Antifungal medicines are used to treat fungal infections

1. ANTIFUNGAL DRUGS
S.SEETARAM SWAMY, M.Pharm.,
Asst. professor,
Dept. of Pharmaceutical Chemistry,
E-mail:seetaram.443@gmail.com

2. •Fungi are eukaryotic cells and therefore represent a more complex
and evolved organism.
• Thousands of fungal species, predominantly parasitic in nature.
•Less frequent than bacterial & Virus but common.
•Mycology - the study of fungi
Four main Characteristics of Fungi
fungi are eukaryotic (they have a nuclei &
mitochondria)
they are heterotrophs (they depend on
other organisms for food)
they are multicellular
they cannot move on their own

3. Fungi may be classified as yeast or moulds:
Yeast like pathogenic
Histoplasmosis
Coccidioidomycosis
Blastomycosis
Cryptococcosis
Candida
Mould group of pathogenic
 Aspergillosis
 Dermatophytes
 Mucormicosis
Therapy of fungal infections usually requires prolonged treatment. Fungal infections
are usually more difficult to treat than bacterial infections, because fungal organisms
grow slowly.

5. Systemic fungal infections: Affect deeper tissues
and organs.
Systemic candidiasis (RTI)
Meningitis, endocarditis
Rhinocerebral mucormycosis (Thrombosis)
Pulmonary aspergillosis
Blastomycosis (lesion of skin)
Histoplasmosis (cough , fever, multiple
pneumonic infiltrates)
Coccidioidomycosis
Pneumocystis carinii pneumonia

6. 6
TYPES OF FUNGAL INFECTIONS
CANDIDA
ASPERGILLUS
CRYPTOCOCCUS
HISTOPLASMA
PNEUMOCYSTIS
STACHYBOTRYS
MICROSPORUM
TRICHOPHYTON

7. Aspergillus fumigatus Infection Aspergillus flavus Infection
ASPERGILLUS
The most common pathogenic species are Aspergillus fumigatus &
Aspergillus flavus. Aspergillus flavus produces aflatoxin which is both
a toxin and a carcinogen and which can potentially contaminate foods
such as nuts.
Aspergillus fumigatus and Aspergillus clavatus can cause
allergic disease.
Aspergillosis is the group of diseases caused by Aspergillus. The
symptoms include fever, cough, chest pain or breathlessness.

8. CRYPTOCOCCUS
•Cryptococcus neoformans can cause a severe form of
meningitis and meningo-encephalitis in patients with HIV
infection and AIDS. The majority of Cryptococcus species live in
the soil and do not cause disease in humans.

9. HISTOPLASMA
Histoplasma capsulatum can
cause histoplasmosis in humans, dogs
and cats.
The fungus is most prevalent in the
Americas, India and southeastern
Asia. It is endemic in certain areas of
the United States. Infection is usually
due to inhaling contaminated air.
PNEUMOCYSTIS
Pneumocystis jirovecii [or] Pneumocystis carinii
can cause a form of pneumonia in people with
weakened immune systems, such as premature
children, the elderly, and AIDS patients.

10. STACHYBOTRYS
Stachybotrys chartarum or "black
mold" can cause respiratory damage
and severe headaches. It frequently
occurs in houses in regions that are
chronically damp.

11. MICROSPORUM
Microsporum canis is
a fungus that can cause tinea
capitis in humans, and
simple ringworm in pets.
The organism's major reservoir
in companion animals is within
domestic cats and dogs.

12. TRICHOPHYTON INFECTION

13. Inhibitor of cell wall
synthesis:
 Caspofungin
Drugs altering membrane
permeability
 Amphotericin-B,
 Nystatin,
 Hamycin
Inhibit nucleic acid
Synthesis
 5 Flucytosine
Disruption of mitotic
spindle
 Griseofulvin
Drugs altering membrane
synthesis
 Inhibition of ergosterol
Trimidazoles
 Fluconazle,
 Itraconazole,
 Voriconazole
Imidazoles
 Ketoconazole,
 Miconazole,
 Clotrimazole.
Inhibition of ergosterol+
lanosterol
 Terbinafine

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15. CHEMICAL STRUCTURES OF ANTIFUNGAL DRUGS

16. SITES OF ACTION OF COMMON ANTIFUNGAL DRUGS

17. 17
SOME ADVERSE REACTIONS OF ANTIFUNGAL DRUGS
Dr.K.Saminathan.M.Pharm, M.B.A, Ph.D

18. N NN
N
N
H3C
CH3
O
O
O
N
N
N
Cl Cl
O
Itraconazole
4-(4-(4-(4-(((2R,4S)-2-((1H-1,2,4-triazol-1-yl)methyl)-2-(3,5-dichlorophenyl)-1,3-dioxolan-4-
yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2-sec-butyl-2H-1,2,4-triazol-3(4H)-one
Chemistry:
Imidazole derivatives:
ketoconazole, miconazole, econazole, clotrimazole
Triazole derivatives: Itraconazole, fluconazole.
Mechanism of action
-Inhibition of sterol 14-alpha-demethylase, a cytochrome P450-
dependent enzyme.

blockade of the synthesis of ergosterol in fungal cell membranes
-The ultimate effect may be fungicidal or fungistatic depending on
the organism and on drug concentration.

19. F
F
C
O
CH2CH2Cl
2,4-difluorobenzyl
ethalene chloride
N
N
H
N
-HCl
(1,2,4-Triazole)
F
F
C
O
CH2CH2
formation
alkoxide
F
F
C
H2C
H2C
O
N
N
N
H
(1,2,4-Triazole)
F
F
C
OH
H2
C N
N
N
N C
H2
Fluconazole
N
N
N
N
N
N
N
N
SYNTHESIS OF FLUCONAZOLE