Irbesartan Crystal Form B

Böcskei, Zsolt; Simon, K Okwute; Rao, R. Balaji; Caron, A.; Rodger, Charles A.; Bauer, Michel

doi:10.1107/s0108270197019884

Cited by 31 publications

(35 citation statements)

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“…This is in line with the findings reported in Ref. [4] indicating that in solid form B the hydrogen atom attached to the nitrogen atom is involved in an intermolecular hydrogen bond. It is worth noting that despite our results it is very difficult to assign one of the forms of Irbesartan to the two species present in solution.…”

Section: Nmr Theoretical Studiessupporting

confidence: 82%

“…[3] The crystal structure of Irbesartan form B (the 2-H tautomer) has been previously determined. [4] The aim of the present study is to thoroughly investigate the room temperature vibrational spectra [Fourier Transform Infrared (FTIR) and Raman] [3] of the supplied sample of Irbesartan (which is a mixture of forms A and B). Theoretical calculations are performed on both forms of Irbesartan.…”

Section: Introductionmentioning

confidence: 99%

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Irbesartan: FTIR and Raman spectra. Density functional study on vibrational and NMR spectra

Franca

Etcheverry

Diez

et al. 2009

J Raman Spectroscopy

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Arterial hypertension is a very common disease, which is treated with different medications such as Irbesartan. This compound is a nonpeptide antagonist of the receptor of the enzyme angiotensin II. The infrared and Raman spectra of this compound were recorded and discussed assisted with density functional theory using the 6-31G * * basis set and animated pictures. Irbesartan exists in two tautomeric forms which can be isolated in the solid state. The vibrational study has been recorded using a mixture of both forms. 13 C, 15 N and 1 H NMR theoretical studies have been performed and compared with previously reported experimental data. Theoretical calculations allowed the determination of the main features of the A and B tautomers of Irbesartan both in the vibrational studies and in the NMR spectroscopy.

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Section: Nmr Theoretical Studiessupporting

confidence: 82%

Section: Introductionmentioning

confidence: 99%

Irbesartan: FTIR and Raman spectra. Density functional study on vibrational and NMR spectra

Franca

Etcheverry

Diez

et al. 2009

J Raman Spectroscopy

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“…For t 1 , the dihedral angle between the tetrazole ring and its adjacent phenyl ring, two values < 408 are observed: 28.18 in the crystal form B of irbesartan [30] and 37.48 in the drug named CS-866.…”

Section: Resultsmentioning

confidence: 94%

Progress in the Understanding of Drug–Receptor Interactions, Part 1: Experimental Charge‐Density Study of an Angiotensin II Receptor Antagonist (C₃₀H₃₀N₆O₃S) atT=17 K

Destro

Soave

Barzaghi

et al. 2005

Chemistry A European J

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An experimental study of the electron-density distribution rho(r) in an angiotensin II receptor antagonist 1 has been made on the basis of single-crystal X-ray diffraction data collected at a low temperature. The crystal structure of 1 consists of infinite ribbons in which molecules are connected by an N-H...N hydrogen bond and several interactions of the C-H...O, C-H...N, and C-H...S type. The molecular conformation, characterized by the syn orientation of a tetrazole and a pyrimidinone ring with respect to a phenyl spacer group, is stabilized by two short SO and SN intramolecular contacts between a substituted thiophene fragment and the other two heterocycles of 1. The electrostatic nature of these interactions is documented. Furthermore, the Laplacian of rho(r) in the plane defined by the sulfur, oxygen, and nitrogen atoms involved in these interactions shows their strongly directional character as the regions of charge concentration on the valence shell of the nitrogen and oxygen atoms directly face the regions of charge depletion on the valence shell of the sulfur atom. All the chemical bonds and the relevant intra- and intermolecular interactions of 1 have been quantitatively described by the topological analysis of rho(r). Simple relationships between the bond path lengths (R(b)) and the values of rho at the bond critical points (rho(bcp)) have been obtained for the 28 C-C bonds, the seven N-C bonds, and the four O-C bonds. For the first two classes of bonds the relationship is in the form of a straight line, whose parameters, for the C-C bonds, agree, within experimental uncertainty, with those previously derived in our laboratory from a 19 K X-ray diffraction study of crystals of a different compound. Maps of the molecular electrostatic potential phi(r) derived from the experimental charge density display features that are important for the drug-receptor recognition of 1.

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“…Originally demonstrated by solution [29] and solid state [6] NMR, it occurs within a tetrazole ring on which the hydrogen is located either adjacent or opposite to the carbon atom. In the solid state [12] the desmotropes build up very different structures indeed, and it is truly surprising what a single proton can cause to the structural arrangement. Despite being rather different in terms of symmetry (form II is triclinic, whereas modification I is trigonal), both structures (Figs.…”

Section: Atropisomers and Desmotropesmentioning

confidence: 99%

Crystallography for Polymorphs

Ochsenbein¹,

Schenk²

2006

Polymorphism

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Irbesartan Crystal Form B

Cited by 31 publications

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Irbesartan: FTIR and Raman spectra. Density functional study on vibrational and NMR spectra

Irbesartan: FTIR and Raman spectra. Density functional study on vibrational and NMR spectra

Progress in the Understanding of Drug–Receptor Interactions, Part 1: Experimental Charge‐Density Study of an Angiotensin II Receptor Antagonist (C₃₀H₃₀N₆O₃S) atT=17 K

Crystallography for Polymorphs

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Irbesartan Crystal Form B

Cited by 31 publications

References 0 publications

Irbesartan: FTIR and Raman spectra. Density functional study on vibrational and NMR spectra

Irbesartan: FTIR and Raman spectra. Density functional study on vibrational and NMR spectra

Progress in the Understanding of Drug–Receptor Interactions, Part 1: Experimental Charge‐Density Study of an Angiotensin II Receptor Antagonist (C30H30N6O3S) atT=17 K

Crystallography for Polymorphs

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Progress in the Understanding of Drug–Receptor Interactions, Part 1: Experimental Charge‐Density Study of an Angiotensin II Receptor Antagonist (C₃₀H₃₀N₆O₃S) atT=17 K