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Small structural modifications can significantly affect the pharmacokinetic properties of drug candidates. This book, written by a medicinal chemist for medicinal chemists, is a comprehensive guide to the pharmacokinetic impact of functional groups, the pharmacokinetic optimization of drug leads, and an exhaustive collection of pharmacokinetic data, arranged according to the structure of the drug, not its target or indication. The historical origins of most drug classes and general aspects of modern drug discovery and development are also discussed. The index contains all the drug names and…mehr
Small structural modifications can significantly affect the pharmacokinetic properties of drug candidates. This book, written by a medicinal chemist for medicinal chemists, is a comprehensive guide to the pharmacokinetic impact of functional groups, the pharmacokinetic optimization of drug leads, and an exhaustive collection of pharmacokinetic data, arranged according to the structure of the drug, not its target or indication. The historical origins of most drug classes and general aspects of modern drug discovery and development are also discussed. The index contains all the drug names and synonyms to facilitate the location of any drug or functional group in the book. This compact working guide provides a wealth of information on the ways small structural modifications affect the pharmacokinetic properties of organic compounds, and offers plentiful, fact-based inspiration for the development of new drugs. This book is mainly aimed at medicinal chemists, but may also be of interest to graduate students in chemical or pharmaceutical sciences, preparing themselves for a job in the pharmaceutical industry, and to healthcare professionals in need of pharmacokinetic data.
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Florencio Zaragoza Dörwald studied chemistry at the Georg-August University in Göttingen, Germany, and Université LouisPasteur, Strasbourg, France, where he obtained his Ph.D. in 1990 on the synthesis of natural products under the guidance of M. Franck-Neumann and M. Miesch. He spent one postdoctoral year in both the groups of A. Pfaltz (University of Basel) and A. P. Marchand (University of North Texas), and then worked on the synthesis of unnatural amino acids at the Technical University of Dresden. From 1994 to 2007 he had a position as a medicinal chemist at Novo Nordisk A/S, Denmark. Currently, he is employed as organic chemist at Lonza AG in Visp, Switzerland.
Inhaltsangabe
PART I: Introduction THE DRUG DISCOVERY PROCESS Pharmacokinetics - Structure Relationship The Future of Small-Molecule Drugs LEAD OPTIMIZATION What Limits/Reduces Oral Bioavailability? What Limits/Reduces Plasma Half-Life? How to Improve bbb-Penetration? How to Avoid CYP Inhibition/Induction? How to Avoid Interaction with the HumanEther-'a-go-go-Related Gene (hERG)? How to Prevent Toxicity? Examples of PK-Optimization in Animals PART II: The Pharmacokinetic Properties of Compound Classes ALKANES Metabolism ALKENES AND ALKYNES Metabolism ARENES Metabolism HALIDES Fluorine Chlorine Bromine Iodine Alkylating Agents AZIDES NITRO COMPOUNDS Metabolism AZO COMPOUNDS TRIAZENES NITRATES AND NITRITES N-NITROSO COMPOUNDS N-OXIDES ALCOHOLS Metabolism PHENOLS ETHERS Metabolism EPOXIDES PEROXIDES THIOLS THIOETHERS Metabolism SULFOXIDES SULFONES ALIPHATIC AMINES Basicity Metabolism Rates of N-Dealkylation QUATERNARY AMMONIUM SALTS AMIDINES GUANIDINES, ACYLGUANIDINES, AND BIGUANIDES Acylguanidines Biguanides ANILINES Metabolism HYDRAZINES, ACYLHYDRAZINES, AND HYDRAZONES ALDEHYDES KETONES CARBOXYLIC ACIDS Metabolism Bioisosteres of Carboxylic Acids Amino Carboxylic Acids, N-Acyl Amino Acids, and Related Compounds CARBOXYLIC ESTERS AMIDES LACTAMS AND IMIDES Pyrazolone Antipyretics Five-Membered Lactams as Nootropics NITRILES CARBONATES CARBAMATES Carbamates as Hypnotics UREAS THIOCARBONYL COMPOUNDS SULFONIC ACIDS SULFONIC ESTERS SULFATES AND SULFAMIC ACIDS PHOSPHONIC ACIDS PHOSPHORIC ACID DERIVATIVES N-(AMINOALKYL)BENZAMIDES, -BENZOATES, AND RELATED COMPOUNDS ARYLALKYLAMINES Antihistaminics: History PHENETHYLAMINES (2-PHENYLETHYLAMINES) Biological Activity of Phenethylamines Metabolism Tetrahydroisochinolines and Related Compounds AMINOALKYLINDOLES AND INDOLE ALKALOIDS PHENOTHIAZINES Metabolism DIBENZAZEPINES AND RELATED TRICYCLIC COMPOUNDS 3-ARYLOXY-2-HYDROXYPROPYLAMINES (B-ADRENERGIC ANTAGONISTS; 'B-BLOCKERS') Metabolism OPIATES N-(CARBOXYALKYL)-a-AMINO ACID AMIDES (PRILS) ANILIDES AND AMIDES OF GLYCINE PEPTIDES, PEPTIDOMIMETICS, AND RELATED OLIGOAMIDES Peptidomimetics Thrombin Inhibitors and Related Compounds OLIGOARYLAMINES, OLIGOARYLAMIDES, OLIGOARYLCARBAMATES, AND OLIGOARYLUREAS IMIDAZOLES TRIAZOLES PYRIDINES, PYRIMIDINES, AND RELATED COMPOUNDS Proton Pump Inhibitors QUINOLINES Tecans Quinazolines NUCLEOSIDE ANALOGS DIHYDROPYRIDINES ARENESULFONAMIDES Antibacterials Diuretics SULFONYLUREAS BENZODIAZEPINES STEROIDS ANTHRACYCLINES ARYLACETIC, BENZOIC, AND RELATED CARBOXYLIC ACIDS (NSAIDS) Salicylates QUINOLONECARBOXYLIC ACIDS (GYRASE INHIBITORS) B-LACTAMS Cephalosporins PROSTAGLANDIN ANALOGS SARTANS STATINS FOLIC ACID ANALOGS (ANTIFOLATES) TAXANES MACROCYCLIC COMPOUNDS
PART I: Introduction THE DRUG DISCOVERY PROCESS Pharmacokinetics - Structure Relationship The Future of Small-Molecule Drugs LEAD OPTIMIZATION What Limits/Reduces Oral Bioavailability? What Limits/Reduces Plasma Half-Life? How to Improve bbb-Penetration? How to Avoid CYP Inhibition/Induction? How to Avoid Interaction with the HumanEther-'a-go-go-Related Gene (hERG)? How to Prevent Toxicity? Examples of PK-Optimization in Animals PART II: The Pharmacokinetic Properties of Compound Classes ALKANES Metabolism ALKENES AND ALKYNES Metabolism ARENES Metabolism HALIDES Fluorine Chlorine Bromine Iodine Alkylating Agents AZIDES NITRO COMPOUNDS Metabolism AZO COMPOUNDS TRIAZENES NITRATES AND NITRITES N-NITROSO COMPOUNDS N-OXIDES ALCOHOLS Metabolism PHENOLS ETHERS Metabolism EPOXIDES PEROXIDES THIOLS THIOETHERS Metabolism SULFOXIDES SULFONES ALIPHATIC AMINES Basicity Metabolism Rates of N-Dealkylation QUATERNARY AMMONIUM SALTS AMIDINES GUANIDINES, ACYLGUANIDINES, AND BIGUANIDES Acylguanidines Biguanides ANILINES Metabolism HYDRAZINES, ACYLHYDRAZINES, AND HYDRAZONES ALDEHYDES KETONES CARBOXYLIC ACIDS Metabolism Bioisosteres of Carboxylic Acids Amino Carboxylic Acids, N-Acyl Amino Acids, and Related Compounds CARBOXYLIC ESTERS AMIDES LACTAMS AND IMIDES Pyrazolone Antipyretics Five-Membered Lactams as Nootropics NITRILES CARBONATES CARBAMATES Carbamates as Hypnotics UREAS THIOCARBONYL COMPOUNDS SULFONIC ACIDS SULFONIC ESTERS SULFATES AND SULFAMIC ACIDS PHOSPHONIC ACIDS PHOSPHORIC ACID DERIVATIVES N-(AMINOALKYL)BENZAMIDES, -BENZOATES, AND RELATED COMPOUNDS ARYLALKYLAMINES Antihistaminics: History PHENETHYLAMINES (2-PHENYLETHYLAMINES) Biological Activity of Phenethylamines Metabolism Tetrahydroisochinolines and Related Compounds AMINOALKYLINDOLES AND INDOLE ALKALOIDS PHENOTHIAZINES Metabolism DIBENZAZEPINES AND RELATED TRICYCLIC COMPOUNDS 3-ARYLOXY-2-HYDROXYPROPYLAMINES (B-ADRENERGIC ANTAGONISTS; 'B-BLOCKERS') Metabolism OPIATES N-(CARBOXYALKYL)-a-AMINO ACID AMIDES (PRILS) ANILIDES AND AMIDES OF GLYCINE PEPTIDES, PEPTIDOMIMETICS, AND RELATED OLIGOAMIDES Peptidomimetics Thrombin Inhibitors and Related Compounds OLIGOARYLAMINES, OLIGOARYLAMIDES, OLIGOARYLCARBAMATES, AND OLIGOARYLUREAS IMIDAZOLES TRIAZOLES PYRIDINES, PYRIMIDINES, AND RELATED COMPOUNDS Proton Pump Inhibitors QUINOLINES Tecans Quinazolines NUCLEOSIDE ANALOGS DIHYDROPYRIDINES ARENESULFONAMIDES Antibacterials Diuretics SULFONYLUREAS BENZODIAZEPINES STEROIDS ANTHRACYCLINES ARYLACETIC, BENZOIC, AND RELATED CARBOXYLIC ACIDS (NSAIDS) Salicylates QUINOLONECARBOXYLIC ACIDS (GYRASE INHIBITORS) B-LACTAMS Cephalosporins PROSTAGLANDIN ANALOGS SARTANS STATINS FOLIC ACID ANALOGS (ANTIFOLATES) TAXANES MACROCYCLIC COMPOUNDS
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