Griseofulvin

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
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 Y
ATC code	D01AA08 D01BA01
PubChem	CID 441140
DrugBank	APRD01004
ChemSpider	389934 Y
UNII	32HRV3E3D5 Y
KEGG	D00209 Y
ChEBI	CHEBI:27779 Y
ChEMBL	CHEMBL562 Y
Chemical data
Formula	C17H17ClO6
Mol. mass	352.766 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3/t8-,17+/m1/s1 Y Key:DDUHZTYCFQRHIY-RBHXEPJQSA-N Y
N(what is this?)  (verify)

Griseofulvin (also known as Grisovin, a proprietary name of Glaxo Laboratories) 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 derived from the mold Penicillium griseofulvum.

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.

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.

Side effects

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 Hives 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

• Grifulvin V
• Gris-PEG
• S-Fulvin
• Crivicin
• Grison-250 (V.I.P Pharma)

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