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MEDICINAL ORGANIC CHEMISTRY > ANTI-FUNGALS > Flashcards

ANTI-FUNGALS Flashcards

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
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Amphotericin B has ____ carbons in its lactone ring.

A

38

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26
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Nystatin has ____ carbons in its lactone ring.

A

38

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27
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

This is the glycosidically linked deoxyaminohexose sugar in polyenes.

A

Mycosamine

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28
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Conjugated double bonds: Natamycin

A

Pentaene

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29
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Conjugated double bonds: Nystatin

A

Hexaene

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30
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Conjugated double bonds:
Amphotericin B

A

Heptaene

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31
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Polyenes have a series of ____ groups on the acid portion of the ring.

A

OH

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32
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Mechanism of action of Polyenes

A
  1. Esterification of ergosterol -> Pore - > Leak of cellular components
  2. False membrane component
33
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Isolated from Streptomyces nodosus

A

Amphotericin B

Fungizone

34
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Amphotericin B is isolated from ____.

A

Streptomyces nodosus

35
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Last option for systemic antifungal therapy due to nephrotoxocity

A

Amphotericin B

36
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Amphotericin B is the last option for antifungal therapy due to its ____.

A

Nephrotoxicity

37
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Amphotericin B is an aqueous colloidal dispersion stabilized by ____.

A

Sodium deoxycholate

38
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Amphotericin B is never admistered ____.

A

Intramuscularly

39
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Colloidal dispersion forms of Amphotericin B

(Cholesterol Sulfate)

A
  1. Amphocil
  2. Amphocyte
40
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Amphotericin B - 7:3 phospholipid mixture

41
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Liposomal form of Amphotericin B

42
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Nystatin is isolated by Hazen and Brown in 1951 from ____.

A

Streptomyces noursei

43
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Isolated from Streptomyces noursei

A

Nystatin

Mycostatin

44
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

The ring (aglycone) of nystatin is called ____.

A

Nystatinolide

45
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Isolated from Streptomyces natalensis

A

Natamycin

Natacyn

46
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Natamycin is isolated from ____.

A

Streptomyces natalensis

47
Q

ANTI-FUNGAL ANTIBIOTICS: POLYENES

Tx of conjunctivitis, blepharitis, and keratitis

A

Natamycin

Natacyn

48
Q

ANTI-FUNGAL ANTIBIOTICS: OTHERS

Isolated from Penicillium griseofulvum

A

Griseofulvin

Grisovin

49
Q

ANTI-FUNGAL ANTIBIOTICS: OTHERS

Griseofulvin is obtained from ____.

A

Penicillium griseofulvum

50
Q

ANTI-FUNGAL ANTIBIOTICS: OTHERS

Mechanism of action of Griseofulvin

A

Mitotic spindle poison

51
Q

ANTI-FUNGAL ANTIBIOTICS: OTHERS

Meal requirement for griseofulvin

A

High-fat meal

GRIS = GREASE = FAT (ALSO LIPOPHILIC)

52
Q

ALLYLAMINES

1% cream/gel for ringworm, athlete’s foot, and jock itch

A

Naftifine HCl

Naftin

53
Q

ALLYLAMINES

Same use as Naftifine but active against ochynomycosis

A

Terbinafine HCl

Lamisil

54
Q

ALLYLAMINES

Thioester of beta-naphtol that inhibits squalene epoxidase

A

Tolnaftate

Tinactin

55
Q

ALLYLAMINES

MOA of allylamines and tolnaftate

A

Squalene epoxidase inhibition

for Ergosterol synthesis

56
Q

AZOLES

Two types of azoles

A
  1. Imidazoles
  2. Triazoles
57
Q

AZOLES

Mechanism of action of azoles

A

Lanosterol 14α-demethylase inhibition

Produces Ignosterol = Toxic sterol

58
Q

AZOLES

New azole under post-marketing surveillance

A

Isavuconazole

59
Q

AZOLES

3 imidazole antifungals

A
  1. Miconazole
  2. Clotrimazole
  3. Ketoconazole
60
Q

AZOLES

Tx for systemic fungal infection and chronic mucocutaneous candidiasis

A

Miconazole Nitrate

Daktarin

61
Q

AZOLES

1st orally active broad spectrum (imidazole)

Cream + Shampoo only; Not available for oral administration anymore

A

Ketoconazole

Nizoral

62
Q

AZOLES

Useful for systemic infection but hepatotoxic

Also: Highly protein bound

A

Ketoconazole

Nizoral

63
Q

AZOLES

Ketoconazole may lead to ____ among male patients.

A

Gynecomastia

64
Q

AZOLES

The bioavailability of Ketoconazole is decreased when taken with ____.

A

Antacids (Basic)

65
Q

AZOLES

Ketoconazole has an antagonistic effect when taken with ____.

A

Amphotericin B

66
Q

AZOLES

Best substitute for ketoconazole

A

Itraconazole

Sporanox

67
Q

AZOLES

____ environment is required for optimum solubilization and oral absorption of itraconazole.

Basic or Acidic

68
Q

AZOLES

2 triazole moieties of itraconazole

A
  • Weakly basic 1,2,4-triazole
  • Non-basic 1,2,4-triazol-3-one
69
Q

AZOLES

Itraconazole is best taken in a/an ____ stomach.

70
Q

AZOLES

Only water soluble azole (bis-triazole) with broad spectrum activity

A

Fluconazole

Diflucan, Funzela

71
Q

AZOLES

Agent of choice for cryptococcal meningitis

A

Fluconazole

Diflucan, Funzela

72
Q

AZOLES

Drug of choice for fungal meningitis

A

Fluconazole

Diflucan, Funzela

73
Q

Large cyclic peptides linked to a long fatty acid

A

Echinocanadins

74
Q

ECHINOCANADINS & PNEUMOCANADINS

Mechanism of action of echinocanadins

A

(1,3)-b-d-glucan synthase inhibition

Cell wall component

75
Q

ECHINOCANADINS & PNEUMOCANADINS

3 Products of echinocanadins

A
  1. Caspofungin
  2. Micafungin
  3. Anidulafungin

Cell wall component

76
Q

AUREOBASIDINS

Aureobasidins are produced by ____.

A

Aureobasidium pullulan

77
Q

AUREOBASIDINS

Aureobasidins have a ____ structure.

A

Cyclic Depsipeptide

78
Q

AUREOBASIDINS

Mechanism of action of aureobasidins

A

Inositol phosphorylceramide (IPC) synthase inhibitor

Non-competitive; For fungal sphingolipid biosynthesis

MEDICINAL ORGANIC CHEMISTRY (17 decks)

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