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Anti infective agent, Classification and reaction.pptx

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Gayatri Patra
Gayatri Patra

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Anti-Infective Agents Gayatri Patra Asst.professor EPCP
Anti-Infective Agents Anti-infective agents are drugs that prevent or treat infections by inhibiting the growth of or killing microorganisms such as bacteria, viruses, fungi, and parasites. These agents act at the site of application, limiting systemic absorption and minimizing side effects. Antiseptics: Antiseptics are chemical agents applied to living tissues (such as skin, mucous membranes, or wounds) to inhibit the growth of or destroy microorganisms, preventing infection without causing significant harm to the tissue. Example: Povidone-iodine, Hydrogen peroxide, Alcohol. Disinfectants: Disinfectants are chemical agents used on non-living surfaces and objects to destroy or inactivate microorganisms, including bacteria, viruses, and fungi. They are not safe for application to living tissues due to their higher toxicity. Example: Sodium hypochlorite (bleach), Phenol.
Local anti-infective agents act by different mechanisms such as: 1. Oxidation of bacterial protoplasm: These agents directly release oxidants that damage bacterial cellular components (Protoplasm). 2. Denaturation of bacterial proteins including enzymes: These are the agents denature bacterial proteins & enzymes by breaking the hydrogen bonds, tertiary or quaternary structures. 3. Detergent-like action( Increasing permeability of bacterial membrane): These are the agents act as surfactants, breaking the lipid bilayer of the bacterial membranes. This increases membrane permeability, causing leakage of essential ions and intracellular content.
Classification Alcohols and related compounds: Alcohol, Isopropyl alcohol, Formaldehyde solution Phenols and their Derivatives: p-Chlorophenol, Hexachlorophene, Hexyl resorcinol Oxidizing agents: Hydrogen peroxide solution, Hydrous benzoyl peroxide Halogen containing compounds: Iodine tincture, Chlorine containing compound- Halazone Cationic surfactants: Benzalkonium chloride, Cetylpyridinium chloride Dyes: Genetian Violet, Methylene blue Nitrogen compounds: Nitrofurazone, Furazolidone
Alcohols and related compounds: Alcohols are widely used antiseptics, especially during dressing of wounds. These act by causing denaturation of proteins. Ethyl and isopropyl alcohols in the con. of 30-70% are used as antiseptics. Structure Activity Relationship (SAR): The activity of alcohols increases with increase in molecular weight and chain length. The potency of aliphatic alcohols increases with lipophilicity. Branching and addition of hydroxy groups decrease the potency.
Alcohols and related compounds: Ethyl Alcohol (Ethanol): CHCHOH Chemical Formula: CHOH Molecular Weight: 46.07 g/mol Appearance: Clear, colorless liquid Used in hand sanitizers, pre-injection skin cleaning, and minor wound care. Used to disinfect surfaces in hospitals, laboratories, and pharmaceutical industries.
Isopropyl alcohol Isopropyl alcohol, also known as isopropanol or 2-propanol, is a widely used antiseptic, disinfectant, and solvent. It is effective against bacteria, viruses, and fungi, making it a common component in hand sanitizers and surface disinfectants. Chemical Formula: (CH)CHOH Molecular Weight: 60.1 g/mol Appearance: Clear, Colorless liquid
Formaldehyde Formaldehyde is a simple organic compound with strong disinfectant and preservative properties. It is widely used in healthcare, laboratories, and industries for sterilization and preservation purposes. Chemical Formula: CHO Molecular Weight: 30.03 g/mol Appearance: Colorless gas or liquid The structure consists of a carbonyl group (C=O) bonded to two hydrogen atoms Mechanism of Action: Formaldehyde cross-links with proteins and nucleic acids, disrupting cell function and leading to microbial death.
Phenols and their Derivatives: Phenols and their derivatives have wide antibacterial properties and antiseptics. They act as germicidals by denaturing the bacterial proteins. Structure Activity Relationship ( SAR): The activity of phenols is related to no. of free hydroxy groups. Halogenation at para position to hydroxy group potentials the activity The antibacterial activity of alkyl phenols increase with increase in size of the alkyl group.
p-Chlorophenol p-Chlorophenol is an aromatic organic compound where a chlorine atom is substituted at the para (4th) position of a phenol ring. Chemical Formula: CHClO Molecular Weight: 128.56 g/mol Appearance: White to off-white crystalline solid It is used as an antiseptic and it is used in combination with camphor as an external antiseptic and anti-irritant.
Hexachlorophene Chemical formula: C13H6Cl6O2 2,2 methylene- bis (3,4,6- trichlorophenol) Hexachlorophene consists of 2 trichlorophenol (C6H2Cl3OH) rings connected by methylene (-CH2-) bridge at the second carbon of each ring It is a white crystaline powder and insoluble in water. It is mainly used in soaps, detergents, creams and emulsions for tropical application.
Synthesis Formaldehyde activation under acidic medium producing a reactive electrophilic intermediate. Electrophilic carbon from formaldehyde reacts with ortho positions of the 2,4,5- trichlorophenol. Methylene Methylene Bridge Formation: A second molecule of trichlorophenol reacts, completing the formation of the bisphenol structure (hexachlorophene).
Hexyl resorcinol Hexylresorcinol is an organic compound that belongs to the resorcinol family, known for its antiseptic and anesthetic properties. It is commonly used in pharmaceutical and personal care products. IUPAC Name: 4-Hexyl resorcinol Molecular Formula: CHO It occurs as white, needle shape crystals with a faint odour. It is freely soluble in water. It is odourless and nonstaining.
Synthesis:
Oxidizing agents: Oxidising agents have germicidal property and are used in treatment of infections caused by anaerobic organisms( dont require oxygen to grow). The most common oxidising agents are Hydrogen peroxide, Potassium permanganate, Zinc peroxide, Hydrousbenzoyl peroxide.
Hydrogen peroxide (H2O2) Hydrogen peroxide is a good disinfectant and sterilant. It is rapidly decomposes releasing nascent oxygen which produces antibacterial action. It is not stable and may undergo decomposition on storage. It is used in the form of carbamate peroxide which releases hydrogen peroxide when come into contact with water. It is mainly used as ear drops to remove slough, ear wax etc. Hydrous Benzoyl Peroxide: It is used topically in the therapy of mild to moderate acne vulgaris and to removes dead skin cells.
Halogen containing compounds Iodine tincture: 2% solution of iodine in alcohol. It is effective over a wide pH range and the bactericidal activity is related to the amount of free iodine generated. Iodine acts by oxidising tyrosine and sulfhydryl groups in proteins causing inactivation.
Halazone Halazone is a chemical compound primarily used as a water disinfectant. It is an organochlorine compound with mild antibacterial properties, commonly employed to purify drinking water. It is a white crystalline powder and chlorine like odour. It is slightly soluble in water.
Halazone Halazone is a chemical compound primarily used as a water disinfectant. It is an organochlorine compound with mild antibacterial properties, commonly employed to purify drinking water. It is a white crystalline powder and chlorine like odour. It is slightly soluble in water.
Bacteria Gram-Positive Bacteria Thick (20-80 nm) Outer Membrane: Absent Lipid Content: Low Gram Staining Result: Retains crystal violet (purple/blue) Gram-Negative Bacteria Thin (5-10 nm) Present High Loses crystal violet; stains with safranin (pink/red)
Cationic Surfactants Cationic surfactants are effective against a number of Gram-possetive and Gram-negative bacteria, fungi and viruses. These cations are absorbed onto the surface of the bacteria resulting in cell membrane disruption, protein denaturation and enzyme inhibitions. The detergent property also helps in cleaning dirty wounds. These compounds have the advantage of having low toxicity, non-staining, high water solubility.
Benzalkonium Chloride (BAK) Benzalkonium Chloride is a widely used quaternary ammonium compound (QAC) with antimicrobial, antiseptic, and surfactant properties. It is commonly found in disinfectants, hand sanitizers, eye drops, and pharmaceutical formulations. Chemical Formula: CHClN (for dodecylbenzyl version) General Formula: CHCHN(R)Cl Where: CHCH Benzyl group N(R) Quaternary ammonium (R = long alkyl chain, typically dodecyl (12-carbon alkyl chain) or tetradecyl) IUPAC Name N-benzyl-N,N-dimethyldodecan-1-aminium chloride
Dyes: Gentian Violet Structure: Gentian violet consists of a triphenylmethane core with three dimethylamino (N(CH)) groups attached to the phenyl rings and a chloride ion. The central carbon is bonded to three phenyl rings, each substituted with a dimethylamino group. IUPAC: [4-(Dimethylamino)phenyl]-bis[4- (dimethylamino)phenyl]methylium chloride Soluble in water and ethanol Gentian violet with antiseptic, antifungal, and staining properties. It is commonly used in microbiology, medicine,
Nitrogen compounds Nitrofurazone is an antimicrobial agent primarily used for the treatment of wounds, burns, and bacterial infections. It belongs to the nitrofuran class of drugs, known for their broad-spectrum antibacterial properties. Nitrofurazone consists of a furan ring substituted with a nitro group (NO) and a hydrazone moiety. The furan ring (CHO) carries a nitro group at position 5, and the hydrazone group is attached at position 2. IUPAC Name N-(5-Nitro-2-furfurylidene)-1-aminohydantoin Topical Antibacterial Agent Used in ointments for skin infections, burns, and wounds.
Anti infective agent, Classification and reaction.pptx

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Anti infective agent, Classification and reaction.pptx

  • 2. Anti-Infective Agents Anti-infective agents are drugs that prevent or treat infections by inhibiting the growth of or killing microorganisms such as bacteria, viruses, fungi, and parasites. These agents act at the site of application, limiting systemic absorption and minimizing side effects. Antiseptics: Antiseptics are chemical agents applied to living tissues (such as skin, mucous membranes, or wounds) to inhibit the growth of or destroy microorganisms, preventing infection without causing significant harm to the tissue. Example: Povidone-iodine, Hydrogen peroxide, Alcohol. Disinfectants: Disinfectants are chemical agents used on non-living surfaces and objects to destroy or inactivate microorganisms, including bacteria, viruses, and fungi. They are not safe for application to living tissues due to their higher toxicity. Example: Sodium hypochlorite (bleach), Phenol.
  • 3. Local anti-infective agents act by different mechanisms such as: 1. Oxidation of bacterial protoplasm: These agents directly release oxidants that damage bacterial cellular components (Protoplasm). 2. Denaturation of bacterial proteins including enzymes: These are the agents denature bacterial proteins & enzymes by breaking the hydrogen bonds, tertiary or quaternary structures. 3. Detergent-like action( Increasing permeability of bacterial membrane): These are the agents act as surfactants, breaking the lipid bilayer of the bacterial membranes. This increases membrane permeability, causing leakage of essential ions and intracellular content.
  • 4. Classification Alcohols and related compounds: Alcohol, Isopropyl alcohol, Formaldehyde solution Phenols and their Derivatives: p-Chlorophenol, Hexachlorophene, Hexyl resorcinol Oxidizing agents: Hydrogen peroxide solution, Hydrous benzoyl peroxide Halogen containing compounds: Iodine tincture, Chlorine containing compound- Halazone Cationic surfactants: Benzalkonium chloride, Cetylpyridinium chloride Dyes: Genetian Violet, Methylene blue Nitrogen compounds: Nitrofurazone, Furazolidone
  • 5. Alcohols and related compounds: Alcohols are widely used antiseptics, especially during dressing of wounds. These act by causing denaturation of proteins. Ethyl and isopropyl alcohols in the con. of 30-70% are used as antiseptics. Structure Activity Relationship (SAR): The activity of alcohols increases with increase in molecular weight and chain length. The potency of aliphatic alcohols increases with lipophilicity. Branching and addition of hydroxy groups decrease the potency.
  • 6. Alcohols and related compounds: Ethyl Alcohol (Ethanol): CHCHOH Chemical Formula: CHOH Molecular Weight: 46.07 g/mol Appearance: Clear, colorless liquid Used in hand sanitizers, pre-injection skin cleaning, and minor wound care. Used to disinfect surfaces in hospitals, laboratories, and pharmaceutical industries.
  • 7. Isopropyl alcohol Isopropyl alcohol, also known as isopropanol or 2-propanol, is a widely used antiseptic, disinfectant, and solvent. It is effective against bacteria, viruses, and fungi, making it a common component in hand sanitizers and surface disinfectants. Chemical Formula: (CH)CHOH Molecular Weight: 60.1 g/mol Appearance: Clear, Colorless liquid
  • 8. Formaldehyde Formaldehyde is a simple organic compound with strong disinfectant and preservative properties. It is widely used in healthcare, laboratories, and industries for sterilization and preservation purposes. Chemical Formula: CHO Molecular Weight: 30.03 g/mol Appearance: Colorless gas or liquid The structure consists of a carbonyl group (C=O) bonded to two hydrogen atoms Mechanism of Action: Formaldehyde cross-links with proteins and nucleic acids, disrupting cell function and leading to microbial death.
  • 9. Phenols and their Derivatives: Phenols and their derivatives have wide antibacterial properties and antiseptics. They act as germicidals by denaturing the bacterial proteins. Structure Activity Relationship ( SAR): The activity of phenols is related to no. of free hydroxy groups. Halogenation at para position to hydroxy group potentials the activity The antibacterial activity of alkyl phenols increase with increase in size of the alkyl group.
  • 10. p-Chlorophenol p-Chlorophenol is an aromatic organic compound where a chlorine atom is substituted at the para (4th) position of a phenol ring. Chemical Formula: CHClO Molecular Weight: 128.56 g/mol Appearance: White to off-white crystalline solid It is used as an antiseptic and it is used in combination with camphor as an external antiseptic and anti-irritant.
  • 11. Hexachlorophene Chemical formula: C13H6Cl6O2 2,2 methylene- bis (3,4,6- trichlorophenol) Hexachlorophene consists of 2 trichlorophenol (C6H2Cl3OH) rings connected by methylene (-CH2-) bridge at the second carbon of each ring It is a white crystaline powder and insoluble in water. It is mainly used in soaps, detergents, creams and emulsions for tropical application.
  • 12. Synthesis Formaldehyde activation under acidic medium producing a reactive electrophilic intermediate. Electrophilic carbon from formaldehyde reacts with ortho positions of the 2,4,5- trichlorophenol. Methylene Methylene Bridge Formation: A second molecule of trichlorophenol reacts, completing the formation of the bisphenol structure (hexachlorophene).
  • 13. Hexyl resorcinol Hexylresorcinol is an organic compound that belongs to the resorcinol family, known for its antiseptic and anesthetic properties. It is commonly used in pharmaceutical and personal care products. IUPAC Name: 4-Hexyl resorcinol Molecular Formula: CHO It occurs as white, needle shape crystals with a faint odour. It is freely soluble in water. It is odourless and nonstaining.
  • 15. Oxidizing agents: Oxidising agents have germicidal property and are used in treatment of infections caused by anaerobic organisms( dont require oxygen to grow). The most common oxidising agents are Hydrogen peroxide, Potassium permanganate, Zinc peroxide, Hydrousbenzoyl peroxide.
  • 16. Hydrogen peroxide (H2O2) Hydrogen peroxide is a good disinfectant and sterilant. It is rapidly decomposes releasing nascent oxygen which produces antibacterial action. It is not stable and may undergo decomposition on storage. It is used in the form of carbamate peroxide which releases hydrogen peroxide when come into contact with water. It is mainly used as ear drops to remove slough, ear wax etc. Hydrous Benzoyl Peroxide: It is used topically in the therapy of mild to moderate acne vulgaris and to removes dead skin cells.
  • 17. Halogen containing compounds Iodine tincture: 2% solution of iodine in alcohol. It is effective over a wide pH range and the bactericidal activity is related to the amount of free iodine generated. Iodine acts by oxidising tyrosine and sulfhydryl groups in proteins causing inactivation.
  • 18. Halazone Halazone is a chemical compound primarily used as a water disinfectant. It is an organochlorine compound with mild antibacterial properties, commonly employed to purify drinking water. It is a white crystalline powder and chlorine like odour. It is slightly soluble in water.
  • 19. Halazone Halazone is a chemical compound primarily used as a water disinfectant. It is an organochlorine compound with mild antibacterial properties, commonly employed to purify drinking water. It is a white crystalline powder and chlorine like odour. It is slightly soluble in water.
  • 20. Bacteria Gram-Positive Bacteria Thick (20-80 nm) Outer Membrane: Absent Lipid Content: Low Gram Staining Result: Retains crystal violet (purple/blue) Gram-Negative Bacteria Thin (5-10 nm) Present High Loses crystal violet; stains with safranin (pink/red)
  • 21. Cationic Surfactants Cationic surfactants are effective against a number of Gram-possetive and Gram-negative bacteria, fungi and viruses. These cations are absorbed onto the surface of the bacteria resulting in cell membrane disruption, protein denaturation and enzyme inhibitions. The detergent property also helps in cleaning dirty wounds. These compounds have the advantage of having low toxicity, non-staining, high water solubility.
  • 22. Benzalkonium Chloride (BAK) Benzalkonium Chloride is a widely used quaternary ammonium compound (QAC) with antimicrobial, antiseptic, and surfactant properties. It is commonly found in disinfectants, hand sanitizers, eye drops, and pharmaceutical formulations. Chemical Formula: CHClN (for dodecylbenzyl version) General Formula: CHCHN(R)Cl Where: CHCH Benzyl group N(R) Quaternary ammonium (R = long alkyl chain, typically dodecyl (12-carbon alkyl chain) or tetradecyl) IUPAC Name N-benzyl-N,N-dimethyldodecan-1-aminium chloride
  • 23. Dyes: Gentian Violet Structure: Gentian violet consists of a triphenylmethane core with three dimethylamino (N(CH)) groups attached to the phenyl rings and a chloride ion. The central carbon is bonded to three phenyl rings, each substituted with a dimethylamino group. IUPAC: [4-(Dimethylamino)phenyl]-bis[4- (dimethylamino)phenyl]methylium chloride Soluble in water and ethanol Gentian violet with antiseptic, antifungal, and staining properties. It is commonly used in microbiology, medicine,
  • 24. Nitrogen compounds Nitrofurazone is an antimicrobial agent primarily used for the treatment of wounds, burns, and bacterial infections. It belongs to the nitrofuran class of drugs, known for their broad-spectrum antibacterial properties. Nitrofurazone consists of a furan ring substituted with a nitro group (NO) and a hydrazone moiety. The furan ring (CHO) carries a nitro group at position 5, and the hydrazone group is attached at position 2. IUPAC Name N-(5-Nitro-2-furfurylidene)-1-aminohydantoin Topical Antibacterial Agent Used in ointments for skin infections, burns, and wounds.