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|Systematic (IUPAC) name
|(2S,6'R)- 7-chloro- 2',4,6-trimethoxy- 6'-methyl- 3H,4'H-spiro [1-benzofuran- 2,1'-cyclohexene]- 3,4'-dione
||B3 (Australia), C (United States)
||POM (UK), ℞-only (U.S.)
||Highly variable (25 to 70%)
||Hepatic demethylation and glucuronidation
| (what is this?) (verify)
Griseofulvin (marketed under the proprietary name Grifulvin V by Orthoneutrogena Labs, according to FDA orange book) is an antifungal drug that is administered orally. It is used both in animals and in humans, to treat fungal infections of the skin (commonly known as ringworm) and nails. It is produced by culture of some strains of the mold Penicillium griseofulvum, from which it was isolated in 1939.
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.
Griseofulvin is used orally only for dermatophytosis. It is ineffective topically. Griseofulvin is reserved for cases with nail, hair or large body surface involvement.
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.
Known side effects of griseofulvin include:
- Can reduce the effectiveness of oral contraceptives as it is a cytochrome p450 enzyme inducer
- Considered unsafe for those with porphyria
- Impairment of performance of routine activities
- Impairment of liver enzymatic activity
- Inability to fall or stay asleep
- Loss of taste sensation
- Oral thrush (yeast infection of the mouth)
- Possibly a teratogen inducing mutations
- Sensitivity to alcohol, with a disulfiram/antabuse-like reaction
- Sensitivity to prolonged sun exposure
- Skin rashes (including Steven- Johnson syndrome)
- Tingling in the hands or feet
- Upper abdominal pain
Common brand names
- Grifulvin V
- Grison-250 (V.I.P Pharma)
- ^ http://books.google.com/books?id=XZ2QB7bu5LwC&pg=PA406
- ^ http://jama.ama-assn.org/content/172/6/532.full.pdf
- ^ Tripathi. Textbook of Pharmacology. Jaypee Brothers. pp. 761–762. ISBN 81-8448-085-7.
- ^