Development of an Efficient and Scalable Process for Preparing Timolol N-Nitrosamine Impurities B, C, E, H, I, J, and Their ADMET Evaluation -Pub

Development of an Efficient and Scalable Process for Preparing Timolol N-Nitrosamine Impurities B, C, E, H, I, J, and Their ADMET Evaluation

Abstract:
The synthesis of N‐nitrosamine impurities in Timolol maleate is a critical aspect of pharmaceutical research and quality assurance. It enables a deeper understanding of impurity formation, facilitates effective risk assessment, and supports the development of robust control strategies. This process is essential for ensuring patient safety, achieving regulatory compliance, and upholding stringent standards of drug quality and reliability. In response to earlier reports, the synthesis of N‐nitrosamine impurities of Timolol has become necessary. The present work outlines a streamlined approach for preparing N‐nitrosamine impurities B, C, E, H, I, and J in a few simple steps, achieving good yields from readily available raw materials. The process employs diethyl malonate in combination with 3,4‐dichloro‐1,2,5‐thiadiazole as key starting components. Theoretical studies on the ADMET properties showed good oral bioavailability of few impurities, and the impurities may likely exhibit respiratory toxicities.

N‐nitrosamine impurities (B, C, E, H, I, J) of timolol maleate are easily synthesized from diethyl malonate and 3,4‐dichloro‐1,2,5‐thiadiazole. Good yields and precise impurity profiling are made possible by the effective technique, which also ensures pharmaceutical safety and strengthens regulatory compliance. Theoretical studies on the ADMET properties showed good oral bioavailability of few impurities, and the impurities may likely exhibit respiratory toxicities.

Open access: Development of an Efficient and Scalable Process for Preparing Timolol N-Nitrosamine Impurities B, C, E, H, I, J, and Their ADMET Evaluation

2 Likes

thanks Naiffer.

To be honest, i am wondering in which way this could be usefull for the nitrosamine case.

Timolol is a secondary amine itself and its presence in the tablet would consume nearly all the available for nitrosation nitrite content. This means, that the possibility for the formation of any of the N-nitroso impurity of timolol is actually negligible.

Please note that the last years we have faced in three projects similar situation (where the API was a secondary amine) and in no one of them we could not identified any quantity of other nitrosamine except the N-nitroso API.

thanks

Christos

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Hola! Yo tuve una experiencia con Esmolol inyectable, en el cual contiene una impureza mayoritaria (Ácido Libre de Esmolol) y encontramos un porcentaje importante de la nitroso-impureza (N-Ácido Libre de Esmolol) en el producto, quizá sean pocos los casos donde aplique y/o valga la pena ahondar en las nitroso impurezas, pero no dejarían de ser importantes si las empresas deciden mantener el registro del producto.