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Penicillins
Content
β-Lactam antibiotics

• Penicillins

– Mechanism of action

– Classification

– Pharmacokinetics

– Clinical uses

Objectives
At the end of this session, students will be able to:

• Classify Penicillins

• Describe the mechanism of action of Penicillins

• Outline the pharmacokinetic profile of Penicillin

• Discuss the clinical uses of Penicillins

β-Lactam antibiotics
• All of the drugs in this group contain a β-lactam ring in their structure

• Inhibit bacterial cell wall synthesis

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Penicillin
• Obtained from Penicillium notatum

• At present obtained from Penicillium chrysogenum

• Consists of sulfur containing thiazolidine ring fused with β-lactam ring having a side chain at C-6

• 6- amino pencillanic acid (6-APA)- active moiety

• Has intact β-lactam ring and amino group at C-6 joined at thiazolidine ring

Mechanism of action

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• Inhibits bacterial cell wall synthesis

• Bacterial cell wall is composed of peptidoglycan

• Peptide chains are cross linked by pentaglycine bridge

• Process of trans bridging - transpeptidation

• Catalysed by penicillin binding protein (PBP)

• Penicillin competes and inhibits PBPs

• Forms imperfect cell wall

• Osmatic drive of fluid

• Bacetrial death by swelling and lysis

• Bactericidal action

Resistance to penicillin
By any of the following mechanism

• Inactivation of β-lactam ring by β-lactamase

• Modification of PBPs

• Reduction in penicillin permeability to reach PBPs

• Activation of antibiotic efflux mechanism

Classification of Penicillins
• Based on antimicrobial spectrum

• Some are stable to gastric acid

• Some are acid labile (give parenterally)

• Some are resistant to β-lactamase

• Others are β-lactamase sensitive

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Narrow spectrum penicillin

Extendend spectrum penicillin

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Pharmacokinetics
Narrow spectrum penicillin

• Penicillin V and G- natural penicillin

• β-lactamase sensitive

• Penicillin G – acid labile

• Easily absorbed

• Wide distribution – except eye, prostrate and CNS

• Excreted through kidneys

Extended spectrum penicillin

• β-lactamase sensitive

• Aminopenicillin – acid stable

• Carboxypenicillin and Ureidopenicillin – acid labile

• Good bioavailability

• Excreted through kidneys

Antimicrobial spectrum
Narrow spectrum penicillin

• Penicillin G and V - Effective against gram positive and gram negative bacteria

• Semisynthetic – Cloxacillin, dicloxacillin, methicillin and nafcillin

• Spectrum of action similar to natural penicillin

Extended spectrum penicillin

• Retains antimicrobial spectrum of penicillin G

• Extended spectrum against gram negative organism

• Amoxycillin – for eradicating H.pylori in duodenal and gastric ulcers

• Piperacillin- antipseudomonal penicillin

Clinical uses
• UTIs, typhoid fever, bacillary dysentry

• Amoxycillin – for eradicating H.pylori in duodenal and gastric ulcers

• Ampicillin – for meningitis by Listeria monocytogenes

• Endocarditis

• Septicemia

• Cellulitis

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Summary
• β-lactam antibiotics are the group of drugs that contain a β-lactam ring in their structure and they act by
inhibiting bacterial cell wall synthesis

• They include – penicillins, cephalosporins, monobactams and cabapenems

• Penicillins are the drug initially obtained from fungus, now obtained by semisynthetic process

• They used in the treatment of UTIs, endocarditis, septicemia

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