What Is Griseofulvin?
Griseofulvin is a white crystalline powder.
Griseofulvin is an aromatic compound with the chemical formula C17H17ClO6, molecular weight 352.77, and CAS number 126-07-8. The IUPAC name of Griseofulvin is (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.
Griseofulvin was discovered in 1939 by Oxford et al. at the University of London in a soil fungus called penicillium griseofulvum. It was subsequently isolated by Bryan et al. in 1946 and identified by Grove et al. in 1947.
Uses of Griseofulvin
Griseofulvin is used as an antifungal agent.
The mechanism of action of griseofulvin is that it acts on the fungal cytoskeleton, inhibiting cell division and thereby preventing fungal growth.
Griseofulvin was once used as an oral drug in Japan. However, Griseofulvin is no longer manufactured and marketed in Japan due to side effects such as headache and dizziness, low drug prices, and the introduction of other antifungal drugs.
Properties of Griseofulvin
Griseofulvin has a melting point of 218-222°C, a boiling point of 570°C, and a density of 1.4 g/cm3. Griseofulvin is insoluble in ethanol, acetone, and benzene, and insoluble in water. Griseofulvin can be extracted with chloroform from penicillium griseofulvum fungi or their cultures.
A new drug that exhibits similar antifungal effects to griseofulvin is terbinafine, which is known to be effective for a shorter period than griseofulvin. On the other hand, it may be more effective than terbinafine for some scalp infections.
Side effects of taking griseofulvin include allergic reactions, nausea, diarrhea, headache, sleep disturbances, and fatigue. It is not recommended for people with liver failure or porphyria. If taken during pregnancy or in the months before pregnancy, it may harm the unborn baby.
Other Information About Griseofulvin
1. How Griseofulvin Is Manufactured
Griseofulvin is obtained industrially by fermentation of the fungus penicillium griseofulvum. The biosynthesis of griseofulvin begins with the synthesis of a six-carbon poly β-keto chain, which undergoes kleisen condensation, aldol condensation, and cycloaromatization to form the benzophenone intermediate. Further methylation, halogenation, and phenol oxidation followed by O-methylation of the tetrahydrofuranone species produced by radical coupling and stereoselective reduction of the olefin yields Griseofulvin.
2. Regulatory Information
Griseofulvin is exempt from all major domestic laws and regulations.
3. Handling and Storage Precautions
Precautions for handling and storage are as follows.
- Seal the container tightly and store it in a dry, cool, and dark place.
- Use only outdoors or in well-ventilated areas.
- Wear protective gloves, protective glasses, protective clothing, and protective masks when using.
- Take care not to inhale dust. If you feel unwell after inhaling, get medical advice and treatment.
- Wash hands thoroughly after handling.
- In case of skin contact, rinse immediately with water.
- In case of eye contact, rinse cautiously with water for several minutes.