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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
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	DB00400
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 O=C2c3c(O[C@@]21C(/OC)=C\C(=O)C[C@H]1C)c(Cl)c(OC)cc3OC
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
Y (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

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

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

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

Known side effects of griseofulvin include:

  Common brand names

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

  References

1. ^ http://books.google.com/books?id=XZ2QB7bu5LwC&pg=PA406
2. ^ http://jama.ama-assn.org/content/172/6/532.full.pdf
3. ^ Tripathi. Textbook of Pharmacology. Jaypee Brothers. pp. 761-762. ISBN 81-8448-085-7. http://jaypeebrothers.com. 
4. ^ [1]

  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