ANTIFUNGAL Flashcards by M.A.Lance Evangelista

used to treat fungal infections such as:
athlete’s foot
ringworm
candidiasis (thrush)
serious systemic

Antifungal drug

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can occur if the patient is on corticosteroid therapy
person who has asthma na nag i-inhaler na may steroid and hindi nagmumog

Candidiasis

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aka Fungal infection
is a condition in which fungi pass the resistance barriers of the human or animal body and establish infections

Mycosis

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Superficial

Org type:

Disease:

Malassezia fur fur

Pityriasis versicolor

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Cutaneous

Org type:

Disease:

Trichophyton
Epidermophyton
Microsporum sp.
Candida albicans

Dermatophytosis
Candidiasis of skin and oral mucous membrane

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Subcutaneous

Org type:

Disease:

Sporothrix schennkii

Sporotrichosis

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Deep

Org type:

Disease:

Blastomyces dermatitidis
Coccidioides immitis
Histoplasma capsulatum
Para coccidioides brasilliensis

Blastomycosis
Coccidioidomycosis
Histoplasmosis
Para coccidioidomycosis

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Deep opportunistic

Org type:

Disease:

Aspergillus sp.
Candida sp.
Cryptococcus neoformans

Aspergillosis
Candidiasis
Cryptococcosis
Zygomycosis

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DOC for Dandruff

Ketoconazole (Nizoral)

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From gardening

Sporotrichosis

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Antifungal Agents

Fatty acids and metal salts
Alkylated or halogenated phenols
Polyenes
Azoles
Allylamines and related compounds
Antibiotics

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Topical agents for dermatophytoses: Fatty acids

PROPIONIC ACID- 3
ZINC PROPIONATE
SODIUM CAPRYLATE
ZINC CAPRYLATE
UNDECYLENIC ACID- 11
TRIACETIN
SALICYLIC ACID AND RESORCINOL
BENZOIC ACID

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SAR

higher molecular weight members have the advantage of having lower volatility
structure similar to sebum
a natural antifungal

Fatty acid

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Sodium & calcium propionates
PRESERVATIVE
for dermatomycosis

Propionic acid

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found in coconut & palm oil
prepared from caprylic acid
Has 8 carbons

Sodium caprylate

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used as topical fungicidal,
astringency of zinc decreases inflammation & wetness

Zinc caprylate

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Fungicide on adhesive tape

Zinc proprionate

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10 UNDECENOIC ACID
Brand name- Decenex, Cruex
- destructive distillation of castor oil

Undecylenic acid

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primarily fungistatic for diaper rash

Undecylenic acid/ Na Undecylenate

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Triacetin aka?

Glyceryl triacetate

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fungicidal properties are due to acetic acid formation, action is self-limiting because esterases are inactivated below a ph of 4.

Triacetin

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antiseptic and keratolytic
commonly combined with benzoic acid to form the Whitfield’s ointment

Salicylic acid

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Salicylic acid

This ointment contains ______, 6% and salicylic acid 6%. in a ______ base.

benzoic acid; petrolatum

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Phenols and their derivatives:

Haloprogin
Ciclopiroxolamine
Clioquinol
Nucleoside antifungal/Flucytosine

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2 mechanism for Flucytosine

Inhibits protein and dna synthesis

orally active antifungal, very narrow spectrum of activity, prone to resistance For serious systemic infections caused by Candida and Cryptococcus sp.

5-Flucytosine

5hFluorocytosine + amphotericin is for?

Cryptococcal meningitis

5-Fluorocytosine + Itraconazole is for?

Chromoblastomycosis

Polyenes:

Amphotericin B Nystatin Natamycin Griseofulvin

SAR Agents that contain in their structure at least 2, and lactone ring

Polyenes

Polyenes 26 membered ring: 38 membered ring:

26- membered ring natamycin(pimaricin) 38-membered ring amphotericin B and nystatin

Based on no. of double bonds broad spectrum antifungal agents with potent activity against yeasts, molds, dermatophytes Systemic activity is limited by: Toxicities, low water solubility, poor chemical stability

Polyenes

act as false membrane component and bind closely with ergosterol, causing membrane disruption. cessation of membrane enzyme activity, and loss of cellular constituents, especially potassium ions Fungi-ergosterol

Polyenes

Pore-Lysis-Kill Fungi

Polyene

BN: Fungizone from Streptomyces nodosus most effective agent in the treatment of systemic fungal infection especially in immunocompromised patients

Amphotericin B

The drug must be administered intravenously and is associated with numerous side effects, ranging from 1. phlebitis at the infusion site and 2. chills 3. NEPHROTOXIC 4. hemolytic activity

Amphotericin B

ability to leach cholesterol from erythrocyte cell membranes

Amphotericin B

binds to ergosterol and alters the permeability of the cell by forming ______-associated pores in the cell membrane.

amphotericin B

Has heptaene

Amphotericin B

BN: Mycostatin 38-membered lactone ring Hexaene

Nystatin

Nystatin aglycone

Nystatinolide

structure similar to amphotericin B active primarily against candida species drug is not readily absorbed For cutaneous and mucocutaneous - ointment, cream, powder Vaginal tablets = vaginal candidiasis

Nystatin

prevents monilial overgrowth caused by the destruction of bacterial microflora of the intestine during tetracycline therapy.

Nystatin+ Tetracycline

1st drug to candida

Nystatin

the smallest macrocycle pentaene From Streptomyces notalensis Amphoteric used topically to treat superficial mycotic infections of the eye.

Natamycin

systemic treatment of tinea infections, refractory ringworm infections of body, nails, hair and feet Its only use is in the systemic treatment of dermatophytosis oral absorption provides systemic effect H.C.

Griseofulvin

administer with a fatty meal* MOA: inhibits fungal cell activity by interfering with mitotic spindle structure

Griseofulvin

ALLYLAMINES & RELATED COMPOUNDS

NAFTIFINE HYDROCHLORIDE, USP TERBINAFINE TOLNAFTATE

SAR presence of naphthalene ring N atom allyl structure

ALLYLAMINES & RELATED COMPOUNDS

inhibits ergosterol synthesis

ALLYLAMINES & RELATED COMPOUNDS

inhibition of squalene epoxide

Allylamine and related compounds

available as 1% topical cream or gel, useful in the treatment of tinea infections

NAFTIFINE HYDROCHLORIDE, USP

available as 1% cream, useful in the treatment of t. pedis, t. corporis, t. cruris

Terbinafine

available as 1% aerosol, 1% powder, 1% cream, 1% solution -cidal in action Thioester of beta naphthol

Tolnaftate

Inhibitor of squalene epoxidase Added to artificial fingernails to prevent ringworm

Tolnaftate

has no Allyl has Amine has Naphthalene NOT TRUE allylamine but can still inhibit squalene epoxidase

Tolnaftate

AZOLE ANTIFUNGALS:

Imidazole - Old Gen Clotrimazole, Miconazole and ketoconazole 1,2,4-triazole- New Gen Itraconazole, Voriconazole and Fluconazole

lower incidence of endocrine effects and nephrotoxic

1,2,4-triazole- New Gen

micromolar (damage of the cell membrane consequent loss of essential cellular constituents)

Fungicidal

nanomolar (inhibition of membrane bound enzymes by low concentration of the azoles

Fungistatic

cidal effect is due to cell membrane damage -static effect is due to inhibition of membrane bound enzymes

Azole antifungals

used in the synthesis of ergosterol

Lanosterol

Amidine N binds heme iron in CP 450

Azole antifungals

at least 2 or 3 aromatic rings, one as halogen substituted

Azole antifungal

Nizoral- cream, shampoo, tablet Oral; systemic mycoses Cream - 2% Enzyme inhibitor A/E: hepatotoxic

Ketoconazole

supplied as topical agent, oral preparation Lotion, cream, tablet GI disturbances when given orally Highly protein bound o Not for systemic infections

Clotrimazole

supplied as 1% cream used for candidiasis

Econazole nitrate

2% cream for vaginal

Butoconazole nitrate (Femstat)

as 1% cream for local tinea infections (Dosage form: cream, ointment)

Sulconazole nitrate

more effective against Torulopsis glabarata, supplied as 6.5% ointment

Tioconazole

presence of a triazole Exclusively for the control of vulvovaginal fungal infection caused by C. albicans

Terconazole

Effective and better tolerated than ketoconazole Oral, alternative to ketoconazole

Itraconazole

This drug should not be given with Antacid & H2 blocker (these 2 will increase pH- basic)

Itraconazole

the only water soluble azo antifungal

Fluconazole

with excellent oral bioavailability more advantageous than itraconazole and ketoconazole

Fluconazole

the treatment of choice for Cryptococcal meningitides, plasma binding is less than 10%

Fluconazole

Water soluble and good cerebrospinal fluid penetration Experiences no hepatic metabolism Not affected by the alteration of GI acidity and the presence of food

Fluconazole

natural products Act as noncompetitive inhibitors of (1,3)-beta-d-glucan synthase

ECHINOCANDINS AND PNEUMOCANDINS

an enzyme complex that forms stabilizing glucan polymers in the fungal cell wall.

ECHINOCANDINS AND PNEUMOCANDINS

cyclic depsipeptide produced by fermentation in cultures of

Aureobasidin A Aureobasidin pullulan

acts as a tight-binding noncompetitive inhibitor of the enzyme inositol phosphorylceramide synthase

Aureobasidin A

enzyme for fungal sphingolipid biosynthesis

Aureobasidin A

pradimycins and benanomycins

Aureobasidin A

Naphthacenequinones (has ketone) that bind mannan in the presence of Ca2 to disrupt the cell membrane in pathogenic fungi.

Aureobasidin A

targets Ergosterol

Polyene

inhibit Ergosterol synthesis

Azo antifungal & allylamine

didikit sa Ergosterol and gagawa ng butas

Amphotericin B

inhibits Beta glucan, mawawala and puputok ang cell wall

Echinocandins

inhibit DNA and Protein synthesis

Flucytosine