|This article needs additional citations for verification. (July 2011)|
|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|
|Bioavailability||Highly variable (25 to 70%)|
|Metabolism||Hepatic demethylation and glucuronidation|
|ATC code||D01 D01|
|Molecular mass||352.766 g/mol|
|(what is this?)|
Griseofulvin (marketed under the proprietary name Grifulvin V by Orthoneutrogena Labs, according to FDA orange book) is an orally administered antifungal drug. It is used both in animals and 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.
It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.
The first step in the biosynthesis of griseofulvin by P. griseofulvin is the synthesis of the 14-carbon poly-β -keto chain by a type I iterative polyketide synthase (PKS) via iterative addition of 6 malonyl-CoA to an acyl-CoA starter unit. The 14-carbon poly-β -keto chain undergoes cyclization/aromatization, using cyclase/aromatase, respectively, through a Claisen and aldol condensation to form the benzophenone intermediate. The benzophenone intermediate is then methylated via S-adenosylmethionine twice to yield griseophenone C. The griseophenone C is then halogenated at the activated site ortho to the phenol group on the left aromatic ring to form griseophenone B. The halogenated species then undergoes a single phenolic oxidation in both rings forming the two oxygen diradical species. The right oxygen radical shifts alpha to the carbonyl via resonance allowing for a stereospecific radical coupling by the oxygen radical on the left ring forming a tetrahydrofuranone species .  The newly formed grisan skeleton with a spiro center is then O-methylated by SAM to generate dehydrogriseofulvin. Ultimately, a stereoselective reduction of the olefin on dehydrogriseofulvin by NADPH affords griseofulvin. 
Known side effects of griseofulvin include:
Common brand names
- Grifulvin V
- Grison-250 (V.I.P Pharma)
- Grisovin-FP (GSK)
- Gris OD 375 (DR.REDDY'S)
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. The drug reaches its site of action only when hair or skin is replaced by the keratin-griseofulvin complex. Griseofulvin then enters 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.
- Michael Ash; Irene Ash (2004). Handbook of Preservatives. Synapse Info Resources. p. 406. ISBN 978-1-890595-66-1.
- Goldman, Leon (6 February 1960). "Current status of Griseofulvin". Journal of the American Medical Association 172 (6): 532. doi:10.1001/jama.1960.03020060022006.
- GB 784618
- U.S. Patent 2,900,304
- U.S. Patent 3,038,839
- U.S. Patent 3,069,328
- U.S. Patent 3,069,329
- J.F. Grove, D. Ismay, J. Macmillan, T.P.C. Mulholland, M.A.T. Rogers, Chem. Ind. (London), 219 (1951).
- Grove, J. F.; MacMillan, J.; Mulholland, T. P. C.; Rogers, M. A. T. (1952). "762. Griseofulvin. Part IV. Structure". Journal of the Chemical Society (Resumed): 3977. doi:10.1039/JR9520003977.
- "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014.
- Birch, Arthur (1953). "Studies in relation to biosynthesis I. Some possible routes to derivatives of orcinol and phloroglucinol". Australian Journal of Chemistry 6 (4): 360. doi:10.1071/ch9530360.
- Dewick, Paul M. (2009). Medicinal Natural Products: A Biosynthetic Approach (3rd ed.). UK: John Wiley & Sons Ltd. ISBN 0-471-97478-1.
- Harris, Constance (1976). "Biosynthesis of Griseofulvin". Journal of the American Chemical Society 98 (17): 5380–5386. doi:10.1021/ja00433a053.
- Tripathi. Textbook of Pharmacology. Jaypee Brothers. pp. 761–762. ISBN 81-8448-085-7.
- 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