INTRODUCTION TO PHARMACOKINETICS

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1 INTRODUCTION TO PHARMACOKINETICS 1

2 2

3 PHARMACOKINETICS 1. ABSORPTION 2. DISTRIBUTION 3. METABOLISM 4. EXCRETION ALL THESE PROCESSES ARE DETERMINED BY THE ABILITY OF A DRUG TO CROSS BIOLOGICAL MEMBRANES 3

4 1. ABSORPTION: transfer of a drug from site of administration to the systemic circulation 4

5 ROUTES OF DRUG ADMINISTRATION ENTERAL: administration into the systemic circulation via the alimentary (digestive) canal Tablets, capsules, solutions, suspensions Oral (PO): by mouth Sublingual (SL): under the tongue Rectal (PR): by suppositories PARENTERAL TOPICAL 5

6 ROUTES OF DRUG ADMINISTRATION ENTERAL PARENTERAL: administration into the systemic circulation via routes other than the alimentary canal Solutions, emulsions, suspensions, aerosols, gases Intravenous (IV): into venous circulation Intramuscular (IM): into the muscle Subcutaneous (SC): under the skin, into the hypodermis Inhalational: via the lungs Intrathecal (IT): into spinal subarachnoid space Epidural: into epidural space outside of dura mater Intrasynovial (Intra-articular): into the joint Intraosseus: into the bone Intraperitoneal (IP): into the abdominal (peritoneal) cavity Intra-arterial (IA): into arterial circulation TOPICAL 6

7 ROUTES OF DRUG ADMINISTRATION ENTERAL PARENTERAL TOPICAL: administration by direct application onto the skin or associated membranes Powders, creams, ointments, gels, sprays, patches Transdermal: across the skin Transmucosal: across the mucous membranes Ophthalmic: onto membranes of the eye Vaginal: onto the membranes of vagina Intrauterine: onto membranes of the uterus lining 7

8 DRUG ABSORPTION Bioavailability is a fraction of unchanged drug reaching the systemic circulation following administration Bioavailability depends Route of administration Drug properties p (lipophilicity, p pk A, formulation) Physiological variables (ph, blood flow, enzymes) Effects of route of administration on absorption and bioavailability: IV = 100% Bioavailability IM, SC, Inhaled = High Bioavailability but < 100% Oral = low and inconsistent i bioavailability il bili and slower absorption First pass effect Requires lipid id solubility Bioavailability varies with GI motility, presence of food GI tract = low ph, lots of enzymes 8

9 FIRST PASS METABOLISM Oral drug administration only Is avoided with parenteral and non-oral drug administration routes Liver - Primary site of drug metabolism in the body Extraction ratio (ER) fraction of drug removed by first pass effect Could be 90% or more of orally administered dose 9

10 FIRST-PASS METABOLISM Alternative routes of administration and first-pass metabolism Sublingual route (avoids first-pass effect) Transdermal route (avoids first-pass effect) Rectal route (decreases first-pass effect by approximately 40 to 60%) Alternative routes Increase bioavailability of drugs with high extraction ratio and Do not significantly affect the bioavailability of drugs with low hepatic extraction 10

11 DISTRIBUTION 2. DISTRIBUTION: movement of a drug from the systemic circulation to various sites in the body 11

12 DISTRIBUTION Distribution is the movement of drugs throughout the body once they are in the general circulation It is reversible transfer of drug between vascular and extra vascular space To sites of action To sites of elimination/metabolism Requires passage through endothelial cells layers Distribution ib ti depends d on Lipid solubility/size of drug Drug pk A and blood/tissue ph Extent of blood perfusion of tissue Extent of binding to plasma binding proteins: albumin, 1-acid glycoprotein 12

13 DISTRIBUTION Distribution into central nervous system blood-brain barrier Only very lipophilic drugs will enter the central nervous system TIGHT JUNCTIONS WIDE JUNCTIONS PERIPHERAL CAPILLARY CAPILLARY IN THE CENTRAL NERVOUS SYSTEM 13

14 DISTRIBUTION TO CELLULAR SITES OF ACTION: LOCAL ANESTHETICS Local anesthetics will more readily reach their sites of action when they are in their LIPID SOLUBLE (UNCHARGED) FORM UNCHARGED DRUG + CHARGED DRUG EXTRACELLULAR Voltage Dependent Sodium Channel NEURONAL MEMBRANE INTRACELLULAR 14

15 LOCAL ANESTHETICS WEAK BASES (pk a ) EXAMPLE: Lidocaine a weak base with a pk a of 7.9. ph < 7.9 C 14 H 23 N 2 O + C 14 H 22 N 2 O ph > Protonated form: charged and lipid insoluble Unprotonated form: uncharged and lipid soluble EXTRACELLULAR EXTRACELLULAR SODIUM CHANNEL INTRACELLULAR INTRACELLULAR 15

16 VOLUME OF DISTRIBUTION Volume of distribution ib ti is a ratio of the amount of drug in the body to the concentration of drug in blood or plasma V d = Total drug dose Plasma concentration This is an apparent and not physical volume (V d for digoxin is ~500 L/70 kg) This parameter characterizes how well the drug is distributed from the systemic circulation 16

17 DISTRIBUTION OF DIFFERENT TYPES OF DRUGS Macromolecular drugs (antibodies, heparin, etc.) V d = 3 L, or 0.04 L/kg Polar small molecule drugs (mannitol) V d = 12 L, or 0.17 L/kg More lipophilic small molecule drugs (diazepam, lidocaine), distributed in total body water V d = 40 L, or 0.57 L/kg Very lipophilic small molecule drugs have very high V d values (larger than the volume of entire body) 17

18 V d AND PROTEIN BINDING The higher the lipophilicity of a drug, the greater is the affinity for plasma proteins Many drugs are normally greater than 90% bound to plasma proteins Drugs extensively bound to plasma proteins usually have lower apparent volume of distribution When several drugs that bind to the same protein are given together, one drug may displace another from the protein binding sites. This causes elevated plasma concentration of the displaced drug, and increased apparent volume of distribution 18

19 DRUG METABOLISM 3. DRUG METABOLISM: biotransformation of the drug with the goal of promoting its elimination via the kidneys 19

20 BIOTRANSFORMATION REACTIONS Biotransformation i reactions occur primarily il but not exclusively in the liver (also in some other organs such as skin and lungs and in some cases, e.g., hydrolysis, in the blood) Phase I reactions make drug more polar by introducing or unmasking functional groups Phase II reactions add endogenous substrate to drug to produce a highly polar conjugate. Usually preceded by phase I reactions, but not always DRUG POLAR METABOLITE 20

21 Types of phase I reactions Hydrolysis reactions PHASE I REACTIONS Catalyzed by esterases (carboxylesterases, cholinesterases) Cleavage of ester or amide bonds in a molecule l via a reaction involving the introduction of water Oxidation reactions Catalyzed by oxidases, dehydrogenases, oxygenases Involves the loss of electrons from the drug and/or introduction of molecular oxygen into the drug molecule The most important Phase I oxidation reaction involves cytochrome P450 enzymes Alcohols (ethanol, methanol) are oxidized by a different family of enzymes that include alcohol and aldehyde dehydrogenases Purposes of Phase I Reactions 1. Expose or introduce functional groups on a drug: -OH, -NH 2, -SH, - COOH 2. Make a drug more hydrophilic 3. Provide sites on a drug for Phase II reactions 4. In most, but NOT ALL cases, metabolism results in drug inactivation 21

22 PHASE I REACTIONS THE CYTOCHROME P450 SYSTEM Bind to drugs and catalyze oxidation reactions Most common Phase I metabolic reactions Three families of cytochrome P450 enzymes CYP1 CYP2 CYP3 Altogether there are more than 15 different kinds of drugmetabolizing cytochrome P450 enzymes in the liver For example: the CYP1 family of cytochrome P450s includes CYP1A1, CYP1A2, and CYP1B1 enzymes Each P450 enzyme can metabolize many different drugs Example: CYP3A4 metabolizes acetaminophen, cocaine, diazepam, testosterone, methadone and many other drugs A single drug can be metabolized by many different cp450 enzymes Example: acetaminophen is a substrate for CYP1A2, CYP2E1, 22 and CYP3A4

23 PHASE II REACTIONS Phase II reactions are reactions of conjugation o the transfer of endogenous substances to functional groups of the drug molecule catalyzed by enzymes call transferases to form polar conjugates which are easily eliminated Important conjugation reactions include: Glucuronidation Glutathione conjugation Acetylation Sulfation Methylation Amino Acid Conjugation UDP-Glucuronic Acid Example: Phase II Glucuronidation Reaction UDP UDP COO - UDP-glucuronyl COO - transferase Substrate Drug Glucuronidated Drug (drug conjugated with glucuronide) 23

24 4. EXCRETION: removal of the drug from the body 24

25 EXCRETION OF DRUG FROM THE BODY Mechanisms of Drug Elimination: i Renal Excretion filtration glomerulus Polar compound Lipophilic compound proximal Loop of distal collecting tubule Henle tubule duct Glomerular Filtration ALL DRUGS except protein- bound Reabsorption = retention No reabsorption = elimination Kidney damage = reduced filtration and decreased drug elimination Tubular Reabsorption Across renal tubule cell layers Active or passive Requires lipid-solubility ph-dependent Active Secretion Proximal tubule Organic acids Organic bases Some drugs secretion reabsorption Nephron of the kidney excretion URINE 25

26 RENAL ELIMINATION OF WEAK ACIDS AND WEAK BASES Kidney All drugs are filtered at the glomerulus Lipid-soluble drugs are reabsorbed in renal tubules by passive diffusioni Ionized (charged) or hydrophilic drugs can t be reabsorbed and are therefore excreted in urine Alkalization of urine (increasing ph) will facilitate excretion of weak acids (e.g., aspirin) is achieved by giving sodium bicarbonate Acidification of urine (decreasing ph) will facilitate the excretion of weak bases (e.g., phencyclidine) is achieved by giving ammonium chloride Urine Normal ph (6.0) Higher ph (8.0) AH A - Blood ph = 7.4 A - + H + Weak acids excretion with urine RENAL TUBULE CELL LAYER 26

27 Mechanisms of Drug Eliminatiion: Biliary Excretion Enterohepatic recirculation Drug Metabolism Excretion with the feces Other routes of drug elimination include lungs, sweat, and breast milk 27

28 ELIMINATION: FIRST-ORDER KINETICS First-order kinetics Is described by an exponential function Elimination is directly proportional to the drug concentration in the body. Higher drug concentrations = more elimination Percentage (fraction) of drug eliminated from the body per unit time is always the same. MOST DRUGS Physiological i l mechanisms responsible for elimination i are not saturated t First-order kinetics Non-linear reduction over time. Same % of drug is eliminated per unit time (e.g., 25%/hr) 28

29 CAPACITY-LIMITED ELIMINATION It occurs when drug elimination pathways become saturated This process is described by zero-order kinetics The rate of elimination does not depend on the concentration of the drug. If C >> K m, then: Rate of elimination i = V max C =V max K m + C V max, maximum elimination i capacity; K m, the drug concentration at which the rate of elimination is 50% of V max ; C, concentration of the drug 29

30 ELIMINATION: ZERO-ORDER KINETICS Zero-order order kinetics Capacity-limited elimination Is described by a linear function Rate of elimination is independent of drug concentration in the body Same amount of drug is eliminated per unit time, regardless of the drug concentration in the body. Physiological elimination pathway becomes saturated (i.e., they reach capacity) Is typical of ethanol (over most of its plasma concentration range), and of phenytoin and aspirin at high therapeutic or toxic concentrations Since elimination is independent of drug concentration, repeated dosing can result in accumulation and toxicity Zero-order kinetics Linear reduction in plasma drug concentration over time. Same amount of drug is eliminated per unittime(eg time (e.g., mg/hr) 30

31 PARAMETERS OF FIRST ORDER KINETICS ELIMINATION Most of pharmacokinetic processes at therapeutic concentrations of drugs are not saturated, and follow first order kinetics Parameters characterizing first order kinetics elimination Clearance Half-life 31

32 CLEARANCE Clearance is a pharmacokinetic parameter that predicts the rate of elimination in relation to drug concentration CL = Rate of elimination C plasma Defined as a volume of fluid from which a drug is removed over a period of time Units volume per unit time: L/min, L/hr 32

33 CLEARANCE Rearranging g the equation for clearance Rate of elimination = CL C plasma The rate of drug elimination is directly proportional to concentration of the drug 33

34 HALF-LIFE Half-life (t 1/2 ) is the time required to decrease the amount of drug in the body by 50% 50% of drug is lost in one half-lifelife 75%% is lost in two half-lives 87.5% is lost in three half-lives 93.75% is lost in four half-lives, etc. HALF-LIVES OF COMMON DRUGS Procaine: 0.01 hrs Acetaminophen: 3 hrs Diazepam: 45 hrs 34

35 PHARMACOKINETIC MODELS Mathematical modeling of pharmacokinetic processes Single-compartment model Two-compartment model Multiple compartment models 35

36 PHARMACOKINETIC MODELS Single-compartment model describes the body as a single compartment May accurately describe the kinetics of certain drugs Confined to a single (vascular) compartment, or Distribution from the vascular compartment into tissues is very rapid k a Absorption V d body k e Elimination 36

37 PHARMACOKINETIC MODELS Two-compartment model describes the body as central and peripheral (or Blood and Tissues) compartments Concentration vs. time curve If serum concentration of the drug is plotted using log scale It will be a straight line with a single compartment model It will be a biphasic i line with a two-compartment t t model Serum con ncentration (logarithm ic scale) Time (linear scale) 37

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