Photodegradation of novel oral anticoagulants under sunlight irradiation in aqueous matrices

Kinetics of photodegradation of novel oral anticoagulants dabigatran, rivaroxaban, and apixaban were studied under simulated solar light irradiation in purified, mineral, and river waters. Dabigatran and rivaroxaban underwent direct photolysis with polychromatic quantum yields of 2.2 × 10−4 and 4.4 ...

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Bibliographic Details
Published in:Chemosphere (Oxford) 2018-02, Vol.193, p.329-336
Main Authors: Yassine, Montaha, Fuster, Laura, Dévier, Marie-Hélène, Geneste, Emmanuel, Pardon, Patrick, Grélard, Axelle, Dufourc, Erick, Al Iskandarani, Mohamad, Aït-Aïssa, Selim, Garric, Jeanne, Budzinski, Hélène, Mazellier, Patrick, Trivella, Aurélien S.
Format: Article
Language:English
Subjects:
Apixaban
Chemical Sciences
Dabigatran
Ecotoxicology
Life Sciences
Material chemistry
Photolysis
Rivaroxaban
Solar light irradiation
Surface water
Toxicology
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Summary:Kinetics of photodegradation of novel oral anticoagulants dabigatran, rivaroxaban, and apixaban were studied under simulated solar light irradiation in purified, mineral, and river waters. Dabigatran and rivaroxaban underwent direct photolysis with polychromatic quantum yields of 2.2 × 10−4 and 4.4 × 10−2, respectively. The direct photodegradation of apixaban was not observed after 19 h of irradiation. Kinetics of degradation of rivaroxaban was not impacted by the nature of the aqueous matrix while photosensitization from nitrate ions was observed for dabigatran and apixaban dissolved in a mineral water. The photosensitized reactions were limited in the tested river water (Isle River, Périgueux, France) certainly due to the hydroxyl radical scavenging effect of the dissolved organic matter. The study of photoproduct structures allowed to identify two compounds for dabigatran. One of them is the 4-aminobenzamidine while the second one is a cyclization product. In the case of rivaroxaban, as studied by very high field NMR, only one photoproduct was observed i.e. a photoisomer. Finally, seven photoproducts were clearly identified from the degradation of apixaban under simulated solar light. •Dabigatran undergoes direct and indirect photolysis, t1/2 is of 24 h in river water.•Direct photolysis is predominant for rivaroxaban, t1/2 is of 2.2 h in river water.•Argatroban is mainly photodegraded by photosensitization.•Structures of main photoproducts have been identified.
ISSN:0045-6535
1879-1298
DOI:10.1016/j.chemosphere.2017.11.036