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Crystal Structure and Physicochemical Properties of Crystalline Form of 2'-O-{; ; ; 3-[(7-chloro- 4-quinolinyl)amino]propyl}; ; ; -9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin A


Filić, Darko; Starčević, Kristina; Pešić, Dijana; Jurmanović, Stella; Meenan, Eugene; Spezzaferri, Alberto; Đilović, Ivica; Prugovečki, Biserka
Crystal Structure and Physicochemical Properties of Crystalline Form of 2'-O-{; ; ; 3-[(7-chloro- 4-quinolinyl)amino]propyl}; ; ; -9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin A // Journal of pharmaceutical sciences, 100 (2011), 7; 2586-2598 doi:10.1002/jps.22511 (međunarodna recenzija, članak, znanstveni)


Naslov
Crystal Structure and Physicochemical Properties of Crystalline Form of 2'-O-{; ; ; 3-[(7-chloro- 4-quinolinyl)amino]propyl}; ; ; -9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin A

Autori
Filić, Darko ; Starčević, Kristina ; Pešić, Dijana ; Jurmanović, Stella ; Meenan, Eugene ; Spezzaferri, Alberto ; Đilović, Ivica ; Prugovečki, Biserka

Izvornik
Journal of pharmaceutical sciences (0022-3549) 100 (2011), 7; 2586-2598

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Crystal structure; crystallography; physicochemical characterization; X-ray powder diffractometry; thermal analysis (DSC and TGA); SEM; stability; solubility; moisture adsorption; Karl Fischer analysis; gas chromatography

Sažetak
The intent of the study was to prepare and characterize crystalline form of 2'-O-{; ; ; 3-[(7-chloro-4-quinolinyl)amino]propyl}; ; ; -9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin A (1), a novel 15-membered azalide derivative with antimalarial activity. The crystalline material was prepared by crystallization from acetonitrile reproducible in high yield and purity. Single crystal X-ray studies, X-ray powder diffractometry, differential scanning calorimetry, thermogravimetric analysis, moisture adsorption, Karl Fischer titration, gas chromatography, scanning electron microscopy, optical microscopy, solubility, and solid-state and solution stability were conducted to investigate physicochemical properties of the existing crystalline form. Crystalline 1 is not hygroscopic, does not contain solvents, is physicochemically stable in solid state for up to 4 weeks, and is highly soluble at pH values below 6 and in biorelevant media (simulated gastric fluid, fed simulated intestinal fluid, and fasted simulated intestinal fluid). Solution stability studies (buffers and biorelevant media) indicated that this compound is stable in solutions at pH values 5–6, and that stability is influenced by pH and temperature.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
119-1193079-1084 - Strukturno istraživanje bioloških makromolekula metodom rentgenske difrakcije (Dubravka Matković-Čalogović, )

Ustanove
Prirodoslovno-matematički fakultet, Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


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