SOME PHYSICAL-CHEMICAL PROPERTIES OF DANTROLENE AND 2 OF ITS ANALOGS

被引:10
|
作者
JANSEN, ACA [1 ]
HILBERS, HW [1 ]
NI, XR [1 ]
VANHELDEN, SP [1 ]
JANSSEN, LHM [1 ]
机构
[1] STATE UNIV UTRECHT,FAC PHARM,DEPT PHARMACEUT CHEM,POB 80082,3508 TB UTRECHT,NETHERLANDS
关键词
CYCLODEXTRIN; BINDING CONSTANT; THERMODYNAMIC INCLUSION DATA; DANTROLENE;
D O I
10.1016/0378-5173(91)90193-R
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
Some physical-chemical properties of dantrolene (1-[[5-(p-nitrophenyl)furfurylidene]amino]hydantoin), p-chlorodantrolene ((des-p-nitro)-p-chlorodantrolene) and o-nitrodantrolene ((des-p-nitro)-o-nitrodantrolene) have been studied. The solubility was measured in the range 20-37-degrees-C, at pH 5.4, 7.4 and 9.4. The solubility was found to increase as a function of pH and temperature. The thermodynamic solubility parameters were determined. Distribution experiments in the system octanol-buffer (20-degrees-C) yielded a value for the logarithm of the partition coefficient of the neutral compound of 1.70 +/- 0.05 and a pK value of 7.5. In the presence of cyclodextrins the solubility increased, indicating complex formation. The corresponding complex formation constants were highest for beta-cyclodextrin, with no detectable pH dependence. The inclusion of p-Cl-dantrolene was also studied using modelling experiments and molecular mechanics calculations. Inclusion of the chlorophenyl group proved to be possible in all cyclodextrins studied; inclusion of the hydantoin part was only feasible with beta- and gamma-cyclodextrin. The calculated energy of interaction indicated that Cl-dantrolene has complete rotational freedom in gamma-cyclodextrin, but limited freedom in alpha- and beta-cyclodextrin.
引用
收藏
页码:193 / 199
页数:7
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