|Trade names||Gris-peg, Grifulvin V|
|ATC code||D01AA08 (WHO) D01BA01 (WHO)|
|Bioavailability||Highly variable (25 to 70%)|
|Metabolism||Liver (demethylation and glucuronidation)|
|Biological half-life||9–21 hours|
|Chemical and physical data|
|Molar mass||352.766 g/mol|
|3D model (Jmol)||Interactive image|
Griseofulvin (trade names: Gris-peg and Grifulvin V) is antifungal medication. It is used both in animals and humans, to treat fungal infections of the skin (commonly known as ringworm) and nail fungus. It is given by mouth.
Griseofulvin was discovered in the culture broth of certain species of the mold Penicillium in 1939. It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system. It is produced industrially by fermenting the fungus Penicillium patulum.
Griseofulvin is used orally only for dermatophytosis. It is ineffective topically. It is reserved for cases with nail, hair, or large body surface involvement.
Known side effects of griseofulvin include:
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.
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-adenosyl methionine (SAM) 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.
- Grifulvin V
- Gris OD 375 (Dr. Reddy's Laboratories)
- Gris-PEG (Valeant Pharmaceuticals)
- Grison-250 (V.I.P Pharma)
- Grisovin-FP (GlaxoSmithKline)
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- 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