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Degradation Studies of Tadalafil: Identification, Isolation and Structure Characterization of Stress Degradation Product using LC-MS, Mass Mediated Prep-HPLC, NMR, HRMS
Corresponding Author(s) : Himabindu Gandham
Asian Journal of Chemistry,
Vol. 33 No. 4 (2021): Vol 33 Issue 4
Abstract
The degradation behaviour of tadalafil performed under different stress conditions according to International Conference on Harmonization guidelines (ICH) was studied. A novel degradation product (DP) of tadalafil was observed only in acidic condition. An isolated degradation product [(R)-3-((1H-indol-3-yl)methyl)-4-(benzo[d][1,3]dioxole-5-carbonyl)-1-methylpiperazine-2,5-dione)] was identified by UPLC-MS technique and its structure was confirmed by high resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) studies. Acquity BEH C18 (50 mm × 2.1 mm, 1.7 μm) column was used in LC-MS, gradient run was performed with mobile phases 0.05% formic acid in acetonitrile and 0.05% formic acid in water, flow rate was 0.6 mL/min. The sample was diluted with acetonitrile and water.
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- ICH,Stability Testing of New Drug Substances and Products Q1A (R2), International Conference on armonization, IFMPA, Geneva (2003).
- ICH Q2 (R1); Validation of Analytical Procedures: Text and Methodology (2005).
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- D.V. Subba Rao, P. Radhakrishnanand and V. Himabindu, Chromatographia, 67, 183 (2008); https://doi.org/10.1365/s10337-007-0478-1
- B. Prasanna Reddy, K. Amarnadh Reddy and M.S. Reddy, Res. Pharm. Biotechnol., 2, 1 (2010).
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References
NIH Consensus Conference Impotence: NIH Consensus Development Panel on Impotence, JAMA, 270, 83 (1993).
A.D. Borthwick, Chem. Rev., 112, 3641 (2012); https://doi.org/10.1021/cr200398y
D. Sriram, Medicinal Chemistry, Pearson Education India, p. 635 (2010).
J.E. Ferguson III and C.C. Carson III, Arab J. Urol., 11, 222 (2013); https://doi.org/10.1016/j.aju.2013.07.009
R.M. Coward and C.C. Carson, Ther. Clin. Risk Manag., 4, 1315 (2008); https://doi.org/10.2147/tcrm.s3336
Y. Wang, Y. Bao, J. Liu, L. Duan and Y. Cui, Low. Urin. Tract Symptoms, 10, 84 (2018); https://doi.org/10.1111/luts.12144.
FDA approves tadalafil for pulmonary arterial hypertension; Drugs.com. Retrieved 2014-11-13.
ICH,Stability Testing of New Drug Substances and Products Q1A (R2), International Conference on armonization, IFMPA, Geneva (2003).
ICH Q2 (R1); Validation of Analytical Procedures: Text and Methodology (2005).
S.W. Baertschi, M.K. Alsante and R.A. Reed, Pharmaceutical Stress Testing: Predicting Drug Degradation, Informa Healthcare: New York, ed. 2 (2011).
D.V. Subba Rao, P. Radhakrishnanand and V. Himabindu, Chromatographia, 67, 183 (2008); https://doi.org/10.1365/s10337-007-0478-1
B. Prasanna Reddy, K. Amarnadh Reddy and M.S. Reddy, Res. Pharm. Biotechnol., 2, 1 (2010).
A. Unnisa, Y. Babu, S.K. Suggu and S. Chaitanya, J. Appl. Pharm. Sci., 4, 72 (2014).
A. Kavitha, D. Vijaya Durga, S. Himabindu, K. Eshvendar, N. Khaleel and D. Pani Kumar, Asian J. Pharm. Clin. Res., 6(Suppl. 2), 326 (2013).