Analytical Workflow for Extractable and Leachable Impurities
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1 Analytical Workflow for Extractable and Leachable Impurities AAPS October 2015, Orlando FL Kyle D Silva The world leader in serving science
2 WHAT are EXTRACTABLES and LEACHABLES? 2
3 3 What is E&L testing for?
4 Areas of concern CONTAMINANT TOXICICITY DRUG EFFICACY Is there risk of harm to the patient? Is there impact on drug potency? 4
5 Extractables & Leachables EXTRACTABLE Chemical released from process equipment, packaging or delivery system; under laboratory extraction conditions. Process must not degrade or deform material. LEACHABLE Chemical that migrates from process equipment, packaging or delivery system; into drug formulation under normal usage conditions. Leachables are typically a subset of extractables. 5
6 Extractables versus Leachables testing EXTRACTABLE LEACHABLE Test the materials Test the product 6
7 Regulations There are as yet no single specific standards or guidance for extractables and leachables testing. 7
8 Extractables & Leachables Assessment Workflow Select Raw Material Risk Assessment Risk? No Extraction Study (Material) Leachable Study (Drug & Placebo) Yes >AET? Yes Toxicological Risk Assessment Yes >AET? No No Yes High Risk? No AET = Analytical Evaluation Threshold Establish E to L Relationship & Acceptance Criteria Assessment Complete 8
9 E&L Regulatory and method landscape National Regulators Methods & Advisory Bodies USP 1663 & 1664 Standardized Extractables Testing Protocol. Pharmaceutical Engineering 34 (2014) Industry Groups 9
10 BPOG Single-use System Extractables Test Guidelines Standardized Extractables Testing Protocol. Pharmaceutical Engineering 34 (2014) 10
11 Analysis of Extractables & Leachables GC-MS GC-HRMS Headspace EI & CI Library Volatile Impurities Semi- Volatile Impurities GC-MS GC-HRMS EI & CI Library ESI & APCI LC-UV LC-MS/MS LC-HRMS Library Non- Volatile Impurities Elemental Impurities ICP-MS ICP-OES 11
12 Our solution is complete for Extractables & Leachables Preparation Volatiles Semi-volatiles Non-Volatiles Elemental Consumables ASE 350 Chromeleon Trace 1300 GC TriPlus 300 ISQ GC-MS Chromeleon Q Exactive GC GC-MS/MS Trace 1300 GC TraceFinder Q Exactive LC-MS/MS Vanquish UHPLC ICS-5000 HPIC Compound Discoverer TraceFinder MZ Cloud icap Q ICP-MS icap ICP-OES Qtegra ISDS MS Certified Vials Columns Ultra-pure GC Resolv & Optima LCMS Solvents Virtuoso 12
13 Experimental O-Ring Extractables Study 13
14 Pharmaceutical O-Rings extractables study 4 O-ring samples A Red B Brown C White D Black Blank (control) Solvents Water 5M NaCl 50% Ethanol 100% Ethanol 1% PS N NaOH 0.1M Phosphoric Acid 40 C for 30 days 14
15 O-ring Extractables Study Semi-volatiles Non-Volatiles Metals Q Exactive GC GC-MS/MS Trace 1310 GC TraceFinder Q Exactive LC- MS/MS Compound Discoverer TraceFinder MZ Cloud icap Q ICP-MS Qtegra ISDS 15
16 GC-MS instrument conditions TRACE 1310 GC Parameters Injection Volume (ml): 1 Liner Single gooseneck Inlet ( C): 280 Carrier Gas, (ml/min): He, 1.2 Oven Temperature Program: Temperature 1 ( o C): 40 Hold Time (min): 1 Temperature 2 ( o C): 320 Rate ( o C/min) 15 Hold Time (min): 10 Thermo Scientific Q Exactive GC Hybrid Quadrupole-Orbitrap GC-MS/MS System Thermo Scientific Trace 1310 GC Thermo Scientific TraceFinder Q Exactive GC MS Parameters Transfer line ( C): 280 Ionization type: EI Ion source( C): 230 Electron energy (ev): 70 Acquisition mode: Full scan Mass range (Da): Mass resolution (FWHM): 60k Lockmass (m/z):
17 Integration of 3 highly successful technologies TRACE 1310 GC rapid heat cycling unique modular injector and detector design 17
18 Integration of 3 highly successful technologies TSQ 8000 Series ExtractaBrite ion source technology Routine grade robustness Removable without breaking vacuum Patented RF lens protects ion guide and quads 18
19 Integration of 3 highly successful technologies Orbitrap mass analyzer technology Incredible HR/AM performance Highly regarded Q Exactive platform 19
20 Breakthrough in GC-MS capability Resolution Mass Accuracy Sensitivity Dynamic Range Up to 120,000 at m/z 200 < 1ppm ppt >6 orders Highest available Maximum selectivity Fast enough for GC! Every scan All concentrations In complex matrix In full scan High selectivity High spectral fidelity Excellent coverage in sample profiling Triple quad grade quantitation in full scan Across the mass range Everyday! 20
21 Scan speed and accurate mass error across a peak Ethyl octanoate m/z
22 Results Semi-volatile extractables 22
23 Compound Discovery and Identification 1. Peak detection 2. Spectral deconvolution 3. Library searching (e.g. NIST, Wiley, custom) 4. % TIC explained using elemental composition and high resolution filtering with accurate mass 23
24 Peak Detection and Candidate Matching Deconvolve TIC Create clean spectrum Library search Candidate Compounds Acquired Library 24
25 High Resolution Filtering Candidate Compounds Subset formulae C 8 H 8 Cl 2 O 2 (m/z *Intensity) explained HRF Score = x 100% (m/z *Intensity) observed 25
26 Example results RT: SM: 7B Relative Abundance Blank control Brown O-Ring Time (min) NL: 6.86E8 TIC MS 03June15_0 08 NL: 2.54E9 TIC MS 03june15_
27 Step 1: Deconvolution of the data TraceFinder first performs an accurate mass deconvolution of the data. Extracts all of the peaks in the chromatogram. Provides a cleaned spectrum for library matching. 27
28 Step 2: Quickly isolate the peaks of interest 2051 peaks were extracted from the brown O-ring sample Heat Map indicates the peaks elevated in the sample. 28
29 Top 10 differential peaks in Brown O-ring Peaks list can also be sorted by fold difference compared with control to isolate the differential peaks that could be low or high intensity. 29
30 Step 3: Identify the compound searching NIST Hits from NIST are sorted based on: Spectral matching High Resolution Filtering (HRF) score. 30
31 Step 3: Identify the compound searching NIST 14 Combined SI and HRF values give an overall score (%) to quickly and confidently identify the compound. Eliminates other hits that would be valid if only SI used. 31
32 Step 4: Fragments can be explained with < 1ppm mass accuracy 32
33 Identifying without a library hit? Confident ID comes from mass accuracy 33
34 Black O ring peak at minutes no clear NIST hit No clear match with low score at 75.7% 34
35 EI & PCI spectra for peak at mins. 35
36 No. of proposed formulae for m/z Top hit = C 20 H 20 O 4 25 No. proposed formulae ppm1 3 ppm 5 ppm 10 ppm 20 ppm Elements used: C (1-30), H (1-60, N (1-5), O (1-5), P (1-2), S (1-2) 36
37 MS/MS m/z to support proposed formula 08OCT15_01 # RT: AV: 10 NL: 1.19E7 T: FTMS + p CI Full ms @hcd10.00 [ ] Relative Abundance >13 fragments can be explained based on C 20 H 20 O C 7 H 5 O = ppm C 9 H 5 O 2 = ppm C 14 H 11 O = ppm C 15 H 11 O 2 = ppm C 17 H 15 O 2 = ppm C 18 H 15 O 3 = ppm m/z 37
38 Summary of identifications in Black and Brown O-rings Sample RT (min) Base Peak (m/z) Search Index HRF Compound Name Formula Base Peak Mass Accuracy (ppm) Molecular ion Mass Accuracy (ppm) Black O Ring No match No match Unknown C 20 H 20 O No match No match Unknown C 20 H 20 O Tetraethylene glycol bis (2 ethylhexanoate) C 24 H 46 O Irganox 1076 C 35 H 62 O ethyl 1 hydroxy 2,3 diphenylcycloprop 2 ene 1 carboxylate C 18 H 16 O Octadecenamide C 18 H 35 NO Brown O Ring Triphenylphosphine oxide C 18 H 15 OP Triphenylphosphine C 18 H 15 P tert butyl 2,6 diisopropylphenol C 16 H 26 O Diethyl phthalate C 12 H 14 O Diphenyl sulfide C 12 H 10 S di(butoxyethyl)adipate C 18 H 34 O Peaks listed are significantly different compared to control. 38
39 Summary of identifications in White and Red O-rings Sample RT (min) Base Peak (m/z) Search Index HRF Compound Name Formula Base Peak Mass Accuracy (ppm) Molecular ion Mass Accuracy (ppm) White O Ring ,4 Dihydrophenacetic acid, 3,5 di t butyl, ethyl ester C 18 H 30 O Butanedioic acid, diethyl ester C 8 H 14 O Red O Ring Ethanone, 1 [4 (1 hydroxy 1 methylethyl)phenyl C 11 H 14 O Methyl stearate C 19 H 38 O di(butoxyethyl)adipate C 18 H 34 O Peaks listed are significantly different compared to control. 39
40 Results Non-Volatile extractables 40
41 LC-MS/MS instrument conditions Equipped with a HESI II ion source. Full scan MS and top3 datadependent HCD MS/MS data were collected. Resolutions of 17,500 and 70,000 Polarity switching. Thermo Scientific Q Exactive Plus Hybrid Quadrupole-Orbitrap LC-MS/MS System. Thermo Scientific UltiMate 3000 UHPLC System 41
42 Mass Accuracy with Polarity Switching (External Calibration) 1 positive + 1 negative scan in <1 second 42
43 MS Scanning Speeds to meet UHPLC Separation Resolution Setting: 35,000 Resolution Setting: 70, Relative Abundance Relative Abundance Time (min) Time (min) Peakwidth (FWHM) ~ 1 sec Scans/peak = 21 Peakwidth (FWHM) ~ 1 sec Scans/peak = 11 43
44 Polarity Switching maintains High Mass Accuracy O O P OH O (M+H) ppm Positive (+) 80 Relative Abundance C 28 H 43 O 4 P MF: (M+NH 4 ) (M+Na) m/z Relative Abundance (M-H) ppm Negative (-) m/z 44
45 Data Analysis For Unknown Quanfirmation Thermo Scientific TraceFinder Software Thermo Scientific Compound Discoverer Thermo Scientific SIEVE Software Quantitation Deconvolution Searching Advanced Unknown Identification Metabolism Differential Analysis PCA Small Molecule Unknown ID & Quantification Spectral Interpretation Libraries & Mass Tables Validated Cloud Library Thermo Scientific Mass Frontier Software High-Resolution Accurate-Mass MS/MS Spectral Libraries MZ Cloud 45
46 Unknown analysis of small molecules Thermo Scientific Compound Discoverer Customizable node based small molecule structure analysis software CD v.1 is for known parent workflows structure analysis CD v.2 will include unknown workflows structure analysis (E&L). Coming end
47 Compound Discoverer Workflow Process Review results Report Elucidate structure C15 H23 N2 O2 [M-e]+1 Intensity [counts] (10^6) C6 H6 N O3 S [M-e]+1 (+Oxidation) C11 H13 N2 O [M-e] C11 H17 N2 O2 S [M-e] C15 H21 N2 O2 [M-e] C11 H17 N2 O3 S [M-e] C11 H14 N O3 [M-e] m/z 47
48 mzcloud Free Advanced high resolution mass spectral database Search spectrum, name, structure, substructure, and m/z Identify compounds even when they are not present in the library through substructure search 48
49 High Resolution E&L Database Contains >1200 common E&L related compounds. Works with TraceFinder and Compound Discoverer for targeted screening. New E&L related compounds are added frequently. 49
50 O-Ring Extractables - Water E:\Parker-O-Ring Leachable\WFI_1 06/24/15 00:17:23 Accucore C18 150X um A: H2O/0.1% FA B: ACN/0.1% FA WFI Control RT: Relative Abundance SM: 5G Control Red Brown White Black Time (min) NL: 3.00E8 Base Peak m/z= F: FTMS + p ESI Full ms [ ] MS WFI_1 NL: 3.00E8 Base Peak m/z= F: FTMS + p ESI Full ms [ ] MS a_red_h2o_01 NL: 3.00E8 Base Peak m/z= F: FTMS + p ESI Full ms [ ] MS b_brown_h2o_1 NL: 3.00E8 Base Peak m/z= F: FTMS + p ESI Full ms [ ] MS c_white_h2o_1 NL: 3.00E8 Base Peak m/z= F: FTMS + p ESI Full ms [ ] MS d_black_h2o_1 50
51 O-Ring Extractables 5M NaCl d_black_nacl_2 06/27/15 22:06:23 Accucore C18 150X um A: H2O/0.1% FA B: ACN/0.1% FA RT: Relative Abundance SM: 5G NL: 1.00E8 Base Peak m/z= F: FTMS + p 9.9 Red ESI Full ms [ ] - m/z= MS a_red_nacl_ NL: 1.00E8 Base Peak m/z= F: FTMS + p Brown ESI Full ms [ ] m/z= MS b_brown_nacl_ NL: 1.00E8 Base Peak m/z= F: FTMS + p White ESI Full ms [ ] - m/z= MS c_white_nacl_ NL: 1.00E8 Base Peak m/z= F: FTMS + p Black ESI Full ms [ ] - m/z= MS d_black_nacl_ Time (min) Control NL: 1.00E8 Base Peak m/z= F: FTMS + p ESI Full ms [ ] - m/z= MS 5M_NaCl_2 51
52 O-Ring Extractables 50% Ethanol E:\Parker-O-Ring Leachable\50EtOH_2 06/25/15 04:50:58 Accucore C18 150X um A: H2O/0.1% FA B: ACN/0.1% FA WFI Control RT: SM: 5G Control NL: 6.00E8 Base Peak F: FTMS + p ESI Full ms [ ] MS 50EtOH_2 Relative Abundance Red White Black Time (min) NL: 6.00E8 Base Peak F: FTMS + p ESI Full ms [ ] MS a_red_50etoh_ NL: 6.00E Base Peak F: FTMS + p ESI Full ms [ ] MS Brown b_brown_50etoh_2 NL: 6.00E8 Base Peak F: FTMS + p ESI Full ms [ ] MS c_white_h2o_2 NL: 6.00E8 Base Peak F: FTMS + p ESI Full ms [ ] MS d_black_50etoh_2 52
53 O-Ring Extractables 100% Ethanol E:\Parker-O-Ring Leachable\100EtOH_2 06/26/15 04:17:58 Accucore C18 150X um A: H2O/0.1% FA B: ACN/0.1% FA WFI Control RT: Relative Abundance SM: 5G Control Red Brown White Black Time (min) 40.0 NL: 8.00E8 Base Peak m/z= F: FTMS + p ESI Full ms [ ] MS 100EtOH_2 NL: 8.00E8 Base Peak m/z= F: FTMS + p ESI Full ms [ ] MS a_red_100etoh_2 NL: 8.00E8 Base Peak m/z= F: FTMS + p ESI Full ms [ ] MS b_brown_50etoh_3 NL: 8.00E8 Base Peak m/z= F: FTMS + p ESI Full ms [ ] MS b_brown_100etoh_2 NL: 8.00E8 Base Peak m/z= F: FTMS + p ESI Full ms [ ] MS d_black_100etoh_2 53
54 BPI+ of Black O-ring in Four Extraction Solutions d_black_50etoh_2 06/25/15 23:12:07 Accucore C18 150X um A: H2O/0.1% FA B: ACN/0.1% FA WFI Control RT: Waters NL: 1.00E9 Base Peak F: FTMS + p ESI Full ms [ ] MS D_Black_H2O_2 Relative Abundance % EtOH % EtOH NL: 1.00E9 Base Peak F: FTMS + p ESI Full ms [ ] MS d_black_50etoh_2 NL: 1.00E9 Base Peak F: FTMS + p ESI Full ms [ ] MS d_black_100etoh_ NL: 1.00E9 Base Peak F: FTMS + p ESI Full ms [ ] MS d_black_nacl_2 5 M NaCl Time (min) 54
55 Powerful Top3 MS/MS for structural elucidation B_Brown_50EtOH_1 08/10/15 19:58:00 Accucore C18 150X um A: H2O/0.1% FA B: ACN/0.1% FA WFI Control Brown O-Ring 50% EtOH RT: Relative Abundance NL: 1.53E9 Base Peak F: FTMS + p ESI Full ms [ ] MS B_Brown_50EtOH _ Time (min) B_Brown_50EtOH_1 #4379 RT: AV: 1 NL: 2.16E8 T: FTMS + p ESI Full ms [ ] 100 Full Scan (+) (M+H) B_Brown_50EtOH_1 #4803 RT: AV: 1 NL: 1.52E9 T: FTMS + p ESI Full ms [ ] (M+H) O P Relative Abundance P C 25 H 21 P Error: -0.7 ppm Relative Abundance C 18 H 15 P Error: -0.1 ppm m/z m/z B_Brown_50EtOH_1 #4364 RT: AV: 1 NL: 2.98E7 T: FTMS + p ESI d Full ms @hcd40.00 [ ] 100 MS/MS (+) B_Brown_50EtOH_1 #4780 RT: AV: 1 NL: 4.62E7 T: FTMS + p ESI d Full ms @hcd40.00 [ ] Relative Abundance Relative Abundance m/z m/z 55
56 Compound Discoverer Workflow for O-Ring leachables Workflow Nodes Workflow Tree 56
57 Automated Identification Compound Discoverer 57
58 Data are directly mirror-plotted versus mzcloud 58
59 Parallel identification through multiple reference sources mzcloud Library Spectrum ChemSpider Search Results E&L Library Results 59
60 Components identified confidently Compound Discoverer allows rapid identification with confident searching of multiple databases in parallel Targeted search compounds can be easily confirmed. High confidence Orbitrap data (<1ppm) combine with mzcloud libraries 60
61 Results Elemental extractables 61
62 Elemental analysis Thermo Scientific icap Q Series ICP-MS Qcell technology for interference reduction Sub ppt detection limits >9 orders dynamic range Robust design to compete with almost any sample matrix Fully compliant Thermo Scientific Qtegra ISDS software Automatic- dilution Full USP 233 & ICH Q3D method capabilities 62
63 icap Q ICP-MS Instrument Configuration Extracts: Water - Analyzed directly 5M NaCl - Analyzed directly 50% Ethanol - Analyzed directly 100% Ethanol - EtOH evaporated 50%, re-dissolved in ultra-pure water Measurement Mode: KED; pure 4.5 ml min-1 Internal standard added online 30ppb Sc, 10 ppb Ga, Y and Lu in 2% HNO3 (4% EtOH added for 50% EtOH samples) All samples were acidified before analysis: 1mL sample, 0.5 ml 65% HNO3, 3.5 ml UPW 63
64 Analysis and QC checks following USP 233 Calibration Range: between 1000-fold and 10-fold dilution of lower limit R 2 better than 0.99 Sensitivity Verification: 0.5x lower limit ±30% of prepared concentration Accuracy Check: Spike recovery of a 0.2 mg/l solution after complete sample acidification routine ±20% of expected concentration Drift Check: Standard 2 (500x dilution) was analyzed every 10 samples ±30% of prepared concentration Quality data, automatically tested 64
65 Results Water and 5M NaCl Reported is concentration in undiluted sample solution Most elements were not detectable Water 5M NaCl 63 Cu 66 Zn 111 Cd 123 Sb 208 Pb 56 Fe 63 Cu 66 Zn 75 As 123 Sb 208 Pb ng ml -1 ng ml -1 ng ml -1 ng ml -1 ng ml -1 ng ml -1 ng ml -1 ng ml -1 ng ml -1 ng ml -1 ng ml -1 Black White Brown Red
66 Results 100% EtOH Reported is concentration in undiluted sample solution Most elements were not detectable 100% EtOH 50% EtOH 63 Cu 66 Zn 111 Cd 123 Sb 208 Pb 63 Cu 66 Zn 111 Cd 123 Sb 208 Pb ng ml -1 ng ml -1 ng ml -1 ng ml -1 ng ml -1 ng ml -1 ng ml -1 ng ml -1 ng ml -1 ng ml -1 ng ml -1 E FF HF S
67 Drift Check 6.5 hour run, 100 samples, 11 drift checks Analyte Av. Recovery [%] RSD [%] Analyte Av. Recovery [%] RSD [%] 7Li Rh Be V Cr Mn Co Ni Cu Zn As Se Mo Pd Cd In Sb W Os Ir Pt Hg Tl Pb Ru
68 Summary Extractable workflow 68
69 Summary GC & LC Orbitrap have superior HRAM, enabling confident identification of extractable unknowns. Empowering software workflows simplify and automate the process of complex identification. Free cloud libraries allow quick qualification of unknowns. Analysis of elemental impurities at the lowest levels is possible with icap Q. 69
70 Webinars SAVE THE DATES 1. Testing for leachables in pharmaceutical contact closure materials; a complete ICP-MS, GC-MS & LC-MS workflow. Wednesday 4th November :30 EST 16:30 CET Dr. Andrew Feilden, Chemistry Operations Director, Smithers Rapra 2. Using GC & LC Orbitrap mass spectrometry to confidently identify leached packaging and process impurities. Wednesday 2nd December :30 EST 16:30 CET Dr. Kate Comstock & Mr. Dominic Roberts, Thermo Fisher Scientific bit.ly/identifyleachables 70
71 E&L Resources Webinars Applications Blogs Regulatory updates White papers And more 71
72 Thank you Andrew Feilden, Smithers Rapra Kate Comstock Daniel Kutscher Dom Roberts 72
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