Structure elucidation of thermal degradation products of amlodipine

Devi, A. Siva Lakshmi; Rao, Yadunandana N.; Satish, M.; Jyothi, G.; Rao, K. Babu; Omdutt, T.

doi:10.1002/mrc.2022

Cited by 12 publications

(3 citation statements)

References 5 publications

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“…A few articles are available on photostability studies of AM, where the thermal degradation kinetics are reported from 0 h to 108 h [17] , [18] , [19] , [20] . There exists report on isolation and characterization of three thermal degradation products of AM, which were formed due to intramolecular reactions and cyclization [21] . Moreover, there are few reports on isolation and characterization of process-related impurities of AM and accelerated stability studies.…”

Section: Introductionmentioning

confidence: 99%

LC, MS n and LC–MS/MS studies for the characterization of degradation products of amlodipine

Tiwari¹,

Shah²,

Bhalani³

et al. 2015

Journal of Pharmaceutical Analysis

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In the present study, comprehensive stress testing of amlodipine (AM) was carried out according to International Conference on Harmonization (ICH) Q1A(R2) guideline. AM was subjected to acidic, neutral and alkaline hydrolysis, oxidation, photolysis and thermal stress conditions. The drug showed instability in acidic and alkaline conditions, while it remained stable to neutral, oxidative, light and thermal stress. A total of nine degradation products (DPs) were formed from AM, which could be separated by the developed gradient LC method on a C18 column. The products formed under various stress conditions were investigated by LC–MS/MS analysis. The previously developed LC method was suitably modified for LC–MS/MS studies by replacing phosphate buffer with ammonium acetate buffer of the same concentration (pH 5.0). A complete fragmentation pathway of the drug was first established to characterize all the degradation products using LC–MS/MS and multi-stage mass (MSn) fragmentation studies. The obtained mass values were used to study elemental compositions, and the total information helped with the identification of DPs, along with its degradation pathway.

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Section: Introductionmentioning

confidence: 99%

LC, MS n and LC–MS/MS studies for the characterization of degradation products of amlodipine

Tiwari¹,

Shah²,

Bhalani³

et al. 2015

Journal of Pharmaceutical Analysis

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“…The compound formed by the aromatization of the ring (pyridine derivative) is the only photoproducts known and described in the literature so far [16] , [17] , [18] . A few studies were performed for thermal degradation of amlodipine showing the formation of 3 [19] or 5 main transformation products [20] .…”

Section: Introductionmentioning

confidence: 99%

Phototransformation of Amlodipine: Degradation Kinetics and Identification of Its Photoproducts

et al. 2014

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Nowadays, monitoring focuses on the primary compounds and does not include degradation products formed during various biological and chemical processes. Transformation products may have the same effects to human health and the environment or sometimes they can be more toxic than the parent compound. Unfortunately, knowledge about the formation of degradation products is still limited, however, can be very important for the environmental risk assessment. Firstly, the photodegradation kinetic of amlodipine was investigated in two experimental conditions: during the exposure to solar radiation and during the exposure to the light emitted by the xenon lamp. In all cases degradation of amlodipine followed a pseudo-first-order kinetics. In the next step, identification of transformation products of amlodipine formed during the exposure to xenon lamp irradiation was performed using ultra high performance liquid chromatography quadrupole time-of-flight mass spectrometry (UHPLC-QTOF-MS). As a result sixteen photoproducts were identified, their structures were elucidated and ultimately the transformation pathway was proposed. Fifteen compounds (out of 16 photoproducts) were newly identified and reported here for the first time; some of those compounds were formed from the first photoproduct, amlodipine pyridine derivative. Several analytes were formed only in acidic or basic conditions. Furthermore, the occurrence of amlodipine and its identified degradation products was investigated in environmental waters. Only one out of 16 compounds was found in wastewater effluent. The possibility of the sorption of examined analytes to sewage sludge particles was discussed based on QSAR.

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“…1,4-Dihydropyridine substance frameworks forming an important class of Ca +2 channel blockers such as Nifedipin and Amlodipine are clinically significant antihypertensive drugs [1][2][3][4]. First synthesis of 1,4-dihydropyridine from an aldehyde, b-keto ester and an amine was described by Hä ntzsch in 1882 [5].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,4-dihydropyridine using microwave-assisted aza-Diels–Alder reaction and its application to Amlodipine

Lee

Kim

2011

Journal of Industrial and Engineering Chemistry

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Structure elucidation of thermal degradation products of amlodipine

Cited by 12 publications

References 5 publications

LC, MS n and LC–MS/MS studies for the characterization of degradation products of amlodipine

LC, MS n and LC–MS/MS studies for the characterization of degradation products of amlodipine

Phototransformation of Amlodipine: Degradation Kinetics and Identification of Its Photoproducts

Synthesis of 1,4-dihydropyridine using microwave-assisted aza-Diels–Alder reaction and its application to Amlodipine

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