Applications Summary Waters Corporation 1
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1 Applications Summary 2012 Waters Corporation 1
2 UPC ² Key Messages UPC² is an exclusive, innovative separations tool which applies Waters proven UPLC technology to the traditional technique of SFC, broadening its applicability and radically improving robustness, sensitivity and throughput resulting in a more universal laboratory tool. UPC² was designed to redefine the classic, specialized technique of SFC to a broad based, general analytical tool across a broad range of compounds and analytical challenges. UPC² comes along with the established portfolio of customer service and support capabilities that ensure successful implementation and usage of this new separations tool. WHY CHANGE, WHY NOW, WHY WATERS UPC² enables scientists to separate, analyze and characterize compounds that challenge GC and LC technologies while significantly reducing the use of toxic solvents Waters Corporation 2
3 Analyze a Diverse Range of Compounds 2012 Waters Corporation 3
4 UPC² Compound Diversity ACQUITY UPC 2 Hybrid 2.1 x 150mm, 1.7µm 1.2mL/min, 45 C, 130 bar UV 230nm, 2µL inj 2012 Waters Corporation 4
5 Stereoselective Separations Using Waters ACQUITY UPC² System 2012 Waters Corporation 5
6 Importance of Chiral Separation Chirality is a fundamental aspect of nature, e.g. proteins, nucleic acids, and polysaccharides are chiral molecules Stereoisomers, including enantiomers and diastereomers, could show different biological activities FDA mandate on developing stereoisomeric drugs states that stereoisomers have to be treated as different chemical entities It is important to separate chiral compounds, especially those of pharmaceutical importance 2012 Waters Corporation 6
7 The Dominance of Chiral Chemical Entities in Pharmaceuticals Global Sales Form of Active ($ Billions) Ingredients Therapy Class Lipitor 12.0 Single enantiomer Cholesterol reducer Zocor 5.9 Single enantiomer Cholesterol reducer Plavix 5.0 Single enantiomer Antithrombotic Nexium 4.8 Single enantiomer Antiulcerant Zyprexa 4.8 Achiral Antipsychotic Norvasc 4.8 Racemate Antihypertensive Seretide/Advair 4.7 Racemate Bronchodilator Single enantiomer Anti-inf lammatory Erypo 4.0 Protein Blood cell stimulant Ogastro 3.8 Racemate Antiulcerant Effexor 3.7 Racemate Antidepressant Total 53.5 C&EN, September 5, 2005, 83 (36), Waters Corporation 7
8 The FDA Mandate..In order to evaluate the pharmacokinetics of a single enantiomer or mixture of enantiomers, manufacturers should develop quantitative assays for analyzing the individual enantiomers in vivo samples at early stage in the drug development processes. FDA s Policy Statement for the Development of New Stereoisomeric Drugs May 1, 1992; Corrections made on January 3, /Guidances/ucm htm 2012 Waters Corporation 8
9 Chiral Separation of Binol using NPLC and UPC NPLC Rs=1.67 AU Experimental Conditions NPLC UPC ² Flow Rate (ml/min) 2 4 AU UPC 2 Rs= Minutes Mobile Phase Hexane:iPrOH (98:2) CO 2 :MeOH (75:25) Pressure (bar) n/a 120 Temp ( o C) Ambient 40 Column CHIRALPAK AS-H (4.6x150 mm, 5µm) Conc.(mg/mL) 2 Inj. Vol. (µl) Waters Corporation 9
10 The UPC² Advantages Successful separation of Binol enantiomers in less than 2 min using a Waters ACQUITY UPC² system UPC² is 9 times faster than NPLC More environmentally sustainable Elimination of hexane More cost effective using UPC² $2.85/analysis for NPLC vs. $0.08/analysis for SFC o Improvement in speed o Inexpensive CO 2 and methanol 2012 Waters Corporation 10
11 Chiral Separation of Binol ( en) 2012 Waters Corporation 11
12 Leveraging Small Particles in Chiral Separation Built on ACQUITY platform UPC² system volume is about 66 µl Warfarin UPC² system dispersion is about 25 µl at 2 ml/min o ACQUITY UPLC is about 16 µl UPC² 0.30 IB3 ( mm, 3 µm) 15% methanol 3 ml/min 120 bar Total analysis time: 18 s o Alliance is about 40 µl The reduced system volume of UPC² minimizes extra-column band broadening AU 0.30 NPLC AD-H ( mm, 5 µm) 70/30 hexane/ethanol 1 ml/min Faster separation leads to more dramatic cost-savings and solvent reduction Minutes 2012 Waters Corporation 12
13 Reduced System Volume Also Allows for Fast Gradients Chiral method development often involves screening of multiple columns and co-solvents Carprofen The example shows a typical screening gradient in 2.5 min Reduced system volume allows for fast gradients using 3 µm packed chiral columns The total run time can be reduced by 67% compared to a traditional SFC system 2012 Waters Corporation 13
14 The Need for Chiral Impurity Determination The single enantiomeric form of a chiral drug is considered an improved chemical entity Higher efficacy Better pharmacological profile More favorable adverse reaction profile The undesired stereoisomers should be considered in the same manner as other organic impurities According to the ICH, the threshold for identification and quantification of organic impurities is 0.1% for the majority of compounds 2012 Waters Corporation 14
15 Enantiomeric Excess (ee) Determination by UPC² AU 0.20 R S R S =7.28 O OH (R) O OH (S) Minutes O Benzyl Mandelate O AU R S Minutes Analyte Benzyl mandelate Isomer R- S- Retention t R (min) Std. Dev % RSD Peak area Peak area (µv*sec) Std. Dev % RSD Waters Corporation 15
16 The UPC² Advantages Better Quantitative Chiral Analysis R- and S-benzyl mandelate enantiomers were separated in less than 1.5 min using a Waters ACQUITY UPC² system Excellent repeatability resulting of pumping system < 0.23% RSD for retention time < 0.5% RSD for peak area Improved detection sensitivity enables the detection of 0.02% enantiomeric impurity Improved pumping system Dynamic + Static BPR design to mitigate pressure fluctuation Optimized detector design with improved thermal control o Less susceptible to environmental temperature variation Injection valve specifically designed for UPC² to reduce pulsation 2012 Waters Corporation 16
17 Enantiomeric Excess (ee) by UPC² ( en) 2012 Waters Corporation 17
18 Chiral Pesticides 25% of the currently used pesticides are chiral Chirality plays an important role in the potency, toxicity, metabolism, and environmental fate of these chiral pesticides Permethrin is a synthetic chemical widely used as an insecticide and an insect repellent Separation of permethrin using NPLC and RPLC was moderately successful 2012 Waters Corporation 18
19 Chiral Separation of Permethrin 0.06 UPC² AU Minutes NPLC SFC Flow rate (ml/min) 1 4 Mobile phase hexane:ethanol=90:10 CO 2 :methanol:dea=9 5:5:0.2 Back Pressure (bar) n/a 120 Temperature ( C) ambient 40 CHIRALCEL OJ-H CHIRALCEL OJ-H Column ( mm, 5 ( mm, 5 µm) µm) Sample Conc. 2 mg/ml Injection volume (µl) 10 AU NPLC Minutes 2012 Waters Corporation 19
20 The UPC² Advantages Baseline resolution of all four permethrin isomers was achieved in less than 6 min using a Waters ACQUITY UPC² system Compared to the chiral HPLC methods, the described SFC method offers a better resolution and a shorter run time The SFC method also eliminated the need for toxic hexane often used in NPLC methods 2012 Waters Corporation 20
21 Chiral Separation of Permethrin ( en) 2012 Waters Corporation 21
22 Drugs of Abuse Analysis by UPC²/MS/MS UPC 2 /MS/MS (ESI) S/N=11.6 S/N= min Challenging by other modes of analysis CE/MS: min GC/MS: min, with derivatization LC/MS/MS: min Faster separation 5 ng/ml for each enantiomer (25 pg on column) 2012 Waters Corporation 22
23 Achiral Separations Using Waters ACQUITY UPC² System 2012 Waters Corporation 23
24 Chromatographic Assay of Tolbutamide Using the ACQUITY UPC² System 2012 Waters Corporation 24
25 Chromatographic Assay of Tolbutamide Since the principles of SFC are similar to those of HPLC, methods should be able to be converted to SFC reducing solvent usage and disposal which will lower cost per analysis while enhancing green initiatives Methods converted to an ACQUITY UPC² solution must maintain data quality and must produce results that are equivalent to the current normal phase method Currently, the United States Pharmacopeia (USP) specifies a normal phase HPLC method for the assay of the drug substance tolbutamide (benzenesulfonamide, CAS# ) This isocratic separation is done at 1.5 ml/min using a 4.0 mm x 300 mm, silica column (L3) with a mobile phase that consists of hexane, water-saturatedhexane, tetrahydrofuran, alcohol and glacial acetic acid (475:475:20:15:9) with a run time of about 20 minutes Like most compendia methods, this method is well proven and reliable, it does however use a complicated mobile phase mixture that contains hexane and THF, solvents that many labs would like to eliminate to support green initiatives and reduce costs 2012 Waters Corporation 25
26 Chromatographic Assay of Tolbutamide Tolbutamide Normal Phase HPLC Taolazamide USP Method Column x 300 mm, silica column (L3) Flow Rate - Isocratic 1.5 ml/min Mobile phase - hexane, water-saturated-hexane, tetrahydrofuran, alcohol, and glacial acetic acid (475:475:20:15:9) AU *Cost per run ~ $ Minutes AU Tolbutamide ACQUITY UPC² Tolazamide UPC² Method Column ACQUITY UPC 2 BEH, 3.0 x 100 mm, 1.7 µm at 50 C Flow Rate ml/min, Backpressure Bar/1740 psi Mobile Phase - 95% Carbon Dioxide: 5% Methanol/IPA (1/1) containing 0.2% TFA Minutes 2 *Cost per run ~ $0.01 1/10 th the run time *Solvent cost per run 2012 Waters Corporation 26
27 Chromatographic Assay of Tolbutamide Using the Waters ACQUITY UPC² system a USP compendia HPLC method was successfully converted to an ACQUITY UPC² method This new ACQUITY UPC² method produced data of equal or better quality than the current HPLC method and was 10 times faster and consumed less solvent When high quality results are produced more quickly, laboratory productivity increases and cost per sample decreases The Waters ACQUITY UPC² system is an ideal solution for laboratories wanting to convert their current normal phase HPLC methods to more efficient and cost effective methods while enhancing health, safety, and environmental concerns 2012 Waters Corporation 27
28 Assay of Tolbutamide ( en) 2012 Waters Corporation 28
29 Chromatographic Purity of Estradiol using the ACQUITY UPC² System 2012 Waters Corporation 29
30 Chromatographic Purity of Estradiol Currently, the United States Pharmacopeias (USP) method for the estimation of chromatographic purity of Estradiol utilizes a 4.6 mm 250 mm silica column that uses a mobile phase consisting of 2,2,4- trimethylpentane, n-butyl chloride and methanol (45:4:1) at 2 ml/min Since many laboratories have a desire to limit the use of aliphatic hydrocarbons and chlorinated solvents, alternative chromatographic techniques, like Supercritical Fluid Chromatography (SFC) must be evaluated Using a newly designed analytical SFC system, ACQUITY UPC², a method for the evaluation of chromatographic purity of Estradiol was developed Results obtained from the ACQUITY UPC² method were directly compared to results obtained for the current USP method for Estradiol impurities. The results from both techniques were similar with the UPC² method showing adequate sensitivity to detect impurities in Estradiol equal to those obtained from the Normal Phase Liquid Chromatography (NPLC) USP method 2012 Waters Corporation 30
31 Chromatographic Purity of Estradiol A sample of Estradiol was prepared and analyzed using the current USP method The results were compared against results obtained with a method developed on an ACQUITY UPC² System using identical sample preparation ACQUITY UPC² method conditions: Column: 2.1 x 150 mm ACQUITY UPC² BEH, 1.7 µm Back pressure: 130 bar (1,885 psi), Temperature: 45 C UV Detection /PDA at 280 nm Gradient Table Time Flow %A %B Curve (min) (ml/min) Waters Corporation 31
32 Chromatographic Purity of Estradiol AU Normal Phase HPLC Cost per run ~ $ Compound RT %Area S/N Unk. Impurity Unk. Impurity Not Found Unk. Impurity Unk. Impurity Not Found Unk. Impurity Unk. Impurity Estradiol Main Impurity Minutes ACQUITY UPC² Cost per run ~ $0.05 Compound RT %Area S/N Unk. Impurity Unk. Impurity Unk. Impurity Unk. Impurity Unk. Impurity Unk. Impurity Estradiol Main Impurity Waters Corporation 32
33 Chromatographic Purity of Estradiol Using an ACQUITY UPC² system, a method for the estimation of the chromatographic purity of Estradiol was developed This ACQUITY UPC² method was 3 times faster than the current normal phase method from the USP In addition to speed, this method reduced the cost per analysis by more than 100 times, primarily by reducing the need for aliphatic hydrocarbons and chlorinated solvents Required sensitivity levels were achieved in the ACQUITY UPC² method with impurities as low as 0.01% of the main peaks being easily detected The ACQUITY UPC² system is an ideal choice for laboratories looking for an alternative to conventional normal phase chromatography 2012 Waters Corporation 33
34 Purity of Estradiol ( en) 2012 Waters Corporation 34
35 Fat Soluble Vitamins 2012 Waters Corporation 35
36 Fat Soluble Vitamins The analysis of fat soluble vitamins (FSV) formulations, typically from capsules, can be a challenging task Current methods employ normal phase and reverse phase liquid chromatography techniques as well as gas chromatography, thin layer chromatography, and colorimetric techniques for these analyses Many laboratories are looking for a viable alternative that lowers the use of organic solvents, provides faster analysis times, and maintains chromatographic data quality Using the ACQUITY UPC² system, a series of FSV formulations were analyzed. Results from these experiments show the ACQUITY UPC² has the potential to replace many of the separation methods in use today 2012 Waters Corporation 36
37 Fat Soluble Vitamins Separation of Vitamin A capsule 3X100 mm Prototype C µm 2.5 ml/min 130 Bar backpressure UV at 254 nm Time %CO 2 % MeOH This formulation of Vitamin A was labeled to be from fish liver oil and contained soy oil, gelatin, glycerin, and water as inactive ingredients. Two forms of vitamin A (cis and trans isomers) were noted and were well resolved from the excipient peaks 2012 Waters Corporation 37
38 Fat Soluble Vitamins Separation of Vitamin A & D3 capsule 3X100 mm Prototype C µm 2.5 ml/min 130 Bar backpressure UV at 254 nm Time %CO 2 % MeOH A formulation containing both Vitamin A and Vitamin D3 was analyzed. Again, two forms of vitamin A (cis and trans isomers) were noted before the excipient peaks. Vitamin D3 elutes well after the bulk of the excipient material. The UPC² system provide enough sensitivity to easily detect the Vitamin D3 peak 2012 Waters Corporation 38
39 Fat Soluble Vitamins Separation of Vitamin E capsule 2.1X50 mm ACQUITY UPC 2 BEH 1.7µm 3.0 ml/min 130 Bar backpressure, UV at 293 nm Time %CO 2 % MeOH A very rapid gradient analysis (~ 30 second run time) that easily separated the 4 tocopherol isomers (d-α, d-β, d-γ, d-δ) was developed for the Vitamin E capsule 2012 Waters Corporation 39
40 Fat Soluble Vitamins Separation of Vitamin K1 tablet 3X100 mm Prototype C µm 99 % CO 2 and 1% MeOH at 2.5 ml/min 130 Bar backpressure UV at 246 nm The Vitamin K1 tablets generated 2 distinct peaks with a simple isocratic method. UV spectra (collected simultaneously along with the UV at 246 nm channel) of both peaks were similar indicating that the peaks were related. Although not confirmed (individual standards of each of the isomers were not available at time of analysis), it is likely that the 2 peaks are the cis and trans isomers of phylloquinone 2012 Waters Corporation 40
41 Fat Soluble Vitamins Waters ACQUITY UPC² System was able to successfully analyze different formulations of fat soluble vitamins Each of the FSV formulations were analyzed rapidly with components of interest resolved from excipent materials This system can greatly streamline FSV analysis by allowing labs to use a single technique to analyze a wide range of FSV formulations 2012 Waters Corporation 41
42 Fat Soluble Vitamins (PSTR ) 2012 Waters Corporation 42
43 Fat Soluble Vitamin Capsules ( en) 2012 Waters Corporation 43
44 ACQUITY UPC² Compliments RP-LC Metoclopramide: Providing an Orthogonal Approach for Achiral Impurity Analysis 2012 Waters Corporation 44
45 Metoclopramide Marketed as Reglan (Wyeth) Generic brands supplied by Major Pharmaceuticals, Mutual Pharma Co., Pliva, and Teva A class of medication called prokinetic agents Antiemetic prescribed to treat heartburn healing of ulcers and sores for people with GERD Nausea and vomiting for patients undergoing chemotherapy US annual sales approximately $13M 2012 Waters Corporation 45
46 Conditions ACQUITY UPC 2 ACQUITY UPLC Reversed Phase Instrument: ACQUITY UPC 2 coupled to SQD Mobile Phase A: CO 2 (tank, medical grade) Modifier B: Methanol with 2g/L ammonium formate Column: UPC 2 BEH 3.0 x 100 mm, 1.7µm Injection Vol.: 1.0 µl Column Temp.: 50 C Flow Rate: 2.5 ml/min Gradient: Time %B Instrument: ACQUITY UPLC System ACQUITY UPLC eλpda Mobile Phase A: 0.25% w/w Ammonium Acetate in Water Mobile Phase B: Acetonitrile Column: 2.1 x 100mm BEH C18, 1.7µm Temperature: 32 C Injection Volume: 1 µl Flow Rate: 500 µl/min Gradient: Time %B *CCM pressure: 1500psi Wavelength: 4.8nm Resolution (compensated nm) CDS: Empower 3 CDS Wavelength: CDS: 4.8nm Resolution Empower 2 Software 2012 Waters Corporation 46
47 AU Metoclopramide SFC vs. RP Metoclopramide Reversed Phase Minutes 12 minutes Metoclopramide ACQUITY UPC 2 AU Minutes 12 minutes 2012 Waters Corporation 47
48 Analysis of Metoclopramide with 0.5% impurities 2-EP, ammonium formate RT Area % Area EP Imp. B EP Imp. D EP Imp. A EP Imp. C Metoclop EP Imp. G Metoclopramide *Imp B *Imp D *Imp A Imp C AU AU AU AU AU API AU EP Imp B EP Imp D EP Imp A EP Imp C EP Imp G Minutes Imp G AU nm *Impurities b, d, a, c will have different relative response factors calculated 2012 Waters Corporation 48
49 The UPC² Advantages ACQUITY UPC² appropriate for achiral pharmaceutical analysis Excellent orthogonal approach to reversed phase LC Essential for generic pharmaceutical companies comparison to innovator drug formulation Impurities can be detected at less than 0.05% area Maintains spectral integrity at low levels Ability to determine relationship to API 2012 Waters Corporation 49
50 Summary UPC² system solution enhances every laboratory s problem solving capability Demonstrated applications show clear advantages over current methodology UPC² system solution offers the necessary attributes required from an analytical system for routine analysis Acquity UPC² system complements Acquity UPLC systems and allows us to offer our customers unparalleled solutions to solve their challenging analytical problems 2012 Waters Corporation 50
51 Questions?? 2012 Waters Corporation 51
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