Low-level determination of 4-chlorobutyl-(S)-[4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxy-but-3yn-2-yl)phenyl] carbamate (4-CTHC) in efavirenz drug substance by LC-MS.
LC-MS
LOD
LOQ
RSD
efavirenz
related substances
validation
Journal
Biomedical chromatography : BMC
ISSN: 1099-0801
Titre abrégé: Biomed Chromatogr
Pays: England
ID NLM: 8610241
Informations de publication
Date de publication:
Jul 2021
Jul 2021
Historique:
revised:
26
01
2021
received:
08
08
2020
accepted:
05
02
2021
pubmed:
19
2
2021
medline:
6
7
2021
entrez:
18
2
2021
Statut:
ppublish
Résumé
A rapid, simple, sensitive, and selective liquid chromatography-tandem mass spectrometry (LC-MS) test method was developed and validated for the trace level determination of 4-chlorobutyl-(S)-[4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxy-but-3yn-2-yl)phenyl] carbamate (4-CTHC). 4-CTHC is a potential genotoxic impurity in efavirenz drug substance and the acceptable level is 2.5 μg ml
Substances chimiques
Alkynes
0
Benzoxazines
0
Carbamates
0
Cyclopropanes
0
efavirenz
JE6H2O27P8
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e5086Subventions
Organisme : Department of Chemistry, School of Science, GITAM (Deemed to be University) Hyderabad
Informations de copyright
© 2021 John Wiley & Sons, Ltd.
Références
Andries, K., Azijn, H., Thielemans, T., Ludovici, D., Kukla, M., Heeres, J., Janssen, P., De Corte, B., Vingerhoets, J., Pauwels, R., & de Béthune, M. P. (2004). TMC125, a novel next-generation nonnucleoside reverse transcriptase inhibitor active against nonnucleoside reverse transcriptase inhibitor-resistant human immunodeficiency virus type 1. Antimicrobial Agents and Chemotherapy, 48, 4680-4686.
Ashok, K. P., Dongala, T., & Katakam, L. N. R. (2020). QbD based development of HPLC method for simultaneous quantification of telmisartan and hydrochlorothiazide impurities in tablets dosage form. Practical Laboratory Medicine, 21, e00169.
Bartos, D., & Gorog, S. (2008). Recent advances in the impurity profiling of drugs. Current Pharmaceutical Analysis, 4, 215-230.
Bhargavi, D., Rao, B. B., Kiran, G., Gouthami, T., & Bakshi, V. (2017). Method development and validation for related impurities of efavirenz by RP-HPLC method. Analytical Chemistry Letters, 7(5), 737-747.
Colón, I., & Richoll, S. M. (2005). Determination of methyl and ethyl esters of methane sulfonic, benzene sulfonic and p-toluenesulfonic acids in active pharmaceutical ingredients by solid-phase micro extraction (SPME) coupled to GC/SIM-MS. Journal of Pharmaceutical and Biomedical Analysis, 39(3-4), 477-485.
De Aquino Ribeiro, J. A., De Campos, L. M. M., Alves, R. J., Lages, G. P., & Pianetti, G. A. (2007). Efavirenz related compound preparation by hydrolysis procedure: Setting reference standards for chromatographic purity analysis. Journal of Pharmaceutical and Biomedical Analysis, 43(1), 298-303. https://doi.org/10.1016/j.jpba.2006.06.010
Dongala, T., Katari, N. K., Palakurthi, A. K., & Jonnalagadda, S. B. (2019a). Development and validation of a generic RP-HPLC PDA method for the simultaneous separation and quantification of active ingredients in cold and cough medicines. Biomedical Chromatography, 33(11), e4641. https://doi.org/10.1002/bmc.4641
Dongala, T., Katari, N. K., Palakurthi, A. K., & Jonnalagadda, S. B. (2019b). Stability-indicating HPLC method for simultaneous quantification of 14 impurities in excedrin tablet formulations and identification of new impurity by LC-MS in accelerated stability studies. Biomedical Chromatography, 33(10), e4608. https://doi.org/10.1002/bmc.4608
Dr Sol Bobst (ToxSci Advisors LLC), Gowri Sukumar (Iterion Therapeutics). (2019). Genotoxic impurities in pharmaceutical products. https://www.europeanpharmaceuticalreview.com/content_author/dr-sol-bobst-toxsci-advisors-llc/
Dudhipala, N., & Janga, K. Y. (2017). Lipid nanoparticles of zaleplon for improved oral delivery by Box-Behnken design: Optimization, in vitro and in vivo evaluation. Drug Development and Industrial Pharmacy, 43(7), 1205-1214. https://doi.org/10.1080/03639045.2017.1304957
Dudhipala, N., Narala, A., Suram, D., & Janga, K. Y. (2016). Biopharmaceutical and preclinical studies of zaleplon as semisolid dispersions with self-emulsifying lipid surfactants for oral delivery. International Journal of Pharmaceutical Sciences and Nanotechnology, 9(1), 3102-3111.
EMEA. (2006). Committee for Medical products for Human Use, Guidelines on the Limits of Genotoxic Impurities. CPMP/SWP/5199/02. https://www.ema.europa.eu/en/documents/scientific-guideline/guideline-limits-genotoxic-impurities_en.pdf
Glowienke, S., Frieauff, W., Allmendinger, T., Martus, H. J., Suter, W., & Mueller, L. (2005). Structure-activity considerations and in vitro approaches to assess the genotoxicity of 19 methane-benzene- and toluene sulfonic acid esters. Mutation Research, 581, 23-34. https://doi.org/10.1016/j.mrgentox.2004.10.004
ICH. (2003). Harmonized Tripartite Guideline Stability Testing of New Drug Substances and Products Q1A(R2), (accessed 9 October 2018), https://www.ich.org/fileadmin/PublicWebSite/ICHProducts/Guidelines/Quality/Q1AR2/Step4/Q1AR2Guideline.pdf
ICH. (2005). ICH Harmonized Tripartite Guideline Validation of Analytical Procedures: Text and Methodology Q2(R1), (accessed 9 October 2018). https://www.ich.org/fileadmin/PublicWebSite/ICHProducts/Guidelines/Quality/Q2R1/Step4/Q2R1Guideline.pdf
Jaishetty, N., Palanisamy, K., Maruthapillai, A., & Jaishetty, R. (2015). Trace level quantification of the (−) 2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluoro-3-butyn-2-ol genotoxic impurity in efavirenz drug substance and drug product using LC-MS/MS. Scientia Pharmaceutica, 84, 456-466. https://doi.org/10.3390/scipharm84030456
Janga, K. Y., Shadambikar, G., Sawant, S., & Murthy, S. N. (2018). Photostability issues in pharmaceutical dosage forms and photostabilization. AAPS PharmSciTech, 19(1), 48-59. https://doi.org/10.1208/s12249-017-0869-z
Kamberi, M., Riley, C. M., Ma, S. X., & Chen, W. C. H. (2004). A validated, sensitive HPLC method for the determination of trace impurities in acetaminophen drug substance. Journal of Pharmaceutical and Biomedical Analysis, 34, 123-128. https://doi.org/10.1016/j.japna.2003.08.015
Katakam, L. N. R., & Dongala, T. (2020). Quality by design with design of experiments approach for the development of a stability-indicating LC method for benzonatate and its impurities in liquid oral dosage form. Separation Science Plus, 3(7), 276-285. https://doi.org/10.1002/sscp.202000023
Kawai, H., Kitayama, T., Tokunaga, E., & Shibata, N. (2011). A new synthetic approach to efavirenz through enantioselective trifluoromethylation by using the Ruppert-Prakash reagent. European Journal of Organic Chemistry, 2011, 5959-5961. https://doi.org/10.1002/ejoc.201101038
Komala, D. R., Janga, K. Y., Jukanti, R., & Bandari, S. (2015). Competence of raloxifene hydrochloride loaded liquisolid compacts for improved dissolution and intestinal permeation. Journal of Drug Delivery Science and Technology, 30(A), 232-241. https://doi.org/10.1016/j.jddst.2015.10.020
Kumar, P., Dwived, S., & Kushnoor, A. (2011). Validation and stability of RP-HPLC method for the determination of efavirenz as bulk drug and in pharmaceutical formulations. International Journal of Pharma and Bio Sciences, 2, 220-231.
Lakshmi, N. R. K., Dongala, T., & Ettaboina, S. K. (2020). Novel stability indicating UHPLC method development and validation for simultaneous quantification of hydrocortisone acetate, pramoxine hydrochloride, potassium sorbate and sorbic acid in topical cream formulation. Talanta Open, 1, 100004. https://doi.org/10.1016/j.talo.2020.100004
Lakshmi, N. R. K., & Padmaja, R. K. (2010). Simultaneous estimation of fluticasone propionate, azelastine hydrochloride, phenylethyl alcohol and benzalkonium chloride by RP-HPLC method in nasal spray preparations. International Journal of Research in Pharmaceutical Sciences, 1, 473-480.
Lakshmi, N. R. K., & Padmaja, R. K. (2014). Development and validation of a stability-indicating LC method for simultaneous determination of related compounds of guaifenesin, terbutaline sulfate and ambroxol HCl in cough syrup formulation. Journal of Saudi Chemical Society, 18, 593-600. https://doi.org/10.1016/j.jscs.2012.01.006
Lakshmi, N. R. K., & Padmaja, R. K. (2015). Stability-indicating method for simultaneous determination of polar and non-polar related compounds of zidovudine in drug substance and drug product tablet form. International Journal of Research in Pharmaceutical Sciences, 6, 5-14.
Modhave, Y., Shahapure, P., Khuroo, A., Kumar, A., & Pillai, M. (2016). Bioanalytical method transfer from the API 3200 TM system to the SCIEX triple quad TM 3500 system and the quantitative bioanalysis of efavirenz. Drug Discovery and Development, 1-6.
Montgomery, E. R., Edmanson, A. L., Cook, S. C., & Hovsepian, P. K. (2001). Development and validation of a reverse-phase HPLC method for analysis of efavirenz and its related substances in the drug substance and in a capsule formulation. Journal of Pharmaceutical and Biomedical Analysis, 25(2), 267-284. https://doi.org/10.1016/S0731-7085(00)00495-7
Mulla, S., Mukhopadhyay, R. N., Kulkarni, S. R., Bhure, S., & Iyer, K. (2014). Synthesis, isolation and characterization of efavirenz in-process impurity due to the presence of tetrahydrofuran as solvent. International Journal of Pharmacy and Pharmaceutical Sciences, 6(1), 426-431.
Pinto, E. C., Dolzan, M. D., Cabral, L. M., Armstrong, D. W., & Sousa, V. P. (2016). Topiramate: A review of analytical approaches for the drug substance, its impurities and pharmaceutical formulations. Journal of Chromatographic Science, 54, 280-290.
Qiu, F., & Norwood, D. L. (2007). Identification of pharmaceutical impurities. Journal of Liquid Chromatography and Related Technologies, 30, 877-935.
Reddiah, C. V., Devi, P. R., Mukkanti, K., & Srinivasu, P. (2017). Development and validation of stability indicating HPLC method for combination tablet dosage form of efavirenz, lamivudine and tenofovir in tablet. International Journal of Pharmaceutical and Phytopharmacological Research, 2, 40-45.
Saira, M., Nath, M. R., Ramkrishana, K. S., Sudesh, B., & Krishnan, I. (2014). Synthesis, isolation and characterization of efavirenz in-process impurity due to the presence of tetrahydrofuran as solvent. International Journal of Pharmacy and Pharmaceutical Sciences, 6, 426-431.
Seshachalam, U., Narasimha Rao, D. V. L., & Chandrasekhar, K. B. (2008). Validated enantiospecific LC method for determination of (R)-enantiomer impurity in (S)-efavirenz. International Journal of Pharmacy Science, 63(2), 107-109.
Sluis-Cremer, N., & Tachedjian, G. (2008). Mechanisms of inhibition of HIV replication by nonnucleoside reverse transcriptase inhibitors. Virus Research, 134, 147-156.
Subramanian, V. B., Katari, N. K., Dongala, T., & Jonnalagadda, S. B. (2020). Stability-indicating RP-HPLC method development and validation for determination of nine impurities in apixaban tablet dosage forms. Robustness study by quality by design approach. Biomedical Chromatography, 34(1), e4827.
Thirupathi, D., & Palakurthi, A. K. (2019). Stability-indicating LC method for the simultaneous determination of methyl paraben, propyl paraben, butylated hydroxytoluene and alpha-tocopherol contents in marijuana capsules. Journal of the Iranian Chemical Society, 17, 631-638.
Thirupathi, D., Palakurthi, A. K., Vytla, V., & Katari, N. K. (2019). A novel UPLC-PDA isocratic method for the quantification fulvestrant in oil-based pre-filled syringe injection matrix formulations. Journal of Analytical Science and Technology, 10(1), 12.