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  1. 1. MAHATMA GANDHI INSTITUE OF PHARMACY, LUCKNOW Presented by:- MOHHAMAD AFAQUE Assistant Professor Department of Pharmaceutical chemistry ( M. PHARM Medicinal Chemistry)
  2. 2. ANTIBIOTICS:- Antibiotics Introduction:- ➢ Antibiotics are chemical substance which is inhibited the growth of micro- organism or to kill the microorganisms are called antibiotics. ➢ The word antibiotics came from the word antibiosis which is discovered by Louis Pastures in 1889. Classification of antibiotics: 1. Based on Chemical structure 2. Based on mechanism of action 3. Based on chemical structure:- a )Β-lactam antibiotic e.g. Penicillin, Cephalosporine. b) Quinolines antibiotics:- e.g. Ciprofloxacin, Norfloxacine
  3. 3.  c) Tetracycline antibiotics:- e.g. Doxycycline, Oxyteracycline.  d) Nitrobenzene antibiotics:- e.g. Chloramphenicol  e) Aminoglycoside antibiotics:- e.g. Streptomycine, Neomycine.  f) Macrolide antibiotics:- e.g. Azithromycine, Erythromycine.  g) Polypeptide antibiotics:- e.g. Bacitracin.  h) Miscelleneous antibiotics:- e.g. Rifampicin, Lincomycin.
  4. 4.  2. Based on mechanism of action:-  a) Inhibit cell synthesis:- e.g. Penicilline, cephalosporine.  b) Cause leankage from cell membrane:- e.g. Polypeptide- bacitracin.  c) Inhibit protein synthesis:- e.g. Tetracycline, chloramphenicol.  d) By interfering with DNA and RNA synthesis: e.g. Actinomycin  e) Inhibit DNAgyrase e.g. Rifampicin  f) Interfere with DNA synthesis e.g. Acyclovir.  g) Interfere with intermediate metabolism e.g. Sulfonamide, sulfones.
  5. 5.  What is Penicillin:-  Penicillin is a β-lactam antibiotic, which is obtained from penicillium notatum.  Penicillin is a group of antibiotic that are commonly used to treat different type of Gram-negative and Gram-positive bacterial infections such as syphilis, pneumonia.  Penicillin was discovered by Alexander Fleming in 1928. General Structure of penicillin:- R C O H N N O S CH3 CH3 COOH Amide Beta-lactam Thiazolidine ring Carboxyl group Side chain
  6. 6. Structure of 6-AMP Benzyl Penicillin (Penicillin-G):- ➢Penicillin-G also known as benzyl penicillin, it is an antibiotic which is used in the treatment of bacterial infections. ➢It is obtained from penicillium notatam. ➢Benzyl penicillin is manufactured by a submerged culture technique using p.chrysogenum in a sterile medium consisting mainly of corn steep liquor, several inorganic salts and lactose. H2N N O S CH3 CH3 COOH
  7. 7. Structure of Penicillin-G:- IUPAC Name:- 6(2-phenylacetamido)-3,3-dimethyl-7-oxy-1-aza-4-thia [3,2,0] heptane-2-carboxylic acid. OR Chemical Name:- 6-(2-phenylacetamido) penicillanic acid H N N O S CH3 CH3 COOH C O H2 C 1 2 3 4 5 6 7
  8. 8. ➢ It is stable in powder forms so must be stored in sterile well closed container in cool, dry place. Brand name:- for penicillin-G sodium 1. Sodium penicillin-G, 2. Novacillin For benzyl penicillin potassium 1. Penicillin, 2. Penicillin-G potassium Formulations:- . Benzyl penicillin i.p Benzyl penicillin injection I.P, B.P
  9. 9. USES:-1. It is used in the treatment of streptococcal infection, Pneumococcal infections, syphilis, tetanus and rat fever. Amoxicillin:- ➢ Amoxicillin is a penicillin derivative which is used to treat different types of bacterial infections which is obtained by gram-positive bacteria. Structure of Amoxicillin:- H N N O S CH3 CH3 COOH C O H C NH2 HO 1 2 3 6 7 4 5
  10. 10. IUPAC Name:- ➢ 6-[2’-amino-2’-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxy-1-aza-4- thiabicycle[3.2.0]heptanes-2-carboxylic acid OR ➢ 6-[2’-amino-2’-(4-hydroxyphenyl) acetamide]penicillanic acid Storage and stability:- ➢ Capsules and pills should be kept at room temperature, and away from light and moisture. ➢ It should not be store in refrigerated.
  11. 11. Types of formulations:- 1. Tablets 2. Suspensions Brand Name:- 1. Amoxil 2. Trimox 3. Novamox Uses:- 1. It is used in the treatment of various types of infections such as pneumonia, nose, ear, skin and urinary infections. 2. It is also used in the treatment of stomach ulcers caused by Helicobacter pylori.
  12. 12. Cloxacillin:- ➢ Cloxacillin is an antibiotic that is used in the treatment of several infections which is caused by beta-hemolytic streptococcal, pneumococcal, and staphylococcal infections. Stability and storage:- ➢ It should be kept away from light and moisture at room temperature 20- 25℃. ➢ It should be stored in refrigerated under temperature 2-8℃. Type of formulations:- 1. Cloxacillin capsules, I.P, B.P 2. Cloxacillin injection, I.P, B.P, 3. Powder
  13. 13. Brand Name:- 1. Tegopen 2. Cloxapen 3. Cloxacillin 4. Klox Uses:- 1. It is used to treat bacterial infections.
  14. 14. Aminoglycoside antibiotics:- ➢ The amino glycoside antibiotics include gentamicin, neomycin and streptomycin. ➢ These compounds attached with two amino groups linked with two or more sugar molecules. ➢ They are very soluble in water and the solutions are quite stable. ➢ They are broad spectrum antibiotics but mainly active against Gram- negative bacteria. Streptomycin:- ➢ Streptomycin is an antibiotic which is produced by streptomyces griseus. ➢ It is an aminoglycoside antibacterial and antimycobaterial agents.
  15. 15. Stability and storage:- ➢ It can be store at room temperature. ➢ It can also be store in refrigerator. Types of formulations:- 1. Powder for injection Brand name:- 1. Brucella Uses:- 1. Streptomycin is used for the treatment of tuberclusis.
  16. 16. Tetracyclines:- ➢Tetracycline is a potent, broad- spectrum antibacterial agent. ➢ It is active against both Gram- positive and Gram- negative bacteria. ➢ They are also used in the treatment of sexually transmitted and Gonococcal diseases, urinary tract infections and bronchitis. ➢ Tetracycline is manufactured by the fermentation of streptomyces or by the catalytic hydrogenolysis of 7-chlorotetracycline in which the chlorine atom present at 7-position is replaced by hydrogen.
  17. 17. General Structure of tetracycline:- 7-Chlorotetracycline R1= Cl, R2= OH, R3= CH3, R4= H 5-Oxytetracycline:- R1= H, R2= OH, R3= CH3, R4= OH O R1 R2 R3 OH R4 OH N OH CONH2 O CH3 CH3 OH 1 2 3 4 5 6 7 8 9 10 11 12
  18. 18. Doxycycline:- ➢ Doxycycline is a broad-spectrum antibiotic drug derived from tetracycline which is inhibit protein synthesis. ➢ It can be used for the treatment of various bacterial infections. ➢ It is a second generation tetracycline it has less toxic than first generation tetracyclines. Storage and stability:- ➢ It should be stored at room temperature between 15-30℃ in air tight, light-resistant containers. Types of formulations:- 1. Capsule, 2. Tablet, 3. Powder
  19. 19. Brand name:- 1. Doryx 2. Oracea 3. Adoxa TT Uses:- Doxycycline is used in several types of infections caused by Gram-positive and Gram-negative bacteria such as: 1. Respiratory tract infections caused by Mycoplasma pneumonia. 2. Typhus fever.
  20. 20. Minocycline:- ➢ Minocycline is a tetracycline derivative, 7-dimethylamino but lacking 5-methyl and hydroxyl groups. ➢ It is effective against tetracycline-resistant staphylococcus infections. Stability and storage:- ➢ It should be store at 4℃ for two days. ➢ It is water soluble produces a clear, yellow to amber solution when heated. Types of formulations:- 1. Capsules 2. Injection 3. Tablets
  21. 21. Brand name:- 1. Minocin 2. Minocin kit 3. Dynacin 4. Solodyn Uses:- 1. Minocycline is used for the treatment of infections which is caused by microorganisms, such as typhus fever, Q fever etc.
  22. 22. Macrolide antibiotics:- ➢These are a group of antibiotics containing a macrocyclic lactone ring with attached deoxy sugars. ➢ These are obtained by various strains of streptomyces and many other compounds. ➢ Macrolide compounds are erythromycin, carbomycin, oleandomycin. ➢ They are mainly active against Gram positive bacteria and also active against a few Gram negative bacteria such as Haemophilus-Brucella group. ➢ The most important of these antibiotics is erythromycin. ➢ Erythromycin is the drug which was obtained in 1952 from streptomyces erythreus.
  23. 23. Erythromycin:- ➢ Erythromycin was isolated in 1952 from the culture of Streptomyces erythreus by Mcguire and co-workers. ➢ Erythromycin is a bacteriostatic macrolide antibiotic. ➢ It is widely used in various infections caused by gram-positive bacteria and gram-negative bacteria. Stability and storage ➢ It should be stored at a temperature below 30℃. Types of formulations:- Tablet 2. Capsules 3. Powder
  24. 24. Brand Name:- 1. Erthyrocin, 2. E-Mycin 3. Ilosone Uses:- ➢ It is also used in STD, like syphilis. ➢ It is used to treat ear, urinary tract and skin infections.
  25. 25. Azithromycin:- ➢ Azithromycin is a broad-spectrum macrolide antibiotic with a long half- life and a high degree of tissue penetration. ➢ It is used in various gram-positive and gram-negative bacterial infections. Storage and stability:- ➢ Azithromycin pills, suspension, and extended-release suspension are kept at room temperature, away from heat and moisture. Types of formulations:- 1. Tablets 2. Suspension,
  26. 26. Brand name:- 1. Zithromax, 2. Zithromax Tri-Pak, 3. Zithromax Z- Pak, 4. Zmax. Uses:- ➢ Azithromycin is used to treat many different types of infections caused by bacteria, such as respiratory infections, skin infections, ear infections, eye infections and STD.
  27. 27. Chloramphenicol Introduction:- ➢ Chloramphenicol is the first, isolated from streptomyces venezuelae bacteria in 1947. ➢ It has a bacteriostatic action, and inhibit the bacterial protein biosynthesis. ➢ It has a broad spectrum of activity, it is mainly used for the treatment of topically for skin and eye infections. ➢ It is a naturally nitro compound, It contain nitro aromatic compound. ➢ It is active against viruses and bacteria. It is the first antibiotic to be synthesized on a large scale.
  28. 28. Structure of chloramphenicol:- IUPAC Name:- 1(4-nitrophenyl)- 2(1,1dichloroacetamido) propan 1,3-diol. Stability and storage:- ➢ It should be stored in tightly closed, light-resistant containers. Formulations: 1. Chloramphenicol capsules, I.P, B.P 2. Chloramphenicol Eye drops, I.P B.P, 3. Chloramphenicol Eye ointment, I.P, B.P . C O2N H OH C H NHCOCHCl2 CH2OH
  29. 29. Brand Names:- Chlorocid, Chloromycetin, Enteromycetin. Uses:- ➢ It is very useful in the treatment of eye and ear infections. ➢ It is used in the treatment of typhoid fever. ➢ Chloramphenicol is sometimes used for rickettsial diseases