2-Methyl-4-(4-methyl-1-piperazinyl)-10<i>H</i>-thieno[2,3-<i>b</i>][1,5]benzodiazepine methanol solvate

Wawrzycka-Gorczyca, Irena; Mazur, Liliana; Kozioł, Anna E.

doi:10.1107/s1600536803028071

Cited by 15 publications

(13 citation statements)

References 5 publications

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“…Olanzapine in fact is a hydrophobic molecule (LogP=2.199 at pH=9) and therefore poorly soluble in its de-protonated form (0.0165 g/L at pH=9). Solubility increases at pH lower than pKa (7.37-4.69): 87.4 g/L and correspondingly LogP decreases (0.3) at pH=5 [12].…”

Section: Hydrated Formsmentioning

confidence: 97%

Thermal Study of Anhydrous and Hydrated Forms of Olanzapine

Cavallari¹,

Fini

Santos³

2013

Pharmaceut Anal Acta

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Section: Hydrated Formsmentioning

confidence: 97%

Thermal Study of Anhydrous and Hydrated Forms of Olanzapine

Cavallari¹,

Fini

Santos³

2013

Pharmaceut Anal Acta

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“…methanol solvate (Wawrzycka-Gorczyca et al, 2004b), olazipinium nicotinate (Ravikumar et al, 2005), olanzapine and its solvates (Wawrzycka-Gorczyca et al, 2006), highly soluble olanzapinium maleate crystalline salts (Thakuria & Nangia, 2011a) and polymorphic form IV of olanzapine (Thakuria & Nangia, 2011b) have been reported. In view of the importance of olanzapine, this paper reports the crystal structure of the title salt, (I),…”

Section: S1 Commentmentioning

confidence: 99%

Olanzapinium dipicrate

et al. 2013

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The asymmetric unit of the title salt [systematic name: 2-methyl-4-(4-methylpiperazin-4-ium-1-yl)-10H-thieno[2,3-b][1,5]benzodiazepinium bis(2,4,6-trinitrophenolate)], C17H22N4S2+·2C6H2N3O7 −, consists of a diprotonated olanzapinium cation and two independent picrate anions. In the cation, the piperazine ring adopts a distorted chair conformation and contains a positively charged N atom with quaternary character and the N atom in the seven-membered 1,5-diazepine ring, which adopts a boat configuration, is also protonated. The dihedral angle between the benzene and thiene rings flanking the diazepine ring is 58.8 (1)°. In one of the picrate anions, a nitro group is disordered over two sets of sites in a 0.748 (5):0.252 (5) ratio, and the benzene ring has a flat envelope conformation with the O− C atom displaced from the mean plane of the other five C atoms [maximum deviation 0.0151 (14) Å] by 0.1449 (14) Å. In the crystal, N—H⋯O hydrogen bonds and weak intermolecular C—H⋯S and C—H⋯O interactions link the components, forming a three-dimensional network.

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“…The crystals formed from the two preparations proved to be olanzapine methanol solvate (1:1). 11 The results of the present work offer more information. Olanzapine precipitates from a saturated methanol solution as a solvate in the form of well-shaped yellow prismatic crystals (Fig.…”

Section: Methanol Solvatementioning

confidence: 64%

“…This proves to be particularly important for olanzapine that exists in a variety of forms. [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] Each form displays unique physicochemical properties influencing bioavailability, purification, stability, and other performances of the drug. Because of its particular ability to interact with solvents, for olanzapine, it appears difficult to forecast which form could be obtained by crystallization from a given solvent, the formation of solvate occurring also after a few days suspen-sion of olanzapine unsolvated crystals in most of the solvents previously examined at room temperature.…”

Section: Discussionmentioning

confidence: 99%

Olanzapine Solvates

Cavallari

Santos

Fini

2013

Journal of Pharmaceutical Sciences

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Olanzapine was crystallized from 12 organic solvents alone or in mixture, by cooling in the freezer, by slow evaporation of the solvent, or by suspending olanzapine powder for some time in the solvent. All the samples thus obtained were examined by thermal analysis (differential scanning calorimetry-DSC and thermogravimetry-TG) to certify the formation of a solvate, the presence of polymorph (form 1 or 2) in the desolvated olanzapine, comparing the different profile of the thermograms, and to calculate the stoichiometry of the possible solvate. According to the DSC thermogram, the solvents can be divided into four classes: those that do not form solvates and leave olanzapine form 1 (ethyl acetate, toluene, diethyl ether, and acetone); those that form solvate and leave form 1 of olanzapine after desolvation (methanol, 1- and 2-propanol); those that after desolvation of the solvate show a polymorph transition in the thermogram indicating the presence of form 2 of olanzapine (ethanol); other solvents (tetrahydrofuran, chloroform, acetonitrile) give solvate thermograms, where this last thermal trace is only poorly evident. With few exceptions, each solvent forms solvate both when pure and in mixture (10%, v/v, in ethyl acetate). Methanol monosolvate displays complex thermogram and thermogravimetric desolvation profiles, depending on the crystallization experimental conditions, used to prepare the solvates. Dichloromethane solvate was found by X-ray diffraction analysis to be amorphous and, on heating during DSC analysis, allowed the crystallization of both form 1 and 2, with different weight ratio, according to the experimental conditions of the solvate preparation.

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2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine methanol solvate

Cited by 15 publications

References 5 publications

Thermal Study of Anhydrous and Hydrated Forms of Olanzapine

Thermal Study of Anhydrous and Hydrated Forms of Olanzapine

Olanzapinium dipicrate

Olanzapine Solvates

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