Identification, isolation and characterization of a new impurity in drug substance resulting from stress stability studies

Vundavilli Jagadeesh Kumar; P Badarinadh Gupta; K Mukkanti; B Shankar Reddy; K S R Pavan Kumar; G K A S S Narayan; Yallappa Somappa Somannavar; G S Siva Kumar; Hemant Kumar Sharma

doi:10.1039/c0ay00467g

Identification, isolation and characterization of a new impurity in drug substance resulting from stress stability studies

Anal Methods. 2011 Jan 1;3(1):181-185. doi: 10.1039/c0ay00467g.

Authors

Vundavilli Jagadeesh Kumar¹, P Badarinadh Gupta¹, K Mukkanti², B Shankar Reddy¹, K S R Pavan Kumar¹, G K A S S Narayan¹, Yallappa Somappa Somannavar¹, G S Siva Kumar¹, Hemant Kumar Sharma¹

Affiliations

¹ Aurobindo Pharma Ltd Research Centre, 313, Bachupally, Qutubullapur Mandal, Hyderabad, 500090, Andhra Pradesh, India. jagadishkumar28@rediffmail.com pavan_kothapalli@rediffmail.com.
² J.N.T.University, Kukatpally, Hyderabad, 500085, Andhra Pradesh, India.

PMID: 32938128
DOI: 10.1039/c0ay00467g

Abstract

A new unknown impurity of cefoxitin formed during a gradient reverse phase high performance liquid chromatography (HPLC) analysis of stress stability samples of the drug substance cefoxitin, and the level of this impurity was found at up to 0.9%. This impurity was identified by LC-MS and characterized by (1H NMR, 13C NMR, LC/MS/MS, elemental analysis and FT-IR). Based on the spectral data, the impurity was named as, 3-[[(2R,3S)-[3-methoxy-3-N-[2-(thiophen-2-yl)acetamido]]-4-oxoazetidin-2-ylthio]-2-[(carbamoyloxy)methyl]]-acrylic acid. The structure of this impurity was also established unambiguously, prepared by isolation and co-injected into HPLC to confirm the retention time. To the best of our knowledge, this impurity has not been reported elsewhere. Structural elucidation of the impurity by spectral data is discussed in detail.