Cyclodextrins in the Pharmaceutical Field

AbstractCyclodextrins (CyDs) are cyclic oligosaccharides, containing a minimum of six D-(+)-glycopyranose units attached by α-1, 4-linkages produced by the action of the cyclodextrin-trans-glycosidase enzyme on a medium containing starch. CyDs are somewhat cone-shaped. The outside of CyDs is hydrophilic and the inside of the cavity is hydrophobic in character. If a molecule fits entirely or at least partially into the cavity, an inclusion complex may be formed. In general, hydrophobic molecules, rather than hydrophilic ones, have a higher affinity to the CyD cavity in aqueous solutions. The CyD complexes thus formed are stabilized by various intermolecular forces, such as hydrophobic interaction, van der Waals forces, hydrogen bonding, release of high energy water molecules in complex formation and release of strain energy in the macromolecular CyD ring. Orally administered CyDs have shown to be harmless, because insignificant amounts are absorbed.Parenterally administered natural CyDs may cause severe ne...

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

[2]  K. Uekama,et al.  Cyclodextrins in drug carrier systems. , 1987, Critical reviews in therapeutic drug carrier systems.

[3]  T. Osa,et al.  Complexation of aromatic carboxylic acids with heptakis(2,6-di-O-methyl)cyclomaltoheptaose in chloroform and water , 1989 .

[4]  T. Nagai,et al.  Inclusion complex of cinnarizine withβ-cyclodextrin in aqueous solution and in solid state , 1984 .

[5]  T. Nagai,et al.  Properties of cyclodextrin polymer as a tabletting aid. , 1984, Chemical & pharmaceutical bulletin.

[6]  I. Sanemasa,et al.  A new method for determining cyclodextrin complex formation constants with electrolytes in aqueous medium. , 1988 .

[7]  W. M. Atkinson,et al.  Solute-induced circular dichroism: drug discrimination by cyclodextrin. , 1984, Analytical chemistry.

[8]  F. Bright,et al.  Thermodynamic study on the effects of beta-cyclodextrin inclusion with anilinonaphthalenesulfonates. , 1989, Analytical chemistry.

[9]  K. Uekama,et al.  Improvement in biopharmaceutics of prednisolone by β- and γ-cyclodextrins , 1984 .

[10]  T Nagai,et al.  Enhancement of bioavailability of cinnarizine from its beta-cyclodextrin complex on oral administration with DL-phenylalanine as a competing agent. , 1985, Journal of pharmaceutical sciences.

[11]  J. Lach,et al.  Interaction of pharmaceuticals with Schardinger dextrins. VI. Interactions of beta-cyclodextrin, sodium deoxycholate, and deoxycholic acid with amines and pharmaceutical agents. , 1966, Journal of pharmaceutical sciences.

[12]  N. Bodor,et al.  The effects of 2-hydroxypropyl-β-cyclodextrin on the solubility and stability of chlorambucil and melphalan in aqueous solution , 1989 .

[13]  K. A. Connors,et al.  Effect of cycloamyloses on apparent dissociation constants of carboxylic acids and phenols: equilibrium analytical selectivity induced by complex formation. , 1976, Journal of pharmaceutical sciences.

[14]  Ying Hu,et al.  Preparation and properties of inclusion compounds of ferrocene and its derivatives with cyclodextrins , 1988 .

[15]  T. Nagai,et al.  Evaluation of bioavailability upon oral administration of cinnarizine-beta-cyclodextrin inclusion complex to beagle dogs. , 1985, Chemical & pharmaceutical bulletin.

[16]  Biopharmaceutical aspects of cyclodextrins , 1990 .

[17]  Y. Aso,et al.  Epimerization and racemization of some chiral drugs in the presence of cyclodextrin and liposomes. , 1989, Chemical & pharmaceutical bulletin.

[18]  Terada Katsuhide,et al.  Molecular behavior, dissolution characteristics and chemical stability of aspirin in the ground mixture and in the inclusion complex with di-O-methyl-β-cyclodextrin , 1986 .

[19]  N. Çelebi,et al.  A study of the inclusion complex of naproxen with β-cyclodextrin , 1988 .

[20]  Mohammad A. Hassan,et al.  Improvement of the in vitro dissolution characteristics of famotidine by inclusion in β-cyclodextrin , 1990 .

[21]  H. Koinuma,et al.  STRUCTUAL ELUCIDATION OF THE INCLUSION COMPLEXES OF TOLBUTAMIDE WITH α- AND β-CYCLODEXTRINS IN AQUEOUS SOLUTION , 1978 .

[22]  M. Kajtár,et al.  Complex formation of phenolphthalein and some related compounds with β-cyclodextrin , 1988 .

[23]  K. Uekama,et al.  Hydrolysis Rate of Ethyl Cinnamates in the Presence of Cyclodextrin , 1976 .

[24]  L. Pannell,et al.  Hydroxypropyl-β-cyclodextrin: preparation and characterization; effects on solubility of drugs , 1986 .

[25]  C. Rhodes,et al.  Potential Pharmaceutical Applications of a New Beta Cyclodextrin Derivative , 1988 .

[26]  J. Lach,et al.  Influence of cyclodextrins on ester hydrolysis. , 1968, Journal of pharmaceutical sciences.

[27]  T Nagai,et al.  Evaluation of cyclodextrin polymer as an additive for furosemide tablet. , 1984, Chemical & pharmaceutical bulletin.

[28]  K. Koizumi,et al.  Inclusion complexes of poorly water-soluble drugs with glucosyl-cyclodextrins. , 1987, Chemical & pharmaceutical bulletin.

[29]  K. Harata,et al.  CRYSTAL AND MOLECULAR STRUCTURE OF 2 : 2 (±) FLURBIPROFEN-β-CYCLODEXTRIN COMPLEX , 1983 .

[30]  J. Ripmeester Variable temperature CP/MAS13C NMR study of cyclodextrin complexes of benzaldehyde , 1988 .

[31]  I. Sanemasa,et al.  Association of Benzene and Alkylbenzenes with Cyclodextrins in Aqueous Medium , 1987 .

[32]  K. Uekama,et al.  Enhanced absorption of phenobarbital from suppositories containing phenobarbital-beta-cyclodextrin inclusion complex. , 1982, Chemical & pharmaceutical bulletin.

[33]  H. Bundgaard,et al.  Inclusion complexation of metronidazole benzoate with β-cyclodextrin and its depression of anhydrate-hydrate transition in aqueous suspensions , 1984 .

[34]  F. Hirayama,et al.  Inclusion Complexation of Prostaglandin F2α with α-and β-Cyclodextrins in Aqueous Solution , 1978 .

[35]  F. Hirayama,et al.  Effects of Cyclodextrins on the Hydrolysis of Prostacyclin and Its Methyl Ester in Aqueous Solution , 1981 .

[36]  K. Uekama,et al.  Enhancement of Oral Bioavailability of Spironolactone by β- and γ-Cyclodextrin Complexations , 1983 .

[37]  D. Duchěne,et al.  Improvement in availability and stability of a dermocorticoid by inclusion in β-cyclodextrin , 1988 .

[38]  F. Hirayama,et al.  Improvement of dissolution characteristics and chemical stability of prostaglandin E1 by .GAMMA.-cyclodextrin complexation. , 1984 .

[39]  J. Beijnen,et al.  Stabilization of mitomycins on complexation with cyclodextrins in aqueous acidic media , 1989 .

[40]  B. D. Anderson,et al.  Inclusion complexes of purine nucleosides with cyclodextrins. I, Complexation and stabilization of a dideoxypurine nucleoside with 2-hydroxypropyl-β-cyclodextrin , 1990 .

[41]  D. Duchěne,et al.  Inclusion of retinoic acid in β-cyclodextrin , 1989 .

[42]  I. Sanemasa,et al.  Association of naphthalene and its methyl derivatives with cyclodextrins in aqueous medium. , 1988 .

[43]  T. Yotsuyanagi,et al.  Effects of drug bindings on esterase activity of human serum albumin. Dissociation constants of the complexes between the protein and drugs such as N-arylanthranilic acids, coumarin derivatives and prostaglandins. , 1979, Chemical & pharmaceutical bulletin.

[44]  G. Hardee,et al.  The interaction of some coumarin anticoagulants with beta-cyclodextrin in phosphate buffers. , 1978, Pharmaceutica acta Helvetiae.

[45]  K. Harata,et al.  The Circular Dichroism Spectra of the β-Cyclodextrin Complex with Naphthalene Derivatives , 1975 .

[46]  F. Hirayama,et al.  Some physicochemical properties of branched β-cyclodextrins and their inclusion characteristics , 1989 .

[47]  T. Imai,et al.  Improvement of dissolution and suppository release characteristics of flurbiprofen by inclusion complexation with heptakis(2,6-di-O-methyl)-beta-cyclodextrin. , 1985, Journal of pharmaceutical sciences.

[48]  S. Hamai Association of Inclusion Compounds of β-Cyclodextrin in Aqueous Solution , 1982 .

[49]  A. Rassat,et al.  Nitroxides. 87. ESR determination of the thermodynamic data for the association of two paramagnetic enantiomers with .beta.-cyclodextrin , 1979 .

[50]  A. Karara,et al.  Characterization, Dissolution and Diffusion Properties of Tolbutamide-β-Cyclodextrin Complex System , 1988 .

[51]  S. Morimoto,et al.  Cannabis. XV: Preparation and stability of Δ9-tetrahydrocannabinol-β-cyclodextrin inclusion complex , 1983 .

[52]  F. Hirayama,et al.  Utilization of Diethyl-β-Cyclodextin as a Sustained-Release Carrier for Isosorbide Dinitrate , 1988 .

[53]  F. Cramer,et al.  Formation of cyclodextrin inclusion compounds of stable nitroxide radicals as monitored by electron-spin resonance spectra , 1979 .

[54]  R. Palepu,et al.  Binding constants of .beta.-cyclodextrin/surfactant inclusion by conductivity measurements , 1989 .

[55]  D. Frank,et al.  Cyclodextrin nephrosis in the rat. , 1976, The American journal of pathology.

[56]  D. Kristol,et al.  Cyclodextrin inclusion complexes: studies of the variation in the size of alicyclic guests , 1989 .

[57]  K. Uekama,et al.  Pharmaceutical evaluation of hydroxyalkyl ethers of β-cyclodextrins , 1988 .

[58]  F. Hirayama,et al.  Improvements of dissolution characteristics and chemical stability of 16,16-dimethyl-trans-delta 2-prostaglandin E1 methyl ester by cyclodextrin complexation. , 1979, Journal of pharmaceutical sciences.

[59]  OtagiriMasaki,et al.  CIRCULAR DICHROISM STUDY ON INCLUSION COMPLEXES OF SOME PROSTAGLANDINS WITH α- AND β-CYCLODEXTRINS , 1977 .

[60]  S. Hamai Inclusion compounds in the systems of .beta.-cyclodextrin-alcohol-pyrene in aqueous solution , 1989 .

[61]  B. Perly,et al.  Anthraquinone sulphonate as a general‐purpose shift reagent for the NMR analysis of cyclodextrins , 1990 .

[62]  Y. Inoue,et al.  NMR Studies of Cyclodextrin Inclusion Complex , 1989 .

[63]  N. Rajagopalan,et al.  A study of the inclusion complex of amphotericin-B with γ-cyclodextrin , 1986 .

[64]  V. Zecchi,et al.  Availability of NSAIDH β‐Cyclodextrin Inclusion Complexes , 1989 .

[65]  Y. Inoue,et al.  Determination of the qualitative host-guest geometrical relationships in cyclomaltohexaose inclusion-complexes on the basis of measurements of intermolecular proton nuclear Overhauser effects , 1987 .

[66]  F. Hirayama,et al.  Improvement of chemical instability of prostacyclin in aqueous solution by complexation with methylated cyclodextrins , 1987 .

[67]  J. Pitha Enhanced water solubility of vitamins A, D, E, and K by substituted cycloamyloses. , 1981, Life sciences.

[68]  I. Apostol,et al.  Suppositories containing β-cyclodextrin complexes. I: Stability studies , 1984 .

[69]  K. Uekama,et al.  Cyclodextrin-induced hemolysis and shape changes of human erythrocytes in vitro. , 1982, Journal of pharmacobio-dynamics.

[70]  N. Purdie,et al.  Solute-induced circular dichroism: complexation of achiral drugs with cyclodextrin. , 1984, Analytical chemistry.

[71]  H. Ueda,et al.  Microcalorimetric and chromatographic investigations of the binding of some pyridine derivatives to cyclodextrins. , 1988, Journal of pharmaceutical and biomedical analysis.

[72]  F. Hirayama,et al.  Effects of cyclodextrins on the acid hydrolysis of digoxin , 1982, The Journal of pharmacy and pharmacology.

[73]  G. Patonay,et al.  Determination of cyclodextrin formation constants using dynamic coupled-column liquid chromatography , 1989 .

[74]  F. Hirayama,et al.  Utilization of cyclodextrin complexation for separation of E, A, and B prostaglandins by ion-exchange liquid chromatography. , 1977, Journal of pharmaceutical sciences.

[75]  Y. Nakai Molecular Behavior of Medicinals in Ground Mixtures with Microcrystalline Cellulose and Cyclodextrins , 1986 .

[76]  Kennath A. Connors Cyclodextrins and their industrial uses: Dominique Duchêne (Editor), Editions de Santé, 19 rue Louis-le-Grand, 75002 Paris, France, 1987, 448 pages, ISBN 2-86411-019-9. , 1988 .

[77]  K. Koizumi,et al.  Enhancement of the hypnotic potency of barbiturates by inclusion complexation with beta-cyclodextrin. , 1980, Chemical & pharmaceutical bulletin.

[78]  H. Bundgaard,et al.  The influence of cyclodextrin complexation on the stability of betamethasone-17-valerate , 1984 .

[79]  S. Szathmary Determination of hydroxypropyl-beta-cyclodextrin in plasma and urine by size-exclusion chromatography with post-column complexation. , 1989, Journal of chromatography.

[80]  M. E. Brown,et al.  Introduction to Thermal Analysis , 1988 .

[81]  M. L. Bender,et al.  Acceleration of phenyl ester cleavage by cycloamyloses. A model for enzymic specificity , 1967 .

[82]  F. Hirayama,et al.  Some pharmaceutical properties of 3-hydroxypropyl- and 2,3-dihydroxypropyl-beta-cyclodextrins and their solubilizing and stabilizing abilities. , 1989, Chemical & pharmaceutical bulletin.

[83]  F. Hirayama,et al.  Utility of 2-hydroxypropyl-beta-cyclodextrin in an intramuscular injectable preparation of nimodipine. , 1990, Chemical & pharmaceutical bulletin.

[84]  R. Bergeron,et al.  The molecular disposition of sodium p-nitrophenolate in the cavities of cycloheptaamylose and cyclohexaamylose in solution , 1976 .

[85]  M. Schwaller,et al.  Kinetics and thermodynamics of the formation of inclusion complexes between cyclodextrins and DNA-intercalating agents. Inclusion of ellipticine in γ-cyclodextrin , 1989 .

[86]  Y. Kotake,et al.  Bimodal inclusion of nitroxide radicals by .beta.-cyclodextrin in water as studied by electron spin resonance and electron nuclear double resonance , 1989 .

[87]  K. Uekama,et al.  Analysis of interfacial transfer and absorption behavior of drugs following dissolution from beta-cyclodextrin complexes. , 1983, Chemical & pharmaceutical bulletin.

[88]  F. Menger,et al.  Aggregation in strong acid. A micelle of carbonium ions , 1979 .

[89]  S. Lincoln,et al.  Inclusion Complexes of the Cyclomalto-Oligosaccharides (Cyclodextrins) , 1988 .

[90]  J. Szejtli,et al.  Stabilisierung fettlöslicher Vitamine mit beta‐Cyclodextrin , 1980 .

[91]  H. Nakanishi,et al.  Circular dichroism spectra of the inclusion complexes of phlorizin in cyclodextrins , 1990 .

[92]  A. Karara,et al.  Characterization, dissolution and bioavailability in rats of ibuprofen-β-cyclodextrin complex system , 1986 .

[93]  W. Saenger,et al.  Inclusion Compounds. XIX.1a The Formation of Inclusion Compounds of α-Cyclodextrin in Aqueous Solutions. Thermodynamics and Kinetics , 1967 .

[94]  Wolfram Saenger,et al.  Cyclodextrin Inclusion Compounds in Research and Industry , 1980 .

[95]  T. Matsue,et al.  Cyclodextrin-Nitrophenol Systems Studied by Polarography , 1977 .

[96]  I. Wadsö,et al.  Microcalorimetric titration of β-cyclodextrine with adamantane-1-carboxylate , 1986 .

[97]  B. Müller,et al.  Solubilization of drugs by modified β-cyclodextrins , 1985 .

[98]  J. Szejtli Cyclodextrins and their inclusion complexes , 1982 .

[99]  K. Uekama,et al.  Stabilization of isosorbide 5-mononitrate in solid state by β-cyclodextrin complexation , 1985 .

[100]  K. Uekama,et al.  Effects of β- and γ-Cyclodextrins on Release of Betamethasone from Ointment Bases , 1984 .

[101]  T. Nagai,et al.  Inclusion compounds of non-steroidal antiinflammatory and other slightly water soluble drugs with alpha- and beta-cyclodextrins in powdered form. , 1975, Chemical & pharmaceutical bulletin.

[102]  L. M. Schwartz,et al.  Acid dissociation of cyclooctaamylose , 1982 .

[103]  F. Hirayama,et al.  Improvement of chemical instability of digitoxin in aqueous solution by complexation with beta-cyclodextrin derivatives. , 1988, Chemical & pharmaceutical bulletin.

[104]  F. Vincieri,et al.  Inclusion complex formation of 1,8-dihydroxyanthraquinone with cyclodextrins in aqueous solution and in solid state. , 1988, Journal of pharmaceutical sciences.

[105]  S. Harada,et al.  Inclusion compounds of lankacidin-group antibiotics with cyclodextrins. , 1985, The Journal of antibiotics.

[106]  F. Hirayama,et al.  Inclusion Complexation of Prostaglandin F2α with γ-Cyclodextrin in Solution and Solid Phases , 1984 .

[107]  R. Bergeron,et al.  Dependence of cycloamylose-substrate binding on charge , 1978 .

[108]  K. Terada,et al.  New Methods for Preparing Cyclodextrin Inclusion Compounds. I. Heating in a Sealed Container , 1987 .

[109]  M. Eftink,et al.  Spectral displacement techniques for studying the binding of spectroscopically transparent ligands to cyclodextrins. , 1986, Analytical biochemistry.

[110]  O. Corrigan,et al.  Mechanism of drug dissolution rate enhancement from β‐cyclodextrin‐drug systems , 1982 .

[111]  N. Higuchi,et al.  Dissolution behavior of prednisolone from solid dispersion systems with cyclodextrins and polyvinylpyrrolidone. , 1986, Chemical & pharmaceutical bulletin.

[112]  K. Koizumi,et al.  Isolation and characterization of hexakis(2,6-di-O-methyl)cyclomaltohexaose and octakis(2,6-di-O-methyl)cyclomalto-octaose, and their over-methylated homologues. , 1990 .

[113]  K. Uekama,et al.  Anomalous dissolution behavior of the diazepam — γ-cyclodextrin complex in polymer solutions , 1984 .

[114]  M. Takada,et al.  Preparation of Solid dispersion Systems of Disopyramide with Polyvinylpyrrolidone and γ-Cyclodextrin , 1988 .

[115]  J. Nakayama,et al.  Induced circular dichroism spectra of the cyclodextrin complexes with 2-Thioxo-1,3-benzodithiole and 2-Selenoxo-1,3-benzodithiole , 1990 .

[116]  Y. Inoue,et al.  Determination of the host-guest geometry in the inclusion complexes of cyclomalto-oligosaccharides with p-nitrophenol in solution , 1988 .

[117]  S. P. Jones,et al.  Polarographic detection of beta-cyclodextrin inclusion complexes , 1986 .

[118]  K. Uekama,et al.  New Perspectives in Cyclodextrin Pharmaceutical Applications , 1990 .

[119]  J. Pitha Amorphous water-soluble derivatives of cyclodextrins: nontoxic dissolution enhancing excipients. , 1985, Journal of pharmaceutical sciences.

[120]  J. Szejtli,et al.  Aggregation of amphotericin B in the presence of γ‐cyclodextin , 1989 .

[121]  K. Uekama,et al.  Inclusion complexes of cinnamic acids with cyclodextrins. Mode of inclusion in aqueous solution. , 1975 .

[122]  Kikuchi Masahiko,et al.  Improvement of oral and rectal bioavailabilities of carmofur by methylated β-cyclodextrin complexations , 1987 .

[123]  F. Hirayama,et al.  Improvement of the oral bioavailability of digitalis glycosides by cyclodextrin complexation. , 1983, Journal of pharmaceutical sciences.

[124]  Y Horiuchi,et al.  Design and in vitro evaluation of slow-release dosage form of piretanide: utility of beta-cyclodextrin:cellulose derivative combination as a modified-release drug carrier. , 1990, Journal of pharmaceutical sciences.

[125]  F. Hirayama,et al.  Improvement of dissolution and absorption characteristics of benzodiazepines by cyclodextrin complexation , 1983 .

[126]  K. Kitamura,et al.  Stabilization of AD-1590, a non-steroidal antiinflammatory agent, in suppository bases by beta-cyclodextrin complexation. , 1986, Chemical and pharmaceutical bulletin.

[127]  T Nagai,et al.  Bioavailability of powdered inclusion compounds of nonsteroidal antiinflammatory drugs with beta-cyclodextrin in rabbits and dogs. , 1978, Chemical & pharmaceutical bulletin.

[128]  B. Hingerty,et al.  “Induced-fit”-type complex formation of the model enzyme α-cyclodextrin , 1976 .

[129]  K. Uekama,et al.  Sustained release of buserelin acetate, a luteinizing hormone‐releasing hormone agonist, from an injectable oily preparation utilizing ethylated β‐cyclodextrin , 1989, The Journal of pharmacy and pharmacology.

[130]  J. Szejtli,et al.  Menadione-γ-cyclodextrin inclusion complex , 1985 .

[131]  Y. Sasaki,et al.  Inclusion compounds of cyclodextrin and azo dyes. IV(b): Nuclear magnetic resonance and circular dichroism spectra of γ-cyclodextrin and orange II in the solution state , 1984 .

[132]  M. Kata,et al.  Increasing the solubility of drugs through cyclodextrin complexation , 1987 .

[133]  L. M. Schwartz,et al.  Acid dissociation of cyclohexaamylose and cycloheptaamylose , 1980 .

[134]  M. E. Brown,et al.  Introduction to Thermal Analysis: Techniques and applications , 1988 .

[135]  F. Hirayama,et al.  Slow-release characteristics of diltiazem from ethylated beta-cyclodextrin complexes. , 1990, Journal of pharmaceutical sciences.

[136]  L. Barcza,et al.  Complex formation of phenol, aniline, and their nitro derivatives with β-cyclodextrin , 1988 .

[137]  J. Szejtli Dimethyl-β-cyclodextrin as parenteral drug carrier , 1983 .

[138]  F. Hirayama,et al.  Inclusion complexes of cyclodextrins with cinnamic acid derivatives: Dissolution and thermal behavior. , 1979 .

[139]  S. Ismail,et al.  Studies of Cyclodextrin Inclusion Complexes: I - Inclusion Complexes Between α- And β-Cyclodextrins and Chloramphenicol in Aqeuous Solutions , 1986 .

[140]  F. Hirayama,et al.  Determination of the Stability Constants for Inclusion Complexes of Cyclodextrins with Various Drug Molecules by High Performance Liquid Chromatography , 1978 .

[141]  M. Huffman,et al.  Comparison of tolbutamide β-cyclodextrin inclusion compounds and solid dispersions: Physicochemical characteristics and dissolution studies , 1990 .

[142]  Y. Inoue,et al.  N.m.r. studies of cycloamylose inclusion-complexes with p-substituted phenols , 1984 .

[143]  A. Harada,et al.  Preparation and properties of inclusion compounds of transition-metal complexes of cycloocta-1,5-diene and norbornadiene with cyclodextrins , 1989 .

[144]  H. Koinuma,et al.  Molecular dynamics of prostaglandin F2.ALPHA.-cyclodextrin complexes in aqueous solution. , 1980 .

[145]  M. Brewster,et al.  An intravenous toxicity study of 2-hydroxypropyl-β-cyclodextrin, a useful drug solubilizer, in rats and monkeys , 1990 .

[146]  Masaki Yamasaki,et al.  Inclusi on complexations of steroid hormones with cyclodextrins in water and in solid phase , 1982 .

[147]  K. A. Connors,et al.  Potentiometric study of molecular complexes of weak acids and bases applied to complexes of alpha-cyclodextrin with para-substituted benzoic acids. , 1982, Journal of pharmaceutical sciences.

[148]  T. Arita,et al.  Dissolution behavior and gastrointestinal absorption of dicumarol from solid dispersion systems of dicumarol-polyvinylpyrrolidone and dicumarol-beta-cyclodextrin. , 1983, Chemical & pharmaceutical bulletin.

[149]  S. Hizukuri,et al.  Some properties and the inclusion behavior of branched cyclodextrins. , 1988, Chemical & pharmaceutical bulletin.

[150]  F. Hirayama,et al.  Ethylated beta-cyclodextrins as hydrophobic drug carriers: sustained release of diltiazem in the rat. , 1987, Journal of pharmaceutical sciences.

[151]  F. Hirayama,et al.  MODIFICATION OF SUBSTITUENT EFFECT BY CYCLODEXTRIN COMPLEXATION IN ALKALINE HYDROLYSIS OF 7-SUBSTITUTED COUMARINS , 1981 .

[152]  L. Szente,et al.  Proceedings of the Eighth International Symposium on Cyclodextrins , 1982 .

[153]  J. Lach,et al.  SCHARDINGER DEXTRIN INTERACTION. IV. INHIBITION OF HYDROLYSIS BY MEANS OF MOLECULAR COMPLEX FORMATION. , 1964, Journal of pharmaceutical sciences.

[154]  F. Hirayama,et al.  Improvement of some pharmaceutical properties of nocloprost by β- and γ-Cyclodextrin Complexation , 1990 .

[155]  N. Purdie,et al.  Cyclodextrin complexation of barbiturates in aqueous solution. , 1984, Analytical chemistry.

[156]  K. Kano,et al.  Spectroscopic Study of Hydrophobic Interaction of Heterocyclic Amine N-Oxides with Cyclodextrins. , 1988 .

[157]  M. Hashida,et al.  Effects of β-cyclodextrin and di-O-methyl-β-cyclodextrin on the percutaneous absorption of butylparaben, indomethacin and sulfanilic acid , 1986 .

[158]  K. Uekama,et al.  Simultaneous determination of complexation equilibrium constants for conjugated guest species by extended potentiometric titration method: on barbiturate-beta-cyclodextrin system. , 1976, Chemical & pharmaceutical bulletin.

[159]  István Lukovits,et al.  Theoretical investigation of inclusion complexes of β-cyclodextrin with alcohols , 1988 .

[160]  H. Frijlink,et al.  The effects of cyclodextrins on drugs absorption. I. In vitro observations , 1989 .

[161]  J. Perrin,et al.  Cycloheptaamylose-barbiturate inclusion complexes: solubility and circular dichroism studies. , 1972, Journal of pharmaceutical sciences.

[162]  S. Davis,et al.  Modification of the aqueous solubility and stability of progabide , 1989 .

[163]  A. Kaifer,et al.  The interactions of surfactant viologens with cyclodextrins , 1989 .

[164]  F. Hirayama,et al.  Improving the aqueous stability of prostaglandin E2 and prostaglandin A2 by inclusion complexation with methylated-beta-cyclodextrins. , 1984, Chemical & pharmaceutical bulletin.

[165]  B. D. Anderson,et al.  Inclusion complexes of purine nucleosides with cyclodextrins II. Investigation of inclusion complex geometry and cavity microenvironment , 1990 .

[166]  Y. Inoue,et al.  A Molecular Orbital Study of Cyclodextrin Inclusion Complexes. I. The Calculation of the Dipole Moments of α-Cyclodextrin Aromatic Guest Complexes , 1988 .

[167]  T. Nagai,et al.  Influence of inclusion of nonsteroidal antiinflammatory drugs with beta-cyclodextrin on the irritation to stomach of rats upon oral administration. , 1978, Chemical & pharmaceutical bulletin.

[168]  K. A. Connors,et al.  Stoichiometric model of α-cyclodextrin complex formation , 1980 .

[169]  K. Uekama,et al.  Improvement in the percutaneous absorption of beclomethasone dipropionate by γ‐cyclodextrin complexation , 1985, The Journal of pharmacy and pharmacology.