Solubility of sulphadiazine in (acetonitrile plus water) mixtures: measurement, correlation, thermodynamics and preferential solvation

被引:20
作者
Ricardo Delgado, Daniel [1 ]
Ivan Caviedes-Rubio, Diego [1 ]
Patricia Ortiz, Claudia [2 ]
Lizeth Parra-Pava, Yarly [3 ]
Angeles Pena, Maria [4 ]
Jouyban, Abolghasem [5 ,6 ,7 ]
Mirheydari, Seyyedeh Narjes [8 ]
Martinez, Fleming [9 ]
Acree, William E., Jr. [10 ]
机构
[1] Univ Cooperat Colombia, Grp Invest GRIAUCC, Programa Ingn Ind, Fac Ingn, Sede Neiva, Neiva Huila, Colombia
[2] Fdn Escuela Tecnol Neiva, Grp Invest Seguridad & Salud Trabajo FET, Neiva Rivera, Colombia
[3] Univ Antonio Narino, Programa Odontol, Sede Buganviles, Neiva, Colombia
[4] Univ Alcala, Dept Ciencias Biomed, Fac Farm, Madrid, Spain
[5] Tabriz Univ Med Sci, Pharmaceut Anal Res Ctr, Tabriz, Iran
[6] Tabriz Univ Med Sci, Fac Pharm, Tabriz, Iran
[7] Tabriz Univ Med Sci, Kimia Idea Pardaz Azarbayjan KIPA Sci Based Co, Tabriz, Iran
[8] Tabriz Univ Med Sci, Drug Appl Res Ctr, Tabriz, Iran
[9] Univ Nacl Colombia, Grp Invest Farmaceut Fis Quim, Dept Farm, Fac Ciencias, Carrera 30 45-03, Bogota, Colombia
[10] Univ North Texas, Dept Chem, Denton, TX 76203 USA
关键词
Sulphadiazine; {acetonitrile (1) + water (2)} mixtures; solubility; Jouyban-Acree model; preferential solvation; Inverse Kirkwood-Buff integrals (IKBI); ENTHALPY-ENTROPY COMPENSATION; BINARY SOLVENT MIXTURES; SULFANILAMIDE SOLUBILITY; DRUG SOLUBILITY; ACID SOLUBILITY; GALLIC ACID; SULFONAMIDES; SULFAMETHAZINE; METHANOL; SULFAMETHIZOLE;
D O I
10.1080/00319104.2019.1594227
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The equilibrium solubility at temperatures from (293.15 to 313.15) K, dissolution thermodynamics and preferential solvation of sulphadiazine (SD) in {acetonitrile (ACN) (1) + water (2)} mixtures is reported. Mole fraction solubility of SD (x(3)) increases when temperature arises and also increases with the ACN proportion increasing. It varies from 4.81 x 10(-6) in neat water to 6.02 x 10(-4) in neat ACN at 298.15 K. Solubility behaviour was adequately correlated by Jouyban-Acree, modified Wilson and non-linear (proposed by Machatha et al.) models and the obtained mean percentage deviations (MPD) are 4.1%, 2.3% and 2.3%, respectively. The comparison of the MPD shows that the prediction using Jouyban-Acree model is more accurate than Jouyban-Acree-Abraham equation for solubility prediction of SD in {ACN (1) + water (2)}. From the variation of solubility with temperature the apparent thermodynamic analysis of dissolution was performed in all the mixtures and neat solvents. Based on the inverse Kirkwood-Buff integrals preferential solvation parameters were calculated. SD is preferentially solvated by water in water-rich mixtures (0.00 x(1) < 0.26) but preferentially solvated by ACN in the interval (0.26 x(1) < 0.65). In ACN-rich mixtures the behaviour is not well defined.
引用
收藏
页码:381 / 396
页数:16
相关论文
共 69 条
[1]  
Avdeef A., 2003, ABSORPTION DRUG DEV
[2]   Preferential solvation in acetonitrile-water mixtures - Relationship between solvatochromic parameters and pK values of carboxylic acids [J].
Barbosa, J ;
Barron, D ;
Berges, R ;
SanzNebot, V ;
Toro, I .
JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1997, 93 (10) :1915-1920
[3]  
Barton A.F. M., 1991, Handbook of Solubility Parameters and Other Cohesion Parameters, V2nd
[4]  
Budavari S., 2001, The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, V13th
[5]   Enthalpy-entropy compensation for the solubility of drugs in solvent mixtures: Paracetamol, acetanilide, and nalidixic acid in dioxane-water [J].
Bustamante, P ;
Romero, S ;
Pena, A ;
Escalera, B ;
Reillo, A .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1998, 87 (12) :1590-1596
[6]   A MODIFICATION OF THE EXTENDED HILDEBRAND APPROACH TO PREDICT THE SOLUBILITY OF STRUCTURALLY RELATED DRUGS IN SOLVENT MIXTURES [J].
BUSTAMANTE, P ;
ESCALERA, B ;
MARTIN, A ;
SELLES, E .
JOURNAL OF PHARMACY AND PHARMACOLOGY, 1993, 45 (04) :253-257
[7]   Solubility and Preferential Solvation of Sulfanilamide, Sulfamethizole and Sulfapyridine in Methanol plus Water Mixtures at 298.15 K [J].
Cardenas, Zaira J. ;
Jimenez, Daniel M. ;
Almanza, Ovidio A. ;
Jouyban, Abolghasem ;
Martinez, Fleming ;
Acree, William E., Jr. .
JOURNAL OF SOLUTION CHEMISTRY, 2016, 45 (10) :1479-1503
[8]   Extended Hildebrand solubility approach applied to some sulphonamides in propylene glycol+water mixtures [J].
Cardenas, Zaira J. ;
Jimenez, Daniel M. ;
Delgado, Daniel R. ;
Pena, Maria A. ;
Martinez, Fleming .
PHYSICS AND CHEMISTRY OF LIQUIDS, 2015, 53 (06) :763-775
[9]  
Chun, 1993, PHYS CHEM PRINCIPLES
[10]  
Connors K A., 2002, Thermodynamics of pharmaceutial systems: An introduction for students of pharmacy