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Interactions Of Ketoprofen And Ibuprofen With β-cyclodextrins In Solution And In The Solid State

P. Mura, B. Gp, A. Manderioli, M. Faucci, G. Bramanti, M. Sorrenti
Published 1998 · Chemistry

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Abstract The complexing, solubilizing and amorphizing abilities towards ketoprofen and ibuprofen of native β -cyclodextrin and some randomly substituted amorphous derivatives (methyl, hydroxyethyl, and hydroxypropyl β -cyclodextrin with an average substitution degree per anhydroglucose unit, respectively of 1.8, 1.6 and 0.9) were determined and compared with those already observed for naproxen. Drug-carrier interactions were studied in aqueous solution by means of phase-solubility analysis and 13 C NMR spectroscopy, and in the solid state using differential scanning calorimetry (DSC), X-ray powder diffractometry and infrared spectroscopy. The strength of the inclusion complexes with β -cyclodextrins ( K 1:1,ibu > K 1:1,nap > K 1:1,keto ) was directly related to the hydrophobic character of the guest (log  P values) and depended on its molecular features. The presence in physical mixtures of a high-energy state of crystalline drug molecularly dispersed in the amorphous carrier was assumed from DSC behaviour. Dissolution rates (dispersed amount method) of the active ingredient from equimolar drug-cyclodextrin physical mixtures and amorphous colyophilized products showed that methyl β -cyclodextrin was the most effective carrier also for ketoprofen and ibuprofen.
This paper references
10.1002/JPS.2600801214
Carbon-13 Nuclear Magnetic Resonance Study of Naproxen Interaction with Cyciodextrins in Solution
G. Bettinetti (1991)
10.1007/978-94-009-5376-5_56
Interaction of tri-O-methyl-β-cyclodextrin with drugs
Y. Nakai (1984)
Inclusion complexes between non steroidal antiinflammatory drugs and β-cyclodextrin
I. Orienti (1991)
10.1016/0378-5173(88)90081-6
Pharmaceutical evaluation of hydroxyalkyl ethers of β-cyclodextrins
A. Yoshida (1988)
10.1016/0378-5173(92)90053-5
Enhancing effects of cyclodextrins on nasal absorption of insulin in rats
T. Irie (1992)
10.1002/JPS.2600750106
Dissolution and partition thermodynamic functions of some nonsteroidal anti-inflammatory drugs.
A. Fini (1986)
10.3109/03639049409050236
Comparative study on Inclusion compounds of 4-Biphenylacetic acid with β-Cyclodextrin, Hydroxypropylated-β-Cyclodextrins, and methylated-β-Cyclodextrins
C. A. Ventura (1994)
10.3109/03639048309039887
Dissociation constants, solubilities and dissolution rates of some selected nonsteroidal antiinflammatories
C. Herzfeldt (1983)
Phase solubility techniques
T. Higuchi (1965)
10.1002/ARDP.19843170314
pH‐Solubility Relationship and Partition Coefficients for some Anti‐Inflammatory Arylaliphatic Acids
A. Chiarini (1984)
10.1111/j.2042-7158.1982.tb04689.x
Mechanism of drug dissolution rate enhancement from β‐cyclodextrin‐drug systems
O. Corrigan (1982)
10.3109/03639049209043682
Thermal behaviour and dissolution properties of naproxen in combinations with chemically modified ß-Cyclodextrins
G. Bettinetti (1992)
10.1007/BF00662225
Comparative study on inclusion complexations of antiinflammatory drug flurbiprofen with β-cyclodextrin and methylated β-cyclodextrins
T. Imai (1984)
10.1002/JPS.2600740312
Application of differential scanning calorimetry to the study of solid drug dispersions.
K. H. Kim (1985)
10.1016/0168-3659(88)90086-7
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.
Kennath A. Connors (1988)
10.1016/0378-5173(86)90232-2
Characterization, dissolution and bioavailability in rats of ibuprofen-β-cyclodextrin complex system
DahNan D. Chow (1986)
Control of NSAID dissolution by beta-cyclodextrin complexation.
V. Zecchi (1988)
10.1021/J100248A029
Cyclodextrin-adamantanecarboxylate inclusion complexes: studies of the variation in cavity size
W. Cromwell (1985)
10.1021/JA01077A028
A NEW SUBSTITUENT CONSTANT, PI, DERIVED FROM PARTITION COEFFICIENTS
T. Fujita (1964)
10.1021/ja00479a043
Complexation of 4-biphenylcarboxylate by cyclohexaamylose. A conductometric and carbon-13 nuclear magnetic resonance spectrometric analysis
R. I. Gelb (1978)
10.1002/ARDP.19893220404
Availability of NSAIDH β‐Cyclodextrin Inclusion Complexes
I. Orienti (1989)
10.1248/CPB.32.832
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
M. Suzuki (1984)
10.1002/JPS.2600780517
Heptakis(2,6-di-O-methyl)-beta-cyclodextrin complexation with the antitumor agent chlorambucil.
A. Green (1989)
10.1111/j.2042-7158.1993.tb05549.x
Stereochemical Aspects of the Molecular Pharmaceutics of Ibuprofen
A. Romero (1993)
10.1111/j.2042-7158.1975.tb09378.x
The concept of dissolution efficiency
K. A. Khan (1975)
10.1248/CPB.23.3062
Inclusion Compounds of Non-Steroidal Antiinflammatory and Other Slightly Water Soluble Drugs with α-and β-Cyclodextrins in Powdered Form
M. Kurozumi (1975)
10.1248/YAKUSHI1947.104.9_990
[Stabilization and reduction of irritant taste of anti-inflammatory drug pirprofen by beta-cyclodextrin complexation].
T. Hibi (1984)



This paper is referenced by
10.1016/j.ejps.2008.02.001
Microspheres for colonic delivery of ketoprofen-hydroxypropyl-beta-cyclodextrin complex.
F. Maestrelli (2008)
10.1080/10610270108027469
Interaction of Naproxen with Crystalline and Amorphous Methylated β-Cyclodextrin in the Liquid and Solid State
P. Mura (2001)
New Mode for Long Path Irradiation and Two Sided Detection for the Determination of Ibuprofen in Pure and Pharmaceutical Drugs using Continuous Flow Feed via the use of ISNAG Fluorometer Instrument Proph
Nagam S. Turkie (2017)
10.1016/J.SNB.2012.09.016
Cyclodextrin based potentiometric sensor for determination of ibuprofen in pharmaceuticals and waters
T. Sousa (2013)
10.5582/ddt
Drug Discoveries & Therapeutics
N. Kokudo (2008)
Design, Formulation And Evaluation Of Controlled Release Tablets Of Selected Non-Steroidal Anti-Inflammatory Drugs
A. Muhammad (2013)
SÍNTESE E CARACTERIZAÇÃO DE HIDROGÉIS DE AMIDO RETROGRADADO E GOMA GELANA UTILIZADOS COMO MATRIZ EM SISTEMAS DE LIBERAÇÃO CÓLON ESPECÍFICA DE FÁRMACOS
Câmpus de Araraquara (2014)
10.1016/J.VIBSPEC.2003.09.002
FTIR study of dibenzofuran-2-carboxylic acid and its complexes with β-cyclodextrin
Íñigo X. García-Zubiri (2003)
10.1016/J.EJPB.2005.08.010
Influence of cyclodextrins and chitosan, separately or in combination, on glyburide solubility and permeability.
N. Zerrouk (2006)
Estabilidad y propiedades fisicoquímicas de complejos de inclusión de ß-ciclodextrinas y sus derivados
Ponce Cevallos (2013)
10.1080/03639040802192798
Development of Glyburide Fast-Dissolving Tablets Based on the Combined Use of Cyclodextrins and Polymers
M. Cirri (2009)
10.1023/A:1026303516401
Diclofenac β-Cyclodextrin Binary Systems: A Study in Solution and in the Solid State
F. Barbato (2003)
10.1016/S0378-5173(98)00390-1
Influence of the preparation method on the physicochemical properties of ketoprofen-cyclodextrin binary systems.
P. Mura (1999)
10.1021/acs.jpcb.6b07913
Conformational Change in the Mechanism of Inclusion of Ketoprofen in β-Cyclodextrin: NMR Spectroscopy, Ab Initio Calculations, Molecular Dynamics Simulations, and Photoreactivity.
T. Guzzo (2016)
10.1016/j.ijpharm.2020.119181
Advantages of the combined use of cyclodextrins and nanocarriers in drug delivery: a review.
P. Mura (2020)
Drug loading into solid carriers using a controlled particle deposition (CPD) method for improved drug dissolution
K. Hussein (2008)
10.1021/ct400073s
Does Dispersion Dominate over H-Bonds in Drug-Surface Interactions? The Case of Silica-Based Materials As Excipients and Drug-Delivery Agents.
M. Delle Piane (2013)
10.1080/03639040701743949
The Improvement of Ibuprofen Dissolution Rate Through Microparticles Spray Drying Processed in an Aqueous System
S. Wikarsa (2008)
10.1016/S0166-3542(01)00218-2
In vitro antiviral efficacy of the ganciclovir complexed with beta-cyclodextrin on human cytomegalovirus clinical strains.
C. Nicolazzi (2002)
10.1002/jps.23329
The effect of parenterally administered cyclodextrins on the pharmacokinetics of coadministered drugs.
Sergey V. Kurkov (2012)
Influence of selected formulation factors on the transdermal delivery of ibuprofen
Aysha Bibi Moosa (2012)
10.1016/j.cplett.2019.136802
Experimental characterization and molecular dynamic simulation of ketoprofen-cyclodextrin complexes
Q. Zhao (2019)
Optimization of Lovastatin Self-Nanoemulsifying Solid Dosage Form.
Maulik J. Patel (2013)
10.1002/JPS.21007
Conformational stability of ibuprofen: assessed by DFT calculations and optical vibrational spectroscopy.
M. L. Vueba (2008)
Maturation of a ketoprofen / beta-cyclodextrin mixture with supercritical carbon dioxide
A. Bounaceur (2017)
10.1016/j.ijpharm.2013.12.043
Impact of in situ granulation and temperature quenching on crystal habit and micromeritic properties of ibuprofen-cationic dextran conjugate crystanules.
A. Abioye (2014)
10.1111/cbdd.12825
Computer‐aided drug design to explore cyclodextrin therapeutics and biomedical applications
A. Abdolmaleki (2017)
10.1016/S0378-5173(02)00294-6
Ibuprofen crystals with optimized properties.
N. Rasenack (2002)
Formulation and hypoglycemic activity of pioglitazone-cyclodextrin inclusion complexes.
A. A. El-Bary (2008)
Controlled Release : Cyclodextrins for oral controlled release
P. Salústio (2011)
10.1016/j.talanta.2004.05.040
In-tube solid phase microextraction using a beta-cyclodextrin coated capillary coupled to high performance liquid chromatography for determination of non-steroidal anti-inflammatory drugs in urine samples.
Y. Fan (2005)
10.1016/J.EJPB.2004.12.005
Cyclodextrin complexes of valdecoxib: properties and anti-inflammatory activity in rat.
Kale Rajendrakumar (2005)
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