Griseofulvin

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Griseofulvin

Systematic (IUPAC) name
(2S,6'R)- 7-chloro- 2',4,6-trimethoxy- 6'-methyl- 3H,4'H-spiro [1-benzofuran-2,1'-cyclohex[2]ene]- 3,4'-dione
Identifiers
CAS number	126-07-8
ATC code	D01AA08 D01BA01
PubChem	441140
DrugBank	APRD01004
ChemSpider	389934
Chemical data
Formula	C17H17ClO6
Mol. mass	352.766 g/mol
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	Highly variable (25 to 70%)
Metabolism	Hepatic demethylation and glucuronidation
Half life	9-21 hours
Excretion	?
Therapeutic considerations
Pregnancy cat.	B3 (Au), C (U.S.)
Legal status	POM (UK), ℞-only (U.S.)
Routes	Oral
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Griseofulvin (also known as Grisovin, a proprietary name of Glaxo Laboratories) is an antifungal drug. It is used both in animals and in humans, to treat fungal infections of the skin (commonly known as ringworm) and nails. It is derived from the mold Penicillium griseofulvum.

It is administered orally.

Contents 1 Mechanism 2 Treatment of fungal infections 3 Potential for cancer treatment 4 Side effects 5 Common brand names 6 See also 7 References 8 External links

[edit] Mechanism

The drug binds to tubulin, interfering with microtubule function, thus inhibiting mitosis.

It binds to keratin in keratin precursor cells and makes them resistant to fungal infections. It is only when hair or skin is replaced by the keratin-griseofulvin complex that the drug reaches its site of action. Griseofulvin will then enter the dermatophyte through energy dependent transport processes and bind to fungal microtubules. This alters the processing for mitosis and also underlying information for deposition of fungal cell walls.

[edit] Treatment of fungal infections

Griseofulvin is used to treat the following fungal infections:
Tinea capitis (ringworm of the scalp)
Tinea corporis (ringworm of the body)
Tinea pedis (athlete's foot)
Tinea unguium (onychomycosis)
Tinea cruris (ringworm of the thigh)
Tinea barbae (barber's itch)

[edit] Potential for cancer treatment

When cancer cells divide (undergo mitosis), they use an unusual mechanism to ensure the correct genetic material is present within each of the resulting tumor cells. Laboratory experiments at the German Cancer Research Center (Deutsches Krebsforschungszentrum, DKFZ) show that griseofulvin causes cancer cells to fail to divide the chromosomes correctly, which eventually leads to tumor cell death. Griseofulvin does not interfere with cell division in healthy cells. The observed effect is not strong, but is significant. Griseofulvin may be combined with other treatments to improve its effectiveness and may lead to the development of more effective future drug treatments with very low toxic side effects^[1].

[edit] Side effects

Known side effects of griseofulvin include:

• Can cause conjoined twins
• Can reduce the effectiveness of oral contraceptives as it a cytochrome p450 enzyme inducer
• Confusion
• Considered unsafe for those with Porphyria
• Diarrhea
• Dizziness
• Fatigue
• Headache
• Hives
• Impairment of performance of routine activities
• Inability to fall or stay asleep
• Itching
• Loss of taste sensation
• Nausea
• Oral thrush (yeast infection of the mouth)
• Possibly a teratogen inducing mutations
• Sensitivity to alcohol, with a disulfiram-like reaction
• Sensitivity to prolonged sun exposure
• Skin rashes
• Swelling
• Tingling in the hands or feet
• Upper abdominal pain
• Vomiting

[edit] Common brand names

• Grifulvin V
• Gris-PEG
• S-Fulvin

Crivicin

[edit] See also

Medicinal mushrooms

[edit] References

1. ^ [1]

[edit] External links

• Griseofulvin (Medline Plus)
• Antifungal drug causes preferential apoptosis of cancer cells (Oncolink Cancer News)
• Anti-fungal Drug May Help Treat Cancer, Say Scientists at UC Santa Barbara
• dermnetnz Mentions alcohol, contraceptive interactions

v • d • e Antifungals (D01 and J02) Wall/ membrane Ergosterol inhibitors Azoles (lanosterol 14 alpha-demethylase inhibitors) Imidazoles topical: Bifonazole, Clomidazole, Clotrimazole#, Croconazole, Econazole, Fenticonazole, Ketoconazole, Isoconazole, Miconazole#, Neticonazole, Oxiconazole, Sertaconazole, Sulconazole, Tioconazole Triazoles topical: (Fluconazole#, Fosfluconazole) systemic: (Fluconazole, Itraconazole, Posaconazole, Voriconazole) Benzimidazoles topical: Thiabendazole Polyene antimycotics (ergosterol binding) topical: (Natamycin, Nystatin#) systemic: (Amphotericin B#) Allylamines (squalene monooxygenase inhibitors) topical: (Amorolfine, Butenafine, Naftifine, Terbinafine) systemic: (Terbinafine) β-glucan synthase inhibitors echinocandins (Anidulafungin, Caspofungin, Micafungin) Intracellular Pyrimidine analogues/ Thymidylate synthase inhibitors Flucytosine# Mitotic inhibitors Griseofulvin# Others Bromochlorosalicylanilide · Methylrosaniline · Tribromometacresol · Undecylenic acid · Polynoxylin · Chlorophetanol · Chlorphenesin · Ticlatone · Sulbentine · Ethyl hydroxybenzoate · Haloprogin · Salicylic acid · Selenium sulfide# · Ciclopirox · Amorolfine · Dimazole · Tolnaftate · Tolciclate · Sodium thiosulfate# · Whitfield's ointment# · Potassium iodide# Tea tree oil • citronella oil • lemon grass • orange oil • patchouli • lemon myrtle PCP: Pentamidine • Dapsone • Atovaquone #WHO-EM. ‡Withdrawn from market. CLINICAL TRIALS: †Phase III. §Never to phase III see also diseases

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