CAO Xiaoxue, JI Shaochang, KUANG Wenjie, LIAO Anping, LAN Ping, ZHANG Jinyan. Solubility and ternary phase diagram of azithromycin dihydrate in water-organic solvent[J]. CIESC Journal, 2019, 70(3): 817-829
CAO Xiaoxue, JI Shaochang, KUANG Wenjie, LIAO Anping, LAN Ping, ZHANG Jinyan. Solubility and ternary phase diagram of azithromycin dihydrate in water-organic solvent[J]. CIESC Journal, 2019, 70(3): 817-829DOI: 10.11949/j.issn.0438-1157.20180910.
Solubility and ternary phase diagram of azithromycin dihydrate in water-organic solvent
The solubility of azithromycinin water+isopropanol and propanon
e+water solvent mixtures were measured at temperatures from 293.15 K to 323.15 K by an analytical method. The water activity of transformation at 293.15
298.15
303.15 and 308.15 K were measured
and the phase diagram of alcohol- azithromycin -water at that temperature was obtained through solubility property. The solubility data were correlated by the modified Apelblat equation
λh
equation and van’t Hoff equation. The results showed that the solubility of azithromycin dihydrate obviously increased with the increase of temperature and the volume fraction of isopropanol and propanone
and the water activity of transformation increased and the coexist area decreased with the increase of temperature. The modified Apelblat equation was the best choice in the correlation of the solubility data.
关键词
Keywords
references
Timoumi S , Mangin D , Peczalski R , et al . Stability and thermophysical properties of azithromycin dihydrate [J ] . Arabian Journal of Chemistry , 2014 , 7 ( 2 ): 189 - 195 .
Gandhi R , Pillai O , Thilagavathi R , et al . Characterization of azithromycin hydrates [J ] . European Journal of Pharmaceutical Sciences , 2002 , 16 ( 3 ): 175 - 184 .
Kobrehel G , Lazarevski G , Dokić S , et al . Synthesis and antibacterial activity of O-methylazithromycin derivatives [J ] . Journal of Antibiotics , 1992 , 45 ( 4 ): 527 - 34 .
Peters D H , Friedel H A , Mctavish D . Azithromycin. A review of its antimicrobial activity, pharmacokinetic properties and clinical efficacy [J ] . Drugs , 1992 , 44 ( 5 ): 750 - 799 .
Liu M J , Yin D P , Fu H L , et al . Solid–liquid equilibrium of azithromycin in water+1,2-propanediol solutions from (289.35 to 319.15) K [J ] . Journal of Molecular Liquids , 2014 , 199 ( 3 / 4 ): 51 - 56 .
Adeli E , Mortazavi S A . Design, formulation and evaluation of azithromycin binary solid dispersions using kolliphor series for the solubility and in vitro dissolution rate enhancement [J ] . Journal of Pharmaceutical Investigation , 2014 , 44 ( 2 ): 119 - 131 .
Montejo-Bernardo J , García-Granda S , Llorente I , et al . On the interaction of azithromycin monohydrate with metallic containers [J ] . Journal of Applied Crystallography , 2006 , 39 ( 6 ): 826 - 830 .
Wang X , Qin Y , Zhang T , et al . Measurement and correlation of solubility of azithromycin monohydrate in five pure solvents [J ] . Journal of Chemical & Engineering Data , 2014 , 59 ( 59 ): 784 - 791 .
Montejobernardo J M , Garciagranda S , Bayodjasanada M S , et al . On the solid state conformation of azithromycin monohydrate and dihydrate pseudopolymorphs [J ] . Zeitschrift für Kristallographie-Crystalline Materials , 2005 , 220 ( 1 ): 66 - 73 .
Aronhime J , Singer C . Crystalline azithromycin, process for manufacture and pharmaceutical compositions thereof [J ] . Differential Equations & Dynamical Systems , 2004 , 21 ( 1 / 2 ): 3 - 13 .
O’Mahony M A , Croker D M , Rasmuson Åke C , et al . Measuring the solubility of a quickly transforming metastable polymorph of carbamazepine [J ] . Organic Process Research & Development , 2013 , 17 ( 3 ): 512 - 518 .
Hanna M , Shan N , Cheney M L , et al . Solubility modeling and solvent effects of allopurinol in 15 neat solvents [J ] . Journal of Chemical & Engineering Data , 2018 , 63 ( 9 ): 3551 - 355 .
Docherty R , Pencheva K , Abramov Y A . Low solubility in drug development: de-convoluting the relative importance of solvation and crystal packing [J ] . Journal of Pharmacy & Pharmacology , 2015 , 67 ( 6 ): 847 - 856 .
Fayjunessa R , Sarkar M R , Sultana R , et al . Study on dissolution improvement of allopurinol by co-grinding and fusion method using solid dispersion technique [J ] . J. Biomed . Pharmaceut. Res . 2013 , 2 , 1 - 7 .
Healy A M , Worku Z A , Kumar D , et al . Pharmaceutical solvates, hydrates and amorphous Forms [J ] . Advanced Drug Delivery Reviews , 2017 , 117 ( 1 ): 25 - 46 .
Neglur R , Hosten E , Aucamp M , et al . Water and the relationship to the crystal structure stability of azithromycin [J ] . Journal of Thermal Analysis & Calorimetry , 2018 , 132 ( 1 ): 373 - 384 .
Zhen M , Chen J , Chen G Q , et al . Solubility ,modeling and solvent effects of allopurinol in 15 neat solvents [J ] . Journal of Chemical & Engineering Data , 2018 , 63 ( 9 ): 3551 - 3558 .
Hazi M T , Lenka M , Sarkar D . Nucleation kinetics from metastable zone widths for sonocrystallization of l-phenylalanine [J ] . Ultrasonics Sonochemistry , 2017 , 36 : 497 - 506 .
Imran S , Hossain A , Mahali K , et al . Role of solubility and solvation thermodynamics on the stability of L-phenylalanine in aqueous methanol and ethanol solutions [J ] . Journal of Molecular Liquids , 2018 , 265 ( 1 ): 693 - 700 .
Li R R , Ye S F , Chen Y F , et al . Solubility of sulfachloropyridazine in pure and binary solvent mixtures and investigation of intermolecular interactions [J ] . Journal of Chemical & Engineering Data , 2018 , 63 ( 6 ): 2002 - 2008 .
Zhang Y Z , Guo X , Tang P , et al . Solubility of 2,5-furandicarboxylic acid in eight pure solvents and two binary solvent systems at 313.15—363.15 K [J ] . Journal of Chemical & Engineering Data , 2018 , 63 ( 5 ): 1316 - 1324 .
Wang X M , Qin Y A , Zhang T W , et al . Measurement and correlation of solubility of azithromycin monohydrate in five pure solvents [J ] . Journal of Chemical & Engineering Data , 2014 , 59 ( 3 ): 784 - 791 .
Xu L X . Content determination of azithromycin granules (Ⅱ) by RP-HPLC [J ] . China Pharmacy , 2013 , 24 ( 36 ): 3447 - 3449
Zhang J , Dang L , Wei H . Solubility of 5-(dithiolan-3-yl) pentanoic acid in the mixed solvents of cyclohexane + ethyl acetate, heptane + ethyl acetate, and hexane + ethyl acetate [J ] . Journal of Chemical & Engineering Data , 2010 , 55 ( 9 ): 4025 - 4028 .
Baluja S , Alnayab E A M , Hirapara A . Solubility and solution thermodynamics of hippuric acid in various solvents from 298.15 K to 328.15 K [J ] . Journal of Molecular Liquids , 2017 , 238 : 84 - 88 .
Chen L Z , Song L , Lan G C , et al . Solubility and metastable zone width measurement of 3,4-bis(3-nitrofurazan-4-yl) furoxan (dntf) in ethanol + water [J ] . Chinese Journal of Chemical Engineering , 2017 , 25 ( 5 ): 646 - 651 .
Xie Y , Shi H W , Du C B , et al . Solubility determination and modeling for 4, 4 -dihydroxydiphenyl sulfone in mixed solvents of (acetone, ethyl acetate, or acetonitrile)+ methanol and acetone + ethanol from (278.15 to 313.15) K [J ] . Journal of Chemical & Engineering Data , 2016 , 61 ( 10 ): 3519 - 3526 .
Yang H , Rasmuson Å C . Solubility of butyl paraben in methanol, ethanol, propanol, ethyl acetate, acetone, and acetonitrile [J ] . Journal of Chemical & Engineering Data , 2010 , 55 ( 11 ): 5091 - 5093 .
Lei Z Y , Hu Y H , Yang W G , et al . Solubility of 2-(2,4,6-trichlorophenoxy)ethyl bromide in methanol, ethanol, propanol, isopropanol, acetonitrile, n -heptane, and acetone [J ] . Journal of Chemical & Engineering Data , 2011 , 56 ( 5 ): 2714 - 2719 .
Buchowski H , Ksiazczak A , Pietrzyk S . ChemInform abstract: Solvent activity along a saturation line and solubility of hydrogen-bonding solids [J ] . Journal of Physical Chemistry , 1980 , 84 ( 9 ): 975 - 979 .
Su J , Chao Q , Luo N , et al . Experimental measurement and modeling of the solubility of biotin in six pure solvents at temperatures from 298.15 K to 333.85 K [J ] . Journal of Chemical & Engineering Data , 2014 , 59 ( 11 ): 3894 - 3899 .
Choi W S , Kim K J . Solubility of Forms I and II of clopidogrel hydrogen sulfate in methanol and 2-propanol mixture [J ] . Journal of Chemical & Engineering Data , 2011 , 56 ( 1 ): 43 - 47 .
Hong M , Xu L , Ren G , et al . Solubility of lansoprazole in different solvents [J ] . Fluid Phase Equilibria , 2012 , 331 ( 1 ): 18 - 25 .
Wilson G M . Vapor-liquid equilibrium. XI. A new expression for the excess free energy of mixing [J ] . Journal of the American Chemical Society , 1964 , 86 ( 2 ): 127 - 130 .
Arrad M , Kaddami M , Goundali B E , et al . Solubility modeling of the binary systems Fe(NO 3 ) 3 –H 2 O, Co(NO 3 ) 2 –H 2 O and the Ternary System Fe(NO 3 ) 3 –Co(NO 3 ) 2 –H 2 O with the extended universal quasichemical (UNIQUAC) model [J ] . Journal of Solution Chemistry , 2016 , 45 ( 4 ): 534 - 545 .
Arrad M , Kaddami M , El Goundali B , et al . Solubility modeling of the systems Ni(NO)-HO and Fe(NO)-Ni(NO)-HO with the extended universal quasichemical (UNIQUAC) model [J ] . Journal of Solution Chemistry , 2017 , 46 ( 6 ): 1220 - 1229 .
Crystallization thermodynamics of L-phenylalanine in methanol-water solvent
Preparation of 3.5-valent vanadium electrolyte via ammonia gas-phase reduction
Predictive model on gas solubility in water-rich phase coexisted with gas hydrates
Machine learning-assisted solvent molecule design for efficient absorption of ethanethiol
Preparation of high-concentration positive electrolyte of vanadium redox flow battery by activating vanadium pentoxide with highly concentrated sulfuric acid
Related Author
CAO Xiaoxue
JI Shaochang
KUANG Wenjie
LIAO Anping
LAN Ping
ZHANG Jinyan
HU Feifei
WANG Cheng
Related Institution
Guangxi Key Laboratory for Polysaccharide Materials and Modifications, Key Laboratory of Chemical and Biological Transformation Process of Guangxi Higher Education Institutes, College of Chemistry and Chemical Engineering, Guangxi University for Nationalities
School of Environmental and Chemical Engineering, Dalian University
National Engineering Research Center for Green Recycling of Strategic Metal Resources, Institute of Process Engineering, Chinese Academy of Sciences
Beijing Integrated Circuit Equipment Innovation Center Co., Ltd.
Chengde Vanadium and Titanium New Materials Co., Ltd.