[Preparation and characterization of (5-methyl-2-oxo-1,3-dioxol-4-yl) methyl thiamine sulfides].
A new type of S-protected thiol-type thiamines (prodrugs), which have a (5-methyl-2-oxo-1,3-dioxol-4-yl) methyl group recognized as a biologically safe promoiety, were designed, prepared, and confirmed to show higher serum thiamine levels after oral administration to rats than after that of thiamine itself and bisbentiamin as standards. Thus it was shown that the promoiety should be also used for improvement of poor oral absorption of drugs with a mercapto group, in addition to the absorption of drugs with carboxyl, amino, and hydroxyl groups.
Uchida
Tetsuro
T
Department of Chemistry, Nagaoka University of Technology, Nagaoka City, Japan.
Tsukamoto
Goro
G
Yamamoto
Koji
K
Kametani
Shun-ichi
S
Maekawa
Hirofumi
H
Nishiguchi
Ikuzo
I
D000284:Administration, Oral; D000818:Animals; D007408:Intestinal Absorption; D008297:Male; D011355:Prodrugs / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics; D051381:Rats; D017207:Rats, Sprague-Dawley; D013329:Structure-Activity Relationship; D013440:Sulfides / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics; D013831:Thiamine / Q000097:blood
D011355:Prodrugs; D013440:Sulfides; D013831:Thiamine