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INTRODUCTION: • Phenylephrine-succinate is a degradation product formed from the reaction between the maleate of chlorpheniramine and phenyleph- rine. It is found in over-the-counter products containing maleates and phenylephrine. • The purpose of this project was to develop a single sample processing method that would allow for injection using multiple LC-MS/MS methods, if necessary, for the quantitation of ibuprofen (IBU), phenylephrine (PE), chlorpheniramine (CHL), and phenyleph- rine-succinate (PES) in rat plasma (NaF/EDTA). CHALLENGES: • Differences in the structures, active functional groups, and acid dissociation constants of the target compounds made it impossible to develop a single solid phase or liquid-liquid extraction method for all four compounds from rat plasma. • Instead, a single protein precipitation method had to be developed to provide “clean” samples that would not cause high back- pressure or blown fittings when injected onto the LC-MS/MS. • The protein precipitation method also required high recovery for the less sensitive compounds (PE and PES) and the addition of an appropriate dilution solvent for the more sensitive compounds (IBU and CHL). • Differences in instrument sensitivity and required ion modes (positive vs. negative) made it necessary to develop three LC-MS/ MS methods that would separate the compounds from matrix components inherently present in protein precipitated samples. METHODS AND INSTRUMENTATION: • Proteins in rat plasma samples (0.05 mL) were precipitated by the addition of dilute trichloroacetic acid. • After centrifugation, portions of the supernatant were transferred to two separate 96 well plates using a Zymark/Caliper Sciclone automated sample handling system. • One plate (for PE and PES) was diluted with an acidified aqueous:organic solution. • The second plate (for IBU and CHL) was diluted with acetonitrile. • PE and PES were resolved from each other and from other matrix components on a Waters Xterra MS C18 analytical column using trifluoroacetic acid in an aqueous rich mobile phase. • CHL and IBU were separated from matrix components on ZORBAX 300-SCX and Luna C 8 analytical columns, respectively, using solvent rich mobile phases. • An AB SCIEX 4000 using an ESI interface detected positive ions (for PE, PES, and CHL) and negative ions (for IBU) in the multiple reaction monitoring mode. • The acquisition times for PE/PES, CHL, and IBU were 3.0, 1.5, and 1.5 minutes, respectively. RESULTS: • A weighted (1/x 2 ) linear regression over the ranges of 0.250-50.0 µg/mL (IBU), 5.00-1000 ng/mL (PE), 1.00-200 ng/mL (CHL), and 2.00-400 ng/mL (PES) was used. • Inter-batch precision (% CV) and accuracy (% Bias) of IBU (Table 1), PE (Table 2), CHL (Table 3), and PES (Table 4) quality control samples met predefined validation acceptance criteria. • Assay selectivity was demonstrated by quantitation of six separate rat plasma lots fortified near the LLOQ and at the high quality control concentrations for all compounds. No significant matrix effect was observed (Tables 5-6). • A post-column infusion demonstrated that IBU, PE, CHL, PES and their respective internal standards did not co-elute with any areas of significant suppression or enhancement. • Samples having a concentration above the upper limit of the calibration standard ranges were diluted with blank control matrix, and results show that samples with concentrations up to 100 µg/mL, 5000 ng/mL, 1000 ng/mL, and 2000 ng/mL for IBU, PE, CHL, PES, respectively, could be quantified after the application of an appropriate dilution factor. • The average extraction recoveries of IBU, PE, CHL, and PES were 48%, 83%, 93%, and 106%, respectively. The average extraction recoveries of d 3 -IBU, d 3 -PE, and d 6 -CHL were 43%, 83%, and 95%, respectively. • Stability evaluations of IBU, PE, CHL, and PES (Table 7) quality control samples met predefined validation acceptance criteria. • Method robustness was demonstrated with multiple column lots, mass spectrometers, and extraction scientists. • The validated batch size was 96 samples. Figure 4. PES Structure Figure 2. PE Structure Figure 3. CHL Structure Figure 1. IBU Structure Figure 5. IBU / d 3 -IBU Extracted Blank Sample (Top) and Extracted LLOQ Sample (Bottom) Figure 6. PE / d 3 -PE Extracted Blank Sample (Top) and Extracted LLOQ Sample (Bottom) Figure 7. CHL / d 6 -CHL Extracted Blank Sample (Top) and Extracted LLOQ Sample (Bottom) Figure 8. PES / d 3 -PE Extracted Blank Sample (Top) and Extracted LLOQ Sample (Bottom) Table 1. IBU Inter-Batch Precision and Accuracy LLOQ QC QC A QC B QC C 0.250 µg/mL 0.750 µg/mL 3.75 µg/mL 37.5 µg/mL Inter-Batch Mean 0.258 0.780 3.95 35.5 Inter-Batch % CV 6.2 4.6 4.3 5.9 Inter-Batch % Bias 3.2 4.0 5.3 -5.3 n 18 18 18 18 Table 2. PE Inter-Batch Precision and Accuracy LLOQ QC QC A QC B QC C 5.00 ng/mL 15.0 ng/mL 75.0 ng/mL 750 ng/mL Inter-Batch Mean 5.47 15.2 74.6 704 Inter-Batch % CV 12.4 5.6 6.5 4.3 Inter-Batch % Bias 9.4 1.3 -0.5 -6.1 n 18 18 18 18 Table 3. CHL Inter-Batch Precision and Accuracy LLOQ QC QC A QC B QC C 1.00 ng/mL 3.00 ng/mL 15.0 ng/mL 150 ng/mL Inter-Batch Mean 0.927 2.88 15.1 147 Inter-Batch % CV 5.5 3.4 4.6 2.8 Inter-Batch % Bias -7.3 -4.0 0.7 -2.0 n 18 18 18 18 Table 4. PES Inter-Batch Precision and Accuracy LLOQ QC QC A QC B QC C 2.00 ng/mL 6.00 ng/mL 30.0 ng/mL 300 ng/mL Inter-Batch Mean 2.03 6.02 31.2 308 Inter-Batch % CV 11.5 8.3 5.5 6.1 Inter-Batch % Bias 1.5 0.3 4.0 2.7 n 18 18 18 18 CONCLUSIONS: • The validated method utilized a single sample processing method and three LC-MS/MS methods to appropriately quantitate all four compounds and eliminate significant matrix interference. • The bioanalytical assay for the quantitation of ibuprofen, phenylephrine, chlorpheniramine, and phenylephrine-succinate in rat plasma (NaF/EDTA) met acceptance criteria for precision, accuracy, sensitivity, selectivity, and stability. • The validation results demonstrate that a precise, accurate, sensitive, selective, rugged and reproducible assay was developed. Table 5. IBU and CHL Matrix Effect Test IBU CHL LLOQ High LLOQ High Lot# 0.250 µg/mL % Dev. 37.5 µg/mL % Dev. 1.00 ng/mL % Dev. 150 ng/mL % Dev. 1 0.242 -3.2 31.9 -14.9 1.00 +0.0 142 -5.3 2 0.262 +4.8 35.0 -6.7 0.988 -1.2 143 -4.7 3 0.244 -2.4 34.8 -7.2 1.02 +2.0 145 -3.3 4 0.240 -4.0 33.0 -12.0 1.11 +11.0 146 -2.7 5 0.249 -0.4 31.0 -17.3 0.983 -1.7 139 -7.3 6 0.227 -9.2 33.2 -11.5 1.05 +5.0 145 -3.3 Mean 0.244 33.2 1.03 143 % CV 4.7 4.7 4.7 1.8 % Theoretical 97.6 88.5 103.0 95.3 n 6 6 6 6 Table 6. PE and PES Matrix Effect Test PE PES LLOQ High LLOQ High Lot# 5.00 ng/mL % Dev. 750 ng/mL % Dev. 2.00 ng/mL % Dev. 300 ng/mL % Dev. 1 6.69 +33.8 663 -11.6 2.06 +3.0 293 -2.3 2 5.25 +5.0 682 -9.1 1.94 -3.0 272 -9.3 3 5.46 +9.2 695 -7.3 2.28 +14.0 312 +4.0 4 5.53 +10.6 658 -12.3 2.02 +1.0 294 -2.0 5 5.48 +9.6 692 -7.7 2.22 +11.0 288 -4.0 6 5.25 +5.0 656 -12.5 2.24 +12.0 302 +0.7 Mean 5.61 674 2.13 294 % CV 9.7 2.6 6.5 4.6 % Theoretical 112.2 89.9 106.5 98.0 n 6 6 6 6 A LC-MS/MS Method for the Quantitation of Ibuprofen, Phenylephrine, Chlorpheniramine, and Phenylephrine-Succinate in Rat Plasma (NaF/Na 2 EDTA) Ginny James, Alan Dzerk, Curtis Sheldon Celerion, Lincoln, NE Table 7. Stability Evaluations Information Requested Data Bench-Top Stability (Short-term Stability) at IBU, CHL, PES: 7 hours Ambient Temperature Under UV-Shielded Light PE: 2 hours Bench-Top Stability (Short-term Stability) in an IBU: 19 hours Ice Water Bath Under UV-Shielded Light PE, CHL, PES: 5 hours Processed Stability (Post-Preparative Stability) IBU: 106 hours in a Polypropylene 96 Well Plate at 5°C PE: 105 hours CHL, PES: 126 hours Processed Stability (Processed Sample Integrity) IBU: 101 hours in a Polypropylene 96 Well Plate at 5°C PE, PES: 157 hours CHL: 107 Freeze-Thaw Stability in Polypropylene Tubes IBU, PE, CHL, PES: 4 freeze (-80°C) Under UV-Shielded Light -thaw (ambient temperature) cycles Long-Term Storage Stability in Polypropylene IBU, PE, CHL, PES: 110 days Tubes at -80°C

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Page 1: a lc-Ms/Ms Method for the Quantitation of Ibuprofen ... · LC-MS/MS methods, if necessary, for the quantitation of ibuprofen (IBU), phenylephrine (PE), chlorpheniramine (CHL), and

IntroductIon:• Phenylephrine-succinateisadegradationproductformedfromthe

reactionbetweenthemaleateofchlorpheniramineandphenyleph-rine.Itisfoundinover-the-counterproductscontainingmaleatesandphenylephrine.

• ThepurposeofthisprojectwastodevelopasinglesampleprocessingmethodthatwouldallowforinjectionusingmultipleLC-MS/MSmethods,ifnecessary,forthequantitationofibuprofen(IBU),phenylephrine(PE),chlorpheniramine(CHL),andphenyleph-rine-succinate(PES)inratplasma(NaF/EDTA).

challenges:• Differencesinthestructures,activefunctionalgroups,andacid

dissociationconstantsofthetargetcompoundsmadeitimpossibletodevelopasinglesolidphaseorliquid-liquidextractionmethodforallfourcompoundsfromratplasma.

• Instead,asingleproteinprecipitationmethodhadtobedevelopedtoprovide“clean”samplesthatwouldnotcausehighback-pressureorblownfittingswheninjectedontotheLC-MS/MS.

• Theproteinprecipitationmethodalsorequiredhighrecoveryforthelesssensitivecompounds(PEandPES)andtheadditionofanappropriatedilutionsolventforthemoresensitivecompounds(IBUandCHL).

• Differencesininstrumentsensitivityandrequiredionmodes(positivevs.negative)madeitnecessarytodevelopthreeLC-MS/MSmethodsthatwouldseparatethecompoundsfrommatrixcomponentsinherentlypresentinproteinprecipitatedsamples.

Methods and InstruMentatIon:• Proteinsinratplasmasamples(0.05mL)wereprecipitatedbythe

additionofdilutetrichloroaceticacid.• Aftercentrifugation,portionsofthesupernatantweretransferred

totwoseparate96wellplatesusingaZymark/CaliperScicloneautomatedsamplehandlingsystem.

• Oneplate(forPEandPES)wasdilutedwithanacidifiedaqueous:organicsolution.

• Thesecondplate(forIBUandCHL)wasdilutedwithacetonitrile.• PEandPESwereresolvedfromeachotherandfromothermatrix

componentsonaWatersXterraMSC18analyticalcolumnusingtrifluoroaceticacidinanaqueousrichmobilephase.

• CHLandIBUwereseparatedfrommatrixcomponentsonZORBAX300-SCXandLunaC8analyticalcolumns,respectively,usingsolventrichmobilephases.

• AnABSCIEX4000usinganESIinterfacedetectedpositiveions(forPE,PES,andCHL)andnegativeions(forIBU)inthemultiplereactionmonitoringmode.

• TheacquisitiontimesforPE/PES,CHL,andIBUwere3.0,1.5,and1.5minutes,respectively.

results:• Aweighted(1/x2)linearregressionovertherangesof

0.250-50.0µg/mL(IBU),5.00-1000ng/mL(PE),1.00-200ng/mL(CHL),and2.00-400ng/mL(PES)wasused.

• Inter-batchprecision(%CV)andaccuracy(%Bias)ofIBU(Table1),PE(Table2),CHL(Table3),andPES(Table4)qualitycontrolsamplesmetpredefinedvalidationacceptancecriteria.

• AssayselectivitywasdemonstratedbyquantitationofsixseparateratplasmalotsfortifiedneartheLLOQandatthehighqualitycontrolconcentrationsforallcompounds.Nosignificantmatrixeffectwasobserved(Tables5-6).

• Apost-columninfusiondemonstratedthatIBU,PE,CHL,PESandtheirrespectiveinternalstandardsdidnotco-elutewithanyareasofsignificantsuppressionorenhancement.

• Sampleshavingaconcentrationabovetheupperlimitofthecalibrationstandardrangesweredilutedwithblankcontrolmatrix,andresultsshowthatsampleswithconcentrationsupto100µg/mL,5000ng/mL,1000ng/mL,and2000ng/mLforIBU,PE,CHL,PES,respectively,couldbequantifiedaftertheapplicationofanappropriatedilutionfactor.

• TheaverageextractionrecoveriesofIBU,PE,CHL,andPESwere48%,83%,93%,and106%,respectively.Theaverageextractionrecoveriesofd3-IBU,d3-PE,andd6-CHLwere43%,83%,and95%,respectively.

• StabilityevaluationsofIBU,PE,CHL,andPES(Table7)qualitycontrolsamplesmetpredefinedvalidationacceptancecriteria.

• Methodrobustnesswasdemonstratedwithmultiplecolumnlots,massspectrometers,andextractionscientists.

• Thevalidatedbatchsizewas96samples.

Figure 4. PES Structure

Figure 2. PE Structure

Figure 3. CHL Structure

Figure 1. IBU Structure

Figure 5. IBU / d3-IBU Extracted Blank Sample (Top) and Extracted LLOQ Sample (Bottom)

Figure 6. PE / d3-PE Extracted Blank Sample (Top) and Extracted LLOQ Sample (Bottom)

Figure 7. CHL / d6-CHL Extracted Blank Sample (Top) and Extracted LLOQ Sample (Bottom)

Figure 8. PES / d3-PE Extracted Blank Sample (Top) and Extracted LLOQ Sample (Bottom)

Table 1. IBU Inter-Batch Precision and Accuracy

LLOQQC QCA QCB QCC 0.250µg/mL 0.750µg/mL 3.75µg/mL 37.5µg/mL

Inter-Batch Mean 0.258 0.780 3.95 35.5

Inter-Batch % CV 6.2 4.6 4.3 5.9

Inter-Batch % Bias 3.2 4.0 5.3 -5.3

n 18 18 18 18

Table 2. PE Inter-Batch Precision and Accuracy

LLOQQC QCA QCB QCC 5.00ng/mL 15.0ng/mL 75.0ng/mL 750ng/mL

Inter-Batch Mean 5.47 15.2 74.6 704

Inter-Batch % CV 12.4 5.6 6.5 4.3

Inter-Batch % Bias 9.4 1.3 -0.5 -6.1

n 18 18 18 18

Table 3. CHL Inter-Batch Precision and Accuracy

LLOQQC QCA QCB QCC 1.00ng/mL 3.00ng/mL 15.0ng/mL 150ng/mL

Inter-Batch Mean 0.927 2.88 15.1 147

Inter-Batch % CV 5.5 3.4 4.6 2.8

Inter-Batch % Bias -7.3 -4.0 0.7 -2.0

n 18 18 18 18

Table 4. PES Inter-Batch Precision and Accuracy

LLOQQC QCA QCB QCC 2.00ng/mL 6.00ng/mL 30.0ng/mL 300ng/mL

Inter-Batch Mean 2.03 6.02 31.2 308

Inter-Batch % CV 11.5 8.3 5.5 6.1

Inter-Batch % Bias 1.5 0.3 4.0 2.7

n 18 18 18 18

conclusIons:• Thevalidatedmethodutilizedasinglesampleprocessing

methodandthreeLC-MS/MSmethodstoappropriatelyquantitateallfourcompoundsandeliminatesignificantmatrixinterference.

• Thebioanalyticalassayforthequantitationofibuprofen,phenylephrine,chlorpheniramine,andphenylephrine-succinateinratplasma(NaF/EDTA)metacceptancecriteriaforprecision,accuracy,sensitivity,selectivity,andstability.

• Thevalidationresultsdemonstratethataprecise,accurate,sensitive,selective,ruggedandreproducibleassaywasdeveloped.

Table 5. IBU and CHL Matrix Effect Test

IBU CHL

LLOQ High LLOQ High

Lot# 0.250µg/mL %Dev. 37.5µg/mL %Dev. 1.00ng/mL %Dev. 150ng/mL %Dev.

1 0.242 -3.2 31.9 -14.9 1.00 +0.0 142 -5.3

2 0.262 +4.8 35.0 -6.7 0.988 -1.2 143 -4.7

3 0.244 -2.4 34.8 -7.2 1.02 +2.0 145 -3.3

4 0.240 -4.0 33.0 -12.0 1.11 +11.0 146 -2.7

5 0.249 -0.4 31.0 -17.3 0.983 -1.7 139 -7.3

6 0.227 -9.2 33.2 -11.5 1.05 +5.0 145 -3.3

Mean 0.244 33.2 1.03 143

% CV 4.7 4.7 4.7 1.8

% Theoretical 97.6 88.5 103.0 95.3

n 6 6 6 6

Table 6. PE and PES Matrix Effect Test

PE PES

LLOQ High LLOQ High

Lot# 5.00ng/mL %Dev. 750ng/mL %Dev. 2.00ng/mL %Dev. 300ng/mL %Dev.

1 6.69 +33.8 663 -11.6 2.06 +3.0 293 -2.3

2 5.25 +5.0 682 -9.1 1.94 -3.0 272 -9.3

3 5.46 +9.2 695 -7.3 2.28 +14.0 312 +4.0

4 5.53 +10.6 658 -12.3 2.02 +1.0 294 -2.0

5 5.48 +9.6 692 -7.7 2.22 +11.0 288 -4.0

6 5.25 +5.0 656 -12.5 2.24 +12.0 302 +0.7

Mean 5.61 674 2.13 294

% CV 9.7 2.6 6.5 4.6

% Theoretical 112.2 89.9 106.5 98.0

n 6 6 6 6

a lc-Ms/Ms Method for the Quantitation of Ibuprofen, Phenylephrine, chlorpheniramine, and Phenylephrine-succinate in rat Plasma (naF/na2 edta) ginny James, alan dzerk, curtis sheldon celerion, lincoln, ne

Table 7. Stability Evaluations

InformationRequested Data

Bench-TopStability(Short-termStability)at IBU, CHL, PES: 7 hours AmbientTemperatureUnderUV-ShieldedLight PE: 2 hours

Bench-TopStability(Short-termStability)inan IBU: 19 hours IceWaterBathUnderUV-ShieldedLight PE, CHL, PES: 5 hours

ProcessedStability(Post-PreparativeStability) IBU: 106 hours inaPolypropylene96WellPlateat5°C PE: 105 hours CHL, PES: 126 hours

ProcessedStability(ProcessedSampleIntegrity) IBU: 101 hours inaPolypropylene96WellPlateat5°C PE, PES: 157 hours CHL: 107

Freeze-ThawStabilityinPolypropyleneTubes IBU, PE, CHL, PES: 4 freeze (-80°C)UnderUV-ShieldedLight -thaw (ambient temperature) cycles

Long-TermStorageStabilityinPolypropylene IBU, PE, CHL, PES: 110 days Tubesat-80°C

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