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Story of penicillin
Story of penicillin
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Penicillins

  1. 1. PENICILLINS
  2. 2. Historical Background Penicillin:Penicillin was the world’s first antibiotic and was discovered bySir Alexander Fleming in 1928 accidently. Alexander Fleming, noticed that one of his experimentalcultures of Staphylococcus was contaminated with mould,which caused the bacteria to lyse. Since mould belongedto the family Penicillium, he named the antibacterialsubstance penicillin. On Friday, September 28, in 1928, Fleming left the lid off ofone of his Petri dishes for several weeks, and a fungal sporelanded on it. After returning from vacation, Fleming noticedthat his Staphylococcus (bacteria) culture was contaminatedwith this fungus which cause the bacteria to die. He thencarefully examined it first.
  3. 3. Then, he grew a pure culture and discovered that it was a Penicilliummould, now known to be Penicillium notatum. He concluded that Penicillium mould must be secreting anantibacterial substance, which he isolated first in crude form ofthe active substance and named it as penicillin. Unfortunately, the substance was also unstable and Flemingwas unable to isolate and purify the compound.Florey and Chain in 1938 by using processes such as freezedryingand chromatography which allowed isolation of pure formof penicillins. Fleming, Florey, and Chain shared the 1945 Nobel Prize for theirmedicinal work on the antibiotic penicillin.
  4. 4. Penicillins are called beta-lactam antibiotics and arecharacterized by three fundamental structural requirements: A) Beta-lactam ring B) Thiazolidine ring C) Side chains (R)
  5. 5. Classification 1. Natural Penicillins: Natural penicillins, the first agents in the penicillin family, are obtained directly from the Penicillium mouldand do not require further modification. e.g., Penicillin G. 2. Semisynthetic Penicillins (i) Acid resistant penicillins (ii) Penicillinase resistant penicillins (iii) Extended spectrum penicillins (a)Aminopenicillins (b)Carboxypenicillins (c) Ureidopenicillins (d)Amidinopenicillins
  6. 6. Natural penicillins Penicillin G (Benzyl penicillin) Penicillin F Penicillin K Penicillin N Penicillin O Penicillin X
  7. 7. Semisynthetic penicillins These penicillins are produced by chemically combining specific side chains in place of benzyl side chain of Penicillin G. (i) Acid resistant penicillins Penicillin V Phenethicillin Propicillin
  8. 8. (ii) Penicillinase resistant penicillins (Anti-staphylococcal penicillins) Oxacillin Cloxacillin Dicloxacillin Flucloxacillin Methicillin Nafcillin
  9. 9. (iii) Extended spectrum penicillins (a) Aminopenicillins Ampicillin Amoxycillin Epicillin Bacampicillin Pivampicillin
  10. 10. (b) Carboxypenicillins Carbenicillin Carfecillin Carindacillin Ticarcillin Temocillin
  11. 11. (c) Ureidopenicillins Azlocillin Mezlocillin Piperacillin (d) Amidinopenicillins Mecillinam Pivmecillinam
  12. 12. Mechanism of action Penicillin blocking the construction of bacterial cell wall by binding with penicillin binding protein and thus weakening and causing break of cell wall, finally killing the bacteria. Inhibit the synthesis of peptidoglycon layer containing NAM &NAGconnected by penicillin binding proteins(PBP). Transpeptidases locatedwithin the cell membraneare responsible forcross linking the peptidoglycan chains of cell wall. Penicillins inactivatethe transpeptidase (PBP) enzymeby covalently bondingto the serine residueswithin the active site.
  13. 13. In absence of penicillins
  14. 14. In presence of penicillins
  15. 15. https://www.youtube.com/watch?v=sEaMnZmPJLI
  16. 16. THERAPEUTIC USES  Skin & soft tissue infections.  Diphtheria, tetanus, gas gangrene.  Intra -abdominal infection, syphilis.  Ear, nose, lungs infections.  Streptococcal infections.  Drug of choice for Anthrax,Trench mouth, Rat bite fever,Actinomycosis
  17. 17. STRUCTURE ACTIVITY RELATIONSHIPS
  18. 18. CHEMICAL DEGRADATION
  19. 19. ADVERSE EFFECTS Diarrhea that is watery or bloody;  Fever, chills, body aches, flu symptoms;  Urinating less than usual or not at all;  Severe skin rash, itching, or peeling;  Agitation, confusion, unusual thoughts or behavior; or  Seizure (black -out or convulsions).  Vomiting , Nausea and Stomach pain.  Headache  Thrush( white patches inside mouth or throat)

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