Metabolism
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This document provides an overview of the process of metabolism. It discusses how metabolism involves two phases - phase I and phase II. Phase I reactions make the drug more polar through processes like oxidation, reduction, and hydrolysis. Phase II then involves conjugating the drug or phase I metabolite with biomolecules like glucuronic acid, sulfate, or amino acids to make it more hydrophilic and easily excreted. The liver is the primary site of drug metabolism, which helps terminate the drug's action and eliminate it from the body.
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This document discusses drug metabolism, which occurs in two phases: Phase I and Phase II reactions. Phase I reactions introduce functional groups like hydroxyl groups and involve oxidation, reduction, and hydrolysis. This is done primarily by cytochrome P450 enzymes in the liver. Phase II reactions conjugate these metabolites to make them more polar and water soluble, through glucuronidation, sulfation, methylation, acetylation, and conjugation with amino acids like glycine. Together, these two phases of metabolism convert lipophilic drugs into more hydrophilic forms that can be more readily excreted from the body. The rate and pathway of a drug's metabolism can be affected by its physicochemical properties as well as environmental and
Drug metabolism Introduction and Types
This document provides an overview of drug metabolism. It defines drug metabolism as the biochemical modification of chemicals occurring through specialized enzyme systems. Drug metabolism involves two phases: phase I reactions functionalize drugs through oxidation, reduction or hydrolysis, making them more polar; phase II or conjugation reactions then conjugate these functionalized drugs to other molecules like glucuronic acid, making them water soluble and excretable. The liver is the primary site of drug metabolism, though other tissues also metabolize drugs. First-pass metabolism by the liver can deactivate drugs before they reach systemic circulation. Drug metabolism transforms lipophilic drugs into more polar, excretable metabolites to prevent accumulation and toxicity.
Xenobiotics Metabolism
1) Xenobiotics are foreign compounds introduced into the body that are metabolized in two phases. Phase 1 involves reactions like hydroxylation and oxidation to make the compound more polar. Phase 2 then conjugates these derivatives with molecules like glucuronic acid or glutathione to further increase polarity for excretion.
2) Cytochrome P450 enzymes, especially in the liver, play a key role in phase 1 as they catalyze reactions like hydroxylation. Phase 2 then involves conjugation through six different pathways such as glucuronidation, sulfation, or glutathione conjugation.
3) The overall purpose is to increase water solubility and excretion of hydrophobic xenobiotics from the body to prevent accumulation in
Drug metabolism Phase II reaction
Glucuronic acid conjugation, Sulfate conjugation, Conjugation with α-Amino acid, Conjugation with glutathione, Acetyl conjugation
6. Methylation
Drug metabolismsvpp
1. Biotransformation converts lipophilic compounds to hydrophilic compounds to facilitate excretion. The liver is the primary site of metabolism.
2. Metabolism occurs in two phases: Phase I performs functionalization reactions like oxidation, reduction, and hydrolysis. Phase II performs conjugation reactions by adding small polar groups like glucuronic acid and sulfate, synthesizing new compounds and further increasing hydrophilicity to facilitate excretion.
3. Factors like age, sex, disease state, and concurrent medications can influence an individual's rate of metabolism by inducing or inhibiting drug-metabolizing enzyme systems.
Biotransformation of toxicants
This document discusses biotransformation and toxicology. It begins by introducing biotransformation as the process by which substances are transformed by chemical reactions in the body. It then discusses the phases of biotransformation - phase 1 adds functional groups to make substances hydrophilic, while phase 2 creates water-soluble compounds for excretion. The liver is the main organ for biotransformation through enzymes like cytochrome P450. Factors like diet, age, and genetics can impact biotransformation. The document provides several examples of biotransformation reactions and their consequences.
Lect. No. 14 & 15 Detoxification & Biotrasformation of Xenobiotics.ppt
1. Detoxification involves metabolizing xenobiotics like drugs and chemicals through phase I and phase II reactions to make them more water soluble and easily excreted.
2. Phase I reactions like oxidation, reduction and hydrolysis are catalyzed by cytochrome P450 enzymes in the liver to produce primary metabolites.
3. Phase II reactions involve conjugating these primary metabolites through processes like glucuronidation, sulfation and methylation to form secondary metabolites that are more polar and excretable. The liver is the primary organ of detoxification.
METABOLISM
biotransformation of drug
Biotransformation/Xenobiotic metabolism/ drug metabolism/detoxification.
-Xenobiotics: a wide variety of foreign compounds to which humans get exposed in day to day life.
-It includes unknown compounds, drugs, environmental pollutants, toxins.
-Many xenobiotics can evoke biological responses.
DEFINITION
The biochemical alteration of drug or xenobiotic in the presence of various enzymes that acts as a catalyst which themselves not consumed in the reaction and there by may activate or deactivate the drug is called biotransformation.
Why Biotransformation is necessary?:
To easily eliminate the drug
To terminate drug action by inactivating it
Consequences of Biotransformation
Active to Inactive:
Phenobarbitone---- Hydroxyphenobarbitone
Inactive (prodrug) to Active :
L-Dopa ---- Dopamine
Parathion -- Paraoxon
Talampicillin -- Ampicillin
Active to equally active:
Diazepam -- Oxazepam
Amitriptyline -- Nortriptyline
Imipramine -- Des-imipramine
Codeine -- Morphine
Sites of biotransformation
In the body: Liver, small and large intestines, lungs, skin, kidney, nasal mucosa & brain.
Liver is considered “metabolite clearing house” for both endogenous substances and xenobiotics.
Intestines are considered “initial site of drug metabolism”.
FIRST PASS METABOLISM:
First pass metabolism or presystemic
metabolism or ‘first pass effect’
After oral administeration many drugs are absorbed from the small intestine - transported first via portal system to the liver, where they undergo extensive metabolism before reaching systemic circulation.
fundamental concepts in drug biotransformation
Lipid soluble drugs are poorly excreted in the urine. They tend to store in fat and/or circulate until they are converted (phase I biotransformation) to more water soluble metabolites or metabolites that conjugate (phase II biotransformation) with water soluble substances.
Water soluble drugs are more readily excreted in the urine. They may be metabolized, but generally not by the CYP enzyme systems.
Enzymes catalyzing phase I biotransformation reactions
Enzymes catalyzing phase I biotransformation reactions include:
cytochrome P-450
aldehyde and alcohol dehydrogenase
deaminases
esterases
amidases
epoxide hydratases
Addition of water
Cleavage of R-O or R-N bond accompanied by addition of H2O
CYTOCHROME P450
The cytochrome P-450 families are referred to using an arabic numeral, e.g., CYP1, CYP2, etc.
Each family has a number of subfamilies denoted by an upper case letter, e.g., CYP2A, CYP2B, etc.
The individual enzymes within each subfamily are denoted by another arabic numeral, e.g., CYP3A1, CYP3A2, etc.
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INTRODUCTION TO BIOTRANSFORMATION OF DRUG (METABOLISM OF PHENYTOIN AND CODEINE)
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- 2. OVERVIEW.. Introduction Process Conclusion Reference 2
- 3. INTRODUCTIon.. Metabolism means chemical alteration of drug in the body. It terminate the drug action. An enzyme catalysed biochemical transformation of drug to hydrophilic or polar & non-absorbable metabolite. Primary sites for metabolism is liver ;others kidney , lungs, plasma. Involves 2 stages.(phase 1 & phase 2) 3
- 4. Process involved Metabolism.. Phase I Phase II Phase I Metabolism.. Non-synthetic reaction where a functional group generated that serves as the active centre for conjugation in Phase II reaction. Structural changes occur to make the drug polar & metabolite may be active or inactive 4
- 5. 5 Phase I Metabolism reaction.. i. Oxidation ii. Reduction iii. Hydrolysis iv. Cyclization OXIDATION.. Addition of Oxygen or removal of Hydrogen. Produces unstable intermediates - Epoxides, Super oxides,quinones. Various oxidation( hydroxylation, oxygenation at C,N or S atom,N-alkylation)etc.
- 6. OXIDATION.. 1.OXIDATION AT NITROGEN ATOM RNH2 O RNHOH Ex-Dapsone. 2.OXIDATION AT SULPHUR ATOM R1 R1 SH2 O S=O R2 R2 Ex-Chloramphenicol. 3.DEALKYLATON AT OXYGEN ATOM ROCH3 O ROH + CH2O Ex-Phenacetin to Paracetamol 6
- 7. REDUCTION.. Addition of Hydrogen / positively charged radical or removal of Oxygen / negatively charged radical 1. Nitro Reduction: Reductase RNo2 RNH2 Ex-Chloramphenicol to aryl amine metabolite. 2.Azo reduction: 7
- 8. HYDROLYSIS… Drug is split combining with water Ester + water Esterases Alcohol & Acid Ex-Atropine to tropic acid. Tropic acid 8
- 9. PHASE II- METABOLISM Drug or phase I metabolite conjugate with biomolecules that derived from carbohydrates, amino acids & make the drug polar. It is synthetic in nature & requires high energy. Occurs mostly in cytosol Gives products that are generally water soluble and easily excreted 9
- 10. CONJUGATED PRODUCTS.. I. Glucuronic acid. II. Acetylation/Methylation. III. Sulphate. IV. Amino acids. ( Glycine, L- Leucine ) 1.CONJUGATION WITH GLUCURONIC ACID: Drug + UDPGA Drug glucuronide + UDP 10
- 11. ACETYLATION: Drugs with Amino or Hydrazine groups. Ex- Dapsone. R-NH2 +N Acetyl transferase R-NHCOCH3 METHYLATION: Drugs with Amino & Phenol groups Ex- Captopril, Dopamine. Enzymes-Methyl transferase CONJUGATION WITH SULFATE: Drug groups-Amino, Hydroxyl. Ex-Chloramphenicol, Warfarin. Enzymes-Sulfotransferases 11
- 12. CONCLUSION.. The metabolism of drugs into more hydrophilic metabolites is essential for the elimination of these compounds from the body and termination of their biological activity. 12
- 13. REFERENCE.. Tripathi.KD Essentials of Medical Pharmacology, Edition-7th,Page no- (22- 25), Jaypee Brothers Medical Publishers Ltd. THANKINGYOU… 13