DRUG METABOLISM. Drug discovery & development solutions FOR DRUG METABOLISM

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1 DRUG METABLISM Drug discovery & development solutions FR DRUG METABLISM

2 Fast and efficient metabolite identification is critical in today s drug discovery pipeline. The goal is to achieve rapid structural identification and complete characterization of major and low-level metabolites in a single analysis. AB SCIEX triple quadrupole-linear ion trap mass spectrometers and accurate mass approaches make that goal a reality. Qual & Quant for the answers you need: Get high-sensitivity quantification and new qualitative capabilities on a single platform the AB SCIEX TripleTF 5600 System and MetabolitePilot Software. Fast and efficient low-level metabolite identification: Acquire predictive MRM (pmrm) and multiple precursor ion and/or neutral loss survey scans in a single analysis, including polarity switching, with the AB SCIEX QTRAP 5500 and LightSight Software. From early discovery to late stage development: Get the information you need to take products from the lab to the clinic with integrated workflows.

3 Simple, clear metabolism workflows The AB SCIEX TripleTF 5600 System and MetabolitePilot Software deliver high sensitivity quantification and new qualitative capabilities on a single platform. The AB SCIEX QTRAP 5500 and LightSight Software use predictive MRM (pmrm) and multiple precursor ion and/or neutral loss survey scans in a single analysis, including polarity switching. AB SCIEX TripleTF 5600 System Accurate mass at the speed and sensitivity of a triple quadrupole: Fast MS and MS/MS acquisition speeds compatible with fast chromatography Resolution over 30,000 External mass accuracy ~1ppm 4 orders of Linear Dynamic Range AB SCIEX QTRAP 5500 System A single platform for drug metabolism and bioanalytical quantification workflows: Targeted and non-targeted workflows Increased sensitivity Increased speed Full quantitative capabilities MetabolitePilot Software Accurate mass data processing and interrogation: Generate cleaner, more relevant data with Multiple Mass Defect Filtering. Store and retrieve critical information in Compound Library & Results Database. Quickly process multiple sample sets in batches. Increase confidence in your results with intelligent scoring and easy-to-visualize color-coding. LightSight Software Exploit the full functionality of QTRAP technology and processing strategies for multiple MetID workflows pmrm high sensitivity targeted approach for really low level detection and confirmation PI/NL (+/-ve polarity switching) structure based filtering approach ideal for reactive metabolite screening Multiple Ion Monitoring (MIM) & Q3 single MS strategies for a non-targeted approach Predict formulae with a high level of chemical intelligence. AB SCIEX TripleTF 5600 System MetabolitePilot Software AB SCIEX QTRAP 5500 System Lightsight Software

4 Drug discovery & development pipeline Metabolite identification is central to many of the activities in the discovery and development pipeline. From rapid structural identification during the discovery process to provide an early perspective on the metabolically labile sites, or soft spots of a drug candidate, to a more complete characterization of the metabolic clearance process to maximize safety and efficacy, there s an ever-increasing demand on throughput. The ability to find, identify and confirm metabolites as fast as possible is critical; not only for the major metabolites, but the very low-level metabolites as well. Being able to do this in a single analysis is a highly sought after goal. With improved strategies for metabolite ID from hybrid triple quadrupole-linear ion trap mass spectrometers and an ever increasing use of accurate mass approaches, these different but complementary mass spectrometric techniques have brought the goal to reality. Application snapshots within the drug discovery & development pipeline 1. EARLY DISCVERY Metabolic Stability GSH Detection 2. LATE STAGE DISCVERY In-vivo Metabolite ID Low-level Metabolite ID 3. DEVELPMENT Definitive Identification Integrated Qual/Quant workflows DRUG DISCVERY PRE-CLINICAL CLINICAL TRIALS FDA REVIEW LARGE-SCALE MANUFACTURING PHASE IV 10,000 CMPUNDS 250 CMPUNDS IND SUBMITTED Phase I 20 To 100 volunteers 5 CMPUNDS Phase II 100 to 500 volunteers Phase III 1,000 To 5,000 volunteers NDA SUBMITTED FDA APPRVED DRUG 5 YEARS 1.5 YEARS 6 YEARS 2 YEARS 2 YEARS Average time in stage

5 Early discovery: metabolic stability screening Metabolic stability assessment Take soft-spot analysis to new levels of speed, efficiency and depth of data with the TripleTF 5600 and MetabolitePilot Software. Apply completely generic methodology to acquire high quality quantitative and qualitative data simultaneously for soft-spot analysis. The AB SCIEX TripleTF 5600 System makes it possible, with TF MS and MS/MS scanning at rates suitable for UPLC. Generate quantitative data on the parent compound from the TF MS scan. Metabolic Stability Rat Liver Microsomes t=5 min Automatically acquire MS/MS data on the major metabolites using high-speed IDA logic. Use accurate mass MS/MS for structural elucidation. A Using a generic IDA method and fast chromatography, metabolic stability profiles were obtained in rat liver microsomes at a substrate concentration of 1 μm at t=0. B A wide range of Imipramine phase I metabolites detected at t=5 minutes by TF MS scan. C The MS/MS spectrum of Imipramine obtained automatically in IDA mode. The high mass accuracy and resolution greatly simplify structure elucidation.

6 Early discovery: reactive metabolite detection Detect low-level reactive metabolites in complex samples using glutathione (GSH) detection with the AB SCIEX QTRAP 5500 System and LightSight Software. The formation of undetected reactive metabolite species can potentially cause idiosyncratic adverse drug reactions (IADRs), which can lead to Black Box warnings and withdrawal of drugs from the market. GSH detection is one of the most sensitive ways of detecting low-level, transient reactive metabolites in complex biological samples. H 3 C H H 2 N NH HN H 3 C NH S NH H S H H 2 N HN NH H Neutral Loss m/z 129 Precursor Ion m/z 272 GSH Adduct Screening 2 Survey scans with polarity switching in 1 injection +EPI m/z 632 +EPI m/z CNL of 129 at 20,000 amu/sec Both triggered via ER scan - Prec + ER + EPI + CNL + ER + EPI - Precursor m/z 272 Total cycle time 1.3 sec High sensitivity GSH adduct screening: Fast scanning and polarity switching with the QTRAP 5500 System enable sensitive detection of GSH-trapped reactive metabolites with a combined precursor ion (negative ion mode, 272 m/z) and neutral loss (positive ion mode, m/z 129) in a single injection. The survey scans are specific to the GSH moiety. They do not require knowledge of parent MS/MS fragmentation, or prediction of metabolites. This provides for comprehensive detection of GSH conjugated metabolites whether predicted or not.

7 Late stage discovery: In vivo metabolite identification Identify metabolites of lead drug candidates for structural elucidation using selective detection techniques such as mass defect filtering with the TripleTF 5600 System. For the first time, multiple mass defect filters can be applied in real time to select peaks for MS/MS data acquisition. There is no need to schedule a second injection to obtain MS/MS information. With the TripleTF 5600 you can detect and characterize major metabolites in vivo with a single injection. A A Minor oxidative metabolite (2.59 minutes) of Carbamazepine detected in protein precipitated plasma. Although eluting just before a major metabolite, multiple mass defect filtering enabled acquisition of MS/MS spectra of both metabolites in the presence of strong matrix interferences. B TF MS scan of peak at 2.59 min in above chromatogram. Large endogenous interferences are present in the scan. Real time mass defect filtering ensures successful acquisition of MS/MS data for the ion of interest in the presence of high background. C The accurate mass MS/MS spectrum of the minor oxidative metabolite obtained in IDA mode using real time mass defect filtering. B C

8 Late stage discovery: low-level metabolite ID In vivo detection in complex matrices Detect low levels of metabolites at clinically relevant concentrations in vivo even in matrices such as bile, plasma, urine and fecal extracts using the QTRAP 5500 System. The predictive MRM (pmrm) survey method on the QTRAP 5500 System is the most sensitive and selective single-injection strategy for identifying metabolites in challenging matrices. Low level in vivo metabolite detection in protein precipitated plasma: extracted ion chromatograms of Carbamazepine metabolites from a 4 mg/kg IV administration in rat, detected by pmrm (176 transitions monitored simultaneously) with the QTRAP 5500 System.

9 Development: definitive in vivo metabolite ID Metabolite characterization in lead compounds Acquire accurate mass data for both parent and fragments in lead compounds with the TripleTF 5600 System and MetabolitePilot Software. An advanced collision cell design and collision energy spread function produce rich MS/MS fragmentation in the low mass range for structure elucidation. Rich fragmentation, high resolution and mass accuracy enable definitive metabolite profiling. Hydroxymidazolam in rat liver microsomes. Excellent accuracy and resolution at the low mass range in MS/MS enables unambiguous assignment of elemental composition.

10 Development: integrated qual/quant workflows Metabolite quantification Estimate metabolite concentrations, without a reference standard, using mass extracted ion chromatograms from high-resolution experiments using the TripleTF 5600 System, MetabolitePilot and MultiQuant Software. TripleTF 5600 System, MetabolitePilot and MultiQuant Software meets the challenge by enabling you to compare the response in the extracted ion chromatogram (XIC) of the metabolite to the parent drug, with high resolution, high resolution and mass accuracy at the low mass range, and more selectivity. Thanks to fast scanning, you can perform these studies under UPLC. Quantification of metabolites and cross-species quantitative comparisons have received greater emphasis due to the Metabolites in Safety Testing (MIST) Guidelines. Estimating metabolite concentrations without a reference standard, however, is challenging. TF MS extracted ion chromatograms of H-Midazolam metabolites and the Midazolam parent. All peaks are automatically integrated and labeled with area counts. Corresponding TF MS scans for the metabolite and parent peaks in Figure 6A. High resolution enables relative quantitation in TF MS mode while reducing or eliminating matrix interference.

11 Biotransformation studies Acquire and process mass spectrometric and UV or radiochromatographic data in the same experiment with the QTRAP 5500 System and LightSight Software and without time-consuming manual procedures. All together now: Correlation of UV and MS data of rat liver microsomal metabolites of Bromocriptine. The Processing Workspace of LightSight Software makes the correlation of UV absorbance, pmrm, and EPI-MS/MS data easy and intuitive.

12 You invest in our technology. We invest in your success. As the world leader in mass spectrometry, AB SCIEX solutions are backed by the industry s most extensive service and support organization. With a network of service professionals, experienced compliance specialists, and over 150 PhD application scientists worldwide, we are dedicated to supporting your technical needs and helping you get the most out of your AB SCIEX systems. AB SCIEX service professionals are recognized as the most highly qualified in the industry. They are certified on our instrument platforms through a rigorous 4-step certification program, with re-certification occurring every two years. This award-winning program helps to ensure that you receive the most efficient, highest-quality, and most up-to-date service available for AB SCIEX products and technology. Choose from flexible service plans and a variety of services for the right level of support for your laboratory s needs and budget. ur customer support network is available to provide expert assistance in the use and application of AB SCIEX products through a comprehensive range of services, including application support, technical service, and training. Whether you access our service and support team by phone, , on-site visits, or through our innovative remote monitoring technology, you can be confident that the AB SCIEX organization will be there for you. For more information, visit For Research Use nly. Not for use in diagnostic procedures AB SCIEX. The trademarks mentioned herein are the property of AB Sciex Pte. Ltd. or their respective owners. AB SCIEX is being used under license /11 Headquarters 110 Marsh Road Foster City CA USA Phone International Sales For our office locations please call the division headquarters or refer to our website at

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