Thermodynamics of Mixing and Solvation of Ibuprofen and Naproxen in Propylene Glycol + Water Cosolvent Mixtures

IUPAC-NIST Solubility Data Series. 102. Solubility of Nonsteroidal Anti-inflammatory Drugs (NSAIDs) in Neat Organic Solvents and Organic Solvent Mixtures

“…Stovall et al 103 also used spectroscopic methods to measure the solubility of ibuprofen in six primary linear alcohols (methanol, ethanol, 1-propanol, 1-pentanol, 1-octanol, and 1-decanol), in two secondary alcohols (2-propanol and 2-butanol), and in one branched primary alcohol (2-methyl-1-propanol) at 298 K and atmospheric pressure. Garzó n and Martínez, 94 Aragón et al, 101 Wang et al, 97 Soltanpour and Jouyban, 109,110 Jouyban et al, 108 Wang et al, 105 Manrique and Martínez, 107 and Manrique et al 111 have also performed ibuprofen solubility measurements at 298 K. Takahashi et al 100 measured the solubility of ibuprofen in diethyl butanedioate, diethyl hexanedioate, diisopropyl hexanedioate, and diethyl decanedioate at 305 K in their study concerning the use of fatty diesters as a means to enhance NSAID permeation through skin.…”

“…There have been several studies 60,91,94,96,101,104,107,111 reporting the solubility of ibuprofen as a function of temperature. Fini et al 60 determined the molar solubility of ibuprofen in 1-octanol at only three temperatures from 278 to 310 K. Garzón and Martínez 94 measured the solubility of ibuprofen in cyclohexane, 1-methylethyl tetradecanoate, trichloromethane and 1-octanol at several temperatures from 293 to 313 K. Aragón et al 101 examined the solubility of ibuprofen in dichloromethane and propanone in the temperature range of 293-313 K. Manrique and co-workers 107,111 reported solubility data for ibuprofen in ethanol and 1,2-propanediol at several temperatures between 293 and 313 K. Gracin and Rasmuson 96 employed a gravimetric method to study the solubility of ibuprofen in methylbenzene, ethyl ethanoate, methanol, ethanol, 2-propanol, propanone, and 4-methyl-2-pentanone.…”

“…Fini et al 60 determined the molar solubility of ibuprofen in 1-octanol at only three temperatures from 278 to 310 K. Garzón and Martínez 94 measured the solubility of ibuprofen in cyclohexane, 1-methylethyl tetradecanoate, trichloromethane and 1-octanol at several temperatures from 293 to 313 K. Aragón et al 101 examined the solubility of ibuprofen in dichloromethane and propanone in the temperature range of 293-313 K. Manrique and co-workers 107,111 reported solubility data for ibuprofen in ethanol and 1,2-propanediol at several temperatures between 293 and 313 K. Gracin and Rasmuson 96 employed a gravimetric method to study the solubility of ibuprofen in methylbenzene, ethyl ethanoate, methanol, ethanol, 2-propanol, propanone, and 4-methyl-2-pentanone. Doma nska et al 91 determined the solubility of ibuprofen in ethanol and 1-octanol at as a function of temperature using a dynamic method that involved placing known amounts of solute and solvent in sealed containers and slowly increasing the temperature until the last crystal disappeared.…”

“…Lejal et al 162 found that naproxen protected Madin-Darby canine cells against HqN1 and H3N2 viral strains, and that naproxen decreased the viral titers in mice lungs after intranasal viral infection. There have been several studies 64,65,92,111,117,[163][164][165][166][167][168][169][170] involving the solubility of naproxen in organic solvents. Perlovich et al 163 measured naproxen solubilities in hexane, benzene, methanol, ethanol, 1-propanol, 1-butanol, 1-pentanol, 1-heptanol, and 1-octanol at 298 K based on spectroscopic methods.…”

“…Bustamante et al 164 reported solubility data for naproxen at 298 K in two saturated hydrocarbons (heptane and cyclohexane), in one aromatic hydrocarbon (benzene), in one alkyl alkanoate (ethyl ethanoate), in one dialkyl ether (1,1′-oxybisethane) and one cyclic ether (1,4-dioxane), in two chloroalkanes (trichloromethane and 1,2-dichloroethane) and one chlorinated aromatic hydrocarbon (chlorobenzene), in six alcohols (methanol, ethanol, 1-pentanol, 1-octanol, 1,2-propanediol, and 1,2,3-propanetriol), in one alkanone (propanone) and one aromatic ketone (acetophenone), and four miscellaneous organic solvents (ethanoic acid, propanoic acid, formamide, and N,N-dimethylformamide). Daniels et al 165 determined the solubility of naproxen in two alkyl alkanoates (methyl ethanoate and butyl ethanoate), in three dialkyl ethers (1,1-oxybisethane, 2,2′-oxybispropane, and 1,1′-oxybisbutane), and two cyclic ethers (tetrahydrofuran and 1,4-dioxane), and in 12 alcohols (1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl-1-propanol, 1-pentanol, 2-pentanol, 3-methyl-1-butanol, 1-hexanol, 1-heptanol, 1-octanol, and 1-decanol) at 298 K. Manrique et al, 111 Yan et al, 168 Fini et al, 60 Mora and Martínez, 167 Claramonte et al, 170 and Aragón et al 166,169 have also performed naproxen solubility measurements at 298 K. Wenkers and Lippold 64 reported solubility data for ten NSAIDs (aspirin, diclofenac, diflunisal, flufenamic acid, ibuprofen, ketoprofen, nabumetone, naproxen, piroxicam, and tenoxicam) in light mineral oil at 305 K.…”