaguchi T, Hayashi K, Watari N, Sumi M. 1987. Dissolution behavior of carbamazepine polymorphs. Yakugaku Zasshi 107:808-813.
10. Lang M, Kampf Jeff W, Matzger Adam J. 2002. Form IV of carbamazepine. J Pharm Sci 91:1186-1190.
11. Laine E, Tuominen V, Ilvessalo P, Kahela P. 1984. Formation of dihydrate from carbamazepine anhydrate in aqueous conditions. Int J Pharm 20:307-314.
12. Kahela P, Aaltonen R, Lewing E, Anttila M, Kristoffersson E. 1983. Pharmacokinetics and dissolution of two crystalline forms of carbamazepine. Int J Pharm 14:103-112.
13. Lake OA, Olling M, Barends DM. 1999. In vitro/in vivo correlations of dissolution data of carbamazepine immediate release tablets with pharmacokinetic data obtained in healthy volunteers. Eur J Pharm Biopharm 48:13-19.
14. Chen X-Q, Venkatesh S. 2004. Miniature device for aqueous and non-aqueous solubility measurements during drug discovery. Pharm Res 21:1758-1761.
15. Brewster M, Anderson W, Pop E, Sawchuk R, Cheung B, Webb A. 1995. Improved oral bioavailability of carbamazepine through the use of chemically modified cyclodextrins. World Meeting on Pharmaceutics, Biopharmaceutics and Pharmaceutical Technology, 1st, Budapest, May 9-11, 1995:627-628.
16. Loescher W, Hoenack D, Richter A, Schulz H-U, Schuerer M, Duesing R, Brewster ME. 1995. New injectable aqueous carbamazepine solution through complexing with 2-hydroxypropyl-b-cyclodextrin: Tolerability and pharmacokinetics after intravenous injection in comparison to a glycofurol-based formulation. Epilepsia 36:255-261.
17. Loescher W, Hoenack D. 1997. Intravenous carbamazepine: Comparison of different parenteral formulations in a mouse model of convulsive status epilepticus. Epilepsia 38:106-113.
18. Steulet AF, Schmutz M, Maitre L, Bernasconi R, Stahl PH. 1991. Intravenous solutions of antiepileptics. Eur. Pat. Appl. 435826 ed.: (Ciba-Geigy A.-G., Switz.) 12 pp.
19. Yalkowsky SH, Krzyzaniak JF, Ward GH. 1998. Formulation-related problems associated with intravenous drug delivery. J Pharm Sci 87:787-795.
20. Akers MJ. 2002. Excipient - Drug interactions in parenteral formulations. J Pharm Sci 91:2283-2300.
21. Johnson JLH, He Y, Yalkowsky SH. 2003. Prediction of precipitation- induced phlebitis: A statistical validation of an in vitro model. J Pharm Sci 92:1574-1581.
22. Yalkowsky SH, Valvani SC, Johnson BW. 1983. In vitro method for detecting precipitation of parenteral formulations after injection. J Pharm Sci 72:1014-1017.
23. Oshida S, Degawa K, Takahashi Y, Akaishi S. 1979. Physico-chemical properties and local toxic effects of injectables. Tohoku J Exp Med 127:301-316.
24. Yalkowsky SH, Valvani SC. 1977. Precipitation of solubilized drugs due to injection or dilution. Drug Intell Clin Pharm 11:417-419.
25. Trivellato E, Malesani L, Concilio C. 1958. Some new esters of chloramphenicol. IV. Pharmacological research on chloramphenicol glycinate. Farmaco [Prat] 13:399-405.
26. Bundgaard H, Larsen C, Thorbek P. 1984. Prodrugs as drug delivery systems. XXVI. Preparation and enzymic hydrolysis of various water-soluble amino acid esters of metronidazole. Int J Pharm 18:67-77.
27. Stella VJ, Kennedy PE. 1987. Water-soluble rapamycin prodrugs. Us Patent 4650803. ed.: (University of Kansas, USA). p 6.
28. Pop E, Soti F, Brewster ME, Barenholz Y, Korablyov V, Mechoulam R, Nadler V, Biegon A. 1996. Derivatives of dexanabinol. II. Salts of amino acid esters containing tertiary and quaternary heterocyclic nitrogen with increased water-solubility. Pharm Res 13:469-475.
29. Hirai K, Koike H, Ishiba T, Ueda S, Makino I, Yamada H, Ichihashi T, Mizushima Y, Ishikawa M, Ishihara Y, Hara Y, Hirose H, Shima N, Doteuchi M. 1991. Amino acid amides of 2-[(2-aminobenzyl) sulfinyl]benzimidazole as acid-stable prodrugs of potential inhibitors of H+/K+ ATPase. Eur J Med Chem 26:143-158.
30. Hutchinson I, Jennings SA, Vishnuvajjala BR, Westwell AD, Stevens MFG. 2002. Antitumor benzothiazoles. 16. Synthesis and pharmaceutical properties of antitumor 2-(4-aminophenyl)benzothiazole amino acid prodrugs. J Med Chem 45:744-747.
31. Pochopin NL, Charman WN, Stella VJ. 1995. Amino acid derivatives of dapsone as water-soluble prodrugs. Int J Pharm 121:157-167.
32. Pochopin NL, Charman WN, Stella VJ. 1994. Kinetics of rearrangement and hydrolysis of amino acid derivatives of prazosin. Int J Pharm 105:169-176.
33. Pochopin NL, Charman WN, Stella VJ. 1994. Pharmacokinetics of dapsone and amino acid prodrugs of dapsone. Drug Metab Dispos 22:770-775.
34. Bradshaw TD, Bibby MC, Double JA, Fichtner I, Cooper PA, Alley MC, Donohue S, Stinson SF, Tomaszewjski JE, Sausville EA, Stevens MFG. 2002. Preclinical evaluation of amino acid prodrugs of novel antitumor 2-(4-amino-3-methylphenyl)-benzothiazoles. Mol Cancer Ther 1:239-246.
35. Bradshaw TD, Westwell AD. 2004. The development of the antitumour benzothiazole prodrug, phortress, as a clinical candidate. Curr Med Chem 11:1009-1021.
36. Speziale AJ, Smith LR. 1963. The reaction of oxalyl chloride with amides. II. Oxazolidinediones and acyl isocyanates. J Org Chem 28:1805-1811.
37. Kukolja S, Lammert SR. 1975. Azetidinone antibiotics. XIV. Removal of a phthaloyl protective group from acid and base sensitive compounds. J Am Chem Soc 97:5582-5583.
38. Zalipsky JJ, Patel DM, Darnowski RJ, Reavey-Cantwell NH. 1976. The pKa determination of methaqualone. J Pharm Sci 65:460-461.
39. Stejskal EO, Tanner JE. 1965. Spin diffusion measurements: Spin echoes in the presence of a timedependent field gradient. J Chem Phys 42:288-292.
40. Yao S, Howlett GJ, Norton RS. 2000. Peptide self-association in aqueous trifluoroethanol monitored by pulsed field gradient NMR diffusion measurements. J Biomol NMR 16:109-119.
41. Momot KI, Kuchel PW. 2003. Pulsed field gradient nuclear magnetic resonance as a tool for studying drug delivery systems. Concepts Magn Reson A 19A:51-64.
42. Wu D, Chen A, Johnson CS, Jr. 1995. An improved diffusion-ordered spectroscopy experiment incorporating bipolar-gradient pulses. J Magn Reson A 115:260-264.
43. Jemal M, Almond RB, Teitz DS. 1997. Quantitative bioanalysis utilizing high-performance liquid chromatography/electrospray mass spectrometry via selected-ion monitoring of the sodium ion adduct [M + Na]+. Rapid Commun Mass Spectrom 11:1083-1088.
44. Li X-F, Ma M, Scherban K, Tam Yun K. 2002. Liquid chromatography- electrospray mass spectrometric studies of ginkgolides and bilobalide using simultaneous monitoring of proton, ammonium and sodium adducts. Analyst 127:641-646.
45. Jonkers N, Govers H, De Voogt P. 2005. Adduct formation in LC-ESI-MS of nonylphenol ethoxylates: Mass spectrometrical, theoretical and quantitative analytical aspects. Anal Chim Acta 531:217-228.
46. Espenson JH. 1981. Chemical kinetics and reaction mechanisms, 1st edition. New York: McGraw-Hill. p 56.
47. Anderson BD, Conradi RA, Johnson K. 1983. Influence of premicellar and micellar association on the reactivity of methylprednisolone 21-hemiesters in aqueous solution. J Pharm Sci 72:448-454.
48. Anderson BD, Conradi RA, Knuth KE, Nail SL. 1995. Strategies in the design of solution-stable, water-soluble prodrugs II: Properties of micellar prodrugs of methylprednisolone. J Pharm Sci 74:375-381.
49. Surakitbanharn Y, McCandless R, Krzyzaniak JF, Dannenfelser RM, Yalkowsky SH. 1995. Self-association of dexverapamil in aqueous solution. J Pharm Sci 84:720-723.
50. Abdul Rasool A, Hussain AA, Dittert LW. 1991. Solubility enhancement of some water-insoluble drugs in the presence of nicotinamide and related compounds. J Pharm Sci 80:387-393.