Extended hildebrand solubility approach: Solubility of theophylline in polar binary solvents

Martin, A.; Newburger, Jerold; Adjei, Akwete

doi:10.1002/jps.2600690503

Cited by 154 publications

(49 citation statements)

References 15 publications

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“…The solubilization efficiency of a cosolvent depends upon the extent to which it weakens the structure of water. Various models have been proposed to estimate the solubility of drugs in cosolvent-water mixtures (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)). While it is not possible to compare all these approaches here, a few important ones are discussed:…”

Section: Introductionmentioning

confidence: 99%

Solubility Improvement of Drugs using N-Methyl Pyrrolidone

Narazaki²,

et al. 2008

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Abstract. The solubilization efficiency of N-methyl pyrrolidone (NMP) has been determined and compared to that of ethanol and propylene glycol for 13 poorly soluble drugs. NMP is found to be a more efficient solubilizer for all the drugs studied. The solubility enhancement as high as about 800-fold is obtained in 20% v/v NMP solution as compared to water. The mechanism of drug solubilization by NMP has also been investigated. It is proposed that NMP enhances drug solubility by simultaneously acting as a cosolvent and a complexing agent. A mathematical model is used to estimate the drug solubility in NMP-water mixture, according to which the total solubility enhancement is a sum of the two effects. This model describes the experimental data well and is more accurate than other models. A large and uniform reduction in the surface tension of water as a function of NMP concentration demonstrates its cosolvent effect. The complexation is supported by the fact that it's strength is affected by the temperature and the polarity of the medium. A strong correlation exists between log K ow of the drugs and the cosolvency coefficients. The correlation between log K ow and the complexation coefficients is weak suggesting that factors such as molecular shape and aromaticity of the drug molecule are significant in determining the complexation strength. This has been confirmed by the absence of a significant complexation between NMP and linear drug-like solutes.

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Section: Introductionmentioning

confidence: 99%

Solubility Improvement of Drugs using N-Methyl Pyrrolidone

Narazaki²,

et al. 2008

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“…Not all researchers parametrize measured solubility data in accordance with eq 4. For example, in the pharmaceutical industry isothermal solubility data may be expressed in terms of the extended Hildebrand solubility parameter approach (Barra et al, 1997;Martin et al, 1980Martin et al, , 1982, the double log-log model (Barzegar-Jalali and Hanaee, 1994), modified Wilson model (Jouyban-Gharamaleki, 1997), or as a power series expansion in mole fraction composition of one of the binary solvent components. Solubility data for select crystalline polycyclic aromatic hydrocarbons dissolved in binary aqueousorganic solvent mixtures were described using the Margules equation in a recently published paper (Fan and Jafvert, 1997) appearing in an environmental science journal.…”

Section: Resultsmentioning

confidence: 99%

Solubility of Anthracene in Multicomponent Solvent Mixtures Containing Propanol, Butanol, and Alkanes

et al. 1999

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Experimental solubilities are reported for anthracene dissolved in ternary solvent mixtures 1-propanol + 2-propanol + cyclohexane and 1-butanol + 2-butanol + cyclohexane, for anthracene dissolved in the heptanary solvent mixture 1-propanol + 2-propanol + 1-butanol + 2-butanol + cyclohexane + heptane + 2,2,4-trimethylpentane, and for anthracene dissolved in binary solvent heptane + 2,2,4-trimethylpentane at 298.15 K. For the two ternary solvent systems anthracene mole fraction solubilities are reported at 19 different ternary compositions spanning the entire mole fraction range. In the case of heptanary solvent system, solubility data was measured at eight solvent compositions. Results of these measurements are used to test the predictive ability of the combined nearly ideal multiple solvent (NIMS)/Redlich-Kister and combined NIMS/BAB equations. Computations showed that both solution models provided reasonably accurate predictions for how the mole fraction solubility varied with solvent compositions. Deviations between predicted and experimental values were on the order of (0.95% for the better of the two predictive equations.

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“…In the formation of salts, transfer of hydrogen atom occurs and it does not occur in the formation of cocrystals. [31] If one component is liquid at room temperature, then the crystals are designated as solvates, and if both components are present in solid form, then crystals are designated as cocrystals. In solvates, one component is present in a liquid form, so they are less stable as compared to cocrystal.…”

Section: Cocrystal Versus Salts Solvates Solid Dispersions and Hydmentioning

confidence: 99%

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Payghan¹

2017

AJP

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The objective of this study was to investigate whether the miscibility of a drug and coformer, as predicted by Hansen solubility parameters (HSPs), can indicate cocrystal formulation. It was also our aim to evaluate various HSPs-based approaches in miscibility predication. It is concerned with some new aspects of solvent properties, and these properties can help predict solvent behavior during the manufacturing processes and will be useful in predicting behavior in many other fields of endeavor. The work on the solubility parameter, in particular, deals with fundamental attractions among materials and should have broad application. To say that hydrogen bonding had no significant effect on solvent retention without defining hydrogen bonding was not satisfactory. To better define hydrogen bonding and polar bonding, a study based on the solubility parameter was initiated. This eventually led to the concept of a three-dimensional (3D) solubility parameter (E). The 3D solubility parameter is has been assumed that ∆E is given by the simple sum of the energies arising from dispersion forces, ∆E d , polar forces, ∆E P , and hydrogen bonding forces, ∆E h. Group contribution method for the estimation of Hansen solubility parameters of pure organic compounds is presented by characteristic groups ensure the prediction of HSP for a broad series of organic compounds, including those having complex multiring, heterocyclic, and aromatic structures. The predictions are exclusively based on the molecular structure of compounds, and no experimental data are needed. Solubility parameters for solutes are obtained by group contribution method. Using Fedor's substituent constants, Hoy's molar attraction constants and Van Kreevalen constants were calculated and are currently used methods. The resultant Δ values of active pharmaceutical ingredient and coformers are compared, and their solid-state miscibility is expressed. Possibility of cocrystal formulation by Krevlens is Δδ < 5MP and Greenhalgh Δδ < 7MP can be predicted.

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Extended hildebrand solubility approach: Solubility of theophylline in polar binary solvents

Cited by 154 publications

References 15 publications

Solubility Improvement of Drugs using N-Methyl Pyrrolidone

Solubility Improvement of Drugs using N-Methyl Pyrrolidone

Solubility of Anthracene in Multicomponent Solvent Mixtures Containing Propanol, Butanol, and Alkanes

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