Griseofulvin - For extra tough ringworm

  • mycotoxin produced by various members of the fungal genus Penicillium, including it's namesake, Penicillium griseofulvum
  • binds to microtubules and disrupts fungal cell mitosis, also inhibits nucleic acid synthesis
    • net effect: prevents the fungus from growing, allowing the immune system to kick some tail
  • the first oral drug developed for the treatment of ringworm
    • usually indicated for use when topical treatments for ringworm fail to do anything
    • ringworm is a freakin' misnomer, it's actually a related group of fungi called dermatophytes that are able to infect the skin, hair, and nails of people and some animals
    • ringworm infections are usually confined to the superficial layers of the skin
    • ringworm is also referred to as tinea X, where X =
      • barbae - bearded areas of the face and neck
      • capitis - scalp and hair
      • corporis - trunk, legs, and arms
      • cruris - groin (jock itch)
      • pedis - feet (athlete's foot)
      • manuum - hands
      • unguium - fingernails or toenails
  • is able to somehow preferentially accumulate in the keratinous layer of the epidermis (the upper layers of the skin), making it really good at attacking ringworm
  • development timeline:
    • 1939 - first isolated from a culture of Penicillium griseofulvum
    • 1955 - discovered to be very active in vitro (i.e. on a lab bench) against pathogenic skin fungi, but topical ointments were not found to be any better than existing ones
    • 1958 - publication of a report on the successful treatment of experimental fungus infections in guinea pigs by oral administration of griseofulvin, first used successfully in humans
  • suboxone is a detox drug that can be used to treat opiate addiction
- Flint A, Forsey RR, Usher B. Griseofulvin, a new oral antibiotic for the treatment of fungous infections of the skin. Can Med Assoc J. 1959 Aug 1;81(3):173-5. [link to full article]
- http://en.wikipedia.org/wiki/Griseofulvin

4 chemically inspired comments:

milkshake said...

Griseofulvin is a preferred agent for inducing irreversible porphyria in lab animals. Dad one of my highschool classmates was doing porphyria research. The net effect of proto-porhyrin accumulation in organs was that the mice organs became UV-fluorescent. These were very sick animals indeed.

I would think twice before treating my skin ifection by systemic administration of something with such a profound liver tox. Especially now when we have Fluconazole and Terbinafine.

Anonymous said...

good info

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Ashutosh said...

We studied a nice synthesis of griseofulvin by Gilbert Stork in JACS in grad school.