Approved by PHARMACY COUNCIL OF INDIA – New delhi

Affiliated to THE TAMILNADU DR MGR MEDICAL UNIVERSITY - Chennai

ARUNAI COLLEGE OF PHARMACY - Tiruvannamalai

Prepared & Lecture by

Unit 1 - ANTIBIOTIC Part 1 – ANTIBIOTIC’S Mr. Murugan
(Associate professor)

MEDICINAL CHEMISTRY-III (BP-601T) - B Pharmacy - VI Sem

 β-

Syllabus:

Historical background, Nomenclature, Stereochemistry, Structure activity relationship, Chemical

degradation, classification and important products of the following classes.

Antibiotic’s

Pervious The Tamilnadu Dr MGR Medical university exam question

Jan – 2022 a) Define Antibiotics. Write about the classification of anti – biotics
b) Write about the synthesis and uses of Sulfacetamide and Sulfamethoxazole (10 mark)

Aug – 2023 Classify antibiotics.

Explain in detail about the chemistry and SAR of cephalosporins (10 mark)

May – 2024 Classify antibiotics.

Explain in detail about the chemistry and SAR of Cephalosporins. (10 mark)
 1822-1895 Louis Pasteur (father of modern microbiology) was one of the first recognized physicians who

observed that bacteria could be used to kill other bacteria, he discoveries of the principles of vaccination,

fermentation.

 1909 Paul Ehrlich (Father of Modern Chemotherapy) discovered the first modern chemotherapeutic agent

Salvarsan for the treatment of syphilis

 1928 Alexander Fleming discovered the antibiotic substance penicillin by observed the killing of

staphylococci by a fungus (Penicillium notatum)

 1932 Domagk discovered Prontosil (sulfonamide-dye). a prodrug. Sulphapyridine was the first

sulphonamide drug to be marketed in 1938.

 1943 Waksman, who in his lifetime discovered over 20 antibiotics. Including streptomycin, neomycin etc.
 Vuillemin proposed - antibiosis (against life) as the biological concept of survival of the fittest, in which

one organism destroys another to preserve itself.

 Waksman proposed “an antibiotic or antibiotic substance is a substance produced by microorganisms,

which has the capacity of inhibiting the growth and even of destroying other microorganism.

 Antibiotics are a class of drugs, which are microbial metabolites / chemical substances produced by a

living organism (bacteria, fungi or actinomycetes) or synthetic analogues, in small doses, that destroy or

suppress the growth and multiplying of disease-causing micro-organisms without serious toxicity to the

host (humans or animals).

 Antibiotic derived from the Greek word antibiosis means “against life”

anti-"against" and bios-"life”

Examples: Penicillin, Cephalosporins,
β- Lactamase inhibitors, Monobactams
Tetracyclines etc.

 antibiotics used to treat bacterial infections and other microbial infections.

 doesn’t effect on viral infections

 In many cases, natural antibiotics has been enhanced through medicinal chemical manipulation of the

original structure, leading to broader antimicrobial spectrum, greater potency, lesser toxicity, more

convenient administration, and additional pharmacokinetic advantage etc.

Antimicrobial agents (AMA): Anti-microbial agents are a drug or substance that can destroy microorganisms

or prevent their growth or multiplication.

 Antimicrobials agents include antibiotics, antiseptics, antivirals, antifungals, etc.

 Disinfectants are antimicrobial agents that are applied to non-living surface

Classification - classified in many ways, which is based on the 1. Source obtained
2. Chemical Nature
3. Mechanism of action
4. Spectrum of activity
5. Organisms against

Antibiotics are classified based on the source obtained from:

1. Natural – obtained from microbes by fermentation process

Fungi: Penicillin, Cephalosporin, etc

Bacteria: Polymyxin B Colistin Aztreonam Bacitracin

Actinomycetes: Aminoglycosides, Macrolides Tetracyclines

2. Semisynthetic - commercially modified natural antibiotics by adding chemical

Ampicillin, Methicillin, Cloxacillin, Oxacillin, etc.

3. Synthetic – commercially synthesized

Chloramphenicol
Chemical structure

1. β-Lactam antibiotics: Penicillin, Cephalosporins, β- Lactamase inhibitors,

2. Aminoglycosides: Streptomycin, Neomycin, Kanamycin, etc.

3. Tetracyclines: Tetracycline, Oxytetracycline, Chlortetracycline, Doxycycline

4. Macrolide antibiotics: Erythromycin, Clarithromycin, Azithromycin, etc.

5. Polypeptide antibiotics: Polymyxin-B, Colistin, Bacitracin,

6. Polyene antibiotics: Nystatin, Amphotericin-B,

7. Quinolones: Ofloxacin, Norfloxacin, Ciprofloxacin etc

8. Miscellaneous: Chloramphenicol, Clindamycin

9. Azole derivatives: Clotrimazole, Ketoconazole, Fluconazole etc

10. Sulpha Drugs: Sulfadiazine, Dapsone (DDS)
11. Nicotinic acid derivatives: Isoniazid, Pyrazinamide, Ethionamide etc
12. Nitro imidazole: Metronidazole, Tinidazole, etc
13. Others: Rifampin, Cycloserine, Linezolid, Trimethoprim, etc.
Mechanism of action

1. Inhibit cell wall synthesis: Penicillin, Cephalosporins, Vancomycin,

2. Damage of cell membranes: Colistin, Bacitracin. Amphotericin B, Nystatin.
3. Inhibit protein synthesis: Tetracyclines, Chloramphenicol, Erythromycin,
4. misreading of m-RNA code: Streptomycin, Gentamicin, etc.
5. Inhibit DNA gyrase: Ciprofloxacin and others.
6. Interfere with DNA function: Rifampin.
7. Interfere with DNA synthesis: Acyclovir, Zidovudine.
8. Interfere intermediary metabolism: Sulfonamides, Sulfones, Metronidazole

Antibiotics are classified based on the Spectrum of activity

1. Narrow-spectrum – effective against only few species of bacteria, fungi or protozoa

Gram positive Penicillin, Erythromycin
Gram Negative Ciprofloxacin, Cefuroxime
2. Broad-spectrum - effective against variety of species of both gram +ve & –ve, fungi
Tetracyclines, Chloramphenicol
Type of organisms against which primarily active

1. Antibacterial:
Bacteriostatic - inhibit the growth of microorganisms by interfering with protein synthesis
Sulfonamides Erythromycin
Tetracyclines Chloramphenicol

Bactericidal – which kill or destroy the microorganism by inhibit the cell wall synthesis.
Penicillins Cephalosporins
Aminoglycosides Vancomycin

An antibiotic which is having bactericidal effect in certain concentration may produce bacteriostatic

effect in lower concentration.

2. Antifungal: Griseofulvin, Amphotericin B, Ketoconazole, etc

3. Antiviral: Acyclovir, Amantadine, Zidovudine, etc.

4. Antiprotozoal:Chloroquine, Pyrimethamine, Metronidazole, Diloxanide, etc

5. Anthelmintic: Mebendazole, Pyrantel, Niclosamide, Diethyl carbamazine, etc

 Category Example Uses

1. β-Lactam antibiotics: Penicillin Bacterial infections

2. Aminoglycosides: Streptomycin RTI, UTI abdominal inflammatory disease

3. Tetracyclines: Tetracycline Pneumonia, amebiasis, ache

4. Macrolide antibiotics: Azithromycin RTI, STDs, Pulmonary diseases

5. Quinolones: Ciprofloxacin RTI, UTI, eye, skin and Diarrhea

6. Miscellaneous: Chloramphenicol Infection of Eye, Ear, skin and minor wound

7. Azole derivatives: Ketoconazole Fungal infection

8. Sulpha Drugs: Sulfadiazine Bacterial infection in skin, UTI, Eye

9. Nicotinic acid derivatives: Isoniazid Tuberculosis

10. Nitro imidazole: Metronidazole GIT,