Characterization of the Solubility and Solid-State Properties of Saccharin Salts of Fluoroquinolones

被引：43

作者：

Romanuk, Carolina B. ^{[1
]}

Manzo, Ruben H. ^{[1
]}

Garro Linck, Yamila ^{[2
]}

Chattah, Ana K. ^{[2
]}

Monti, Gustavo A. ^{[2
]}

Olivera, Maria E. ^{[1
]}

机构：

[1] Univ Nacl Cordoba, Fac Ciencias Quim, Dept Farm, RA-5000 Cordoba, Argentina

[2] Univ Nacl Cordoba, Fac Matemat Astron & Fis, RA-5000 Cordoba, Argentina

来源：

JOURNAL OF PHARMACEUTICAL SCIENCES | 2009年 / 98卷 / 10期

关键词：

saccharin salts; solid state; solubility; zwitterionic; fluoroquinolone derivatives; hydrogen bond; NMR; heteronuclear correlation; METAL-IONS; ELECTROPHORETIC BEHAVIOR; NMR; ANTIMICROBIALS; CIPROFLOXACIN; COMPLEXATION; QUINOLONES; PREDICTION; SERIES;

D O I：

10.1002/jps.21688

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Saccharinates salts of the fluoroquinolone antibiotics norfloxacin, ciprofloxacin, ofloxacin, and enrofloxacin were obtained as pure crystalline anhydrous solids with sweet taste. The products were characterized by one- ((13) C) and two-dimensional (H-1-C-13) dimensions solid state Nuclear Magnetic Resonance and infrared spectroscopy showing ionic interactions between the saccharine amide and the fluoroquinolone piperazine. Several intermolecular bindings were also identified. Thermal behavior and powder X-ray diffraction provided complementary evidences of salt formation. The series of products showed improved properties with respect to water solubility. A solubility model was developed. These salts would be a good way forward to developing more suitable formulations of these APIs. (C) 2009 Wiley-Liss, Inc. and the American Pharmacists Association J Pharm Sci 98:3788-3801, 2009

引用

页码：3788 / 3801

页数：14

共 50 条

[31] Characterization of Pharmaceutical Cocrystals and Salts by Dynamic Nuclear Polarization-Enhanced Solid-State NMR Spectroscopy
Zhao, Li
Hanrahan, Michael P.
Chakravarty, Paroma
DiPasquale, Antonio G.
Sirois, Lauren E.
Nagapudi, Karthik
Lubach, Joseph W.
Rossini, Aaron J.
CRYSTAL GROWTH & DESIGN, 2018, 18 (04) : 2588 - 2601
[32] Characterization of Pharmaceutical Compounds by Solid-state NMR
Vogt, Frederick G.
EMAGRES, 2015, 4 (02): : 255 - 268
[33] An update on solid-state characterization of the polyphenol pterostilbene
Catenacci, Laura
Sorrenti, Milena
Milanese, Chiara
Valentino, Caterina
Vicatos, Alexios I.
Caira, Mino R.
Bonferoni, Maria Cristina
JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY, 2022, 71
[34] Solid-state characterization of a novel chemotherapeutic drug
Marini, A
Berbenni, V
Bruni, G
Maggioni, A
Cofrancesco, P
Sinistri, C
Orlandi, A
Villa, M
JOURNAL OF PHARMACEUTICAL SCIENCES, 2003, 92 (03) : 577 - 584
[35] Arginine Complexes with Simvastatin: Apparent Solubility, In Vitro Dissolution and Solid State Characterization
Affandi, Meor Mohd Redzuan Meor Mohd
Tripathy, Minaketan
Majeed, Abu Bakar Abdul
CURRENT DRUG DELIVERY, 2018, 15 (01) : 77 - 86
[36] Solid-state amorphization of rebamipide and investigation on solubility and stability of the amorphous form
Xiong, Xinnuo
Xu, Kailin
Li, Shanshan
Tang, Peixiao
Xiao, Ying
Li, Hui
DRUG DEVELOPMENT AND INDUSTRIAL PHARMACY, 2017, 43 (02) : 283 - 292
[37] Solid-state versatility in tranexamic acid drug: structural and thermal behavior of new salts and cocrystals
Nechipadappu, Sunil Kumar
Balasubramanian, Sridhar
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2023, 79 : 78 - 97
[38] Zwitterionic Cocrystals of Flavonoids and Proline: Solid-State Characterization, Pharmaceutical Properties, and Pharmacokinetic Performance
He, Hongyan
Huang, Ying
Zhang, Qi
Wang, Jian-Rong
Mei, Xuefeng
CRYSTAL GROWTH & DESIGN, 2016, 16 (04) : 2348 - 2356
[39] Developments in solid-state NMR
Ramanathan K.V.
Resonance, 2015, 20 (11) : 1040 - 1052
[40] Developments in Solid-State NMR
Ramanathan, K. V.
RESONANCE-JOURNAL OF SCIENCE EDUCATION, 2015, 20 (11): : 1040 - 1052

← 1 2 3 4 5 →