Analytical Methods for Determination of Apremilast from Bulk, Dosage Form and Biological Fluids: A Critical Review

References

• An, I.; Harman, M.; Ibiloglu, I. Case Report Bullous Hemorrhagic Dermatosis Induced by Enoxaparin. Indian Dermatol. Online J 2018, 9, 347–350. DOI: 10.4103/idoj.IDOJ.
   Google Scholar
• Poole, R. M.; Ballantyne, A. D. Apremilast: First Global Approval. Drugs 2014, 74, 825–837. DOI: 10.1007/s40265-014-0218-4.
   PubMed Web of Science ®Google Scholar
• Om, A.; Hill, D.; Feldman, S. R. Chapter 7, Apremilast. In Therapy for Severe Psoriasis. 2014, 12. DOI: 10.1016/j.chtm.2016.07.032.
   Google Scholar
• Zerilli, T.; Ocheretyaner, E. Apremilast (Otezla): A New Oral Treatment for Adults with Psoriasis and Psoriatic Arthritis. PT. 2015, 40, 495–500.
   PubMedGoogle Scholar
• Monograph, P. PrOTEZLA® Apremilast. Celgene Corp. 2017, 1–55.
   Google Scholar
• De Luca, G.; Cariddi, A.; Campochiaro, C.; et al. Efficacy and Safety of Apremilast for Behçet’s Syndrome: A Real-Life Single-Centre Italian Experience. Rheumatology 2019. 59, 171–175. DOI: 10.1093/rheumatology/kez267.
   Google Scholar
• Maloney, N. J.; Zhao, J.; Tegtmeyer, K.; Lee, E. Y.; Cheng, K. Off-Label Studies on Apremilast in Dermatology: A Review. J. Dermatol. Treat. 2019, 1–10. DOI: 10.1080/09546634.2019.1589641.
   PubMed Web of Science ®Google Scholar
• Saporito, R. C.; Cohen, D. J. Apremilast Use for Moderate-to-Severe Atopic Dermatitis in Pediatric Patients. Case Rep. Dermatol. 2016, 8, 179–184. DOI: 10.1159/000446836.
   PubMed Web of Science ®Google Scholar
• Abrouk, M.; Farahnik, B.; Zhu, T. H.; Nakamura, M.; Singh, R.; Lee, K.; Lucking, S.-M.; Blossom, J.; Liao, W.; Koo, J.; et al. Apremilast Treatment of Atopic Dermatitis and Other Chronic Eczematous Dermatoses. J. Am. Acad. Dermatol. 2017, 77, 177–180. DOI: 10.1016/j.jaad.2017.03.020.
   PubMed Web of Science ®Google Scholar
• Knuckles, M. L. F.; Levi, E.; Soung, J. Treating Moderate Plaque Psoriasis: prospective 6-Month Chart Review of Patients Treated with Apremilast. J. Dermatol. Treat. 2019, 30, 430–434. DOI: 10.1080/09546634.2018.1528326.
   PubMed Web of Science ®Google Scholar
• Majid, I.; Imran, S.; Batool, S. Apremilast is Effective in Controlling the Progression of Adult Vitiligo: A Case Series. Dermatol. Ther. 2019. 32. DOI: 10.1111/dth.12923.
   PubMed Web of Science ®Google Scholar
• Navarro-Triviño, F. J.; Cuenca-Barrales, C.; Vega-Castillo, J. J.; Ruiz-Villaverde, R. Chronic Hand Eczema and Hepatogenic Pruritus with Good Response to Apremilast. Dermatol. Ther. 2019, 32, e12879. DOI: 10.1111/dth.12879.
   Web of Science ®Google Scholar
• Narang, T.; Kaushik, A.; Dogra, S. Apremilast in Chronic Recalcitrant Erythema Nodosum Leprosum: A Report of Two Cases. Br. J. Dermatol. 2019, 0–2. DOI: 10.1111/bjd.18233.
   Web of Science ®Google Scholar
• Calleja Algarra, A.; Aragón Miguel, R.; Velasco Tamariz, V.; et al. Apremilast as a New Treatment Option for Acrodermatitis Continua of Hallopeau. Australas. J. Dermatol. 2019, 2. DOI: 10.1111/ajd.12990.
   Web of Science ®Google Scholar
• Okazaki, S.; Osawa, R.; Nakajima, H.; Nakajima, K.; Sano, S. Favorable Response to Apremilast in a Patient with Refractory Psoriasis Verrucosa. J. Dermatol. 2019, 46, 544–547. DOI: 10.1111/1346-8138.14877.
   PubMed Web of Science ®Google Scholar
• Eto, A.; Nakao, M.; Furue, M. Three Cases of Palmoplantar Pustulosis Successfully Treated with Apremilast. J. Dermatol. 2019, 46, e29–e30. DOI: 10.1111/1346-8138.14516.
   PubMed Web of Science ®Google Scholar
• Siyuan, N.; Jing Junzhi, G. L. Stable Crystal Form II of the Apremilast, Not Containing Solvate, and Method of Its Receiving. RU Patent 000,2673,889, December 3, 2018.
   Google Scholar
• Monika, O.; Piotr, G.; Przemyslaw, S.; Dominika, P.; Marcin, S.; Arkadiusz, M. Crystalline Forms of Apremilast. EP 345,520,9A1, March 3, 2019.
   Google Scholar
• Bubna, A. Apremilast: A Dermatologic Perspective. Indian J. Drugs Dermatol. 2016, 2, 75. DOI: 10.4103/2455-3972.196166.
   Google Scholar
• Thomas, J.; Jacob, S. E. Apremilast. J. Dermatol. Nurses Assoc. 2017, 9, 154–156. DOI: 10.1097/JDN.0000000000000308.
   Web of Science ®Google Scholar
• Pharmacology, C. Center for Drug Evaluation and Clinical Pharmacology and Biopharmaceutics Review (S). 2013, 1–183. Application No.: NDA 205437.
   Google Scholar
• Landge, S. B.; Dahale, S. B.; Jadhav, S. A.; Solanki, P. V.; Bembalkar, S. R.; Mathad, V. T. Development and Validation of Stability Indicating Rapid RP-LC Method for Determination of Process and Degradation Related Impurities of Apremilast, an anti-Inflammatory Drug. AJAC. 2017, 08, 380–394. DOI: 10.4236/ajac.2017.86029.
   Google Scholar
• Druk Bank Apremilast. https://www.drugbank.ca/drugs/DB05676. Accessed September 10, 2019.
   Google Scholar
• EMA. Assessment Report : Otezla. 2014;44(November). http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/003746/WC500182629.pdf.
   Google Scholar
• Chaudhari, S. R.; Shirkhedkar, A. A. Design of Experiment Avenue for Development and Validation of RP-HPLC-PDA Method for Determination of Apremilast in Bulk and in in-House Tablet Formulation. J. Anal. Sci. Technol. 2019, 10, 10. DOI: 10.1186/s40543-019-0170-8.
   Web of Science ®Google Scholar
• Shakeel, F.; Haq, N.; Alanazi, F. K.; Alsarra, I. A. Solubility and Thermodynamic Function of Apremilast in Different (Transcutol + Water) Cosolvent Mixtures: Measurement, Correlation and Molecular Interactions. J. Ind. Eng. Chem. 2017, 56, 99–107. DOI: 10.1016/j.jiec.2017.07.002.
   Web of Science ®Google Scholar
• Shakeel, F.; Haq, N.; Alanazi, F. K.; Alsarra, I. A. Solubility and Thermodynamics of Apremilast in Different Mono Solvents: Determination, Correlation and Molecular Interactions. Int. J. Pharm. 2017, 523, 410–417. DOI: 10.1016/j.ijpharm.2017.03.067.
   PubMedGoogle Scholar
• Madan, J.; Pawar, A.; Patil, R.; Awasthi, R.; Dua, K. Preparation, Characterization and in Vitro Evaluation of Tablets Containing Microwave-Assisted Solid Dispersions of Apremilast. Polym. Med. 2019, 48, 17–24. DOI: 10.17219/pim/99801.
   Google Scholar
• Wang, F. Y.; Zhang, Q.; Zhang, Z.; Gong, X.; Wang, J. R.; Mei, X. Solid-State Characterization and Solubility Enhancement of Apremilast Drug-Drug Cocrystals. CrystEngComm 2018, 20, 5945–5948. DOI: 10.1039/C8CE00689J.
   Web of Science ®Google Scholar
• Jirát, J.; Ondo, D.; Babor, M.; Ridvan, L.; Šoóš, M. Complex Methodology for Rational Design of Apremilast-Benzoic Acid Co-Crystallization Process. Int. J. Pharm. 2019, 570, 118639. DOI: 10.1016/j.ijpharm.2019.118639.
   PubMedGoogle Scholar
• Siddiqui, M. R.; AlOthman, Z. A.; Rahman, N. Analytical Techniques in Pharmaceutical Analysis: A Review. Arab. J. Chem. 2017, 10, S1409–S1421. DOI: 10.1016/j.arabjc.2013.04.016.
   Web of Science ®Google Scholar
• Moosavi, S. M.; Ghassabian, S. Linearity of Calibration Curves for Analytical Methods: A Review of Criteria for Assessment of Method Reliability, Calibration and Validation of Analytical Methods - A Sampling of Current Approaches, Mark T. Stauffer, IntechOpen, 2018. DOI: 10.5772/intechopen.72932.
   Google Scholar
• Chen, L. G.; Wang, Z.; Wang, S.; Li, T.; Pan, Y.; Lai, X. Determination of Apremilast in Rat Plasma by UPLC-MS-MS and Its Application to a Pharmacokinetic Study. J. Chromatogr. Sci. 2016, 54, 1336–1340. DOI: 10.1093/chromsci/bmw072.
   PubMed Web of Science ®Google Scholar
• Iqbal, M.; Ezzeldin, E.; Al-Rashood, S. T. A.; Imam, F.; Al-Rashood, K. A. Determination of Apremilast in Rat Plasma by UPLC-MS/MS in ESI-Negative Mode to Avoid Adduct Ions Formation. Bioanalysis 2016, 8, 1499–1508. DOI: 10.4155/bio-2016-0098.
   PubMed Web of Science ®Google Scholar
• Sridhar, T.; Edem Balaraju, L. Chromatographic Method Development and Validation of Assay of Apremilast in Bulk and Tablet Dosage Form. EJBPS. 2016, 3, 348–353.
   Google Scholar
• Chakravarthy, V. A.; Bb, V. S.; A, P. K. Development and Validation of Ultraviolet-Visible Spectroscopic Method for the Estimation of Assay of Sugammadex Sodium, Apremilast, Riociguat, and Vorapaxar Sulfate Drugs in Active Pharmaceutical Ingredient Form. Asian J. Pharm. Clin. Res. 2017, 10, 241–250. DOI: 10.22159/ajpcr.2017.v10i2.15502.
   Google Scholar
• Panchumarthy, R.; Sulthana S.; Babu, PS. Development and Validation of Stability-Indicating UV Spectrophotometric Method for Determination of Apremilast in Bulk and Pharmaceutical Dosage Form. Indian J Res Pharm Biotechnol. 2017, 5(1), 47–53.
   Google Scholar
• Intwala, J. K.; Doshi, D. B. Development and Validation of Sophisticated Analytical Method for the Estimation of Apremilast. Pharma Sci. Monit. 2017, 8, 267–276. http://www.pharmasm.com/current_issue.php?archive=55.
   Google Scholar
• Tanaji, D.; Nandgude, P. Formulation and Development Modified Release Apremilast Pellets. Asian J. Pharm. Free Full Text Artic. Asian J. Pharm. 2019, 12, 6–12. DOI: 10.22377/ajp.v12i04.2915.
   Google Scholar
• Bhole, R. P.; Naksakhare, S. R.; Bonde, C. G. A Stability Indicating HPTLC Method for Apremilast and Identification of Degradation Products Using MS/MS. Int. j. pharm. sci. res. 2019, 11, 1861–1869.
   Google Scholar
• Xiong, K.; Ma, X.; Cao, N.; Liu, L.; Sun, L.; Zou, Q.; Wei, P. Identification, Characterization and HPLC Quantification of Impurities in Apremilast. Anal. Methods 2016, 8, 1889–1897. DOI: 10.1039/C5AY01759A.
   Web of Science ®Google Scholar
• Anwer, M. K.; Mohammad, M.; Ezzeldin, E.; Fatima, F.; Alalaiwe, A.; Iqbal, M. Preparation of Sustained Release Apremilast-Loaded PLGAlga Nanoparticles: In Vitro Characterization and in Vivo Pharmacokinetic Study in Rats. IJN. 2019, 14, 1587–1595. DOI: 10.2147/IJN.S195048.
   Google Scholar
• Priyanka, N.; Neeraja, P.; Mangilal, T.; Kumar, M. R. Formulation and Evaluation of Gel Loaded with Microspheres of Apremilast for Transdermal Delivery System. Asian j. pharm. clin. res. 2019, 12, 411–417.
   Google Scholar
• Hoffmann, M.; Kumar, G.; Schafer, P.; Cedzik, D.; Capone, L.; Fong, K.-L.; Gu, Z.; Heller, D.; Feng, H.; Surapaneni, S.; et al. Disposition, Metabolism and Mass Balance of [14C]Apremilast following Oral Administration. Xenobiotica 2011, 41, 1063–1075. DOI: 10.3109/00498254.2011.604745.
   PubMed Web of Science ®Google Scholar
• Tang, M.; Hu, P.; Huang, S.; Zheng, Q.; Yu, H.; He, Y. Development of an Extended-Release Formulation for Apremilast and a Level A in Vitro–in Vivo Correlation Study in Beagle Dogs. Chem. Pharm. Bull. 2016, 64, 1607–1615. DOI: 10.1248/cpb.c16-00519.
   PubMed Web of Science ®Google Scholar
• Liu, Y.; Zhou, S.; Assaf, M.; Nissel, J.; Palmisano, M. Impact of Renal Impairment on the Pharmacokinetics of Apremilast and Metabolite M12. Clin. Pharmacol. Drug Dev. 2016, 5, 469–479. DOI: 10.1002/cpdd.256.
   PubMed Web of Science ®Google Scholar
• Lu, Y.; Shen, X.; Hang, T.; Song, M. Identification and Characterization of Process-Related Substances and Degradation Products in Apremilast: Process Optimization and Degradation Pathway Elucidation. J. Pharm. Biomed. Anal. 2017, 141, 70–78. DOI: 10.1016/j.jpba.2017.03.067.
   PubMed Web of Science ®Google Scholar
• Badhe, P.; Aher, S.; Saudagar, R. B. Analytical Method of Apremilast : A Review. Journal of Drug Delivery and Therapeutics. 2019, 9, 1116–1119. DOI: 10.22270/jddt.v9i3-s.3144
   Google Scholar
• Foroughbakhshfasaei, M.; Szabó, Z. I.; Tóth, G. Validated LC Method for Determination of Enantiomeric Purity of Apremilast Using Polysaccharide-Type Stationary Phases in Polar Organic Mode. Chromatographia 2018, 81, 1613–1621. DOI: 10.1007/s10337-018-3546-9.
   Web of Science ®Google Scholar
• Wu, Y. D.; Zhang, X. L.; Liu, X. H.; et al. The Preparation, Characterization, Structure and Dissolution Analysis of Apremilast Solvatomorphs. Acta Crystallogr. Sect. C Struct. Chem. 2017, 73, 305–313. DOI: 10.1107/S2053229617002984.
   Web of Science ®Google Scholar
• Kushwaha, A. S.; Repka, M. A.; Narasimha Murthy, S. A Novel Apremilast Nail Lacquer Formulation for the Treatment of Nail Psoriasis. AAPS PharmSciTech 2017, 18, 2949–2956. DOI: 10.1208/s12249-017-0776-3.
   PubMed Web of Science ®Google Scholar
• Chaudhari, S. R.; Shirkhedkar, A. A. Of Box-Behnken Design for Validation of High-Performance Thin-Layer Chromatography/Densitometry Method for Robustness Determination of Apremilast in Bulk and in House Tablets. PHME. 2017, 9, 09–15. DOI: 10.5530/phm.2018.1.3.
   Google Scholar
• Annapurna, M. M.; Pradhan, D. P.; Sushmitha, M. A New Stability Indicating RP-HPLC Method for the Determination of Apremilast-an Antirheumatic Drug. Res. J. Pharm. Technol. 2017, 10, 1160–1164. DOI: 10.5958/0974-360X.2017.00209.8.
   Google Scholar
• Shinde, P.; Shirke, S. D. An. Du, A Novel HPLC Method for Estimation of Genotoxic Impurity 3- Acetamidobenzene 1, 2 Dicarboxylic Acid in Key Starting Material 3-Acetamidopthalic Anhydride of Apremilast API. Indian Drugs 2018, 10, 42–46.
   Google Scholar
• Siouffi, A. M. High Performance Liquid Chromatography. Handbook Food Sci. Technol. 2005, 4, 859–900.
   Google Scholar
• Anerao, A.; Telange, V.; Bondre, N. International Journal of Current Medical and Pharmaceutical Stability-Indicating Related Substances Method of Apremilast by HPLC and Synthesis and Chracterization of Related Impurities Using Mass and NMR Spectroscopy. Int. J. Curr. Med. Pharm. Res. 2017, 3, 1378–1385.
   Google Scholar
• https://www.accessdata.fda.gov/scripts/cder/dissolution/dsp_SearchResults.cfm. Published 2017. Accessed September 23, 2019.
   Google Scholar