Griseofulvin

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Griseofulvin
Griseofulvin.svg
Griseofulvin 3D.png
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
Clinical data
Trade names Gris-peg
AHFS/Drugs.com monograph
MedlinePlus a682295
Pregnancy cat. B3 (Australia), C (United States)
Legal status POM (UK), ℞-only (U.S.)
Routes Oral
Pharmacokinetic data
Bioavailability Highly variable (25 to 70%)
Metabolism Hepatic demethylation and glucuronidation
Half-life 9-21 hours
Identifiers
CAS number 126-07-8 YesY
ATC code D01AA08 D01BA01
PubChem CID 441140
DrugBank DB00400
ChemSpider 389934 YesY
UNII 32HRV3E3D5 YesY
KEGG D00209 YesY
ChEBI CHEBI:27779 YesY
ChEMBL CHEMBL562 YesY
Chemical data
Formula C17H17ClO6 
Mol. mass 352.766 g/mol
 YesY (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.[1][2]

Mechanism[edit]

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.

Uses[edit]

Griseofulvin is used orally only for dermatophytosis. It is ineffective topically. Griseofulvin is reserved for cases with nail, hair or large body surface involvement.[3]

Potential for cancer treatment[edit]

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.[4]

Side effects[edit]

Known side effects of griseofulvin include:

  • Can reduce the effectiveness of oral contraceptives as it is a cytochrome p450 enzyme inducer
  • Confusion
  • Considered unsafe for those with porphyria
  • Diarrhea
  • Dizziness
  • Fatigue
  • Headache
  • Urticaria
  • Impairment of performance of routine activities
  • Impairment of liver enzymatic activity
  • 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/antabuse-like reaction
  • Sensitivity to prolonged sun exposure
  • Skin rashes (including Steven- Johnson syndrome)
  • Swelling
  • Tingling in the hands or feet
  • Upper abdominal pain

Common brand names[edit]

  • Grifulvin V
  • Gris-PEG
  • S-Fulvin
  • Crivicin
  • Grison-250 (V.I.P Pharma)
  • Grisovin-FP (GSK)
  • Gris OD 375 (DR.REDDY'S)

References[edit]

  1. ^ Michael Ash; Irene Ash (2004). Handbook of Preservatives. Synapse Info Resources. p. 406. ISBN 978-1-890595-66-1. 
  2. ^ Goldman, Leon (6 February 1960). "Current status of Griseofulvin". Journal of the American Medical Association 172 (6): 532. doi:10.1001/jama.1960.03020060022006. 
  3. ^ Tripathi. Textbook of Pharmacology. Jaypee Brothers. pp. 761–762. ISBN 81-8448-085-7. 
  4. ^ http://www.dkfz.de/en/presse/pressemitteilungen/2007/download/dkfz_pm_07_43_e.pdf

External links[edit]