title: Isolation and characterization of a degradation product of deflazacort.
abstract: Deflazacort (DFZ) is an oxazoline derivative of prednisolone with anti-inflammatory and immunosuppressive activity. The aim of this study was to investigate and to identify the main degradation product of DFZ, and to evaluate the anti-inflammatory effect of both DFZ and its major degradation product (namely DDP1). DFZ was subjected to alkaline and acid degradation. In 0.1 N NaOH, DFZ was immediately degraded and 99.0% of product DDP1 was detected by high performance liquid chromatography (HPLC). The HPLC method was ideal to separate the primary and other minor degradation products and was carried out using C18 column, mobile phase consisting of water: acetonitrile: (60:40, v/v) with flow rate of 1.0 mL/min and detection at 244 nm. DDP1 was isolated and identified as 21-hydroxy deflazacort (21-OH-DFZ) by NMR, IR and LCMS. The in vivo pharmacological assays showed that both DFZ as 21-OH-DFZ are active in in vivo and in vitro inflammatory models, but 21-OH-DFZ is more potent than DFZ.
authors: Universidade Federal de Santa Catarina, Centro de Ciências da Saúde. Programa de Pós-Graduação em Farmácia, Campus Universitário - Trindade, Florianópolis, SC Brasil. CEP 80.040-970. amarilis_paulino@yahoo.com.br
authors: A S
authors: AS
authors: Paulino
authors: G
authors: G
authors: Rauber
authors: A M
authors: AM
authors: Deobald
authors: N
authors: N
authors: Paulino
authors: A C H F
authors: AC
authors: Sawaya
authors: M N
authors: MN
authors: Eberlin
authors: S G
authors: SG
authors: Cardoso
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000494:pharmacology; D001681:Biological Assay; D002470:Cell Survival / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D004355:Drug Stability; D004487:Edema / Q000139:chemically induced / Q000517:prevention & control; D006868:Hydrolysis; D007202:Indicators and Reagents; D007249:Inflammation / Q000188:drug therapy; D009569:Nitric Oxide / Q000378:metabolism; D011282:Pregnenediones / Q000737:chemistry* / Q000494:pharmacology; D051381:Rats; D013056:Spectrophotometry, Ultraviolet
chemical_list: D000893:Anti-Inflammatory Agents; D007202:Indicators and Reagents; D011282:Pregnenediones; D009569:Nitric Oxide; C021988:deflazacort