Solubility of Lovastatin in Ethyl Acetate, Propyl Acetate, Isopropyl Acetate, Butyl Acetate, <i>sec</i>-Butyl Acetate, Isobutyl Acetate, <i>tert</i>-Butyl Acetate, and 2-Butanone, between (285 and 313) K

Nti-Gyabaah, Joseph; Chiew, Yee C.

doi:10.1021/je800120p

Cited by 21 publications

(12 citation statements)

References 17 publications

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“…The available experimental solubility data for lovastatin ,− in 18 pure solvents are reported in Table . To identify the conceptual segment numbers for lovastatin, we regress the solubility data of four solvents, i.e., ethyl acetate, acetone, methanol, and 1-octanol.…”

Section: Resultsmentioning

confidence: 99%

COSMO-SAC Sigma Profile Generation with Conceptual Segment Concept

Islam

Chen

2014

Ind. Eng. Chem. Res.

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Solvation thermodynamics-based models for predicting liquid-phase nonidealities and fluid-phase equilibria are gaining attention in modern chemical process and product development. Among this class of thermodynamic models, COSMO-RS and COSMO-SAC are two variants used extensively in industry. A key input to these models is the so-called sigma profile, i.e., a histogram of charge density distribution over the molecular surface. Typically, sigma profiles are generated from quantum mechanical calculations with molecular structure and conformation information as inputs to the calculation. We present an alternative approach for generating sigma profiles from experimental fluid-phase equilibrium data, i.e., solubility. Specifically, we incorporate the conceptual segment concept of NRTL-SAC activity coefficient model into sigma profile generation. We generate "apparent" sigma profiles from linear combination of sigma profiles of conceptual segments represented by reference molecules selected for hydrophobic, polar attractive, polar repulsive, and hydrophilic conceptual segments. Conceptual segment numbers of the molecule of interest are identified from regression of available experimental data. We show applicability of this sigma profile generation approach with solubility modeling for four drug molecules: caffeine, aspirin, paracetamol, and lovastatin.

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Section: Resultsmentioning

confidence: 99%

COSMO-SAC Sigma Profile Generation with Conceptual Segment Concept

Islam

Chen

2014

Ind. Eng. Chem. Res.

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“…16,17 Thermodynamic behavior, including the pK a and solubility of solid Pharms in water or other solvents, plays a pivotal role in the design of drug compounds. [21][22][23] This article is a continuation of our systematic study on the solubilities of Pharms and the pK a of these Pharms with the Bates-Schwarzenbach spectrophotometric method. 24 ' EXPERIMENTAL PROCEDURES Materials.…”

Section: ' Introductionmentioning

confidence: 99%

“…The prediction methods usually also need the values of p K a , which are dependent on the buffer and method used. Thus, the prediction of solubility, especially as a function of pH, is more complicated. , Thermodynamic behavior, including the p K a and solubility of solid Pharms in water or other solvents, plays a pivotal role in the design of drug compounds. − …”

Section: Introductionmentioning

confidence: 99%

Solubility of Sparingly Soluble Drug Derivatives of Anthranilic Acid

2011

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This work is a continuation of our systematic study of the solubility of pharmaceuticals (Pharms). All substances here are derivatives of anthranilic acid, and have an anti-inflammatory direction of action (niflumic acid, flufenamic acid, and diclofenac sodium). The basic thermal properties of pure Pharms, i.e., melting and glass-transition temperatures as well as the enthalpy of melting, have been measured with the differential scanning microcalorimetry technique (DSC). Molar volumes have been calculated with the Barton group contribution method. The equilibrium mole fraction solubilities of three pharmaceuticals were measured in a range of temperatures from 285 to 355 K in three important solvents for Pharm investigations: water, ethanol, and 1-octanol using a dynamic method and spectroscopic UV-vis method. The experimental solubility data have been correlated by means of the commonly known G(E) equation: the NRTL, with the assumption that the systems studied here have revealed simple eutectic mixtures. pK(a) precise measurement values have been investigated with the Bates-Schwarzenbach spectrophotometric method.

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“…Thermodynamic behaviour, including pK a and solubility of solid pharmaceuticals in liquid solvents, play an important role in the design of Ph compounds, as well as in the development and optimization of drug manufacturing processes [17,[29][30][31]. The pK a values are useful for physico-chemical measurements describing the extent of ionization of the functional groups with respect to pH.…”

Section: Introductionmentioning

confidence: 99%