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
Chemical data
Formula C17H17O6 
Mol. mass 352.766 g/mol
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

Griseofulvin (also known as Grisovin) is an antifungal drug. It is used both in animals and in humans, to treat ringworm infections of the skin and nails. It is derived from the mold Penicillium griseofulvum.

It is administered orally.

Contents

[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] 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.

[edit] Side effects

Known side effects of griseofulvin include:

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

[edit] External links

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