The effect of solution environment and the electrostatic factor on the crystallisation of desmotropes of irbesartan

Andrea M. Araya-Sibaja; Mariola Urgellés; Felipe Vásquez-Castro; Felipe Vargas-Huertas; José Roberto Vega-Baudrit; Teodolito Guillén-Girón; Mirtha Navarro-Hoyos; Silvia L. Cuffini

doi:10.1039/c8ra10146a

The effect of solution environment and the electrostatic factor on the crystallisation of desmotropes of irbesartan

Andrea M. Araya-Sibaja
, Mariola Urgellés
, Felipe Vásquez-Castro
, Felipe Vargas-Huertas
, José Roberto Vega-Baudrit
, Teodolito Guillén-Girón
, Mirtha Navarro-Hoyos
, Silvia L. Cuffini

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

The experimental conditions necessary for stabilising irbesartan (IBS) tautomers in solution and selectively obtaining the desmotropic crystal forms are presented herein. 1H and 2H tautomers were stabilized in specific solution conditions and the 2H-tetrazole⋯imidazole interaction was confirmed by solution-state NMR. The results showed that highly polar and polarisable solvents (higher values of the electrostatic factor (EF)) lead to the crystallisation of IBS form B. Furthermore, the variations of pH in methanol, in turn, determined the crystallisation of desmotropes A and/or B.

Original language	English
Pages (from-to)	5244-5250
Number of pages	7
Journal	RSC Advances
Volume	9
Issue number	9
DOIs	https://doi.org/10.1039/c8ra10146a
State	Published - 2019

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title = "The effect of solution environment and the electrostatic factor on the crystallisation of desmotropes of irbesartan",

abstract = "The experimental conditions necessary for stabilising irbesartan (IBS) tautomers in solution and selectively obtaining the desmotropic crystal forms are presented herein. 1H and 2H tautomers were stabilized in specific solution conditions and the 2H-tetrazole⋯imidazole interaction was confirmed by solution-state NMR. The results showed that highly polar and polarisable solvents (higher values of the electrostatic factor (EF)) lead to the crystallisation of IBS form B. Furthermore, the variations of pH in methanol, in turn, determined the crystallisation of desmotropes A and/or B.",

author = "Araya-Sibaja, \{Andrea M.\} and Mariola Urgell{\'e}s and Felipe V{\'a}squez-Castro and Felipe Vargas-Huertas and Vega-Baudrit, \{Jos{\'e} Roberto\} and Teodolito Guill{\'e}n-Gir{\'o}n and Mirtha Navarro-Hoyos and Cuffini, \{Silvia L.\}",

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year = "2019",

doi = "10.1039/c8ra10146a",

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volume = "9",

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TY - JOUR

T1 - The effect of solution environment and the electrostatic factor on the crystallisation of desmotropes of irbesartan

AU - Araya-Sibaja, Andrea M.

AU - Urgellés, Mariola

AU - Vásquez-Castro, Felipe

AU - Vargas-Huertas, Felipe

AU - Vega-Baudrit, José Roberto

AU - Guillén-Girón, Teodolito

AU - Navarro-Hoyos, Mirtha

AU - Cuffini, Silvia L.

PY - 2019

Y1 - 2019

N2 - The experimental conditions necessary for stabilising irbesartan (IBS) tautomers in solution and selectively obtaining the desmotropic crystal forms are presented herein. 1H and 2H tautomers were stabilized in specific solution conditions and the 2H-tetrazole⋯imidazole interaction was confirmed by solution-state NMR. The results showed that highly polar and polarisable solvents (higher values of the electrostatic factor (EF)) lead to the crystallisation of IBS form B. Furthermore, the variations of pH in methanol, in turn, determined the crystallisation of desmotropes A and/or B.

AB - The experimental conditions necessary for stabilising irbesartan (IBS) tautomers in solution and selectively obtaining the desmotropic crystal forms are presented herein. 1H and 2H tautomers were stabilized in specific solution conditions and the 2H-tetrazole⋯imidazole interaction was confirmed by solution-state NMR. The results showed that highly polar and polarisable solvents (higher values of the electrostatic factor (EF)) lead to the crystallisation of IBS form B. Furthermore, the variations of pH in methanol, in turn, determined the crystallisation of desmotropes A and/or B.

UR - https://www.scopus.com/pages/publications/85061966388

U2 - 10.1039/c8ra10146a

DO - 10.1039/c8ra10146a

M3 - Artículo

AN - SCOPUS:85061966388

SN - 2046-2069

VL - 9

SP - 5244

EP - 5250

JO - RSC Advances

JF - RSC Advances

IS - 9

ER -

The effect of solution environment and the electrostatic factor on the crystallisation of desmotropes of irbesartan

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