Research progress in quality control of nucleoside antiviral drugs

doi:10.19803/j.1672-8629.2022.06.23

Abstract

Abstract: In recent years, nucleoside antiviral drugs have been increasingly developed, and the related quality control standards have also been improved. Based on 2020 edition of Pharmacopeia of people's Republic of China (ChP2020), 43 edition of the United States Pharmacopeia (USP43), 10.0 edition of European Pharmacopeia (EP10.0), 17 edition of Japanese Pharmacopeia (JP17) and relevant domestic and foreign guidelines, the inclusion of nucleoside antiviral drugs in these pharmacopoeias was summarized, while the critical elements of quality control, such as identification, assay and genotoxic impurities, were analyzed in general and related substances in particular so as to provide reference for the research and development of more accurate quality control methods for nucleoside antiviral drugs.

Key words: nucleoside antiviral drugs, pharmacopoeia, quality control, identification, assay, related substances, genotoxic impurities

CLC Number:

R917

HUANG Lu, LIU Bo, WANG Yan, FAN Huihong, ZHANG Qingsheng. Research progress in quality control of nucleoside antiviral drugs[J]. Chinese Journal of Pharmacovigilance, 2022, 19(6): 692-696.

References

[1] TAN DX, HARDELAND R.Targeting host defense system and rescuing compromised mitochondria to increase tolerance against pathogens by melatonin may impact outcome of deadly virus infection pertinent to COVID-19[J]. Molecules, 2020, 25(19): 4410.
[2] GU H, FADA BJ.Specificity in ubiquitination triggered by virus infection[J]. Int J Mol Sci, 2020, 21(11): 4088.
[3] TRILLA A, TRILLA G, DAER C.The 1918 "Spanish flu" in Spain[J]. Clin Infect Dis, 2008, 47(5): 668-673.
[4] CHEN BC, CHEN LS.Research status and development trend of antiviral drugs[J]. Herald of Medicine(医药导报), 2011, 30(9): 1119-1124.
[5] YU HC, ZHANG W, JIN XL, et al.Analysis of 97 cases of adverse drug reactions induced by thioctic acid injection and its related factors[J]. Chinese Journal of Pharmacovigilance(中国药物警戒), 2018, 15(4): 52-55,59.
[6] Chinese Pharmacopoeia Commission.Pharmacopoeia of People's Republic of China 2020
(中华人民共和国药典2020年版), Vol Ⅱ[M] Vol Ⅱ[M]. Beijing: China Medical Science Press, 2020.
[7] U.S.Pharmacopoeia Convention. U.S. Pharmacopoeia 43[M]. The United States Pharmacopeial Convention, 2020.
[8] European Pharmacopoeia Commission.European Pharma-copoeia[M]. 10.0 edition. Strasbourg: European Directorate for Quality Medicines, 2019.
[9] Pharmaceuticals and Medical Devices Agency of Japan. The Japanese Pharmacopoeia[M]. 17th ed. Tokyo: the Ministry of Health, Labor and Welfare, 2016.
[10] LO MK, FELDMANN F, GARY JM, et al. Remdesivir (GS-5734) protects African green monkeys from Nipah virus challenge[J]. Sci Transl Med, 2019, 11(494): eaau9242.
[11] LAMB YN.Remdesivir: first approval[J]. Drugs, 2020, 80(13): 1355-1363.
[12] ZHANG ST, NI MX, RUAN QP.Enzymatic synthesis of nucleotide drugs[J]. Progress in Pharmaceutical Sciences(药学进展), 2005, 29(2): 56-62.
[13] WANG L, BUCHANAN S, MEYERHOFF ME.Detection of high-charge density polyanion contaminants in biomedical heparin preparations using potentiometric polyanion sensors[J]. Anal Chem, 2008, 80(24): 9845-9847.
[14] HU CQ.Developments on analysis of polymers of B-lactam antibiotics[J]. Chinese Journal of New Drugs(中国新药杂志), 2008, 17(24): 2098-2102.
[15] OUYANG Q, SHEN XX.HPLC determination of emtricitabine enantiomer by chirality column[J]. Chin J Pharm Anal(药物分析杂志), 2007, 27(11): 1698-1700.
[16] ZHU GG.Determination of the related substances in vidarabine monophosphate for injection by HPLC[J]. Evaluation and Analysis of Drug-use in Hospitals of China(中国医院用药评价与分析), 2015, 15(7): 857-859.
[17] JIAO XW, LIANG WY.Determination of related substances in vidarabine monophosphate for injection by HPLC[J]. China Pharmacist(中国药师), 2015, 18(4): 652-655.
[18] BAKER MM, HAMMAD SF, BELAL TS.Development and validation of a versatile HPLC-DAD method for simultaneous determination of the antiviral drugs daclatasvir, ledipasvir, sofosbuvir and ribavirin in presence of seven potential impurities. Application to assay of dosage forms and dissolution studies[J]. Drug Dev Ind Pharm, 2019, 45(7): 1111-1119.
[19] ICH steering committee. ICH harrnonised tripartite guideline:Impurities in new drug products: Q3B (R2) [EB/OL]. (2006-06)[2021-08-31].https://www.ema.europa.eu/en/documents/scientific-guideline/ich-q-3-b-r2-impurities-new-drug-products-step-5_en.pdf.[20] GAO M, YAN XD, JIN SZ, et al. Application of liquid chromatography-mass spectrometry in drug related substances analysis[J]. Drug Evaluation Research(药物评价研究), 2012, 35(1): 63-66.
[21] TAO L, HUANG F, SONG WF, et al.Determination of related substances in entecavir oral preparation by liquid chromatography-tandem mass spectrometry[J]. Journal of Instrumental Analysis(分析测试学报), 2014, 33(3): 362-366.
[22] CHEN D, KANG LJ, ZHANG L, et al.Determination of 9-propenyladenine in tenofovir disoproxil fumarate by LC-MS[J]. Chinese Journal of Pharmaceuticals(中国医药工业杂志), 2014, 45(10): 959-961.
[23] AL AZZAM KM, SAAD B, MAKAHLEAH A, et al.Assay and stability-indicating micellar electrokinetic chromatography method for the simultaneous determination of valacyclovir, acyclovir and their major impurity guanine in pharmaceutical formulations[J]. Biomed Chromatogr, 2010, 24(5): 535-543.
[24] CARVALHO AZ, EL-ATTUG MN, ZAYED SE, et al.Micellar electrokinetic chromatography method development for determination of impurities in ritonavir[J]. J Pharm Biomed Anal, 2010, 53(5): 1210-1216.
[25] ZHAO R.UPLC in pharmaceutical analysis[J]. Heilongjiang Medicine Journal(黑龙江医药), 2014, 27(2): 283-285.
[26] CHU WM.Study of UPLC method on related substances in aciclovir[J]. Guangzhou Chemical Industry(广州化工), 2015, 43(23): 172-175.
[27] SHEN J, WU QH, CHEN YH, et al.Drug use and transfusion safety of blood donors[J]. Chinese Journal of Pharmacovigilance(中国药物警戒), 2020, 17(4): 249-252, 256.
[28] US Food and Drug Administration. Liquid chromatography-high resolution mass spectrometry (LC-HRMS) method for the determination of six nitrosamine impurities in ARB drugs[EB/OL]. (2019-05-21)[2021-08-31]. https://www.fda.gov/media/125478/download.
[29] LIU KL, LIANG JW, WANG S, et al.Study on the quantitative structure-genetic toxicity relationships of pyrrolizidine alkaloids[J]. Chinese Journal of Pharmacovigilance(中国药物警戒), 2019, 16(6): 321-324.
[30] LIU X, LI C, HAN H, et al.Advances on genotoxic impurities of sulfonate esters in pharmaceuticals[J]. J Se Pu, 2018, 36(10): 952-961.
[31] SZEKELY G, AMORES DSM, GIL M, et al.Genotoxic impurities in pharmaceutical manufacturing: sources, regulations, and mitigation[J]. Chem Rev, 2015, 115(16): 8182-8229.
[32] WUTZLER P, THUST R.Genetic risks of antiviral nucleoside analogues--a survey[J]. Antiviral Res, 2001, 49(2): 55-74.
[33] JIANG L, WU X, HE F, et al.Genetic evidence for genotoxic effect of entecavir, an anti-hepatitis B virus nucleotide analog[J]. PLoS One, 2016, 11(1): e0147440.
[34] VENUGOPAL N, VIJAYA BRA, MADHAVI G.Development and validation of a systematic UPLC-MS/MS method for simultaneous determination of three phenol impurities in ritonavir[J]. J Pharm Biomed Anal, 2014, 90: 127-133.
[35] 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.
[36] KAKADIYA PR, CHANDRASHEKHAR TG, GANGULY S.Low level determinations of methyl methanesulfonate and ethyl methanesulfonate impurities in emtricitabine active pharmaceutical ingredient by LC/MS/MS using electrospray ionization[J]. Anal Chem Insights, 2011, 6: 21-28.
[37] LIU B, ZHANG T, HUANG L, et al.Determination of 7 N- nitrosoamines in metformin hydrochloride sustained release tablets by LCHRMS[J]. Chinese Journal of Pharmacovigilance(中国药物警戒), 2021, 18(5): 454-458, 468.
[38] HU CQ.Current status and prospects of chemical impurity control[J]. SCIENTIA SINICA Chimica(中国科学:化学), 2010, 40(6): 679-687.