Citation: | RUAN Xiaoling, ZHENG Xiangyuan, XU Jie, DING Li, ZHENG Feng. Advances in analytical techniques for the determination of genotoxic impurities in pharmaceuticals[J]. Journal of China Pharmaceutical University, 2016, 47(3): 267-274. DOI: 10.11665/j.issn.1000-5048.20160303 |
[1] |
Bouder F.Regulating impurities in pharmaceutical products:a tolerability of risk approach[J].Expert Rev Clin Pharmacol,2008,1(2):241-250.
|
[2] |
Mueller L,Mauthe RJ,Riley CM,et al.A rationale for determining,testing,and controlling specific impurities in pharmaceuticals that possess potential for genotoxicity[J].Regul Toxicol Pharmacol,2006,44(3):198-211.
|
[3] |
Committee for Medicinal Products for Human Use(CHMP).Guidelines on the limits of genotoxic impurities(CPMP/SWP/5199/02)[S].London:European Medicines Agency Evaluation of Medicines for Human Use(EMEA),2006.
|
[4] |
U.S.Food and Drug Administration,Department of Health and Human Services,Center for Drug Evaluation and Research(CDER).Guidance for industry:genotoxic and carcinogenic impurities in drug substances and products:recommended approaches(draft)[S].Silver Spring:U.S.Food and Drug Administration,2008.
|
[5] |
Benigni R,Bossa C,Tcheremenskaia O,et al.Development of structural alerts for the in vivo micronucleus assay in rodents,EUR 23844 EN[R].Luxenbourg:Office for the Official Publications of the European Communities,2009.
|
[6] |
Benigni R,Bossa C.Mechanisms of chemical carcinogenicity and mutagenicity:a review with implications for predictive toxicology[J].Chem Rev,2011,111(4):2507-2536.
|
[7] |
Skett PW,Smith RJ,Webb ML.Low level measurement of potent toxins[M]//Smith RJ,Webb ML.Analysis of Drug Impurities.Oxford:Blackwell Publishing,2007:82-123.
|
[8] |
Wang Y.Determination of organic volatile impurities in azasetron hydrochloride[J].Chin J Pharm Anal(药物分析杂志),2004,24(3):293-295.
|
[9] |
Liu DQ,Sun M,Kord AS.Recent advances in trace analysis of pharmaceutical genotoxic impurities[J].J Pharm Biomed Anal,2010,51(5):999-1014.
|
[10] |
Frost RP,Hussain MS,Raghani AR.Determination of pharmaceutical process impurities by solid phase microextraction gas chromatography[J].J Sep Sci,2003,26(12/13):1097-1103.
|
[11] |
Ho TD,Yehl PM,Chetwyn NP,et al.Determination of trace level genotoxic impurities in small molecule drug substances using conventional headspace gas chromatography with contemporary ionic liquid diluents and electron capture detection[J].J Chromatogr A,2014,1361:217-228.
|
[12] |
Lee KC,Cheuk MW,Chan W,et al.Determination of glucosinolates in traditional Chinese herbs by high-performance liquid chromatography and electrospray ionization mass spectrometry[J].Anal Bioanal Chem,2007,386(7/8):2225-2232.
|
[13] |
Venugopal N,Reddy AVB,Madhavi G,et al.Trace level quantification of 1-(3-chloropropyl)-4-(3-chlorophenyl)piperazine HCl genotoxic impurity in trazodone using LC-MS/MS[J].Arab J Chem,2014,575:1-8.
|
[14] |
Cappiello A,Famiglini G,Palma P,et al.A new liquid chromatography-mass spectrometry approach for generic screening and quantitation of potential genotoxic alkylation compounds without derivatization[J].J Pharm Biomed Anal,2012,1255(17):286-290.
|
[15] |
van Wijk AM,Niederländer HA,Siebum AH,et al.A new derivatization reagent for LC-MS/MS screening of potential genotoxic alkylation compounds[J].J Pharm Biomed Anal,2013,74(4):133-140.
|
[16] |
van Wijk AM,Niederländer HA,van Ogten MD,et al.Sensitive CE-MS analysis of potentially genotoxic alkylation compounds using derivatization and electrokinetic injection[J].Anal Chimi Acta,2015,874:75-83.
|
[17] |
Raman NV,Prasad AV,Reddy KR,et al.Sensitive derivatization methods for the determination of genotoxic impurities in drug substances using hyphenated techniques[J].J Pharm Biomed Anal,2014,89:276-281.
|
[18] |
Harigaya K,Yamada H,Yaku K,et al.Novel sensitive determination method for a genotoxic alkylating agent,4-chloro-1-butanol,in active pharmaceutical ingredients by LC-ICP-MS employing iodo derivatization[J].Anal Sci,2014,30(3):377-382.
|
[19] |
Li W.Trace analysis of residual methyl methanesulfonate,ethyl methanesulfonate and isopropyl methanesulfonate in pharmaceuticals by capillary gas chromatography with flame ionization detection[J].J Chromatogr A,2004,1046(1/2):297-301.
|
[20] |
Wollein U, Schramek N. Simultaneous determination of alkyl mesilates and alkyl besilates in finished drug products by direct injection GC/MS[J].Eur J Pharm Sci,2012,45(1/2):201-204.
|
[21] |
Ramakrishna K,Raman NV,Rao KM,et al.Developmentand validation of GC-MS method for the determination of methyl methanesulfonate and ethyl methanesulfonate in imatinib mesylate[J].J Pharm Biomed Anal,2008,46(4):780-783.
|
[22] |
Raman NV,Prasad AV,Reddy KR,et al.Determination of genotoxic alkyl methane sulfonates and alkyl paratoluene sulfonates in lamivudine using hyphenated techniques[J].J Pharm Anal,2012,2(4):314-318.
|
[23] |
Raman NV,Reddy KR,Prasad AV,et al.Development and validation of RP-HPLC method for the determination of genotoxic alkyl benzenesulfonates in amlodipine besylate[J].J Pharm Biomed Anal,2008,48(1):227-230.
|
[24] |
García A,Rupérez FJ,Ceppa F,et al.Development of chromatographic methods for the determination of genotoxic impurities in cloperastine fendizoate[J].J Pharm Biomed Anal,2012,61(5):230-236.
|
[25] |
Kakadiya PR,Reddy BP,Singh V,et al.Low level determinations of methyl methanesulfonate and ethyl methanesulfonate impurities in lopinavir and ritonavir active pharmaceutical ingredients by LC/MS/MS using electrospray ionization[J].J Pharm Biomed Anal,2011,55(2):379-384.
|
[26] |
Guo T,Shi YY,Zheng L,et al.Rapid and simultaneous determination of sulfonate ester genotoxic impurities in drug substance by liquid chromatography coupled to tandem mass spectrometry:comparison of different ionization modes[J].J Chromatogr A,2014,1355:73-79.
|
[27] |
European Directorate for Quality and Medicines&HealthCare(EDQM).Methyl,ethyl and isopropyl methanesulfonate in methanesulfonic acid[S]//European Pharmacopoeia 8.0.Strasbourg:Council of Europe,2011.
|
[28] |
Colon 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].J Pharm Biomed Anal,2005,39(3/4):477-485.
|
[29] |
Lee CR,Guivarch F,Van Dau CN,et al.Determination of polar alkylating agents as thiocyanate/isothiocyanate derivatives by reaction headspace gas chromatography[J].Analyst,2003,128(7):857-863.
|
[30] |
Alzaga R,Ryan RW,Taylor-Worth K,et al.A generic approach for the determination of residues of alkylating agents in active pharmaceutical ingredients by in situ derivatization-headspace-gas chromatography-mass spectrometry[J].J Pharm Biomed Anal,2007,45(3):472-479.
|
[31] |
European Directorate for Quality and Medicines&HealthCare(EDQM).Methyl,ethyl and isopropyl methanesulfonate in active substances[S]//European Pharmacopoeia 8.0.Strasbourg:Council of Europe,2012.
|
[32] |
An JG,Sun MJ,Bai L,et al.A practical derivatization LC/MS approach for determination of trace level alkyl sulfonates and dialkyl sulfates genotoxic impurities in drug substances[J].J Pharm Biomed Anal,2008,48(3):1006-1010.
|
[33] |
Reddy VB,Venugopal N,Madhavi G.A selective and sensitive LC-MS/MS method for the simultaneous determination of two potential genotoxic impurities in celecoxib[J].J Anal Sci Technol,2014,5(1):1-8.
|
[34] |
Lakshmi KJ,Devi PR,Mukkanti K.Quantitative determination of residual hydrazine content in cilazapril by ion chromatography[J].Orient J Chem,2010,26(3):1001-1006.
|
[35] |
Kean T, Miller JH, Skellern GG, et al. Acceptance criteria for levels of hydrazine in substances for pharmaceutical use and analytical methods for its determination[J].Pharmeur Sci Notes,2006(2):23-33.
|
[36] |
Liu M,Ostovic J,Chen EX,et al.Hydrophilic interaction liquid chromatography with alcohol as a weak eluent[J].J Chromatogr A,2009,1216(12):2362-2370.
|
[37] |
Matsui F,Robertson DL,Lovering EG.Determination of hydrazine in pharmaceuticals III:hydralazine and isoniazid using glc[J].J Pharm Sci,1983,72(8):948-951.
|
[38] |
Sun M,Bai L,Terfloth GJ,et al.Matrix deactivation:a general approach to improve stability of unstable and reactive pharmaceutical genotoxic impurities for trace analysis[J].J Pharm Biomed Anal,2010,52(1),30-36.
|
[39] |
Oh JA,Park JH,Shin HS.Sensitive determination of hydrazine in water by gas chromatography-mass spectrometry after derivatization with ortho-phthalaldehyde[J].Anal Chim Acta,2013,769(6):79-83.
|
[40] |
Oh JA,Shin HS.Simple and sensitive determination of hydrazine in drinking water by ultra-high-performance liquid chromatography-tandem mass spectrometry after derivatization with naphthalene-2,3-dialdehyde[J].J Chromatogr A,2015,1395:73-78.
|
[41] |
Klick S.Evaluation of different injection techniques in the gas chromatographic determination of thermo labile trace impurities in a drug substance[J].J Pharm Biomed Anal,1995,13(4/5):563-566.
|
[42] |
Xiao KP,Xiong Y,Liu FZ,et al.Efficient method development strategy for challenging separation of pharmaceutical molecules using advanced chromatographic techniques[J].J Chromatogr A,2007,1163(1/2):145-156.
|
[43] |
Rao RN,Raju AN,Narshima R.Isolation and characterization of process related impurities an degradation products of bicalutamide and development of RP-HPLC method for impurity profile study[J].J Pharm Biomed Anal,2008,46(3):505-519.
|
[44] |
Spangler M,Mularz E.A validated,stability-indicating method for the assay of dexamethasone in drug substance and drug product analyses,and the assay of preservatives in drug product[J].Chromatographia,2001,54(5):329-334.
|
[45] |
Petkovska R,Cornett C,Dimitrovska A.Development and validation of rapid resolution RP-HPLC method for simultaneous determination of atorvastatin and related compounds by use of chemometrics[J].Anal Lett,2008,41(6):992-1009.
|
[46] |
Bai L,Sun M,An J,et al.Enhancing the detection sensitivity of trace analysis of pharmaceutical genotoxic impurities by chemical derivatization and coordination ion spray-mass spectrometry[J].J Chromatogr A,2010,1217(3):302-306.
|
[47] |
Wu L,Liu DQ,Vogt FG,et al.Gas-phase derivatization via the Meerwein reaction for selective and sensitive LC-MS analysis of epoxides in active pharmaceutical ingredients[J].J Pharm Biomed Anal,2011,56(5):1106-1111.
|
[48] |
Khan SJ,Weinberg HS,Bedford EC.Aqueous-phase aminolysis:approach for the analysis of epoxides in water[J].Anal Chem,2006,78(8):2608-2616.
|
[49] |
Khan M,Jayasree K,Reddy KV,et al.A validated CE method for determining dimethylsulfate a carcinogen and chloroacetyl chloride a potential genotoxin at trace levels in drug substances[J].J Pharm Biomed Anal,2012,58(2):27-33.
|
[50] |
Fu M,Lu Q,Hewitt E,et al.Ultra high performance liquid chromatography coupled with high resolution quantitation mass spectrometry method development and validation for determining genotoxic 2,5-dichlorobenzoyl chloride in MLN9708 drug substance[J].J Pharm Biomed Anal,2014,89(4):233-239.
|
[51] |
Tang L,Kim A,Miller SA,et al.Development and validation of a specific and sensitive GC-FID method for the determination of impurities in 5-chlorovaleroyl chloride[J].J Pharm Biomed Anal,2010,53(3):309-314.
|
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