Identification of Monomethyl Sulfate and Sulfate Impurities in Zidebactam Using LC–MS and Application of Mixed-Mode Liquid Chromatography with Charged Aerosol Detection and Ion Chromatography for Quantification
Zidebactam (ZID), a novel β-lactam enhancer drug being developed to treat infections caused by Gram-negative bacteria, currently is in phase III clinical development. Two ionic impurities observed in liquid chromatography with charged aerosol detector (CAD) analysis were identified through liquid-ch...
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| Veröffentlicht in: | Chromatographia 2020-02, Vol.83 (2), p.219-228 |
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| creator | Ahirrao, Vinod K. Rane, Vipul P. Patil, Kiran R. Jadhav, Rajiv A. Bhamare, Vijay S. Yadav, Dharamvir S. Yeole, Ravindra D. |
| description | Zidebactam (ZID), a novel β-lactam enhancer drug being developed to treat infections caused by Gram-negative bacteria, currently is in phase III clinical development. Two ionic impurities observed in liquid chromatography with charged aerosol detector (CAD) analysis were identified through liquid-chromatography mass spectrometry (LC–MS) as sulfate (SO
4
−2
) and monomethyl sulfate (CH
3
OSO
3
−1
, MMS). There genesis was attributed to the use of pyridine sulfur trioxide as a reagent in ZID synthesis. A new chromatographic method using mixed-mode stationary phase and CAD was developed and validated. The separation of ionic impurities was achieved on Obelisc-N column using buffer gradient. The new method was found to be simple, specific, sensitive, precise, accurate and robust for controlling these impurities in new drug substance. Accuracy of the method was verified by comparing the results with that of ion chromatography (IC) with conductivity detector. The IC method was employed to monitor the impurities in ZID drug substance used for clinical trials and stability analysis.
Graphic abstract |
| doi_str_mv | 10.1007/s10337-019-03836-4 |
| format | Article |
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4
−2
) and monomethyl sulfate (CH
3
OSO
3
−1
, MMS). There genesis was attributed to the use of pyridine sulfur trioxide as a reagent in ZID synthesis. A new chromatographic method using mixed-mode stationary phase and CAD was developed and validated. The separation of ionic impurities was achieved on Obelisc-N column using buffer gradient. The new method was found to be simple, specific, sensitive, precise, accurate and robust for controlling these impurities in new drug substance. Accuracy of the method was verified by comparing the results with that of ion chromatography (IC) with conductivity detector. The IC method was employed to monitor the impurities in ZID drug substance used for clinical trials and stability analysis.
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4
−2
) and monomethyl sulfate (CH
3
OSO
3
−1
, MMS). There genesis was attributed to the use of pyridine sulfur trioxide as a reagent in ZID synthesis. A new chromatographic method using mixed-mode stationary phase and CAD was developed and validated. The separation of ionic impurities was achieved on Obelisc-N column using buffer gradient. The new method was found to be simple, specific, sensitive, precise, accurate and robust for controlling these impurities in new drug substance. Accuracy of the method was verified by comparing the results with that of ion chromatography (IC) with conductivity detector. The IC method was employed to monitor the impurities in ZID drug substance used for clinical trials and stability analysis.
Graphic abstract</description><subject>Amides</subject><subject>Analytical Chemistry</subject><subject>Biochemical Research Methods</subject><subject>Biochemistry & Molecular Biology</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry, Analytical</subject><subject>Chromatography</subject><subject>Impurities</subject><subject>Laboratory Medicine</subject><subject>Life Sciences & Biomedicine</subject><subject>Liquid chromatography</subject><subject>Mass spectrometry</subject><subject>Original</subject><subject>Pharmacy</subject><subject>Physical Sciences</subject><subject>Proteomics</subject><subject>Reagents</subject><subject>Robust control</subject><subject>Science & Technology</subject><subject>Stability analysis</subject><subject>Sulfur trioxide</subject><issn>0009-5893</issn><issn>1612-1112</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>AOWDO</sourceid><recordid>eNqNkc1u1DAUhSNEJYaWF2BliSUK-CeJk2UV_kaaEUKlGzaRx76ecZXYqe2ozK7v0FfjCXgSPBNUqi5QV9e2znfs45Nlrwl-RzDm7wPBjPEckybHrGZVXjzLFqQiNCeE0OfZAmPc5GXdsBfZyxCu0pY2VbXIfi0V2Gi0kSIaZ5HTaO2sGyDu9j26mHotIiBh1f16OYyTN9FAQMaiH0bBRsgoBnQZjN2iVfv79m59cUTOx7F_aGx-gsrXTgFamevJKNTuvBtEdFsvxt0e3Zi4S2fCbyHB4F1wPfoAEeTR4mC5TPMRpZ1H3ybxIMVZdqJFH-DV33maXX76-L39kq--fl6256tcMtLEvKS4UrQuRNMoqdimxEyopuBcy3oDdQWSUUUYEyKphKrrQhe6KinnRFU1l-w0ezP7jt5dTxBid-Umb9OVHWUlq3D64iKp6KySKVDwoLvRm0H4fUdwd2ivm9vrUnvdsb3uANUzdAMbp4M0YCXcg6m-klBeco4PxbYmHnO3brIxoW-fjiY1m9UhKewW_L8M_3neHzcaw00</recordid><startdate>20200201</startdate><enddate>20200201</enddate><creator>Ahirrao, Vinod K.</creator><creator>Rane, Vipul P.</creator><creator>Patil, Kiran R.</creator><creator>Jadhav, Rajiv A.</creator><creator>Bhamare, Vijay S.</creator><creator>Yadav, Dharamvir S.</creator><creator>Yeole, Ravindra D.</creator><general>Springer Berlin Heidelberg</general><general>Springer Nature</general><general>Springer Nature B.V</general><scope>AOWDO</scope><scope>BLEPL</scope><scope>DTL</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-2507-2719</orcidid><orcidid>https://orcid.org/0000-0002-0597-1303</orcidid><orcidid>https://orcid.org/0000-0002-2163-7428</orcidid></search><sort><creationdate>20200201</creationdate><title>Identification of Monomethyl Sulfate and Sulfate Impurities in Zidebactam Using LC–MS and Application of Mixed-Mode Liquid Chromatography with Charged Aerosol Detection and Ion Chromatography for Quantification</title><author>Ahirrao, Vinod K. ; Rane, Vipul P. ; Patil, Kiran R. ; Jadhav, Rajiv A. ; Bhamare, Vijay S. ; Yadav, Dharamvir S. ; Yeole, Ravindra D.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c319t-5206d284a99dcd3b503ad9477fc8be86ec32d133aad28ad884f4f652771d687c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Amides</topic><topic>Analytical Chemistry</topic><topic>Biochemical Research Methods</topic><topic>Biochemistry & Molecular Biology</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry, Analytical</topic><topic>Chromatography</topic><topic>Impurities</topic><topic>Laboratory Medicine</topic><topic>Life Sciences & Biomedicine</topic><topic>Liquid chromatography</topic><topic>Mass spectrometry</topic><topic>Original</topic><topic>Pharmacy</topic><topic>Physical Sciences</topic><topic>Proteomics</topic><topic>Reagents</topic><topic>Robust control</topic><topic>Science & Technology</topic><topic>Stability analysis</topic><topic>Sulfur trioxide</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ahirrao, Vinod K.</creatorcontrib><creatorcontrib>Rane, Vipul P.</creatorcontrib><creatorcontrib>Patil, Kiran R.</creatorcontrib><creatorcontrib>Jadhav, Rajiv A.</creatorcontrib><creatorcontrib>Bhamare, Vijay S.</creatorcontrib><creatorcontrib>Yadav, Dharamvir S.</creatorcontrib><creatorcontrib>Yeole, Ravindra D.</creatorcontrib><collection>Web of Science - Science Citation Index Expanded - 2020</collection><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><collection>CrossRef</collection><jtitle>Chromatographia</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ahirrao, Vinod K.</au><au>Rane, Vipul P.</au><au>Patil, Kiran R.</au><au>Jadhav, Rajiv A.</au><au>Bhamare, Vijay S.</au><au>Yadav, Dharamvir S.</au><au>Yeole, Ravindra D.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identification of Monomethyl Sulfate and Sulfate Impurities in Zidebactam Using LC–MS and Application of Mixed-Mode Liquid Chromatography with Charged Aerosol Detection and Ion Chromatography for Quantification</atitle><jtitle>Chromatographia</jtitle><stitle>Chromatographia</stitle><stitle>CHROMATOGRAPHIA</stitle><date>2020-02-01</date><risdate>2020</risdate><volume>83</volume><issue>2</issue><spage>219</spage><epage>228</epage><pages>219-228</pages><issn>0009-5893</issn><eissn>1612-1112</eissn><abstract>Zidebactam (ZID), a novel β-lactam enhancer drug being developed to treat infections caused by Gram-negative bacteria, currently is in phase III clinical development. Two ionic impurities observed in liquid chromatography with charged aerosol detector (CAD) analysis were identified through liquid-chromatography mass spectrometry (LC–MS) as sulfate (SO
4
−2
) and monomethyl sulfate (CH
3
OSO
3
−1
, MMS). There genesis was attributed to the use of pyridine sulfur trioxide as a reagent in ZID synthesis. A new chromatographic method using mixed-mode stationary phase and CAD was developed and validated. The separation of ionic impurities was achieved on Obelisc-N column using buffer gradient. The new method was found to be simple, specific, sensitive, precise, accurate and robust for controlling these impurities in new drug substance. Accuracy of the method was verified by comparing the results with that of ion chromatography (IC) with conductivity detector. The IC method was employed to monitor the impurities in ZID drug substance used for clinical trials and stability analysis.
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| subjects | Amides Analytical Chemistry Biochemical Research Methods Biochemistry & Molecular Biology Chemistry Chemistry and Materials Science Chemistry, Analytical Chromatography Impurities Laboratory Medicine Life Sciences & Biomedicine Liquid chromatography Mass spectrometry Original Pharmacy Physical Sciences Proteomics Reagents Robust control Science & Technology Stability analysis Sulfur trioxide |
| title | Identification of Monomethyl Sulfate and Sulfate Impurities in Zidebactam Using LC–MS and Application of Mixed-Mode Liquid Chromatography with Charged Aerosol Detection and Ion Chromatography for Quantification |
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