Pharmacokinetics and metabolism in drug design:
Gespeichert in:
| Format: | Buch |
|---|---|
| Sprache: | English |
| Veröffentlicht: |
Weinheim
Wiley-VCH
2012
|
| Ausgabe: | 3., rev. and updated ed. |
| Schriftenreihe: | Methods and principles in medicinal chemistry
51 |
| Schlagworte: | |
| Online-Zugang: | Inhaltstext Inhaltsverzeichnis |
| Beschreibung: | 257 S. Ill., graph. Darst. 240 mm x 170 mm |
| ISBN: | 9783527329540 3527329544 |
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| 650 | 4 | |a Drugs |x Metabolism | |
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IMAGE 1
CONTENTS
A PERSONAL FOREWORD IX
1 PHYSICOCHEMISTRY 1
1.1 PHYSICOCHEMISTRY A N D PHARMACOKINETICS 2
1.2 PARTITION A N D DISTRIBUTION COEFFICIENTS AS M E A S U R E S
O F LIPOPHILICITY 2
1.3 LIMITATIONS O N T H E U S E O F 1-OCTANOL 5
1.4 FURTHER U N D E R S T A N D I N G O F LOG P 6
1.4.1 UNRAVELING T H E PRINCIPAL CONTRIBUTIONS TO LOG P 6
1.4.2 H Y D R O G E N BONDING 7
1.4.3 POLAR SURFACE AREA 8
1.4.4 MOLECULAR SIZE A N D SHAPE 9
1.5 ALTERNATIVE LIPOPHILICITY SCALES 10
1.6 COMPUTATIONAL SYSTEMS TO D E T E R M I N E LIPOPHILICITY 10
1.7 M E M B R A N E SYSTEMS TO STUDY D R U G BEHAVIOR 10
1.8 DISSOLUTION A N D SOLUBILITY 12
1.9 T H E BCS CLASSIFICATION A N D CENTRAL ROLE O F PERMEABILITY 13
REFERENCES 15
2 PHARMACOKINETICS 19
2.1 SETTING T H E SCENE 2 0
2.2 INTRAVENOUS ADMINISTRATION: VOLUME O F DISTRIBUTION 21
2.3 INTRAVENOUS ADMINISTRATION: CLEARANCE 2 2
2.4 INTRAVENOUS ADMINISTRATION: CLEARANCE A N D HALF-LIFE 23
2.5 INTRAVENOUS ADMINISTRATION: INFUSION 2 4
2.6 ORAL ADMINISTRATION 26
2.7 REPEATED DOSES 2 7
2.8 DEVELOPMENT O F T H E U N B O U N D (FREE) D R U G MODEL 2 9
2.9 U N B O U N D D R U G A N D D R U G ACTION 2 9
2.10 U N B O U N D D R U G MODEL A N D BARRIERS TO EQUILIBRIUM 3 2
2.11 P H A R M A C O D Y N A M I C MODELS 3 4
HTTP://D-NB.INFO/1014518091
IMAGE 2
VI C O N T E N T S
2.12 SLOW OFFSET C O M P O U N D S 3 5
2.13 FACTORS GOVERNING U N B O U N D D R U G CONCENTRATION 3 8
REFERENCES 4 0
3 ABSORPTION 4 1
3.1 T H E ABSORPTION PROCESS 4 2
3.2 DISSOLUTION 4 2
3.3 M E M B R A N E TRANSFER 4 4
3.4 BARRIERS TO M E M B R A N E TRANSFER 4 9
3.5 P R O D R U G S TO INCREASE ORAL ABSORPTION 51
3.6 ACTIVE TRANSPORT 5 5
3.7 MODELS FOR ABSORPTION ESTIMATION 56
3.8 ESTIMATION O F ABSORPTION POTENTIAL A N D O T H E R COMPUTATIONAL
APPROACHES 5 6
REFERENCES 5 7
4 DISTRIBUTION 61
4.1 M E M B R A N E TRANSFER ACCESS TO T H E TARGET 62
4.2 BRAIN PENETRATION 63
4.2.1 ACCUMULATION O F LOWER PERMEABILITY C O M P O U N D S I N T O T H
E BRAIN 6 7
4.2.2 DISTRIBUTION INTO T U M O R S 6 8
4.2.3 VOLUME O F DISTRIBUTION A N D DURATION 70
4.2.4 DISTRIBUTION A N D T MAX 7 7
REFERENCES 78
5 CLEARANCE 81
5.1 T H E CLEARANCE PROCESSES 8 2
5.2 ROLE O F TRANSPORT PROTEINS I N D R U G CLEARANCE 8 3
5.3 INTERPLAY BETWEEN METABOLIC A N D RENAL CLEARANCE 8 7
5.4 ROLE O F LIPOPHILICITY I N D R U G CLEARANCE 8 7
5.5 ACTIVE METABOLITES 8 8
5.6 BALANCING T H E RATE O F RENAL A N D METABOLIC CLEARANCE
A N D POTENCY 91
REFERENCES 101
6 RENAL CLEARANCE 103
6.1 KIDNEY A N A T O M Y A N D FUNCTION 103
6.2 LIPOPHILICITY A N D REABSORPTION BY T H E KIDNEY 105
6.3 EFFECT O F CHARGE O N RENAL CLEARANCE 106
6.4 PLASMA PROTEIN BINDING A N D RENAL CLEARANCE 106
6.5 BALANCING RENAL CLEARANCE A N D ABSORPTION 108
6.6 RENAL CLEARANCE A N D D R U G DESIGN 109
REFERENCES 110
IMAGE 3
CONTENTS V I I
7 METABOLIC (HEPATIC) CLEARANCE 111
7.1 SYMBOLS 111
7.2 FUNCTION O F METABOLISM (BIOTRANSFORMATION) 112
7.3 CYTOCHROME P450 112
7.3.1 CATALYTIC SELECTIVITY O F CYP2D6 115
7.3.2 CATALYTIC SELECTIVITY O F CYP2C9 117
7.3.3 CATALYTIC SELECTIVITY O F CYP3A4 119
7.4 O T H E R OXIDATIVE METABOLISM PROCESSES 126
7.4.1 ALDEHYDE OXIDASE 126
7.4.2 FLAVIN-CONTAINING MONOOXYGENASES 130
7.4.3 M O N O A M I N E OXIDASES 133
7.5 OXIDATIVE METABOLISM A N D D R U G DESIGN 138
7.6 NONSPECIFIC ESTERASES 138
7.6.1 FUNCTION O F ESTERASES 138
7.6.2 ESTER D R U G S AS INTRAVENOUS A N D TOPICAL
AGENTS 140
7.7 P R O D R U G S TO AID M E M B R A N E TRANSFER 142
7.8 ENZYMES CATALYZING D R U G CONJUGATION 144
7.8.1 GLUCURONOSYL- A N D SULFOTRANSFERASES 144
7.8.2 METHYL TRANSFERASES 147
7.8.3 GLUTATHIONE-S-TRANSFERASES 148
7.9 STABILITY TO CONJUGATION PROCESSES 149
7.10 P H A R M A C O D Y N A M I C S A N D CONJUGATION 152
REFERENCES 153
8 TOXICITY 159
8.1 TOXICITY FINDINGS 160
8.1.1 PHARMACOLOGIC MECHANISM-BASED TOXICITY 160 8.1.2
CHEMOTYPE-DEPENDENT TOXICITY 161
8.1.3 METABOLISM-INDUCED TOXICITY 164
8.2 STRUCTURE-TOXICITY ANALYSES 167
8.3 REACTIVE METABOLITE SCREENING I N D R U G DISCOVERY 171
8.4 STRUCTURAL ALERTS/TOXICOPHORES I N D R U G DESIGN 173
8.5 DEALING WITH REACTIVE METABOLITE POSITIVES I N D R U G DISCOVERY;
RISK A S S E S S M E N T STRATEGIES - EFFECT O F DAILY DOSE 173 8.6
DEALING W I T H REACTIVE METABOLITE POSITIVES I N D R U G DISCOVERY;
RISK A S S E S S M E N T STRATEGIES - C O M P E T I N G DETOXICATION
PATHWAYS 182
8.7 STRATIFICATION O F TOXICITY 183
8.8 TOXICITY PREDICTION: COMPUTATIONAL TOXICOLOGY 183
8.9 TOXICOGENOMICS 184
8.10 P H A R M A C O G E N O M I C S 185
8.11 E N Z Y M E INDUCTION A N D D R U G DESIGN 186
8.12 E N Z Y M E INHIBITION A N D D R U G DESIGN 191
8.12.1 QUASI-IRREVERSIBLE INHIBITION 191
IMAGE 4
VIII C O N T E N T S
8.12.2 IRREVERSIBLE CYP INACTIVATION VIA APOPROTEIN A N D / O R H E M E
COVALENT MODIFICATION 193 8.12.3 CYP INHIBITION B Y NITROGEN-CONTAINING
HETEROCYCLES 195 REFERENCES 202
9 PREDICTING H U M A N PHARMACOKINETICS 209
9.1 OBJECTIVES O F PREDICTING H U M A N PHARMACOKINETICS 2 1 0
9.2 ALLOMETRIC SCALING O F PRECLINICAL I N VIVO PK PARAMETERS 211
9.2.1 VOLUME O F DISTRIBUTION 211
9.2.2 CLEARANCE 214
9.3 PREDICTION O F H U M A N PK PARAMETERS U S I N G I N VITRO DATA 2 2
0
9.3.1 PREDICTING H U M A N VOLUME O F DISTRIBUTION F R O M I N VITRO
DATA 220
9.3.2 PREDICTING H U M A N CLEARANCE F R O M H U M A N I N VITRO DATA
222
9.3.3 SPECIES SCALING: INCORPORATING DIFFERENCES I N METABOLIC CLEARANCE
223
9.4 ELIMINATION HALF-LIFE 224
9.5 MOVING FORWARD 224
REFERENCES 2 2 5
10 ADME SCREENING 229
10.1 T H E H I G H - T H R O U G H P U T SYNTHESIS A N D SCREENING TREND
10.2 T H E CONCEPT O F A D M E SPACE 231
10.3 D R U G METABOLISM A N D DISCOVERY SCREENING SEQUENCES 10.4
PHYSICOCHEMISTRY 234
10.4.1 SOLUBILITY 2 3 5
10.4.2 IONIZATION 236
10.4.3 LIPOPHILICITY 236
10.4.4 POLAR SURFACE AREA 237
10.5 ABSORPTION/PERMEABILITY 238
10.6 METABOLISM, INDUCTION, A N D INHIBITION 239
10.7 TRANSPORTERS 240
10.8 PROTEIN BINDING 242
10.9 PHARMACOKINETICS 243
10.10 IN SILICO APPROACHES TO ADME 243
10.10.1 QSAR APPROACHES TO ADME 244
10.10.2 THEORETICAL MODELS FOR PREDICTING METABOLISM 244 10.10.3
PHYSIOLOGICALLY-BASED PHARMACOKINETIC MODELING 245
REFERENCES 246
230
233
INDEX 251 |
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| id | DE-604.BV040120907 |
| illustrated | Illustrated |
| indexdate | 2024-07-21T00:31:45Z |
| institution | BVB |
| isbn | 9783527329540 3527329544 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-024977003 |
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| physical | 257 S. Ill., graph. Darst. 240 mm x 170 mm |
| publishDate | 2012 |
| publishDateSearch | 2012 |
| publishDateSort | 2012 |
| publisher | Wiley-VCH |
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| series | Methods and principles in medicinal chemistry |
| series2 | Methods and principles in medicinal chemistry |
| spelling | Pharmacokinetics and metabolism in drug design ed. by Dennis A. Smith ... 3., rev. and updated ed. Weinheim Wiley-VCH 2012 257 S. Ill., graph. Darst. 240 mm x 170 mm txt rdacontent n rdamedia nc rdacarrier Methods and principles in medicinal chemistry 51 Arzneimitteldesign - Pharmakokinetik - Biotransformation Drugs Design Drugs Metabolism Pharmacokinetics Pharmakokinetik (DE-588)4115557-9 gnd rswk-swf Biotransformation (DE-588)4006908-4 gnd rswk-swf Arzneimitteldesign (DE-588)4278218-1 gnd rswk-swf Arzneimitteldesign (DE-588)4278218-1 s Pharmakokinetik (DE-588)4115557-9 s Biotransformation (DE-588)4006908-4 s DE-604 Smith, Dennis Arnold Sonstige (DE-588)172378125 oth Methods and principles in medicinal chemistry 51 (DE-604)BV035418617 51 X:MVB text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3870446&prov=M&dok_var=1&dok_ext=htm Inhaltstext DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=024977003&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Pharmacokinetics and metabolism in drug design Methods and principles in medicinal chemistry Arzneimitteldesign - Pharmakokinetik - Biotransformation Drugs Design Drugs Metabolism Pharmacokinetics Pharmakokinetik (DE-588)4115557-9 gnd Biotransformation (DE-588)4006908-4 gnd Arzneimitteldesign (DE-588)4278218-1 gnd |
| subject_GND | (DE-588)4115557-9 (DE-588)4006908-4 (DE-588)4278218-1 |
| title | Pharmacokinetics and metabolism in drug design |
| title_auth | Pharmacokinetics and metabolism in drug design |
| title_exact_search | Pharmacokinetics and metabolism in drug design |
| title_full | Pharmacokinetics and metabolism in drug design ed. by Dennis A. Smith ... |
| title_fullStr | Pharmacokinetics and metabolism in drug design ed. by Dennis A. Smith ... |
| title_full_unstemmed | Pharmacokinetics and metabolism in drug design ed. by Dennis A. Smith ... |
| title_short | Pharmacokinetics and metabolism in drug design |
| title_sort | pharmacokinetics and metabolism in drug design |
| topic | Arzneimitteldesign - Pharmakokinetik - Biotransformation Drugs Design Drugs Metabolism Pharmacokinetics Pharmakokinetik (DE-588)4115557-9 gnd Biotransformation (DE-588)4006908-4 gnd Arzneimitteldesign (DE-588)4278218-1 gnd |
| topic_facet | Arzneimitteldesign - Pharmakokinetik - Biotransformation Drugs Design Drugs Metabolism Pharmacokinetics Pharmakokinetik Biotransformation Arzneimitteldesign |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=3870446&prov=M&dok_var=1&dok_ext=htm http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=024977003&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| volume_link | (DE-604)BV035418617 |
| work_keys_str_mv | AT smithdennisarnold pharmacokineticsandmetabolismindrugdesign |