Open Access

Journal of Molecular Liquids, volume 360, pages 119548

Effect of pH, temperature and native cyclodextrins on aqueous solubility of baricitinib

Garibyan Anna ¹

Delyagina Ekaterina ^{1, 2}

Agafonov Mikhail ¹

Khodov Ilya A. ¹

Terekhova Irina V ¹

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G.A. Krestov Institute of Solution Chemistry of RAS, Ivanovo, Russian Federation |

Ivanovo State University, Russian Federation |

Publication type: Journal Article

Publication date: 2022-08-01

Elsevier

Journal: Journal of Molecular Liquids

Quartile SCImago

Quartile WOS

Impact factor: 6

ISSN: 01677322, 18733166

DOI: 10.1016/j.molliq.2022.119548

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Materials Chemistry

Electronic, Optical and Magnetic Materials

Physical and Theoretical Chemistry

Spectroscopy

Atomic and Molecular Physics, and Optics

Condensed Matter Physics

Abstract

• Baricitinib is a novel drug recommended in 2017 for treatment inflammatory diseases. • Aqueous solubility of baricitinib is poor and pH dependent. • Native cyclodextrins were used to improve the baricitinib solubility. • β-CD is more effective solubilizer compared with α-CD and γ-CD. • Application of CDs as solubilizers results in decreasing membrane permeability. Baricitinib is a novel drug recommended in 2017 for the treatment of rheumatoid arthritis and other inflammatory diseases. The application of baricitinib can be restricted by its poor aqueous solubility. In this work, it was demonstrated that solubility of baricitinib is pH dependent. Baricitinib is very slightly soluble at pH 4–12 and freely soluble in the acidic and strongly alkaline media due to the ability to protonation and dissociation, respectively. Native cyclodextrins were used to improve the physicochemical properties of baricitinib. For the first time, host–guest complexes of baricitinib with α-, β- and γ-cyclodextrins were investigated by means of 1 H NMR, capillary electrophoresis and solubility methods. The stoichiometric composition and thermodynamic parameters of complex formation of baricitinib with cyclodextrins in the different buffers were obtained. Simultaneous determination of the binding constants of β-cyclodextrin with different ionized forms of BCN was performed by means of the capillary electrophoresis technique. The influence of cyclodextrin structure and ionization state of baricitinib on the inclusion complex formation was analyzed. The effect of cyclodextrins on solubility and membrane permeability of baricitinib was revealed.

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Citations by journals

	1 2 3
International Journal of Molecular Sciences	International Journal of Molecular Sciences, 3, 30% International Journal of Molecular Sciences 3 publications, 30%
Molecules	Molecules, 2, 20% Molecules 2 publications, 20%
Russian Journal of Physical Chemistry A	Russian Journal of Physical Chemistry A, 2, 20% Russian Journal of Physical Chemistry A 2 publications, 20%
Molecular Pharmaceutics	Molecular Pharmaceutics, 1, 10% Molecular Pharmaceutics 1 publication, 10%
Journal of Molecular Liquids	Journal of Molecular Liquids, 1, 10% Journal of Molecular Liquids 1 publication, 10%
International Journal of Nanomedicine	International Journal of Nanomedicine, 1, 10% International Journal of Nanomedicine 1 publication, 10%
	1 2 3

Citations by publishers

	1 2 3 4 5
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 5, 50% Multidisciplinary Digital Publishing Institute (MDPI) 5 publications, 50%
Pleiades Publishing	Pleiades Publishing, 2, 20% Pleiades Publishing 2 publications, 20%
American Chemical Society (ACS)	American Chemical Society (ACS), 1, 10% American Chemical Society (ACS) 1 publication, 10%
Elsevier	Elsevier, 1, 10% Elsevier 1 publication, 10%
Dove Medical Press	Dove Medical Press, 1, 10% Dove Medical Press 1 publication, 10%
	1 2 3 4 5

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Garibyan A. et al. Effect of pH, temperature and native cyclodextrins on aqueous solubility of baricitinib // Journal of Molecular Liquids. 2022. Vol. 360. p. 119548.

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Garibyan A., Delyagina E., Agafonov M., Khodov I. A., Terekhova I. V. Effect of pH, temperature and native cyclodextrins on aqueous solubility of baricitinib // Journal of Molecular Liquids. 2022. Vol. 360. p. 119548.

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RIS Copy

TY - JOUR

DO - 10.1016/j.molliq.2022.119548

UR - https://doi.org/10.1016%2Fj.molliq.2022.119548

TI - Effect of pH, temperature and native cyclodextrins on aqueous solubility of baricitinib

T2 - Journal of Molecular Liquids

AU - Garibyan, Anna

AU - Delyagina, Ekaterina

AU - Agafonov, Mikhail

AU - Khodov, Ilya A.

AU - Terekhova, Irina V

PY - 2022

DA - 2022/08/01 00:00:00

PB - Elsevier

SP - 119548

VL - 360

SN - 0167-7322

SN - 1873-3166

ER -

BibTex

Cite this

BibTex Copy

@article{2022_Garibyan,

author = {Anna Garibyan and Ekaterina Delyagina and Mikhail Agafonov and Ilya A. Khodov and Irina V Terekhova},

title = {Effect of pH, temperature and native cyclodextrins on aqueous solubility of baricitinib},

journal = {Journal of Molecular Liquids},

year = {2022},

volume = {360},

publisher = {Elsevier},

month = {aug},

url = {https://doi.org/10.1016%2Fj.molliq.2022.119548},

pages = {119548},

doi = {10.1016/j.molliq.2022.119548}

}

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Publisher

Elsevier

Journal

Journal of Molecular Liquids

Quartile SCImago

Quartile WOS

Impact factor

ISSN

01677322 (Print)
18733166 (Electronic)

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