H-1 and C-13 nuclear magnetic resonance studies of the sites of protonation in itraconazole and fluconazole

Authors
Inkmann, E Holzgrabe, U
Citation
E. Inkmann et U. Holzgrabe, H-1 and C-13 nuclear magnetic resonance studies of the sites of protonation in itraconazole and fluconazole, J PHARM B, 20(1-2), 1999, pp. 297-307
Citations number
7
Categorie Soggetti
Chemistry & Analysis
Journal title
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
ISSN journal
07317085 → ACNP
Volume
20
Issue
1-2
Year of publication
1999
Pages
297 - 307
Database
ISI
SICI code
0731-7085(199906)20:1-2<297:HACNMR>2.0.ZU;2-3
Abstract
H-1 and C-13 nuclear magnetic resonance spectra of itraconazole were measur ed in neutral solution, and upon addition of varying amounts of deuterated hydrochloride acid. The comparison of the chemical shift in the different s olutions revealed the high proton affinity of the piperazine nitrogen N26. Upon addition of a surplus of acid, the triazole ring was protonated. Corre sponding observations were made for fluconazole. (C) 1999 Elsevier Science B.V. All rights reserved.