Physicochemical characterization of berberine chloride: A perspective in the development of a solution dosage form for oral delivery

AAPS PharmSciTech

Volumn 11, Issue 3, 2010, Pages 1466-1475

  Battu, Sunil Kumar ^a   Repka, Michael A ^b,c   Maddineni, Sindhuri ^b   Chittiboyina, Amar G ^b   Avery, Mitchell A ^b,c   Majumdar, Soumyajit ^b,c  

^a Pharmaceutical RandD   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

^c UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

berberine chloride; complexation; cyclodextrin; solubility; surfactants

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; BERBERINE CHLORIDE; CETRIMIDE; CYCLODEXTRIN; DODECYL SULFATE SODIUM; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; DRUG DOSAGE FORM; DRUG FORMULATION; DRUG SCREENING; DRUG SOLUBILITY; DRUG SOLUTION; DRUG STABILITY; PH; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; STOICHIOMETRY; TEMPERATURE DEPENDENCE;

ADMINISTRATION, ORAL; BERBERINE; BETA-CYCLODEXTRINS; DRUG COMPOUNDING; EXCIPIENTS; SOLUTIONS;

EID: 78649907355     PISSN: None     EISSN: 15309932     Source Type: Journal    
DOI: 10.1208/s12249-010-9520-y     Document Type: Article

References (46)

1. F Zuo N Nakamura T Akao M Hattori 2006 Pharmacokinetics of berberine and its main metabolites in conventional and pseudo germ-free rats determined by liquid chromatography/ion trap mass spectrometry Drug Metab Dispos 34 12 2064 2072 1:CAS:528:DC%2BD28Xht1yltLnO 10.1124/dmd.106.011361 16956957 (Pubitemid 44837767)
2. J Dostál S Man P Seckárová D Hulová M Necas M Potácek, et al. 2004 Berberine and coptisine free bases J Mol Struct 687 1-3 135 142 10.1016/j.molstruc.2003.09.018 (Pubitemid 38167251)
3. K Hayashi K Minoda Y Nagaoka T Hayashi S Uesato 2007 Antiviral activity of berberine and related compounds against human cytomegalovirus Bioorg Med Chem Lett 17 6 1562 1564 1:CAS:528:DC%2BD2sXit1yktbY%3D 10.1016/j.bmcl.2006.12.085 17239594
4. TC Birdsall GS Kelly 1997 Berberine: therapeutic potential of an alkaloid found in several medicinal plants Altern Med Rev 2 2 94 103
5. CT Taylor DC Winter MM Skelly DP O'Donoghue GC O'Sullivan BJ Harvey, et al. 1999 Berberine inhibits ion transport in human colonic epithelia Eur J Pharmacol 368 1 111 118 1:CAS:528:DyaK1MXhvVCmsbk%3D 10.1016/S0014-2999(99) 00023-0 10096776 (Pubitemid 29106421)
6. QL Tran Y Tezuka JY Ueda NT Nguyen Y Maruyama K Begum, et al. 2003 In vitro antiplasmodial activity of antimalarial medicinal plants used in Vietnamese traditional medicine J Ethnopharmacol 86 2-3 249 252 10.1016/S0378-8741(03)00045-X 12738095 (Pubitemid 36542885)
7. WH Ko XQ Yao CW Lau WI Law ZY Chen W Kwok, et al. 2000 Vasorelaxant and antiproliferative effects of berberine Eur J Pharmacol 399 2-3 187 196 1:CAS:528:DC%2BD3cXksFGit7o%3D 10.1016/S0014-2999(00)00339-3 10884519 (Pubitemid 30407040)
8. J Sanchez-Chapula 1996 Increase in action potential duration and inhibition of the delayed rectifier outward current IK by berberine in cat ventricular myocytes Br J Pharmacol 117 7 1427 1434 1:CAS:528:DyaK28XisFentro%3D 8730735
9. PL Tsai TH Tsai 2004 Hepatobiliary excretion of berberine Drug Metab Dispos 32 4 405 412 1:CAS:528:DC%2BD2cXis1ehtbY%3D 10.1124/dmd.32.4.405 15039293 (Pubitemid 38420274)
10. GY Pan ZJ Huang GJ Wang JP Fawcett XD Liu XC Zhao, et al. 2003 The antihyperglycaemic activity of berberine arises from a decrease of glucose absorption Planta Med 69 7 632 636 1:CAS:528:DC%2BD3sXmvVektL4%3D 10.1055/s-2003-41121 12898419 (Pubitemid 37041059)
11. S Jantova L Cipak M Cernakova D Kost'alova 2003 Effect of berberine on proliferation, cell cycle and apoptosis in HeLa and L1210 cells J Pharm Pharmacol 55 8 1143 1149 1:CAS:528:DC%2BD3sXmvFGntr0%3D 10.1211/ 002235703322277186 12956905 (Pubitemid 36998656)
12. V Kettmann D Kosfalova S Jantova M Cernakova J Drimal 2004 In vitro cytotoxicity of berberine against HeLa and L1210 cancer cell lines Pharmazie 59 7 548 551 1:CAS:528:DC%2BD2cXlvVOmsL0%3D 15296093
13. E Kupeli M Kosar E Yesilada K Husnu C Baser 2002 A comparative study on the anti-inflammatory, antinociceptive and antipyretic effects of isoquinoline alkaloids from the roots of Turkish Berberis species Life Sci 72 6 645 657 1:CAS:528:DC%2BD38XptFersrg%3D 10.1016/S0024-3205(02)02200-2 12467905 (Pubitemid 35441232)
14. E Yesilada E Kupeli 2002 Berberis crataegina DC. root exhibits potent anti-inflammatory, analgesic and febrifuge effects in mice and rats J Ethnopharmacol 79 2 237 248 10.1016/S0378-8741(01)00387-7 11801387 (Pubitemid 34136956)
15. Y-C Lu Q Lin G-S Luo Y-Y Dai 2006 Solubility of berberine chloride in various solvents J Chem Eng Data 51 2 642 644 1:CAS:528:DC%2BD28XhsFyrsA%3D%3D 10.1021/je0504360
16. V Misik L Bezakova L Malekova D Kostalova 1995 Lipoxygenase inhibition and antioxidant properties of protoberberine and aporphine alkaloids isolated from Mahonia aquifolium Planta Med 61 4 372 373 1:CAS:528:DyaK2MXnvFWrtLw%3D 10.1055/s-2006-958107 7480190
17. L Ma P Xiao B Guo J Wu F Liang S Dong 1999 Cerebral protective effects of some compounds isolated from traditional Chinese herbs Zhongguo Zhong Yao Za Zhi 24 4 238 239 1:CAS:528:DyaK1MXjt1Knsrw%3D 12205950 56-inside back cover
18. SA Doggrell 2005 Berberine-a novel approach to cholesterol lowering Expert Opin Investig Drugs 14 5 683 685 1:CAS:528:DC%2BD2MXltFyisrs%3D 10.1517/13543784.14.5.683 15926873 (Pubitemid 40790288)
19. WB Alan TT Cormac JB David 1997 Non-antibiotic anti-diarrhoeal drugs: factors affecting oral bioavailability of berberine and loperamide intestinal tissue Adv Drug Deliv Rev 23 111 120 10.1016/S0169-409X(96)00429-2 (Pubitemid 27046997)
20. GY Pan GJ Wang XD Liu JP Fawcett YY Xie 2002 The involvement of P-glycoprotein in berberine absorption Pharmacol Toxicol 91 4 193 197 1:CAS:528:DC%2BD38XosVShs74%3D 10.1034/j.1600-0773.2002.t01-1-910403.x 12530470 (Pubitemid 35216922)
21. BJ Gurley A Swain MA Hubbard DK Williams G Barone F Hartsfield, et al. 2008 Clinical assessment of CYP2D6-mediated herb-drug interactions in humans: effects of milk thistle, black cohosh, goldenseal, kava kava, St. John's wort, and Echinacea Mol Nutr Food Res 52 7 755 763 1:CAS:528:DC%2BD1cXpsFOntLs%3D 10.1002/mnfr.200600300 18214849
22. M Ye S Fu R Pi F He 2009 Neuropharmacological and pharmacokinetic properties of berberine: a review of recent research J Pharm Pharmacol 61 7 831 837 1:CAS:528:DC%2BD1MXpt1Wrtrc%3D 10.1211/jpp.61.07.0001 19589224
23. Hamer DHLGS. Infectious diarrhea and bacterial food poisoning. In: Feldman M, Scharschmidt BF, Sleisenger MH, editors. Sleisinger and Fordtran's gastrointestinaland liver disease. 6th ed. Philadelphia: WB Saunders; 1998. p. 1594-632.
24. EL Liebelt 1998 Clinical and laboratory evaluation and management of children with vomiting, diarrhea, and dehydration Curr Opin Pediatr 10 5 461 469 1:STN:280:DyaK1M%2FjsFKntQ%3D%3D 10.1097/00008480-199810000-00002 9818241 (Pubitemid 28468171)
25. JM Streit RN Jones MA Toleman LS Stratchounski TR Fritsche 2006 Prevalence and antimicrobial susceptibility patterns among gastroenteritis- causing pathogens recovered in Europe and Latin America and Salmonella isolates recovered from bloodstream infections in North America and Latin America: report from the SENTRY Antimicrobial Surveillance Program (2003) Int J Antimicrob Agents 27 5 367 375 1:CAS:528:DC%2BD28XktVyjt7o%3D 10.1016/j.ijantimicag.2005. 12.004 16647842
26. SK Battu MA Repka S Majumdar RY Madhusudan 2007 Formulation and evaluation of rapidly disintegrating fenoverine tablets: effect of superdisintegrants Drug Dev Ind Pharm 33 11 1225 1232 1:CAS:528: DC%2BD2sXhtlOjs7nN 10.1080/03639040701377888 18058319 (Pubitemid 350208742)
27. NA Patel NJ Patel RP Patel RK Patel 2010 The formulation and evaluation of topical berberine hydrochloride products Pharm Technol. 34 60 69 1:CAS:528:DC%2BC3cXhslWns70%3D
28. T Higuchi KA Connors 1965 Phase-solubility techniques Adv Anal Chem Instrum 4 117 212 1:CAS:528:DyaF2MXktlGitrg%3D
29. Koide T, Iwata M, Maekawa K, Saito H, Tanimoto T, Okada S. [Berberine Hydrochloride Reference Standard (Control 001) of National Institute of Health Sciences]. Kokuritsu Iyakuhin Shokuhin Eisei Kenkyusho Hokoku. 2001(119):97-100. (Pubitemid 34101132)
30. AN Tripathi L Chauhan PP Thankachan R Barthwal 2007 Quantum chemical and nuclear magnetic resonance spectral studies on molecular properties and electronic structure of berberine and berberrubine Magn Reson Chem 45 8 647 655 1:CAS:528:DC%2BD2sXot1OmsL4%3D 10.1002/mrc.2019 17559166
31. A Avdeef 2001 Physicochemical profiling (solubility, permeability and charge state) Curr Top Med Chem 1 4 277 351 1:CAS:528:DC%2BD3MXms1Khs7o%3D 10.2174/1568026013395100 11899112
32. J Fernandes CR Gattass 2009 Topological polar surface area defines substrate transport by multidrug resistance associated protein 1 (MRP1/ABCC1) J Med Chem 52 4 1214 1218 1:CAS:528:DC%2BD1MXhsFWgurY%3D 10.1021/jm801389m 19193010
33. BC Hancock P York RC Rowe 1997 The use of solubility parameters in pharmaceutical dosage form design Int J Pharm 148 1 21 1:CAS:528: DyaK2sXivVyjs7c%3D 10.1016/S0378-5173(96)04828-4 Invited Review (Pubitemid 27152212)
34. R Mannhold GI Poda C Ostermann IV Tetko 2009 Calculation of molecular lipophilicity: state-of-the-art and comparison of log P methods on more than 96,000 compounds J Pharm Sci 98 3 861 893 1:CAS:528:DC%2BD1MXjt1eisLo%3D 10.1002/jps.21494 18683876
35. A Jain Y Ran SH Yalkowsky 2004 Effect of pH-sodium lauryl sulfate combination on solubilization of PG-300995 (an anti-HIV agent): a technical note AAPS PharmSciTech 5 3 e45 10.1208/pt050345 15760078
36. CO Rangel-Yagui HWL Hsu A Pessoa Jr LC Tavares 2005 Micellar solubilization of ibuprofen-influence of surfactant head groups on the extent of solubilization Braz J Pharm Sci 41 2 237 246 1:CAS:528:DC%2BD2MXhtFGlur%2FI
37. Duchene D, Glomot FCV. Cyclodextrins and their industrial uses. In: Duchene D, editor. Pharmaceutical applications of cyclodextrins. 1st ed. France: Paris; 1987.
38. M Masson T Loftsson G Masson E Stefansson 1999 Cyclodextrins as permeation enhancers: some theoretical evaluations and in vitro testing J Control Release 59 1 107 118 1:CAS:528:DyaK1MXisVOntbk%3D 10.1016/S0168-3659(98) 00182-5 10210727 (Pubitemid 29187198)
39. VD Wagh SV Ghadlinge 2009 Taste masking methods and techniques in oral pharmaceuticals: current perspectives J Pharm Res 2 6 1049 1054 1:CAS:528:DC%2BC3cXpvFyjsLk%3D
40. AR Patel PR Vavia 2008 Preparation and evaluation of taste masked famotidine formulation using drug/beta-cyclodextrin/polymer ternary complexation approach AAPS PharmSciTech 9 2 544 550 1:CAS:528:DC%2BC3cXnslGjtLg%3D 10.1208/s12249-008-9078-0 18431648
41. Y Nagase M Hirata K Wada H Arima F Hirayama T Irie, et al. 2001 Improvement of some pharmaceutical properties of DY-9760e by sulfobutyl ether beta-cyclodextrin Int J Pharm 229 1-2 163 172 1:CAS:528:DC%2BD3MXntlKntr0%3D 10.1016/S0378-5173(01)00851-1 11604269 (Pubitemid 32972091)
42. T Loftsson D Hreinsdottir M Masson 2005 Evaluation of cyclodextrin solubilization of drugs Int J Pharm 302 1-2 18 28 1:CAS:528:DC%2BD2MXpvVWju7w%3D 10.1016/j.ijpharm.2005.05.042 16099118 (Pubitemid 41244817)
43. RK Sharma JB Wooten VL Baliga X Lin WG Chan MR Hajaligol 2004 Characterization of chars from pyrolysis of lignin Fuel 83 11-12 1469 1482 1:CAS:528:DC%2BD2cXjvFOgsr8%3D 10.1016/j.fuel.2003.11.015
44. PCB Page D Barros BR Buckley BA Marples 2005 Organocatalysis of asymmetric epoxidation mediated by iminium salts: comments on the mechanism Tetrahedron: Assymetry 16 21 3488 3491 10.1016/j.tetasy.2005.08.053 (Pubitemid 41681124)
45. VE Juan Hikawczuk PC Rossomando OS Giordano JR Saad 2002 neo-Clerodane diterpenoids from Baccharis flabellata Phytochemistry 61 4 389 394 1:CAS:528:DC%2BD38XnsF2ltb8%3D 10.1016/S0031-9422(02)00241-8 12377231 (Pubitemid 35230795)
46. LA Miller RL Carrier I Ahmed 2007 Practical considerations in development of solid dosage forms that contain cyclodextrin J Pharm Sci 96 7 1691 1707 1:CAS:528:DC%2BD2sXnsFSqtrc%3D 10.1002/jps.20831 17243148 (Pubitemid 47122948)