1. Synthesis 0f Heterocyclic Drugs
(Ketoconazole And
Metronidazole) • Presented By:
• Gandham Malasree
• M Pharmacy
• I year I sem
• Regd no: 620209502002
• Dept of Pharmaceutical Chemistry
AU COLLEGE OF PHARMACEUTICAL SCIENCES, VISAKHAPATNAM

2. contents
• Introduction
• Ketoconazole
• Synthesis of ketoconazole
• Metronidazole
• Synthesis of metronidazole

3. INTRODUCTION
A Heterocyclic compounds are those which has atoms of at least two different
elements as members of its ring.
Heterocyclic chemistry is a branch of organic chemistry dealing with the
synthesis, properties, and applications of these heterocycles.

4.  Ketoconazole was first oral azole effective broad spectrum antifungal introduced into clinical
use.
 It is distinguished from triazoles by its greater tendency to inhibit mammalian cytochrome
P450 enzymes; that is, it is less selective for fungal P450 than are newer azoles.
 Oral administration has been replaced by itraconazole for treatment of all mycoses except
when lower cost of ketoconazole outweighs advantage of itraconazole.
 Effective against
• Dermatophytosis, Deep mycosis , Candidiasis
KETOCONAZOLE

5. Structure of KETOCONAZOLE
Molecular Formula: C26H28Cl2N4O4
1-(4-(4-((2-((1H-imidazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-
1,3-dioxolan-4- yl)methoxy)phenyl)piperazin-1-yl)ethanone

6. MECHANISM OF ACTION

7. PROPERTIES
 Molecular weight : 531.4 g/mol
 State : solid
 Color : white crystal or powder
 Melting point : 146 ̊C
 Solubility : soluble in organic solvents

8. SYNTHESIS OF KETOCONAZOLE

9. USES
• Orally Effective broad-spectrum antifungal drug.
• Mucocutaneous candidiasis (immune disorder of T cell).
• Used to inhibit excessive production of glucocorticoids in patients with Cushing's syndrome
(hypercortisolism).
• Used to treat fungal infections of the skin such as jock itch, seborrhea, dermatophytosis
(ringworm),and mycosis.

10. •Metronidazole (flagyl) is a synthetic antiprotozoal and antibacterial agent,( l-β-
hydroxyethyl)-2-methyl-5-nitroimidazole.
•It belongs to the group of nitro imidazoles.
METRONIDAZOLE

11. Structure of METRONIDAZOLE
Molecular Formula: C6H9N3O3

12. MECHANISM OF ACTION
• Metronidazole acts by inhibiting nucleic acid synthesis by disrupting the DNA of microbial
cells.
• This function only occurs when metronidazole is partially reduced, and because this reduction
usually happens only in anaerobic cells, it has relatively little effect upon human cells or
aerobic cells.

13. PROPERTIES
 Molecular weight : 171.5 g/mol
 State : solid
 Color : white or pale-yellow crystal
 Melting point : 160.5 ̊C
 Solubility : soluble in organic solvents

14. SYNTHESIS OF METRONIDAZOLE

15. USES
Mainly used as antibiotics knows as nitroimidazoles.
Oral tablets used to treat vaginal infections in women.
Used to treat G.I tract and reproductive system infections such as amebiasis (intestine
infection) and trichomoniasis (sexually transmitted infection).
It works by stopping the growth of bacteria and protozoal infection.
Used to treat infected insect bites, skin ulcers, bed sores and wounds.

16. THANK YOU