Document Detail


HPLC analysis of the nitrosation products of chlordiazepoxide.
MedLine Citation:
PMID:  2604839     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Products originated from Chlordiazepoxide (I) hydrochloride/sodium nitrite interaction were analyzed by HPLC. The studied reactions were carried out in diluted hydrochloric acid solutions at pH values ranging between 0.5-5.0. Depending on the reaction pH values and molar ratios it was possible to find and assess variable amounts of the N-nitrosochlordiazepoxide (II), the dihydroquinazoline (III) and the lactam (IV). The highest degree of N-nitrosation was found at pH 3.5. At this pH value the yields of (II) were respectively 54.8% and 18.3% when the drug (I)/nitrite molar ratios were correspondingly 0.41 and 0.25. When the reaction was performed in concentrations which is possible to find in the gastric juice of patients taking (I) together with nitrite-rich foods the yield of (II) at pH 3.5 was 2.5%. Since in the meantime the genotoxicity of (II) was proved, "in vivo" formation of N-nitrosochlordiazepoxide (II) represents a potential risk not to be underestimated.
Authors:
M Mazzei; A Balbi; G Roma; M Di Braccio; L Robbiano
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Farmaco (Società chimica italiana : 1989)     Volume:  44     ISSN:  0014-827X     ISO Abbreviation:  Farmaco     Publication Date:  1989 Sep 
Date Detail:
Created Date:  1990-02-22     Completed Date:  1990-02-22     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  8912641     Medline TA:  Farmaco     Country:  ITALY    
Other Details:
Languages:  eng     Pagination:  883-91     Citation Subset:  IM    
Affiliation:
Istituto di Scienze Farmaceutiche, Università di Genova, Italy.
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MeSH Terms
Descriptor/Qualifier:
Chlordiazepoxide / analogs & derivatives*,  analysis
Chromatography, High Pressure Liquid
Hydrogen-Ion Concentration
Nitrosation
Nitroso Compounds / analysis,  chemical synthesis
Chemical
Reg. No./Substance:
0/Nitroso Compounds; 58-25-3/Chlordiazepoxide

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