Cocrystal Hydrate of an Antifungal Drug, Griseofulvin, with Promising Physicochemical Properties

Cocrystal Hydrate of an Antifungal Drug, Griseofulvin, with Promising Physicochemical Properties
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DOI:
10.1021/cg3012124
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发表时间:
2012-12-01
影响因子:
3.8
通讯作者:
Tan, Reginald B. H.
Tan, Reginald B. H.
中科院分区:
化学2区
文献类型:
--
作者:
Aitipamula, Srinivasulu;Vangala, Venu R.;Tan, Reginald B. H.

文献摘要

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抗真菌药物灰黄霉素(GF)与人工甜味剂乙酰磺胺(Ace-H)共结晶,得到GF和Ace-H按2:1的化学比例共结晶的一水化合物。用差示扫描量热法和热重法对该共晶进行了表征,并用单晶x射线衍射法对其晶体结构进行了表征。Ace-H分子在晶体结构中呈烯醇形式。共晶水合物表现出显著的热稳定性,这是由于晶体结构中存在强氢键。(GF)的溶解速率(2)。与母体GF相比,Ace-H水合物得到了显著改善,在37℃时,共晶水合物的溶解度大于GF的溶解度。此外,在不同的相对湿度条件下,共晶水合物的稳定性可达13周。Ace-H显著的热稳定性、提高的溶解度和溶出率以及药物可接受性使其成为(GF)(2)。Ace-H水合物是开发GF配方的优选固体形式(新加坡专利申请201107310-3(参考文献1))。
Cocrystallization of an antifungal drug, griseofulvin (GF), with an artificial sweetener, acesulfame (Ace-H), resulted in a cocrystal monohydrate with GF and Ace-H in a 2:1 stoichiometric ratio. The cocrystal was characterized by differential scanning calorimetry and thermogravimetric analysis, and its crystal structure was determined by single-crystal X-ray diffraction. The Ace-H molecule is in its enol form in the crystal structure. The cocrystal hydrate shows remarkable thermal stability, which was traced to strong hydrogen bonds in the crystal structure. The dissolution rate of the (GF)(2).Ace-H hydrate is significantly improved compared to that of the parent GF, and the aqueous solubility of the cocrystal hydrate is greater than the solubility of GF at 37 degrees C. Furthermore, the cocrystal hydrate is found to be stable at different relative humidity conditions for up to 13 weeks. The remarkable thermal stability, improved solubility and dissolution rate, and pharmaceutical acceptability of Ace-H make the (GF)(2).Ace-H hydrate a preferable solid form for development of GF formulations (Singapore patent application 201107310-3 (ref 1)).