Photochemistry of desonide, a non-fluorinated steroidal anti-inflammatory drug.
The photochemistry of anti-inflammatory drug desonide (De, 1) was studied in aerobic as well as in anaerobic condition with different irradiation wavelengths (254, 310 nm) in acetonitrile and 2-propanol. All photoproducts obtained were isolated and characterized on the basis of IR, (1)H-, (13)C-NMR spectroscopy and elemental analysis study. The products were: 11beta,21-dihydroxy-16alpha,17alpha-(1-methylethylidenedioxy)-1,5-cyclopregn-3-ene-2,20-dione 2 (254 nm), 11beta-hydroxy-16alpha,17alpha-(1-methylethylidenedioxy)androsta-1,4-diene-3-one 3 (310 nm/2-propanol), 17beta-hydroperoxy-11beta-hydroxy-16alpha,17alpha-(1-methylethylidenedioxy)androsta-1,4-diene-3-one 4 (310 nm/O(2)/2-propanol). Cyclohexadienone moiety in ring A and keto group at C(17) were found to be deeply modified by UV light therefore, loss of biological activity both during storage and in vivo can not be ruled out.
Iqbal
Jawaid
J
Department of Chemistry, Organic Chemistry Section, Aligarh Muslim University, Aligarh 202002, UP, India. jawaid.iqbal0@lycos.com
Husain
Adil
A
Gupta
Anamika
A
D019840:2-Propanol / Q000737:chemistry; D000097:Acetonitriles / Q000737:chemistry; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry* / Q000494:pharmacology; D003898:Desonide / Q000737:chemistry* / Q000494:pharmacology; D004355:Drug Stability; D015394:Molecular Structure; D010100:Oxygen / Q000378:metabolism; D010777:Photochemistry
D000097:Acetonitriles; D000894:Anti-Inflammatory Agents, Non-Steroidal; D003898:Desonide; D019840:2-Propanol; D010100:Oxygen; C032159:acetonitrile