Interaction of fentanyl with various cyclodextrins in aqueous solutions

Water‐soluble fentanyl citrate salt has been used in sublingual or buccal formulations for the breakthrough pain treatment. However, fentanyl absorption through the lipid mucosal membrane may be improved by enhancing the non‐ionic lipophilic fentanyl base solubility. Therefore, the interaction between cyclodextrins (CDs) and fentanyl base has been evaluated to obtain basic information for its application.

[1]  Thorsteinn Loftsson,et al.  Cyclodextrins as functional excipients: methods to enhance complexation efficiency. , 2012, Journal of pharmaceutical sciences.

[2]  Haiyan Li,et al.  Structure-based in silico model profiles the binding constant of poorly soluble drugs with β-cyclodextrin. , 2011, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[3]  K. Higashi,et al.  Effects of cogrinding with β-cyclodextrin on the solid state fentanyl. , 2010, Journal of pharmaceutical sciences.

[4]  Y. Sueishi,et al.  NMR spectroscopic characterization of inclusion complexes of hydroxy-substituted naphthalenes with native and modified β-cyclodextrins , 2009 .

[5]  Bridget A. Becker,et al.  NMR characterization of the host–guest inclusion complex between β‐cyclodextrin and doxepin , 2008, Magnetic resonance in chemistry : MRC.

[6]  P. Crooks,et al.  Development of a GC-MS Assay for the Determination of Fentanyl Pharmacokinetics in Rabbit Plasma after Sublingual Spray Delivery , 2008, The AAPS Journal.

[7]  R. Guy,et al.  Ex vivo evaluation of bioadhesive films for buccal delivery of fentanyl. , 2007, Journal of controlled release : official journal of the Controlled Release Society.

[8]  Abu T M Serajuddin,et al.  Salt formation to improve drug solubility. , 2007, Advanced drug delivery reviews.

[9]  Thorsteinn Loftsson,et al.  Cyclodextrins as pharmaceutical solubilizers. , 2007, Advanced drug delivery reviews.

[10]  G. Aronoff,et al.  Evidence-based oral transmucosal fentanyl citrate (OTFC) dosing guidelines. , 2005, Pain medicine.

[11]  H. Nakanishi,et al.  Application of ultra-high magnetic field for saccharide molecules: 1H NMR spectra of 6-O-alpha-D-glucopyranosyl-cyclomaltoheptaose and -cyclomaltohexaose. , 2005, Carbohydrate research.

[12]  L. Vlahos,et al.  Transdermal therapeutic fentanyl-system (TTS-F). , 2004, In vivo.

[13]  V. Stella,et al.  Effect of Cyclodextrin Charge on Complexation of Neutral and Charged Substrates: Comparison of (SBE)7M-β-CD to HP-β-CD , 2001, Pharmaceutical Research.

[14]  Y. Vander Heyden,et al.  Preparation and in-vitro release rate of fentanyl-cyclodextrin complexes for prolonged action in epidural analgesia. , 2003, International journal of pharmaceutics.

[15]  J. Elguero,et al.  Fentanyl and its analogue N-(1-phenylpyrazol-3-yl)-N-[1-(2-phenylethyl)-4-piperidyl]propanamide: 1H- and 13C-NMR spectroscopy, X-ray crystallography, and theoretical calculations. , 2003, Chemical & pharmaceutical bulletin.

[16]  Q. Guo,et al.  The Driving Forces in the Inclusion Complexation of Cyclodextrins , 2002 .

[17]  S. Neya,et al.  Dimerization and α-Cyclodextrin Inclusion of Propantheline Bromide as Studied by NMR and Molecular Modeling , 1999 .

[18]  H. Schneider,et al.  NMR Studies of Cyclodextrins and Cyclodextrin Complexes. , 1998, Chemical reviews.

[19]  J. Szejtli Introduction and General Overview of Cyclodextrin Chemistry. , 1998, Chemical reviews.

[20]  F. Hirayama,et al.  Cyclodextrin Drug Carrier Systems. , 1998, Chemical reviews.

[21]  E. Kharasch,et al.  Fentanyl metabolism by human hepatic and intestinal cytochrome P450 3A4: implications for interindividual variability in disposition, efficacy, and drug interactions. , 1997, Drug metabolism and disposition: the biological fate of chemicals.

[22]  J. Lees,et al.  Subcutaneous fentanyl and sufentanil infusion substitution for morphine intolerance in cancer pain management , 1995, PAIN®.

[23]  Carol L. Davis,et al.  Oxford Textbook of Palliative Medicine , 1994, British Journal of Cancer.

[24]  T. Osa,et al.  Ferrocene-appended cyclodextrins. The effects of temperature, organic solvent, length of spacer, and cavity size on the complexation behavior , 1993 .

[25]  B. Müller,et al.  Interaction of NSA with cyclodextrins and hydroxypropyl cyclodextrin derivatives , 1991 .

[26]  B. Müller,et al.  Effect of hydrotropic substances on the complexation of sparingly soluble drugs with cyclodextrin derivatives and the influence of cyclodextrin complexation on the pharmacokinetics of the drugs. , 1991, Journal of pharmaceutical sciences.

[27]  K. A. East,et al.  Oral Transmucosal Fentanyl Citrate (Lollipop) Premedication in Human Volunteers , 1989, Anesthesia and analgesia.

[28]  J. Bonica,et al.  Management of cancer pain. , 1984, Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer.

[29]  Maurice R. Eftink,et al.  Cyclodextrin–adamantanecarboxylate inclusion complexes: A model system for the hydrophobic effect , 1982 .

[30]  D. McClain,et al.  Intravenous fentanyl kinetics , 1980, Clinical pharmacology and therapeutics.

[31]  G. Hall Fentanyl and the metabolic response to surgery. , 1980, British journal of anaesthesia.

[32]  K. A. Connors,et al.  trans-Cinnamic acid--alpha-cyclodextrin system as studied by solubility, spectral, and potentiometric techniques. , 1980, Journal of pharmaceutical sciences.

[33]  T. Higuchi,et al.  Phase solubility techniques , 1965 .