Chiroptical and vibrational spectroscopic study of genuine and counterfeit medicines containing tadalafil

Králík, František; Jirmásek, Patrik; Kuchař, Martin; Setnička, Vladimı́r

doi:10.1002/chir.22828

Cited by 4 publications

(2 citation statements)

References 37 publications

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“…The results revealed that the counterfeit drugs contained a lower amount of tadalafil than that declared by the producer. 140…”

Section: Resultsmentioning

confidence: 99%

“…The results revealed that the counterfeit drugs contained a lower amount of tadalafil than that declared by the producer. 140 ECD and VCD were used to study (−)-brevianamide B (294) ( Figure 83) prepared by reduction and stereoselective oxidation from (+)-brevianamide A, isolated from Penicillium brevicompactum. The ECD bands are due to the (S) spiroindoxyl quaternary center which allowed confirming the AC.…”

Section: Nitrogenated Compoundsmentioning

confidence: 99%

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Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Río

Joseph‐Nathan

2021

Natural Product Communications

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Although demonstrated in 1975, vibrational circular dichroism (VCD) finally started to popularize during this century as a reliable tool to determine the absolute configuration (AC) of organic molecules. This research field continues to be a very dynamic one, in particular for the study of natural products which are a unlimited source of chiral molecules. It therefore turns of interest to summarize the accomplishments published in recent years and to comment on some eventual difficulties that emerged in rare cases to complete the AC determination task. Therefore the aim of this review is to update VCD results for the AC assignment of natural products published from 2015 to 2019, a period in which VCD was reported in some 126 publications involving almost 300 molecules. They are organized according the type of studied metabolite allowing an easily search. The molecules correspond to 28 monoterpenes concerning 17 papers, to 42 sesquiterpenes in 14 papers, to 51 diterpenes in 19 publications, to 5 other terpenoids in three papers, to 48 aromatic molecules in 15 reports, to 20 polyketides in 10 publications, to 27 miscellaneous formulas also in 10 papers, and to 76 nitrogen containing compounds, which include alkaloids and their synthetic analogs, in 38 articles. The landscape of reviewed molecules is quite wide as it goes from simple monoterpenes, like borneol or camphor, to very relevant biological molecules like the alkaloid cocaine or tadalafil samples to distinguish genuine and counterfeit Cialis®. In addition, 5 natural products and a simple derivative published outside the reviewed period, were used to illustrate some aspects of density functional theory calculations.

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“…The results revealed that the counterfeit drugs contained a lower amount of tadalafil than that declared by the producer. 140…”

Section: Resultsmentioning

confidence: 99%

Section: Nitrogenated Compoundsmentioning

confidence: 99%

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Río

Joseph‐Nathan

2021

Natural Product Communications

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Structure of heroin in a solution revealed by chiroptical spectroscopy

et al. 2020

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In this work, the 3‐D structure of the well‐known opioid drug heroin in a solution was investigated. The goal was to provide a complete and detailed description of the stable conformers with their relative abundances. This knowledge is very important from the pharmaceutical and forensic point of view as it could help significantly with deeper understanding of heroin's metabolism and the development of antagonist medicines for the case of an overdose. As heroin is a chiral compound with five stereogenic centres, the methods of chiroptical spectroscopy supplemented by density functional theory (DFT) calculations were applied to study its conformations in chloroform solution. The selected chiroptical methods, namely, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD), are inherently sensitive to the 3‐D structure of small‐ to medium‐sized chiral organic molecules. A thorough conformational analysis revealed four stable conformers of heroin in chloroform solution, where the conductor‐like polarizable continuum model of the solvent was used for all the calculations. The simulated ultraviolet (UV), infrared (IR), ECD, and VCD spectra were compared with the experimental ones and very good agreement was found, which enabled a detailed structure description and interpretation of the spectra. Chiroptical spectroscopy in combination with DFT calculations proved to be a very sensitive tool for the analysis of the 3‐D structure of heroin in a solution in contrast with conventional spectroscopic methods. Especially, the application of VCD seems to be a promising approach for monitoring structural changes, for instance, those caused by solvents or interactions with other agents.

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Facing Counterfeit Medications in Sexual Medicine. A Systematic Scoping Review on Social Strategies and Technological Solutions

2021

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Introduction:The counterfeit phenomenon is a largely under-reported issue, with potentially large burden for healthcare. The market for counterfeit drugs used in sexual medicine, most notably type 5 phosphodiesterase inhibitors (PDE5i), is rapidly growing. Aims: To report the health risks associated with the use of counterfeit medications, the reasons driving their use, and the strategies enacted to contain this phenomenon. Methods: A systematic scoping review of the literature regarding counterfeit PDE5i was carried between January and June 2021, then updated in August 2021. Main Outcome Measure: We primarily aimed to clarify the main drivers for counterfeit PDE5i use, the health risks associated, and the currently available strategies to fight counterfeiters. Results: One hundred thirty-one records were considered for the present scoping review. Production of fake PDE5i is highly lucrative and the lacking awareness of the potential health risks makes it a largely exploitable market by counterfeiters. Adulteration with other drugs, microbial contamination and unreliable dosages make counterfeit medications a cause of worry also outside of the sexual medicine scope. Several laboratory techniques have been devised to identify and quantify the presence of other compounds in counterfeit medications. Strategies aimed at improving awareness, providing antitampering packaging and producing non-falsifiable products, such as the orodispersible formulations, are also described. Clinical implications: Improving our understanding of the PDE5i counterfeit phenomenon can be helpful to promote awareness of this issue and to improve patient care. Strengths & Limitations: Despite the systematic approach, few clinical studies were retrieved, and data concerning the prevalence of counterfeit PDE5i use is not available on a global scale. Conclusion:The counterfeit phenomenon is a steadily growing issue, with PDE5i being the most counterfeited medication with potentially large harmful effects on unaware consumers. Sansone A, Cuzin B, and Jannini EA.

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Chiroptical and vibrational spectroscopic study of genuine and counterfeit medicines containing tadalafil

Cited by 4 publications

References 37 publications

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Structure of heroin in a solution revealed by chiroptical spectroscopy

Facing Counterfeit Medications in Sexual Medicine. A Systematic Scoping Review on Social Strategies and Technological Solutions

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