MEDICINAL CHEMISTRY – III B. Pharma 6th Semester PDF Notes

Scope: This subject is designed to impart fundamental knowledge on the structure, chemistry, and therapeutic value of drugs. The subject emphasis on modern techniques of rational drug design like quantitative structure-activity relationship (QSAR), Prodrug concept, combinatorial chemistry, and Computer-aided drug design (CADD). The subject also emphasizes the chemistry, mechanism of action, metabolism, adverse effects, Structure-Activity Relationships (SAR), therapeutic uses, and synthesis of important drugs.

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

1.  Understand the importance of drug design and different techniques of drug design.

2.  Understand the chemistry of drugs with respect to their biological activity.

3.  Know the metabolism, adverse effects, and therapeutic value of drugs.

4.  Know the importance of SAR of drugs.

Course Content:

Study of the development of the following classes of drugs, Classification, mechanism of action, uses of drugs mentioned in the course,
Structure-activity relationship of the selective class of drugs as specified in the course and synthesis of drugs superscripted by (*)

MEDICINAL CHEMISTRY- III UNIT – I

Antibiotics

Historical background, Nomenclature, Stereochemistry, Structure-activity relationship, Chemical degradation classification, and important products of the following classes.

β-Lactam antibiotics:
Penicillin, Cephalosporins, β-  Lactamase inhibitors, Monobactams

Aminoglycosides: Streptomycin, Neomycin, Kanamycin

Tetracyclines: Tetracycline, Oxytetracycline, Chlortetracycline, Minocycline, Doxycycline

MEDICINAL CHEMISTRY- III UNIT – II

Antibiotics

Historical background, Nomenclature, Stereochemistry, Structure-activity relationship, Chemical degradation classification, and important products of the following classes.

Macrolide: Erythromycin Clarithromycin, Azithromycin.

Miscellaneous: Chloramphenicol*, Clindamycin.

Prodrugs: Basic concepts and application of prodrugs design.

Antimalarials: Etiology of malaria.

Quinolines: SAR, Quinine sulphate, Chloroquine*, Amodiaquine, Primaquine phosphate, Pamaquine*, Quinacrine hydrochloride, Mefloquine.

Biguanides and dihydro triazines: Cycloguanil pamoate, Proguanil.

Miscellaneous: Pyrimethamine, Artesunete, Artemether, Atovoquone.

MEDICINAL CHEMISTRY- III UNIT – III

Anti-tubercular Agents

Synthetic anti-tubercular agents: Isoniozid*, Ethionamide, Ethambutol, Pyrazinamide, Para amino salicylic acid.*

Antitubercular antibiotics: Rifampicin, Rifabutin, Cycloserine Streptomycine, Capreomycin sulphate.

Urinary tract anti-infective agents

Quinolones: SAR of quinolones, Nalidixic Acid,Norfloxacin, Enoxacin, Ciprofloxacin*, Ofloxacin, Lomefloxacin, Sparfloxacin, Gatifloxacin, Moxifloxacin

Miscellaneous:
Furazolidine, Nitrofurantoin*, Methanamine.

Antiviral agents:

Amantadine hydrochloride,  Rimantadine hydrochloride, Idoxuridine trifluoride, Acyclovir*, Gancyclovir, Zidovudine, Didanosine, Zalcitabine, Lamivudine, Loviride, Delavirding, Ribavirin, Saquinavir, Indinavir, Ritonavir.

MEDICINAL CHEMISTRY- III UNIT – IV

Antifungal agents:

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

Synthetic Antifungal agents: Clotrimazole, Econazole, Butoconazole, Oxiconazole Tioconozole, Miconazole*, Ketoconazole, Terconazole, Itraconazole, Fluconazole, Naftifine hydrochloride, Tolnaftate*.

Anti-protozoal Agents: Metronidazole*, Tinidazole, Ornidazole, Diloxanide, Iodoquinol, Pentamidine Isethionate, Atovaquone, Eflornithine.

Anthelmintics: Diethylcarbamazine citrate*, Thiabendazole, Mebendazole*, Albendazole, Niclosamide, Oxamniquine, Praziquantal, Ivermectin.

Sulphonamides and Sulfones

Historical development, chemistry, classification and SAR of Sulfonamides: Sulphamethizole, Sulfisoxazole, Sulphamethizine, Sulfacetamide*, Sulphapyridine, Sulfamethoxaole*, Sulphadiazine, Mefenide acetate, Sulfasalazine.

Folate reductase inhibitors: Trimethoprim*, Cotrimoxazole.

Sulfones: Dapsone*.

MEDICINAL CHEMISTRY- III UNIT – V

Introduction to Drug Design

Various approaches are used in drug design.

Physicochemical parameters used in quantitative structure activity relationships (QSAR) such as partition coefficient, Hammet’s electronic parameter, Taft’s steric parameter, and Hansch analysis.

Pharmacophore modeling and docking techniques.

Combinatorial Chemistry:  Concept and applications of combinatorial chemistry: solid phase and solution phase synthesis.

BP607P. MEDICINAL CHEMISTRY- III (Practical)

I. Preparation of drugs and intermediates

1. Sulphanilamide

2. 7-Hydroxy, 4-methyl coumarin

3. Chlorobutanol

4. Triphenyl imidazole

5. Tolbutamide

6. Hexamine

II. Assay of drugs

1. Isonicotinic acid hydrazide

2. Chloroquine

3. Metronidazole

4. Dapsone

5. Chlorpheniramine maleate

6. Benzyl penicillin

III. Preparation of medicinally important compounds or intermediates by Microwave irradiation technique

IV. Drawing structures and reactions using chem draw®

V. Determination of physicochemical properties such as logP, clogP, MR, Molecular weight,
Hydrogen bond donors and acceptors for class of drugs course content using drug
design software Drug likeliness screening (Lipinskies RO5)

Recommended Books (Latest Editions)

1.  Wilson and Giswold’s Organic medicinal and Pharmaceutical Chemistry.

2.  Foye’s Principles of Medicinal Chemistry.

3.  Burger’s Medicinal Chemistry, Vol I to IV.

4.   Introduction to principles of drug design- Smith and Williams.

5.  Remington’s Pharmaceutical Sciences.

6.  Martindale’s extra pharmacopoeia.

7.  Organic Chemistry by I.L. Finar, Vol. II.

8.  The Organic Chemistry of Drug Synthesis by Lednicer, Vol. 1-5.

9.   Indian Pharmacopoeia.

10. Textbook of practical organic chemistry- A.I.Vogel.

Also, Visit: Medicinal Chemistry Notes