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MEDICINAL ORGANIC CHEMISTRY > ANTI-FUNGALS > Flashcards

ANTI-FUNGALS Flashcards

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1
Q

Study of fungi

A

Mycology

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2
Q

TOPICALS: FATTY ACIDS

Natural antifungal agent that is part
of the innate immune system

A

Sebum

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3
Q

TOPICALS: FATTY ACIDS

0.1% fungicidal, present in sweat

A

Propionic Acid

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4
Q

TOPICALS: FATTY ACIDS

Fungicide on adhesive tapes

A

Zinc Proprionate

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5
Q

TOPICALS: FATTY ACIDS

Cream-colored granules for superficial dermatomycoses

A

Sodium caprylate

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6
Q

TOPICALS: FATTY ACIDS

Fine white powder fungicide that is unstable in moisture

A

Zinc caprylate

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7
Q

TOPICALS: FATTY ACIDS

From the destructive distillation of castor oil (tangan-tangan; ricinoleic acid)

A

Undecylenic Acid

(10-undecenoic acid, Decenex, Cruex)

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8
Q

TOPICALS: FATTY ACIDS

Glyceryl Triacetate

Enzactin, Fungacetin

A

Triacetin

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9
Q

TOPICALS: FATTY ACIDS

Only antifungal that cannot penetrate the skin

A

Benzoic Acid

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10
Q

TOPICALS: FATTY ACIDS

Properties of salicylic acid and resorcinol

A
  • Salicylic Acid: antifungal, keratolytic
  • Resorcinol: antiseptic, keratolytic
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11
Q

TOPICALS: FATTY ACIDS

AP-AP Solution

A

Salicylic Acid + Resorcinol + Benzoic Acid

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12
Q

TOPICALS: FATTY ACIDS

Whitfield’s Ointment

A

Salicylic Acid + Benzoic Acid
(+ Base: White Petrolatum)

1:1

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13
Q

TOPICALS

Interfere with cell membrane integrity and function in susceptible fungi

A

Phenol and its derivatives

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14
Q

TOPICALS: PHENOL & DERIVATIVES

For superficial tinea infection

A

Haloprogin

Halotex

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15
Q

TOPICALS: PHENOL & DERIVATIVES

Substitute for iodoform

A

Clioquinol

Vioform

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16
Q

TOPICALS: PHENOL & DERIVATIVES

For jock itch, athlete’s foot, and vaginitis (3%)

A

Clioquinol

Vioform

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17
Q

TOPICALS: PHENOL & DERIVATIVES

Second line agent for onychomycosis (ringworm of the nails)

A

Ciclopirox olamine

Loprox

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18
Q

TOPICALS: PHENOL & DERIVATIVES

Agent of choice for:
* Cutaneous candidiasis
* Tinea corporis
* Tinea cruris
* Tinea pedis
* Tinea versicolor

A

Ciclopirox olamine

Loprox

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19
Q

TOPICALS: NUCLEOSIDE

For systemic Candida and
Cryptococcus spp. infections

Antimetabolite

A

Flucytosine

5-FC, Ancobon

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20
Q

TOPICALS: NUCLEOSIDE

Flucytosine is a prodrug that will be converted to ____.

A

5-Fluorouracil

5-FU

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21
Q

TOPICALS: NUCLEOSIDE

Mechanism of action of flucytosine

A

Inhibition of DNA and protein synthesis

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22
Q

ANTI-FUNGAL ANTIBIOTICS

Polyenes are isolated from soil bacterium ____.

A

Streptomyces

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23
Q

ANTI-FUNGAL ANTIBIOTICS

These are isolated from Streptomyces

A

Polyenes

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24
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Natamycin has ____ carbons in its lactone ring.

A

26

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25
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Amphotericin B has ____ carbons in its lactone ring.
38
26
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Nystatin has ____ carbons in its lactone ring.
38
27
# ANTI-FUNGAL ANTIBIOTICS: POLYENES This is the glycosidically linked deoxyaminohexose sugar in polyenes.
Mycosamine
28
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Conjugated double bonds: Natamycin
Pentaene
29
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Conjugated double bonds: Nystatin
Hexaene
30
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Conjugated double bonds: Amphotericin B
Heptaene
31
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Polyenes have a series of ____ groups on the acid portion of the ring.
OH
32
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Mechanism of action of Polyenes
1. Esterification of ergosterol -> Pore - > Leak of cellular components 2. False membrane component
33
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Isolated from Streptomyces nodosus
Amphotericin B | Fungizone
34
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Amphotericin B is isolated from ____.
Streptomyces nodosus
35
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Last option for systemic antifungal therapy due to nephrotoxocity
Amphotericin B
36
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Amphotericin B is the last option for antifungal therapy due to its ____.
Nephrotoxicity
37
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Amphotericin B is an aqueous colloidal dispersion stabilized by ____.
Sodium deoxycholate
38
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Amphotericin B is never admistered ____.
Intramuscularly
39
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Colloidal dispersion forms of Amphotericin B | (Cholesterol Sulfate)
1. Amphocil 2. Amphocyte
40
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Amphotericin B - 7:3 phospholipid mixture
Abelcet
41
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Liposomal form of Amphotericin B
AmBisome
42
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Nystatin is isolated by Hazen and Brown in 1951 from ____.
Streptomyces noursei
43
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Isolated from Streptomyces noursei
Nystatin | Mycostatin
44
# ANTI-FUNGAL ANTIBIOTICS: POLYENES The ring (aglycone) of nystatin is called ____.
Nystatinolide
45
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Isolated from Streptomyces natalensis
Natamycin | Natacyn
46
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Natamycin is isolated from ____.
Streptomyces natalensis
47
# ANTI-FUNGAL ANTIBIOTICS: POLYENES Tx of conjunctivitis, blepharitis, and keratitis
Natamycin | Natacyn
48
# ANTI-FUNGAL ANTIBIOTICS: OTHERS Isolated from Penicillium griseofulvum
Griseofulvin | Grisovin
49
# ANTI-FUNGAL ANTIBIOTICS: OTHERS Griseofulvin is obtained from ____.
Penicillium griseofulvum
50
# ANTI-FUNGAL ANTIBIOTICS: OTHERS Mechanism of action of Griseofulvin
Mitotic spindle poison
51
# ANTI-FUNGAL ANTIBIOTICS: OTHERS Meal requirement for griseofulvin
High-fat meal | GRIS = GREASE = FAT (ALSO LIPOPHILIC)
52
# ALLYLAMINES 1% cream/gel for ringworm, athlete's foot, and jock itch
Naftifine HCl | Naftin
53
# ALLYLAMINES Same use as Naftifine but active against ochynomycosis
Terbinafine HCl | Lamisil
54
# ALLYLAMINES Thioester of beta-naphtol that inhibits squalene epoxidase
Tolnaftate | Tinactin
55
# ALLYLAMINES MOA of allylamines and tolnaftate
Squalene epoxidase inhibition | for Ergosterol synthesis
56
# AZOLES Two types of azoles
1. Imidazoles 2. Triazoles
57
# AZOLES Mechanism of action of azoles
Lanosterol 14α-demethylase inhibition | Produces Ignosterol = Toxic sterol
58
# AZOLES New azole under post-marketing surveillance
Isavuconazole
59
# AZOLES 3 imidazole antifungals
1. Miconazole 2. Clotrimazole 3. Ketoconazole
60
# AZOLES Tx for systemic fungal infection and chronic mucocutaneous candidiasis
Miconazole Nitrate | Daktarin
61
# AZOLES 1st orally active broad spectrum (imidazole) | Cream + Shampoo only; Not available for oral administration anymore
Ketoconazole | Nizoral
62
# AZOLES Useful for systemic infection but hepatotoxic | Also: Highly protein bound
Ketoconazole | Nizoral
63
# AZOLES Ketoconazole may lead to ____ among male patients.
Gynecomastia
64
# AZOLES The bioavailability of Ketoconazole is decreased when taken with ____.
Antacids (Basic)
65
# AZOLES Ketoconazole has an antagonistic effect when taken with ____.
Amphotericin B
66
# AZOLES Best substitute for ketoconazole
Itraconazole | Sporanox
67
# AZOLES ____ environment is required for optimum solubilization and oral absorption of itraconazole. | Basic or Acidic
Acidic
68
# AZOLES 2 triazole moieties of itraconazole
* Weakly basic 1,2,4-triazole * Non-basic 1,2,4-triazol-3-one
69
# AZOLES Itraconazole is best taken in a/an ____ stomach.
empty
70
# AZOLES Only water soluble azole (bis-triazole) with broad spectrum activity
Fluconazole | Diflucan, Funzela
71
# AZOLES Agent of choice for cryptococcal meningitis
Fluconazole | Diflucan, Funzela
72
# AZOLES Drug of choice for fungal meningitis
Fluconazole | Diflucan, Funzela
73
Large cyclic peptides linked to a long fatty acid
Echinocanadins
74
# ECHINOCANADINS & PNEUMOCANADINS Mechanism of action of echinocanadins
(1,3)-b-d-glucan synthase inhibition | Cell wall component
75
# ECHINOCANADINS & PNEUMOCANADINS 3 Products of echinocanadins
1. Caspofungin 2. Micafungin 3. Anidulafungin | Cell wall component
76
# AUREOBASIDINS Aureobasidins are produced by ____.
Aureobasidium pullulan
77
# AUREOBASIDINS Aureobasidins have a ____ structure.
Cyclic Depsipeptide
78
# AUREOBASIDINS Mechanism of action of aureobasidins
Inositol phosphorylceramide (IPC) synthase inhibitor | Non-competitive; For fungal sphingolipid biosynthesis

MEDICINAL ORGANIC CHEMISTRY (17 decks)

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