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image of Identification, Isolation, Structure Characterization, and Chromatographic Separation of a New Highly Analogous Impurity of the Ubrogepant

Abstract

Background

Ubrogepant is a regulated peptide receptor antagonist associated with the calcitonin gene, granted approval in the United States for the specific treatment of migraine headaches.

Objective

An impurity found in the alkali hydrolysis of drug dosage forms has a structure very similar to that of ubrogepant. This research aims to characterize this analogous impurity utilizing NMR and LC-MS spectroscopy tools. Moreover, it is critical to develop an extremely sensitive and superior resolution analytical procedure for identifying and determining the amount of analogous impurity in pharmaceutical products.

Method

The ubrogepant impurity was identified using an optimized chromatographic method that relies on reversed-phase HPLC with UV detection. This technique utilized a charged surface hybrid (CSH) technology column operating in gradient elution mode. A mixture of A-channel (0.1% trifluoroacetic acid) and B-channel (acetonitrile and water, 80:20% v/v) constituted the eluent. The analogous impurity was isolated through fraction collection, purified using flash chromatography, and characterized using NMR (1D and 2D) and LC-MS.

Results

The analogous impurity was successfully separated from the ubrogepant peak with a resolution above 2.0. The concentration of the impurity was approximately 10% compared to the ubrogepant peak after alkaline stressing at room temperature for 30 minutes. NMR (1D 13C NMR and 1H, 2D HMBC, HSQC, NOESY, and COSY) and LC-MS analysis characterized the ubrogepant impurity, revealing it to be an epimer of ubrogepant. The developed approach was highly sensitive, allowing for the quantification of the ubrogepant impurity even at a concentration of 0.2 µg/mL.

Conclusion

The approach demonstrated a remarkable degree of precision, linearity, specificity, and accuracy. This new impurity deserves special attention because of its striking similarity to the active ingredient, ubrogepant.

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Identification, Isolation, Structure Characterization, and Chromatographic Separation of a New Highly Analogous Impurity of the Ubrogepant
Bentham Science Publishers ; https://doi.org/10.2174/0115734110324919240918112907
/content/journals/cac/10.2174/0115734110324919240918112907
/content/journals/cac/10.2174/0115734110324919240918112907
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  • Article Type:     Research Article
Keywords: NOESY ; LC-MS ; flash chromatography ; Ubrogepant ; NMR ; epimer ; HPLC

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