A comparative study of enol aldehyde formation from betamethasone, dexamethasone, beclomethasone and related compounds under acidic and alkaline conditions

Steroids

Volumn 74, Issue 1, 2009, Pages 30-41

  Chen, Bin ^a   Li, Min ^a   Lin, Mingxiang ^a   Tumambac, Gilbert ^a   Rustum, Abu ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Beclomethasone; Betamethasone; Corticosteroids; Dexamethasone; Enol aldehyde

Indexed keywords

ALDEHYDE DERIVATIVE; BECLOMETASONE; BECLOMETASONE DIPROPIONATE; BETAMETHASONE; BETAMETHASONE DIPROPIONATE; DEXAMETHASONE; DEXAMETHASONE 17,21 DIPROPIONATE; ENOL ALDEHYDE; UNCLASSIFIED DRUG;

ACIDITY; ALKALINITY; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; MASS SPECTROMETRY;

BECLOMETHASONE; BETAMETHASONE; DEXAMETHASONE; HYDROGEN-ION CONCENTRATION; ISOMERISM; MOLECULAR STRUCTURE;

EID: 57249103316     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2008.09.009     Document Type: Article

References (17)

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11. The knowledge has been obtained through the studies of in-house steroid family drug products in our group. Some of the results from the studies are being published.
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13. n (n is usually 2 to 3) fragmentation patterns can be used as a very effective molecular fingerprinting tool for structural elucidation during the identification of steroid impurities in our laboratory. The details of the work will be published elsewhere.
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16. 13C NMR signals are assigned (Table 3) with the help of relevant 2D NMR data. On the other hand, the NMR signals of the E-isomer could not be assigned in their entirety due to its low amount and signal overlap with the signals of the Z-isomer. The determination of the ratio between the two isomers is based on the peak area of the Z- aldehyde signal (s, 9.59 ppm) vs. that of the E-aldehyde signal. (s, 9.68 ppm).
17. 13C NMR, 2D HSQC, and 1D NOE experiments. The determination of the ratio between the two isomers is based on the peak area of the Z- aldehyde signal (s, 9.62 ppm) vs. that of the E-aldehyde signal. (s, 9.70 ppm).