Benefits of methylated cyclodextrins in the development of midazolam pharmaceutical formulations

Journal of Pharmaceutical Sciences

Volumn 102, Issue 7, 2013, Pages 2102-2111

  Mathiron, David ^a   Marçon, Frédéric ^a,b   Dubaele, Jean marc ^b   Cailleu, Dominique ^a   Pilard, Serge ^a   Djedaïni pilard, Florence ^a  

^a UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

^b AMIENS UNIVERSITY HOSPITAL   (France)

Author keywords

Cyclodextrins; Formulation; HPLC; Inclusion compounds; Mass spectrometry; Midazolam; NMR; Solubility; Stability

Indexed keywords

2,6 O DIMETHYL BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; GAMMA CYCLODEXTRIN; MIDAZOLAM; RANDOMIZED METHYLATED BETA CYCLODEXTRIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG DEGRADATION; DRUG FORMULATION; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY;

EID: 84879019946     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23558     Document Type: Article

References (26)

1. Wermeling DP, Record KA, Kelly TH, Archer SM, Clinch T, Rudy AC. 2006. Pharmacokinetics and pharmacodynamics of a new intranasal midazolam formulation in healthy volunteers. Anesth Analg 103:344-349.
2. The European Agency for the Evaluation of Medicinal Products. 2006. Assessment of the paediatric needs: Anaesthesiology. Doc. Ref: EMEA/405166/2006.
3. Marçon F, Mathiron D, Pilard S, Lemaire-Hurtel AS, Dubaele JM, Djedaini-Pilard F. 2009. Development and formulation of a 0.2% oral solution of midazolam containing γ-CD. Int J Pharm 379:244-250.
4. Loftsson T, Gudmundsdóttir H, Sigurjónsdóttir JF, Sigurdsson HH, Sigfússon SD, Másson M, Stefánsson E. 2001. Cyclodextrin solubilization of benzodiazepines: Formulation of midazolam nasal spray. Int J Pharm 212:29-40.
5. Kaartama R, Turunen E, Toljamo K, Kokki H, Lehtonen M, Ranta VP, Savolainen J, Jarvinen K, Jarho P. 2012. The effect of hydroxypropyl-beta-cyclodextrin and sucrose on the sublingual absorption of midazolam in rabbits. Eur J Pharm Biopharm 81:178-183.
6. Thummel KE, O'Shea D, Paine MF, Shen DD, Kunze KL, Perkins JD, Wilkinson GR. 1996. Oral first-pass elimination of midazolam involves both gastrointestinal and hepatic CYP3A-mediated metabolism. Clin Pharmacol Ther 59:491-502.
7. Fujii J, Inotsume N, Nakano M. 1988. Relative bioavailability of midazolam following sublingual versus oral administration in healthy volunteers. J Pharmacobiodyn 11:206-209.
8. Brosius KK, Bannister CF. 2003. Midazolam premedication in children: A comparison of two oral dosage formulations on sedation score and plasma midazolam levels. Anesth Analg 96:392-395.
9. 9-tetrahydrocannabinol in rabbits. Eur J Pharm Sci 26:71-77.
10. Loftsson T, Brewster ME. 1996. Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. J Pharm Sci 85:1017-1025.
11. Kaukonen AM, Kilpelainen I, Mannermaa JP. 1997. Water-soluble β-cyclodextrins in paediatric oral solutions of spironolactone: Solubilization and stability of spironolactone in solutions of β-cyclodextrin derivatives. Int J Pharm 159:159-170.
12. Scalia S, Tursilli R, Iannuccelli V. 2007. Complexation of the sunscreen agent, 4-methylbenzylidene camphor with cyclodextrins: Effect on photostability and human stratum corneum penetration. J Pharm Biomed Anal 44:29-34.
13. Loftsson T, Vogensen SB, Brewster ME, Konrádsdóttir F. 2007. Effects of cyclodextrins on drug delivery through biological membranes. J Pharm Sci 96:2532-2546.
14. Boulmedarat L, Bocho A, Lesieur S, Fattal E. 2005. Evaluation of buccal methyl-β-cyclodextrin toxicity on human oral epithelial cell culture model. J Pharm Sci 94:1300-1309.
15. Djedaini-Pilard F, Nevers MC, Weisse S, Grassi J, Perly B, Créminon C. 2003. Development of sensitive enzyme immunoassays allowing specific detection for methyl derivatives of cyclomaltoheptaose. Carbohydr Res 338:2091-2099.
16. Loftsson T, Hreinsdottir D, Masson M. 2005. Evaluation of cyclodextrin solubilization of drugs. Int J Pharm 302:18-28.
17. Djedaini-Pilard F, Lin SZ, Perly B, Wouessidjewe D. 1990. High field NMR techniques for the investigation of a beta-cyclodextrin-indomethacin inclusion complex. J Pharm Sci 79:643-646.
18. Péan C, Creminon C, Djedaïni-Pilard F, Pradelles P, Perly B. 1999. NMR investigation of the inclusion of thyroxine and derivatives in natural and chemically modified cyclodextrins. J Inclusion Phenom 33:307-319.
19. Kurkov SV, Loftsson T. 2012. Cyclodextrins. Int J Pharm. [Epub ahead of print]
20. Cézard C, Trivelli X, Aubry F, Djedaini-Pilard F, Dupradeau FY. 2011. Molecular dynamics studies of native and substituted cyclodextrins in different media: 1. Charge derivation and force field performances. Phys Chem Chem Phys 13:15103-15121.
21. Brewster ME, Loftsson T. 2007. Cyclodextrins as pharmaceutical solubilizers. Adv Drug Deliv Rev 59:645-666.
22. Amato ME, Djedaïni-Pilard F, Perly B, Scarlata G. 1992. High field NMR and molecular modelling study of the inclusion complexes of the nootropic drug tenilsetam in cyclodextrins. J Chem Soc, Perkin Trans 2 2065-2069.
23. Ali SM, Upadhyay SK. 2008. Complexation study of midazolam hydrochloride with β-cyclodextrin: NMR spectroscopic study in solution. Magn Reson Chem 46:676-679.
24. Orive MM, Gallo B, Alonso RM, Vicente F, Viré JC, Patriarche GJ. 1989. Spectrophotometric study of the acid-base equilibria of an imidazobenzodiazepine, midazolam, and its determination in pharmaceutical formulations. Microchim Acta 97:181-190.
25. Stella VJ, He Q. 2008. Cyclodextrins. Toxicol Pathol 36:30-42.
26. Frömming KH, Szejtli J. 1994. Cyclodextrins in pharmacy. Dordrecht, The Netherlands: Kluwer Academic Publishers.