N. Hayase et al., NEWLY DISCOVERED PHOTODEGRADATION PRODUCTS OF NIFEDIPINE IN-HOSPITAL PRESCRIPTIONS, Journal of pharmaceutical sciences, 83(4), 1994, pp. 532-538
New photodegradation products of nifedipine (1) have been isolated. Th
ey were found in tablets dispensed in the pulverized form by hospitals
. 1 decomposed concurrently into six components after storage of 30 da
ys under exposure to normal room light. The main photoproduct was a ni
troso derivative (2) and others were minor. Preparative thin-layer chr
omatography has been used to isolate the six photodegradation products
. The chemical structures of these isolated compounds were identified
or estimated by comparison with authentic samples and/or using UV, IR,
H-1 NMR, mass spectroscopy, melting point determination, and elementa
ry analysis. From these analyses, it was found that 1 was converted in
to a cis-azoxy derivative (4), a trans-azoxy derivative (5), a N,N'-di
oxide derivative (6) and a lactam derivative (7) in addition to 2 and
a nitro derivative (3). Furthermore, it is proposed that 2 is mainly r
esponsible for the formation of these new products (4-7) by photochemi
cal condensation.