Reichardt's dye and its reactions with the alkylating agents 4-chloro-1-butanol, ethyl methanesulfonate, 1-bromobutane and Fast Red B - A potentially useful reagent for the detection of genotoxic impurities in pharmaceuticals

Journal of Pharmacy and Pharmacology

Volumn 61, Issue 4, 2009, Pages 533-537

  Corrigan, Damion K ^a   Whitcombe, Michael J ^a   McCrossen, Sean ^b   Piletsky, Sergey ^a  

^a CRANFIELD UNIVERSITY   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Alkylating agents; Genotoxic impurities; Pharmaceuticals and reichardt's dye; UV vis spectroscopy

Indexed keywords

4 CHLORO 1 BUTANOL; ACETONITRILE; ALKYLATING AGENT; DYE; MESYLIC ACID ETHYL ESTER; N,N DIMETHYLFORMAMIDE; PARACETAMOL; REICHARDT DYE; UNCLASSIFIED DRUG; 1 BROMOBUTANE; 2,6 DIPHENYL 4 (2,4,6 TRIPHENYL 1 PYRIDINIO)PHENOLATE; 2,6-DIPHENYL-4-(2,4,6-TRIPHENYL-1-PYRIDINIO)PHENOLATE; 4-CHLORO-1-BUTANOL; BROMINATED HYDROCARBON; CHLORBUTOL; CHROMOGENIC SUBSTRATE; DIAZONIUM COMPOUND; DRUG DERIVATIVE; FAST RED B; MUTAGENIC AGENT; PYRIDINIUM DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; DRUG ABSORPTION; DRUG IMPURITY; DRUG MONITORING; GENOTOXICITY; SPECTROPHOTOMETRY; ULTRAVIOLET SPECTROSCOPY; CHEMISTRY; DRUG CONTAMINATION; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ALKYLATING AGENTS; CHEMISTRY, PHARMACEUTICAL; CHLOROBUTANOL; CHROMOGENIC COMPOUNDS; DIAZONIUM COMPOUNDS; DRUG CONTAMINATION; ETHYL METHANESULFONATE; HYDROCARBONS, BROMINATED; MAGNETIC RESONANCE SPECTROSCOPY; MUTAGENS; PYRIDINIUM COMPOUNDS;

EID: 85047681851     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/jpp.61.04.0017     Document Type: Article

References (12)

1. Elder DP et al. Control and analysis of alkyl esters of alkyl and aryl sulfonic acids in novel active pharmaceutical ingredients (API). J Pharmaceut Biomed Anal 2008; 46: 1-8.
2. Kirkland D, Snodin D. Setting limits for genotoxic impurities in drug substances: Threshold-based and pragmatic approaches. Int J Pharmaceut Med 2004; 18: 197-207.
3. Callon I, Richoll SM. Determination of methyl and ethyl esters of methanesulfonic, benzenesulfonic and p-toluenesulfonic acids in active pharmaceutical ingredients by solid-phase microextraction (SPME) coupled to GC/SIM-MS. J Pharmaceut Biomed Anal 2005; 39(3-4): 477-485.
4. Taylor TE et al. Low level determination of r-toluenesulfonate and benzenesulfonate esters in drug substance by high performance liquid chromatography/mass spectrometry. J Chromatogr A 2006; 1119: 231-237.
5. European Medicines Agency, Committee for Medicinal Products for Human Use (CHMP). Guidelines on the limits of genotoxic impurities, 2006.
6. Elder DP et al. Control and analysis of alkyl and benzyl halides and other related reactive organohalides as potential genotoxic impurities in active pharmaceutical ingredients. J Pharmaceut Biomed Anal 2008; 48: 497-507.
7. Jacobson-Kram D, McGovern T. Toxicological overview of impurities in pharmaceutical products. Adv Drug Deliv Rev 2007; 59: 38-42.
8. Muller L et al. A rationale for determining, testing and controlling specific impurities in pharmaceuticals that possess potential for genotoxicity. Regulat Toxicol Pharmacol 2006; 44: 198-211.
9. McGovern TM, Jacobson-Kram D. Regulation of genotoxic and carcinogenic impurities in drug substances and products. Trends Anal Chem 2006; 25: 790-795.
10. Reichardt C et al. Syntheses and UV-visible spectroscopic properties of new 'flurophillic' fluorine- and perfluoroalkyl-substituted solvatochromic pyridinium N-phenolate betaine dyes. J Phys Organic Chem 2001; 14: 737-751.
11. 6. Green Chem 2001; 3: 210-215.
12. Linert W et al. Alkylation of pyridinium-N-phenoxide betaine dyes with iodomethane: substituent, solvent and temperature dependence. J Phys Organic Chem 1992; 5: 275-284.