Course: BP602T: Medicinal Chemistry III - Theory
Semester: VI (Sixth)

Scope:
This subject is designed to impart fundamental knowledge on the structure, chemistry, and therapeutic value of drugs. The subject emphasizes structure-activity relationships (SAR), mechanism of action, synthesis of important drugs, and an introduction to drug design.

Objectives:
Upon completion of the course, the student shall be able to:

1. Understand the importance of SAR of drug molecules in respect to their pharmacological activity.

2. Understand the chemical nomenclature, stereochemistry, and metabolism of drug molecules.

3. Know the synthetic pathways of selected drug molecules.

4. Get acquainted with the chemistry of recent drugs.

Course Content:

UNIT I (10 Hours)

• Antibiotics:

  • Historical background, nomenclature, stereochemistry, SAR, chemical degradation classification and important products of the following classes:

  • β-Lactam antibiotics: Penicillins (Penicillin G, Penicillin V, Cloxacillin, Ampicillin, Amoxicillin), Cephalosporins (Cephalexin, Cefixime, Cefaclor, Ceftriaxone, Cefepime), β-Lactamase inhibitors (Clavulanic acid, Sulbactam, Tazobactam), Monobactams (Aztreonam), Carbapenems (Imipenem, Meropenem).

  • Aminoglycosides: Streptomycin, Neomycin, Kanamycin, Amikacin, Gentamicin, Tobramycin.

  • Tetracyclines: Tetracycline, Oxytetracycline, Chlortetracycline, Doxycycline, Minocycline.

UNIT II (10 Hours)

• Antibiotics (Continued):

  • Macrolides: Erythromycin, Clarithromycin, Azithromycin.

  • Miscellaneous: Chloramphenicol, Clindamycin, Lincomycin, Vancomycin.

  • Polypeptide antibiotics: Bacitracin, Polymyxin B.

  • Antifungal antibiotics: Amphotericin-B, Nystatin, Griseofulvin.

• Prodrugs:

  • Basic concepts and application of prodrug design.

  • Drug latentiation.

UNIT III (10 Hours)

• Antimalarials:

  • Etiology of malaria.

  • Classification, SAR and synthesis of the following: Chloroquine, Pamaquine, Amodiaquine, Primaquine, Proguanil, Cycloguanil, Pyrimethamine, Mefloquine, Artemisinin and its derivatives.

• Anti-tubercular Agents:

  • Synthetic anti-tubercular agents: Isoniazid*, Ethionamide, Ethambutol*, Pyrazinamide*, Para aminosalicylic acid*.

  • Anti-tubercular antibiotics: Rifampicin, Rifabutin, Cycloserine, Streptomycin, Capreomycin sulphate.

• Urinary tract anti-infective agents:

  • Classification, SAR and synthesis of the following: Quinolones (Nalidixic acid*, Norfloxacin, Ciprofloxacin*, Ofloxacin*, Lomefloxacin, Sparfloxacin, Gatifloxacin, Moxifloxacin), Nitrofurantoin*.

• Antiviral agents:

  • Classification, SAR and synthesis of the following: Amantadine, Rimantadine, Idoxuridine, Acyclovir*, Ganciclovir, Zidovudine, Didanosine, Lamivudine, Stavudine, Saquinavir, Indinavir, Ritonavir, Nevirapine, Efavirenz, Ribavirin.

UNIT IV (08 Hours)

• Antifungal agents:

  • Classification, SAR and synthesis of the following: Azoles (Clotrimazole*, Miconazole, Ketoconazole*, Itraconazole, Fluconazole), Allylamines (Terbinafine*, Naftifine), Others (Tolnaftate, Griseofulvin, Nystatin, Amphotericin B, Ciclopirox olamine).

• Anti-protozoal agents:

  • Classification, SAR and synthesis of the following: Metronidazole*, Tinidazole, Diloxanide furoate*, Iodoquinol, Pentamidine, Suramin, Miltefosine.

• Anthelmintics:

  • Classification, SAR and synthesis of the following: Mebendazole*, Albendazole*, Thiabendazole, Pyrantel pamoate*, Praziquantel, Diethylcarbamazine citrate*, Ivermectin.

UNIT V (07 Hours)

• Sulphonamides and Sulphones:

  • History, nomenclature, classification, SAR, mechanism of action, adverse effects.

  • Synthesis of: Sulfanilamide*, Sulfacetamide*, Sulfapyridine, Sulfadiazine*, Sulfamethoxazole*, Sulfisoxazole, Sulfasalazine. Co-trimoxazole.

  • Sulphones: Dapsone*.

• Introduction to Drug Design:

  • Various approaches used in drug design.

  • Physicochemical parameters used in QSAR: lipophilicity, electronic parameters, steric parameters.

  • QSAR (Quantitative Structure Activity Relationship) - Basic introduction, Hansch & Free-Wilson analysis.

  • Concept of bioisosterism.

(* denotes synthesis of the drug)

Recommended Books (Latest Editions):

1. Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry.

2. Foye's Principles of Medicinal Chemistry.

3. Burger's Medicinal Chemistry and Drug Discovery.

4. An Introduction to Medicinal Chemistry by Graham L. Patrick.

5. Medicinal Chemistry by Ashutosh Kar.

6. Medicinal Chemistry by S. S. Kadam et al.

7. Synthesis of Essential Drugs by R. S. Vardanyan and V. J. Hruby.

8. Pharmaceutical Chemistry - III (Medicinal Chemistry) by P. V. K. et al. (for Indian context).

9. Medicinal Chemistry by D. Sriram and P. Yogeeswari.

Important Note:

• This syllabus is based on the PCI guidelines. Individual universities might have minor variations or additional recommended readings.

• Always refer to the syllabus provided by your specific university or college for the most accurate and up-to-date information.

• The practical component for this subject would be covered under BP606P (Medicinal Chemistry III - Practical).