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ANTIFUNGAL DRUGS
1
3
Mr.Ganesh D.Mote
Monera is a kingdom that contains 
unicellular organisms with a 
prokaryotic cell organization, (having 
no nuclear membrane), such as 
bacteria
eukaryotic one-celled 
living organisms 
distinct from 
multicellular plants 
and animals: protozoa, 
slime molds, and 
eukaryotic algae taxonomic kingdom 
comprising all living 
or extinct animals
Plants, also called green plants (Viridiplantae
 in Latin), are living multicellular 
organisms of thekingdom Plantae.
1. OVER VIEW OF FUNGAL
Lack chlorophyll, leaves, true stems, and 
roots, reproduce by spores, and live as 
saprotrophs or parasites
2
Mr.Ganesh D.Mote
3
THE FUNGI KINGDOM
Mycology - the study of fungi
fungi - singular
fungus - plural
1) fungi are eukaryotic
•they have a nuclei & mitochondria
2) they are heterotrophs
•they depend on other organisms for food
3) they are multicellular
4) they cannot move on their own
4 Main Characteristics of Fungi
1. OVER VIEW OF FUNGAL
Mr.Ganesh D.Mote
4
Major Types of 
Mycoses
superficial
cutaneous
subcutaneous
systemic
opportunistic
1. OVER VIEW OF FUNGAL INFECTION
Mr.Ganesh D.Mote
PATHOGENIC FUNGAI
1. CANDIDA
2. ASPERGILLUS
3. CRYPTOCOCCUS
4. HISTOPLASMA
5. PNEUMOCYSTIS
6. STACHYBOTRYS
7. MICROSPORUM
8. TRICHOPHYTON
5
2. TYPES OF FUNGAL INFECTIONS 
Mr.Ganesh D.Mote
1). CANDIDA
Candida species cause infections in
individuals with deficient immune
systems. Th1-type cell-mediated
immunity (CMI) is required for clearance
of a fungal infection.
6
2. TYPES OF FUNGAL INFECTIONS 
CANDIDA INFEC TIONS
7
2). ASPERGILLUS
•The most common pathogenic species are Aspergillus fumigatus and
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. 
•Some Aspergillus species cause disease on grain crops,especially
maize,and synthesize mycotoxins including aflatoxin.
•Aspergillosis is the group  of  diseases  caused  by  Aspergillus.  The
symptoms include fever,  cough,  chest  pain  or  breathlessness.
Usually, only patients with weakened immune systems or with other lung
conditions are susceptible.
2. TYPES OF FUNGAL INFECTIONS 
Mr.Ganesh D.Mote
8
2. TYPES OF FUNGAL INFECTIONS 
9
Aspergillus
fumigatus Infection
Aspergillus flavus
Infection
2. TYPES OF FUNGAL INFECTIONS 
Mr.Ganesh D.Mote
10
3. 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.
• Cryptococcus neoformans is the major human and animal pathogen.
Cryptococcus laurentii and Cryptococcus albidus have been known to
occasionally cause moderate-to-severe disease in human patients with
compromised immunity.
•Cryptococcus gattii is endemic to tropical parts of the continent of
Africa and Australia and can cause disease in non-
immunocompromised people.
2. TYPES OF FUNGAL INFECTIONS
Mr.Ganesh D.Mote
11 CRYPTOCOCCUS  INFECTION
2. TYPES OF FUNGAL INFECTIONS
Mr.Ganesh D.Mote
12
CRYPTOCOCCUS INFECTIONS
2. TYPES OF FUNGAL INFECTIONS
Mr.Ganesh D.Mote
4. HISTOPLASMA
Histoplasma capsulatum can cause
histoplasmosis in humans, dogs and
cats.
Infection is usually due to inhaling
contaminated air.
2. TYPES OF FUNGAL INFECTIONS
13
Mr.Ganesh D.Mote
14
2. TYPES OF FUNGAL INFECTIONS
HISTOPLASMA INFECTIONSMr.Ganesh D.Mote
15
5. 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.
2. TYPES OF FUNGAL INFECTIONS
Mr.Ganesh D.Mote
16
2. TYPES OF FUNGAL INFECTIONS
PNEUMOCYSTISMr.Ganesh D.Mote
6. STACHYBOTRYS
Stachybotrys chartarum or "black mold"
can cause respiratory damage and
severe headaches. It frequently occurs in
houses in regions that are chronically
damp.
2. TYPES OF FUNGAL INFECTIONS
17 Mr.Ganesh D.Mote
18
7. MICROSPORUM
Microsporum canis is
a fungus that can
cause tinea capitis in
humans, and
simple ringworm in pets.
2. TYPES OF FUNGAL INFECTIONS
Mr.Ganesh D.Mote
MICROSPORUM CANIS INFECTION
2. TYPES OF FUNGAL INFECTIONS
19
Mr.Ganesh D.Mote
20
The fungus genus Trichophyto
n rubrum is characterized by
the development of both
smooth-walled macro-
and microconidia.
Macroconidiaare mostly borne
laterally directly on the hyphae
or on short pedicels, and are
thin- or thick-
walled, clavate to fusiform, and
range from 4 to 8 by 8 to
50 μm in size
8. TRICHOPHYTON
2. TYPES OF FUNGAL INFECTIONS
Mr.Ganesh D.Mote
2. TYPES OF FUNGAL INFECTIONS
TRICHOPHYTON INFECTION
21
22
5.CLASSIFICATION
Mr.Ganesh D.Mote
Chemical classification with structure
Mr.Ganesh D.Mote23
1.Antifunal antibiotics
a.Polyene antibiotics
b.Other antifungal antibiotics
griseofulvin
2.Allyl amines
Mr.Ganesh D.Mote24
terbinafine
Tolnaftate
25
3. CHEMICAL STRUCTURES AZOLE ANTIFUNGAL DRUGS
Mr.Ganesh D.Mote
5.CLASSIFICATION OF ANTIFUNGAL
Con…
26
Mr.Ganesh D.Mote
27
6.SITES OF ACTION OF COMMON ANTIFUNGAL DRUGS
Con…
POLYENES
IMIDAZOLES
TRIAZOLE
ALLYLAMINES
OTHER
GLUCAN
SYNTHASE
INHIBITORS
BIND TO ERGOSTEROL
AND FORM PORES
(CHANNELS)
Mr.Ganesh D.Mote
6.SITES OF ACTION OF COMMON ANTIFUNGAL DRUGS
ALLYLAMINES
IMIDAZOLES
TRIAZOLE
POLYENES
28
GLUCAN
SYNTHASE
INHIBITORS
29
6.SITES OF ACTION OF COMMON ANTIFUNGAL DRUGS
Mr.Ganesh D.Mote
FLUCYTOSINE
IMIDAZOLES
TRIAZOLES
POLYENES
CANDINS
GRISEOFULVIN
OTHERS
30
7. ANTI FUNGAL DRUGS MECHANISAM
Mr.Ganesh D.Mote
31
8.MECHANISM OF AMPHOTERICIN B
Several amphotericin B molecules
bind to ergosterol in the plasma
membranes of sensitive fungal cells.
There, they form pores (channels)
that require hydrophobic
interactions between the lipophilic
segment of the polyene antibiotic
and the sterol.
The pores disrupt membrane
function, allowing electrolytes
(particularly potassium) and small
molecules to leak from the cell,
resulting in cell death.
Mr.Ganesh D.Mote
Flucytosine enters fungal cells via a
cytosine-specific permease an enzyme not
found in mammalian cells.
Flucytosine is then converted by a series of
steps to 5-fluorodeoxyuridine 5'-
monophosphate.
This false nucleotide inhibits thymidylate
synthase, thus depriving the organism
of thymidylic acid an essential DNA
component.
Note: [Amphotericin B increases cell
permeability, allowing more 5-FC to
penetrate the cell. Thus, 5-FC and
amphotericin B are synergistic.]
9.MECHANISM OF FLUCYTOSINE
32
Mr.Ganesh D.Mote
10.MECHANISM OF KETOCONAZOLE
Azoles are predominantly fungistatic.
They inhibit C-14 α-demethylase (a
cytochrome P450 enzyme), thus
blocking the demethylation of
lanosterol to ergosterol the principal
sterol of fungal membranes.
This inhibition disrupts membrane
structure and function and, thereby,
inhibits fungal cell growth.
[Note:In addition to blocking fungal
ergosterol synthesis, the drug also
inhibits human gonadal and adrenal
steroid synthesis, leading to
decreased testosterone and cortisol
production. In addition, ketoconazole
inhibits cytochrome P450]
33 Dr.K.Saminathan.M.Pharm, M.B.A, Ph.D
Mr.Ganesh D.Mote
Terbinafine inhibits fungal
squalene epoxidase, thereby
decreasing the synthesis of
ergosterol .
This plus the accumulation of
toxic amounts of squalene
result in the death of the
fungal cell.
11.MECHANISM OF TERBINAFINE
34
Mr.Ganesh D.Mote
35
It is only fungistatic, and it causes a
number of significant drug
interactions.
Griseofulvin accumulates in newly
synthesized, keratin-containing
tissue, where it causes disruption
of the mitotic spindle and
inhibition of fungal mitosis .
12. MECHANISM OF GRISEOFULVIN
Mr.Ganesh D.Mote
36
13. SOME ADVERSE REACTIONS OF ANTIFUNGAL DRUGS
Mr.Ganesh D.Mote
37
14. SOME ADVERSE REACTIONS OF AMPHOTERICIN B.
Mr.Ganesh D.Mote
38
POLYENES
Mr.Ganesh D.Mote
39
IMIDAZOLES
Mr.Ganesh D.Mote
40
TRIAZOLE ALLYLAMINES
Mr.Ganesh D.Mote
41
Β-3-GLUCAN SYNTHASE
INHIBITORS
Mr.Ganesh D.Mote
42
Griseofulvin Flucytosine
Dr.K.Saminathan.M.Pharm, M.B.A, Ph.D
Mr.Ganesh D.Mote
SAR OF AZOLE ANTIFUNGAL AGENTS
1. The basic structural requirement for members of the azole class is a weakly basic
imidazole or 1,2,4-triazole ring (pKaof 6.5–6.8) bonded by a nitrogen–carbon
linkage to the rest of the structure.
2. At the molecular level, the amidine nitrogen atom (N-3 in the imidazoles, N-4 in
the triazoles) is believed to bind to the heme iron of enzyme-bound cytochrome
P450 to inhibit activation of molecular oxygen and prevent oxidation of steroidal
substrates by the enzyme.
3. The most potent antifungal azoles possess two or three aromatic rings, at least
one of which is halogen substituted (e.g., 2,4-dichlorophenyl, 4-chlorophenyl,
2,4-difluorophenyl), and other nonpolar functional groups.
4. Only 2, and/or 2,4 substitution yields effective azole compounds.
5. The halogen atom that yields the most potent compounds is fluorine, although
functional groups such as sulfonic acids have been shown to do the same.
6. Substitution at other positions of the ring yields inactive compounds.
7. Presumably, the large nonpolar portion of these molecules mimics the nonpolar
steroidal part of the substrate for lanosterol 14-demethylase, lanosterol, in shape
and size.
8. The nonpolar functionality confers high lipophilicity to the antifungal azoles.
9. The free bases are typically insoluble in water but are soluble in most organic
solvents, such as ethanol.
10.Fluconazole, which possesses two polar triazole moieties, is an exception, in that
it is sufficiently water soluble to be injected intravenously as a solution of the
free base.
43
Clotrimazole
Fluconazole
Mechanism action of squaline epoxidase(allyl
amines and lanoseterol 14 ά demethylase
inhibitor(Azoles derivatives)
Mr.Ganesh D.Mote44
Synthesis of Ketoconazole
45
Cl
Cl
C
O
CH2Br
2-bromo-1-(2,4-dichlorophenyl)ethanone
CH2OH
HC
H2C OH
OH
propane-1,2,3-triol
Cl
Cl
C CH2Br
O
O
CH2OH
(2-(bromomethyl)-2-(2,4-
dichlorophenyl)-1,3-dioxolan-4-
yl)methanol
C
O
Cl
Cl
Cl
C
O
O
CH2COO
C
H2
N
N
Cl
Cl
C
O
O
C
H2
N
N
H2
C O SO2CH3
CH3SO3Cl
Mr.Ganesh D.Mote46
1-(3,4-dichlorophenyl)-2-(1H-
imidazol-1-yl)ethanone
Cl C
O
H2
C N
Cl
N
Cl C
H
OH
H2
C N
Cl
N
1-(3,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol
NaBH4
Cl
Cl
H2
CBr
1-(bromomethyl)-2,4-dichlorobenzene
Synthesis of Miconazole
Mr.Ganesh D.Mote47
2-Naphthol thiophosgene
N-methyl 3-toludine
O
Cl
S
O-naphthalen-2-yl carbonochloridothioate
O
N
S
CH3
CH3
O-naphthalen-2-yl methyl(m-tolyl)carbamothioate
Synthesis of Tolnaftate
Thank you
Mr.Ganesh D.Mote48

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