Characterization of two new potential impurities of Valsartan obtained under photodegradation stress condition

Bianchini, Romina M.; Castellano, Patricia M.; Kaufman, Teodoro S.

doi:10.1016/j.jpba.2011.04.017

Cited by 19 publications

(15 citation statements)

References 25 publications

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“…Prior to chemical analysis, samples of the biodegradation test were filtered (cut-off 0.45 mm, Sartorius, Goettingen, Germany) in order to meet the conditions for DOC measurements, and measured continually over the course of the 28-day test period. Samples of the irradiation experiments were measured directly after irradiation for fixed time periods (2,4,8,16,32, 64 and 128 min).…”

Section: Doc Measurementmentioning

confidence: 99%

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Recalcitrant pharmaceuticals in the aquatic environment: a comparative screening study of their occurrence, formation of phototransformation products and their in vitro toxicity

Bergheim¹,

Gminski²,

Spangenberg³

et al. 2014

Environ. Chem.

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Environmental context. Many pharmaceuticals on the market have not undergone detailed evaluation for potential aquatic toxicity. We found that most tested pharmaceuticals were persistent, that phototransformation products were likely to be formed as a result of UV treatment of wastewater and that some transformation products were more toxic to bacteria than their precursor pharmaceutical compound. Thus UV treatment of wastewater does not seem appropriate to completely degrade or transform micropollutants into harmless compounds.Abstract. Data allowing for a complete environmental risk assessment of pharmaceuticals and their photoderatives in the environment are still scarce. In the present study, in vitro toxicity and both bio-and photopersistence of various pharmaceuticals (aciclovir, allopurinol, cetirizine, cimetidine, fluconazole, hydrochlorothiazide, lisinopril, phenytoin, primidone, ranitidine, sotalol, sulpiride, tramadol and valsartane) as well as their phototransformation products were evaluated in order to fill data gaps and to help prioritise them for further testing. Twelve out of the fourteen compounds investigated were found to be neither readily nor inherently biodegradable in the Organisation of Economic Cooperation and Development-biodegradability tests. The study further demonstrates that the photo-induced transformation of the pharmaceuticals was faster upon irradiation with a Hg lamp (UV light) than with a Xe lamp emitting a spectrum that mimics sunlight. Comparing the non-irradiated with the respective irradiated solutions, a higher acute and chronic toxicity against bacteria was found for the irradiated solutions of seven compounds (cetirizine, cimetidine, hydrochlorothiazide, ranitidine, sulpiride, tramadol and valsartane). No cyto-and genotoxic effects were found in human cervical (HeLa) and liver (Hep-G2) cells for any of the investigated compounds or their phototransformation products. This comparative study documents that phototransformation products can arise as a result of UV treatment of wastewater containing these pharmaceuticals. It further demonstrates that some phototransformation products may have a higher environmental risk potential than the respective parent compounds because some phototransformation products exhibited a higher bacterial toxicity.

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Section: Doc Measurementmentioning

confidence: 99%

“…A strong new signal with a corresponding [M þ H] þ ion of m/z 414 was detected in the LC-MS analysis for the 16-min sample but not for the 128-min sample. Recently, Bianchini et al [32] clarified the chemical structure of two PTPs of valsartane with one PTP showing the same signal with a corresponding m/z of 414…”

Section: Toxicitymentioning

confidence: 99%

Recalcitrant pharmaceuticals in the aquatic environment: a comparative screening study of their occurrence, formation of phototransformation products and their in vitro toxicity

Bergheim¹,

Gminski²,

Spangenberg³

et al. 2014

Environ. Chem.

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“…A similar ring‐forming process was observed during the photolysis of TES when its biphenyl 2‐carboxylic acid group was photocyclized to a benzo[ c ]chromen‐6‐one derivative (Fig. ) . The mechanism of the degradation was explained by the promotion of π electrons to a nonbonding orbital yielding two aryl radicals, and the attack by one of them on the adjacent carbonyl of the carboxyclic group, which resulted in a cyclized degradation product .…”

Section: Stability Studiesmentioning

confidence: 57%

“…Some authors concluded that this drug was photostable, even after irradiating at 254 nm for 10 days . Others noticed that VAS showed photolability and described two previously unknown degradates, detected by HPLC and identified by IR, NMR, and MS methods . Such differences may be explained by the fact that VAS was obtained from various sources and that different analytical methods were used.…”

Section: Stability Studiesmentioning

confidence: 99%

“…Degradation products were observed in solutions of VAS exposed to UV–Vis radiation from a metal halide lamp. The formation of DP‐3 resulted from light‐induced decarboxylation of VAS, whereas DP‐4 was formed from DP‐3 by further degradation of the tetrazole ring with the loss of nitrogen and cyclization onto the neighbor biphenyl moiety …”

Section: Stability Studiesmentioning

confidence: 99%

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Analysis of Sartans: A Review

Muszalska

Sobczak

Dołhań

et al. 2014

Journal of Pharmaceutical Sciences

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A Multivariate Curve Resolution Approach to the Study of the Degradation Kinetics of Valsartan under Photolytic and Acid Conditions

Bianchini

Kaufman

2013

Int J of Chemical Kinetics

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The analysis of UV‐spectrophotometric data with second‐order chemometrics techniques, including multivariate curve resolution with alternating least‐squares (MCR‐ALS) and hybrid hard‐ and soft MCR (HS‐MCR), was examined as an alternative tool for studying the kinetics of drug degradation under stress conditions, employing valsartan (VAL) as a model drug. Despite small structural and spectroscopic differences between VAL and its degradation products, MCR‐ALS and HS‐MCR were able to detect the generation of two photoneutral degradation products (DP‐1 and DP‐2) and a single acid hydrolysis product (DP‐3), providing good approximations to their pure spectra and concentration profiles, from which estimations of the kinetic profiles and rate constants were obtained. Kinetic models based on first‐order reactions explained the degradation processes. MCR‐ALS and HS‐MCR analyses yielded similar rate constants; however, the latter was capable of more properly fitting the experimental data to a kinetic model in the case of drug photolysis. The results were confirmed by comparison with data obtained by HPLC analysis of the degraded samples.

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Characterization of two new potential impurities of Valsartan obtained under photodegradation stress condition

Cited by 19 publications

References 25 publications

Recalcitrant pharmaceuticals in the aquatic environment: a comparative screening study of their occurrence, formation of phototransformation products and their in vitro toxicity

Recalcitrant pharmaceuticals in the aquatic environment: a comparative screening study of their occurrence, formation of phototransformation products and their in vitro toxicity

Analysis of Sartans: A Review

A Multivariate Curve Resolution Approach to the Study of the Degradation Kinetics of Valsartan under Photolytic and Acid Conditions

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