Characterization of impurities and degrandants using mass spectrometry:
Gespeichert in:
| Weitere Verfasser: | |
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| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Hoboken, NJ
Wiley
2011
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| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XXII, 462 S. Ill., graph. Darst. |
| ISBN: | 9780470386187 9780470921371 |
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| 020 | |a 9780470386187 |9 978-0-470-38618-7 | ||
| 020 | |a 9780470921371 |c oBook |9 978-0-470-92137-1 | ||
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| 245 | 1 | 0 | |a Characterization of impurities and degrandants using mass spectrometry |c ed. by Birendra N. Pramanik ... |
| 264 | 1 | |a Hoboken, NJ |b Wiley |c 2011 | |
| 300 | |a XXII, 462 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
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Datensatz im Suchindex
| _version_ | 1804142944366624768 |
|---|---|
| adam_text | CONTENTS
PREFACE
xv
CONTRIBUTORS
xvii
ACRONYMS
xix
PART I METHODOLOGY
1.
Introduction to Mass Spectrometry
3
Scott A. Smith, Ruth Waddell Smith, Yu Xia, and Zheng Ouyang
1.1.
History
3
1.1.1.
Atomic Physics
4
1.1.2.
Early Applications
7
1.1.3.
Organic Structural Analysis
7
1.1.4.
The Biological Mass Spectrometry Revolution
8
1.2.
Ionization Methods
9
1.3.
Mass Spectrometer Types
10
1.3.1.
Magnetic Sector Mass Spectrometers
10
1.3.2.
Quadrupole Mass Filter and Quadrupole Ion Trap
Mass Spectrometers
14
1.3.3.
Time-of-Flight Mass Spectrometers
19
1.3.4.
Fourier Transform Ion Cyclotron Resonance
Mass Spectrometers
22
1.3.5.
Orbitrap Mass Spectrometers
25
1.4.
Tandem Mass Spectrometry
28
1.4.1.
Ion Isolation
29
1.4.2.
Ion-Molecule Collisions and Collision-Induced
Dissociation
30
1.4.3.
Electron Capture Dissociation and Electron Transfer
Dissociation
32
1.5.
Separation Techniques Coupled to Mass Spectrometry
35
1.5.1.
Gas Chromatography-Mass Spectrometry
35
1.5.2.
Liquid Chromatography-Mass Spectrometry
37
1.5.3.
Capillary Electrophoresis-Mass Spectrometry
42
1.5.4.
Ion Mobility Spectrometry-Mass Spectrometry
45
VI
CONTENTS
1.6.
Prospects for Mass Spectrometry
48
References
51
2.
LC Method Development and Strategies
59
Gang Xue and Yining Zhao
2.1.
Introduction
59
2.2.
Column,
pH,
and Solvent Screening
60
2.2.1.
Resolution: Goal of Separation
60
2.2.2.
Screening: Systematic Approach to
Seeking Selectivity
60
2.2.3.
Screening Instrumentation and Controlling Software
67
2.3.
Gradient and Temperature Optimization
69
2.4.
Orthogonal Screening
70
2.4.1.
Method Orthogonality
71
2.4.2.
Selection of Orthogonal Methods
72
2.4.3.
Impurity Orthogonal Screening
74
2.5.
High-Efficiency Separation
76
2.6.
Conclusions
78
References
78
3.
Rapid Analysis of Drug-Related Substances using Desorption
Electrospray Ionization and Direct Analysis in Real Time
Ionization Mass Spectrometry
81
Hao Chen and Jiwen Li
3.1.
Introduction
81
3.2.
Ionization Apparatus, Mechanisms, and General Performance
83
3.2.1.
Desorption Electrospray Ionization
(DESI)
83
3.2.2.
Direct Analysis in Real Time (DART)
85
3.3.
Drug Analysis in Biological Matrices using
DESI
and DART
87
3.3.1.
DESI
Application
88
3.3.2.
DART Application
89
3.4.
High-Throughput Analysis
92
3.5.
Chemical Imaging and Profiling
94
3.6.
Future Perspectives
101
References
101
4.
Orbitrap High-Resolution Applications
109
Robert J. Strife
4.1.
Historical Anecdote
109
4.2.
General Description of Orbitrap Operating Principles
110
4.3.
The Orbitrap is a Fourier Transform Device
112
CONTENTS
VM
4.4.
Performing Experiments in Trapping
Devices
113
4.4.1.
Raw HPLC Data Look Like Infusion Data
114
4.4.2.
How Much Mass Resolution Should Be
Used During HPLC
114
4.5.
Determining Elemental Compositions of Unknowns Using
an Orbitrap
1
1
5
4.6.
Orbitrap Figures of Merit in Mass Measurement
117
4.6.1.
Accuracy
П7
4.6.2.
Precision
118
4.6.3.
Discussion
118
4.7.
HPLC Orbitrap MS: Accurate Mass Demonstration and
Differentiation of Small Molecule Formulas Very
Proximate in Mass/Charge Ratio Space
121
4.8.
Determination of Trace Contaminant Compositions by
Simple Screening HPLC-MS and Infusion
Orbitrap MS
122
4.9.
Determining Substructures: Orbitrap Tandem Mass
Spectrometry (MS )
124
4.10.
Multianalyzer (Hybridized) System: The Linear Ion
Trap/Orbitrap for MS/MS and Higher-Order MS ,
η
> 2 127
4.11.
Mass Mapping to Discover Impurities
129
4.12.
The Current Practice of Orbitrap Mass Spectrometry
131
4.13.
Conclusion
132
References
132
5.
Structural Characterization of Impurities and Degradation
Products in Pharmaceuticals Using High-Resolution LC-MS
and Online Hydrogen/Deuterium Exchange Mass
Spectrometry
135
Guodong Chen and Birendra
N.
Pramanik
5.1.
Introduction
135
5.2.
Characterization of Impurities
137
5.2.1.
Mometasone Furoate
137
5.2.2.
Enol Tautomer Impurity in Hepatitis
С
Virus (HCV) Protease Inhibitor
152
5.3.
Characterization of Degradation Products
155
5.3.1.
Everninomicin
156
5.3.2.
Posaconazole
164
5.4.
Conclusions
176
References
177
VIU
CONTENTS
6. Isotope Patten
Recognition on Molecular Formula
Determination for
Structurai
Identification of Impurities
183
Ming
Си
6.1.
Introduction
183
6.2.
Three Basic Approaches to Isotope Pattern Recognition
184
6.2.1.
With Centriod Data
185
6.2.2.
With Profile Data without Peak Shape Calibration
187
6.2.3.
With Profile Data with Peak Shape Calibration
189
6.3.
The Importance of Lineshape Calibration
190
6.3.1.
Lineshape Calibration Using Standards
191
6.3.2.
Lineshape Self-Calibration
193
6.4.
Spectral Accuracy
194
6.5.
Formula Determination with Quadrupole MS
194
6.5.1.
Impurity Identification with LC-MS
195
6.5.2.
Impurity Identification with GC-MS
200
6.5.3.
Pros and Cons of Determination of Elemental
Decomposition (DEC) with Quadrupole MS
201
6.6.
Formula Determination with High-Resolution MS
203
6.7.
Conclusions and Future Directions
208
References
208
PART II APPLICATION
7.
Practical Application of Very High-Pressure Liquid
Chromatography Across the Pharmaceutical
Development-Manufacturing Continuum
215
Brent
Kleintop
and Qinggang Wang
7.1.
Introduction
215
7.2.
Theory and Benefits of VHPLC
217
7.3.
VHPLC Method Development
220
7.3.1.
Adapting Existing HPLC Methods to VHPLC
220
7.3.2.
Developing New VHPLC Methods
224
7.4.
Other Practical Considerations
226
7.5.
VHPLC Method Validation
227
7.6.
Summary
229
References
229
8.
Impurity Identification for Drug Substances
231
David W.
Berberich,
Tao Jiang, Joseph McClurg, Frank
Moser,
and R. Randy
Wilhelm
8.1.
Introduction
231
CONTENTS
IX
8.2.
Case Studies
232
8.2.1.
Identification of Impurities in Each Synthetic
Step of Drug Substance during Process Development
232
8.2.2.
Impurity ID by LC/MS during Exploratory
Chemistry: Evaluation of New Raw Materials
237
8.2.3.
Impurity Identification during Accelerated
Stability Studies
243
8.3.
Conclusions
249
References
250
9.
Impurity Identification in Process Chemistry
by Mass Spectrometry
251
David Q. Liu, Mingjiang Sun, and Lianming Wu
9.1.
Introduction
251
9.2.
Experimentation
252
9.2.1.
Liquid Chromatography Conditions
252
9.2.2.
LC-MS Systems
253
9.2.3.
GC-MS System
253
9.2.4.
Accurate Mass
253
9.2.5.
Online H/D Exchange LC-MS
254
9.3.
Applications
254
9.3.1.
Identification of Reaction Byproducts
by Data-Dependent LC/MS
254
9.3.2.
Online H/D Exchange Aids Structural Elucidation of
Process Impurities
257
9.3.3.
LC-MS for Chemical Reaction Impurity Fate Mapping
260
9.3.4.
GC-MS for Impurity Profiling of Small-Molecule
Starting Materials
262
9.3.5.
Identification of a Process Impurity that Impacts
Downstream Formulation
265
9.3.6.
Differential Fragmentation between Sodiated
and Protonated Molecules as a Means of Structural
Elucidation
267
9.4.
Concluding Remarks
275
Acknowledgments
275
References
276
10.
Structure Elucidation of Pharmaceutical Impurities
and
Dégradants
in Drug Formulation Development
279
Changkang Pan, Frances Liu, and Michael Motto
10.1.
Importance of Drug Degradation Studies in Drug Development
279
10.2.
Drug Degradation Studies in Formulation Development
281
CONTENTS
10.2.1.
Drug
Substance-Excipient Interaction
281
10.2.2.
Small Unknown Peaks (~0.1%) (Low-Dose Drugs
< 1
mg per Dose)
282
10.2.3.
Busy LC Chromatogram with Multiple Peaks
(Combination Drug Products)
282
10.2.4.
Modification of Non-MS-Compatible LC Methods
282
10.2.5.
Uncontrollable Multiple Chemical Reactions in
Stability Samples
283
10.2.6.
Separation Interference and Contamination
Induced by
Excipients
283
10.2.7.
Peak Isolation and NMR Confirmation for
Late-Phase Projects
284
10.3.
Complexity of Impurity Identification in Drug Development
284
10.3.1.
Drug Substance (DS) Degradation
284
10.3.2.
DS-Excipient Interaction
285
10.3.3.
DS-Residual Solvent Interaction
287
10.3.4.
DS-Solvent Impurity Interaction
287
10.3.5.
Metal Ion-Catalyzed Reaction
289
10.3.6.
DS-Excipient Impurity Interaction
289
10.3.7.
DS-Salt Interaction
291
10.3.8.
DS-Preservative Interaction
291
10.3.9.
Preservative-Excipient Interaction
292
10.3.10.
Excipient
Degradation
292
10.3.11.
Leachables and Extractables
293
10.4.
Strategy for Structure Elucidation of Unknowns
295
10.4.1.
Non-MS-Compatible Method versus MS-Compatible
Method
295
10.4.2.
Selection of Ionization Mode (ESI or APCI,
Positive or Negative)
298
10.4.3.
Multiple Approaches for Structure Elucidation
298
10.4.4.
Structure Confirmation
299
10.5.
Hyphenated Analytical Techniques Used in Drug Development
300
10.5.1.
LC-MS/MS for Fragmentation Pathways
302
10.5.2.
High-Resolution MS for Chemical Formula/Elemental
Composition
302
10.5.3.
SEC/CLND or HPLC/CLND: Nitrogen-Specific
Detection
304
10.5.4.
GC-MS with
ΕΙ
-CI
Combination
305
10.5.5.
Headspace GC-MS: Volatile Compounds
305
10.5.6.
NMR and LC-NMR
306
10.5.7.
TD-GC/MS: Chemical Reactions Attributing
to Weight Loss in TGA
307
10.6.
Case Studies
307
CONTENTS
ХІ
10.6.1. LC-MS, GC-MS, and LC-NMR
Studies of a Drug
Degradation Product
307
10.6.1.1.
LC-MS Analysis
308
10.6.1.2.
GC-MS Analysis
308
10.6.1.3.
LC-NMR Analysis
308
10.6.2.
Strategy for Identification of Leachables in
Packaged Liquid Formulation
ЗІЗ
10.6.3.
Characterization of Methionine Oxidation in
Parathyroid Hormone Formulation
316
10.6.3.1.
Oxidation, Isolation, and Digestion
ofPTHl-34
316
10.6.3.2.
Mass Assignment of PTHI-34 Oxidized
Variants
317
10.6.3.3.
Mass Assignment of CNBr Digested
Peptide
Fragments
318
10.6.3.4.
LC-MS/MS Studies of ¡on Fragments
from Oxidized Peptides
322
Acknowledgment
326
References
326
11.
Investigation of Degradation Products and Extractables
in Developing Topical OTC (Over the Counter) and NCE
(New Chemical Entity) Consumer Healthcare
Medication Products
337
Fa Zhang
11.1.
Introduction
337
1
1.2.
Oxidatively Induced Coupling of Miconazole Nitrate
with Butylated Hydroxytoluene in
a Topica!
Ointment
338
11.2.1.
HPLC-MS Screening
339
11.2.2.
Organic Synthesis
341
11.2.3.
Degradation Mechanism
344
1
1.3.
Extractables from Rubber Closures of a Prefilled
Semisolid
Drug Applicator
347
11.3.1.
Isolation of the Extractables
348
11.3.2.
Structural Identification of Extractables
5
and
6 348
11.3.3.
Structural Identification of Extractables
7
and
8 349
11.3.4.
Structural Identification of Extractable
9 351
11.4.
New Degradation Products and Pathways of Vitamin
D
and
Its Analogs
352
11.4.1.
Thermal Isomerization of Vitamin D, in DMSO
355
11.4.2.
Autoxidation of Isotachysterol
356
XII CONTENTS
11.4.2.1.
Mechanism of hot achy
st er
ol
Autoxidation
362
11.4.3.
Thermal Degradation of Ecalcidene
364
11.4.4.
Acid-Induced Degradation of Ecalcidene
368
11.4.5.
Iodine-Induced Degradation of Ecalcidene
370
11.4.5.1.
cis/trans-Isomerization of Ecalcidene
371
11.4.5.2.
cis/trans-Isomerization of Previtamin
иЗ-Туре
Isomer 24 372
11.5.
Reductive Degradation of a 1,2,4-Thiadiazolium
Derivative
376
11.6.
Conclusions
382
References
383
12.
Characterization of Impurities and
Dégradants
in
Protein Therapeutics by Mass Spectrometry
391
Li Tao, Michael Ackerman, Wei Wu, Peiran Liu, and Reb Russell
12.1.
Introduction to Therapeutic Proteins
391
12.2.
Recent Advances in Mass Spectrometry
392
12.3.
Impurities
393
12.3.1.
Endotoxin
394
12.3.2.
Residual
DNA 394
12.3.3.
Residual HCP
395
12.4.
Degradation Products
395
12.4.1.
Chemical Degradation
396
12.4.1.1.
Deamidation/lsomerization
396
12.4.1.2.
Protein Fragmentation
400
12.4.1.3.
Oxidation
401
12.4.2.
Variants Caused by Posttranslational Modification
404
12.4.2.1.
Case Study: Characterization of
S-Thiolation on Secreted Proteins from
E. coli
406
12.4.2.2.
TM307
408
12.4.2.3.
TM485
408
12.4.2.4.
TM358 and TM687
410
12.5.
Conclusions
413
References
413
13.
Identification and Quantification of
Dégradants
and Impurities in Antibodies
427
David M. Hambly and Himanshu S. Gadgil
13.1.
Introduction to Antibodies and Protein Drugs
427
CONTENTS
ХІІІ
13.1.1.
Antibody
Classification
and Subtypes
427
13.1.2.
Antibody Structure
428
13.1.3.
Antibody-Domain Structure
429
13.1.4.
Recombinant
Antibody Production
429
13.1.5.
Methods for Characterizing Antibody Degradation
and Impurity
430
13.2.
Overview of Degradations and Impurities
in Protein Drugs and Antibodies
431
13.2.1.
Chemical Degradations and Impurities
431
13.2.1.1.
Methkmine Oxidation
431
13.2.1.2.
Disulfide Bonds or Reduced
Cysteine
432
¡3.2.1.3.
Deamidation of Asparagine and
Glutaminę
432
13.2.1.4.
lsomerization of Aspartic Acid and
Glutamic Acid
433
13.2.1.5.
Amide Backbone Hydrolysis Reactions
433
13.2.1.6.
Glycation of
Lysine
Residues
433
13.2.1.7.
C-Terminal
Lysine
Variants
434
13.2.1.8.
Carbohydrate Variants
434
13.3.
Methods Used to Identify and Quantitate Degradations and
Impurities
435
13.3.1.
Whole-Protein Mass Analysis Methods
435
13.3.1.1.
Carbohydrate Variation
435
13.3.1.2.
Detection of
Lysine
C-terminal
Variants
and Glycated
Lysine
437
13.3.1.3.
Detection of Disulfide Bond Variants
in ¡gG2 Antibodies
437
13.3.2.
Methods for Evaluating the Mass of Protein
Fragments
438
13.3.2.1.
Limited Digestion Method for Antibodies
438
13.3.2.2.
Limited and Reduced Method for
Antibodies
440
13.3.2.3.
Reduced Protein Mass Analysis AA
13.3.3.
Methods for Evaluating Peptides for Impurities
and Degradations
443
13.3.3.1.
Reduced and Alkylated
Peptide
Mapping
443
13.4.
Conclusions
450
Appendix
450
References
453
INDEX
461
|
| any_adam_object | 1 |
| author2 | Pramanik, Birendra N. 1944- |
| author2_role | edt |
| author2_variant | b n p bn bnp |
| author_GND | (DE-588)1013353269 |
| author_facet | Pramanik, Birendra N. 1944- |
| building | Verbundindex |
| bvnumber | BV036455543 |
| classification_rvk | VS 5300 |
| ctrlnum | (OCoLC)740988201 (DE-599)BVBBV036455543 |
| dewey-full | 543.6502461519 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 543 - Analytical chemistry |
| dewey-raw | 543.6502461519 |
| dewey-search | 543.6502461519 |
| dewey-sort | 3543.6502461519 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
| format | Book |
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| id | DE-604.BV036455543 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T22:39:49Z |
| institution | BVB |
| isbn | 9780470386187 9780470921371 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-020327553 |
| oclc_num | 740988201 |
| open_access_boolean | |
| owner | DE-11 DE-703 |
| owner_facet | DE-11 DE-703 |
| physical | XXII, 462 S. Ill., graph. Darst. |
| publishDate | 2011 |
| publishDateSearch | 2011 |
| publishDateSort | 2011 |
| publisher | Wiley |
| record_format | marc |
| spelling | Characterization of impurities and degrandants using mass spectrometry ed. by Birendra N. Pramanik ... Hoboken, NJ Wiley 2011 XXII, 462 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Pharmazeutische Analyse (DE-588)4174139-0 gnd rswk-swf Massenspektrometrie (DE-588)4037882-2 gnd rswk-swf Arzneimittelanalyse (DE-588)4003116-0 gnd rswk-swf Massenspektrometrie (DE-588)4037882-2 s Pharmazeutische Analyse (DE-588)4174139-0 s Arzneimittelanalyse (DE-588)4003116-0 s DE-604 Pramanik, Birendra N. 1944- (DE-588)1013353269 edt Erscheint auch als Online-Ausgabe 978-0-470-92136-4 Erscheint auch als Online-Ausgabe, EPUB 978-0-470-92297-2 Digitalisierung UB Bayreuth application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=020327553&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Characterization of impurities and degrandants using mass spectrometry Pharmazeutische Analyse (DE-588)4174139-0 gnd Massenspektrometrie (DE-588)4037882-2 gnd Arzneimittelanalyse (DE-588)4003116-0 gnd |
| subject_GND | (DE-588)4174139-0 (DE-588)4037882-2 (DE-588)4003116-0 |
| title | Characterization of impurities and degrandants using mass spectrometry |
| title_auth | Characterization of impurities and degrandants using mass spectrometry |
| title_exact_search | Characterization of impurities and degrandants using mass spectrometry |
| title_full | Characterization of impurities and degrandants using mass spectrometry ed. by Birendra N. Pramanik ... |
| title_fullStr | Characterization of impurities and degrandants using mass spectrometry ed. by Birendra N. Pramanik ... |
| title_full_unstemmed | Characterization of impurities and degrandants using mass spectrometry ed. by Birendra N. Pramanik ... |
| title_short | Characterization of impurities and degrandants using mass spectrometry |
| title_sort | characterization of impurities and degrandants using mass spectrometry |
| topic | Pharmazeutische Analyse (DE-588)4174139-0 gnd Massenspektrometrie (DE-588)4037882-2 gnd Arzneimittelanalyse (DE-588)4003116-0 gnd |
| topic_facet | Pharmazeutische Analyse Massenspektrometrie Arzneimittelanalyse |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=020327553&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT pramanikbirendran characterizationofimpuritiesanddegrandantsusingmassspectrometry |