Solubility prediction of salicylic acid in water-ethanol-propylene glycol mixtures using the Jouyban-Acree model Page: 318
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Faculty of Pharmacy and Drug Applied Research Center', Tabriz University of Medical Sciences, Tabriz, Iran, Faculty of
Pharmacy2, The University of Sydney, Sydney, Australia, Kimia Research Institute3, Tabriz, Iran, Department of Chemistry4,
University of North Texas, Denton, USA
Solubility prediction of salicylic acid in water-ethanol-propylene glycol
mixtures using the Jouyban-Acree model
A. JouvBAN1, N. Y. K. CHEW2, H. K. CHAN2, M. KHOUBNASABJAFARI3, W. E. ACAREE JR4
Received April 22, 2005, accepted May 3, 2005
Dr. A. Jouyban, Faculty of Pharmacy, Tabriz Universtty of Medical Sciences, Tabriz 51664, Iran
ajouyban @hotmail. com
Pharmazie 61: 318-321 (2006)
To show the applicability of a solution model, i.e. the Jouyban-Acree model, for predicting the solubi-
lity of a solute in ternary solvent systems based on model constants computed using solubility data of
the solute in binary solvent systems, the solubility of salicylic acid in water-ethanol, water-propylene
glycol, ethanol-propylene glycol mixtures was determined. A minimum number of three data points
from each binary system was used to calculate the binary interaction parameters of the model. Then
the solubility in other binary solvent compositions and also in a number of ternary solvents was pre-
dicted, and the mean percentage deviation (MPD) was calculated as an accuracy criterion. The overall
MPD (SD) was 7.3 (7.3)% and those of a similar predictive model was 15.7 (11.5)%. The mean
difference between the proposed and a previous model was statistically significant (paired t-test,
p < 0.004).
Solubility data of pharmaceuticals are required in many
industrial processes including liquid drug formulations and
adding a cosolvent to the aqueous solution is one of the
most common methods to alter the solubility. When a bi-
nary solvent mixture is not able to dissolve the desired
amount of a drug, addition of a second cosolvent is neces-
sary. As a general rule, the higher the concentration of the
cosolvent, the more is the increase in the solubility of the
poorly soluble drug. However, because of toxicity consid-
erations and also the cost of the process, the concentration
of the cosolvent should be kept as low as possible and
usually less than 50% v/v of the liquid formulations (Ru-
bino 1990). A method often used to optimise the solvent
composition of binary and/or ternary solvent mixtures is
the trial and error approach which is time-consuming. In
addition, in many cases at the first stages of a new drug
development processes, the scarcity of the available
amount of the drug is another limiting factor. An attempt
has been made to reduce the number of experimental data
required to facilitate the solubility prediction of drugs in
mixed solvent systems (Jouyban et al. 2002). In the pre-
vious work, the model constants of a solution model, so
called Jouyban-Acree model, were calculated using solubi-
lity data of anthracene in sub-binary solvent mixtures, and
then the model constants were used to predict the solubi-
lity of anthracene in the corresponding ternary solvent
mixtures using an extended form of the Jouyban-Acree
model. Anthracene is a polycyclic aromatic hydrocarbon
and relatively non-polar solute compared to drug mole-
cules and the solvent systems employed were alkane and
alkanol mixtures. The produced prediction percentage er-
rors were 1.5 and 3.7%. The previous results on the accu-
racy of the Jouyban-Acree model on polar and semi-polar!
non-polar systems showed that the higher the polarity of
the system is, the higher is the error associated with the
model (Barzegar-Jalali and Jouyban-Gh. 1996). Therefore,
it is expected that the solubility prediction of a semi-polar
drug molecule in a ternary aqueous solvent mixture based
on model constants calculated using sub-binary solubility
data produces a higher prediction error compared to the
result of a similar work on anthracene solubility data. The
solubilty of salicylic acid in binary solvent mixtures has
been reported at 30.6 C by Paruta et al. (1964), however,
the data was for binary aqueous mixtures and no data has
been reported for ethanol-propylene glycol mixtures so far.
To check the applicability of the prediction method, the
solubility of salicyclic acid in water-ethanol, water-propy-
lene glycol, ethanol-propylene glycol and a limited num-
ber of water-ethanol-propylene glycol mixtures was deter-
mined as a model system. The accuracy of the proposed
method was also compared with that of a previously pub-
lished method by Williams and Amidon (1984).
2. Investigations, results and discussion
2.1. Computational methods
A solution model (i.e. the Jouyban-Acree model) was
used to correlate different physico-chemical properties in
mixed solvent systems which is briefly reviewed in a re-
cent paper (Jouyban et al. 2005). Its basic form to calcu-
late a solute solubility in a binary solvent mixture is:
n Xm = fl nX +f2ln X2+ ff2 E Si(ft -f2)'
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Jouyban, Abolghasem; Chew, Nora Yat Knork; Chan, H.; Khoubnasabjafari, M. & Acree, William E. (William Eugene). Solubility prediction of salicylic acid in water-ethanol-propylene glycol mixtures using the Jouyban-Acree model, article, 2006; [Eschborn, Germany]. (digital.library.unt.edu/ark:/67531/metadc282593/m1/1/: accessed July 27, 2017), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT College of Arts and Sciences.