QuickView for Griseofulvin (compound)

Summary
General Info

PubChem

PubChem Compound 3512

Name:	Griseofulvin
PubChem Compound ID:	3512
Description:	An antifungal antibiotic. Griseofulvin may be given by mouth in the treatment of tinea infections.
Molecular formula:	C₁₇H₁₇ClO₆
Molecular weight:	352.766 g/mol
Synonyms:	LABOTEST-BB LT00244818; BAS 00463344; MLS000028436; 78739-00-1; Griseostatin; Grisowen; Gris-PEG; NSC34533; Griseofulvin; NSC41728. show more » LABOTEST-BB LT00244818; BAS 00463344; MLS000028436; 78739-00-1; Griseostatin; Grisowen; Gris-PEG; NSC34533; Griseofulvin; NSC41728; NCI60_003070; Grisovin; Spiro[benzofuran-2(3H),1'-[2]-cyclohexene]-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl; SMR000058317; Grifulvin V; Gricin; Spiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl-, (1'S-trans)-; Polygris; Fulcin; Fulvicin; Griseo show less «

DrugBank

Identification

Name:	Griseofulvin
Name (isomeric):	DB00400
Drug Type:	small molecule
Description:	An antifungal antibiotic. Griseofulvin may be given by mouth in the treatment of tinea infections.
Synonyms:	Griseofulvinum [INN-Latin]; Griseofulvine [INN-French]; Griseofulvina [INN-Spanish]
Brand:	Fulvina, Fulvicin, Grifulvin, Grisactin Ultra, Lamoryl, Fungivin, Neocid, Griseofulvin forte, Grisofulvin, Sporostatin, Grisefuline, Gricin, Griseo, Grisetin, Grizeofulvin, Sporostatin xan, Grisactin, Gresfeed, Fulvican grisactin, Gris-PEG, Fulvicin-U/F, Griscofulvin, Likuden, Poncyl, Spirofulvin, Neo-Fulcin, Fulvicin-P/G, Griseomix, Delmofulvina, Grisovin, Amudane, Fulvistatin, Greosin, Grifulvin V, Grysio, Fulvicin P/G, Guservin, Fulcin, Fulvinil, Fulvicin U/F, Murfulvin, Biogrisin-fp, Grisovin FP, Fulcine, Grifulin, Griseofulvin-forte, Curling factor, Likunden, Xuanjing
Category:	Antibacterial Agents, Antibiotics, Antifungal
CAS number:	126-07-8

Pharmacology

Indication:	For the treatment of ringworm infections of the skin, hair, and nails, namely: tinea corporis, tinea pedis, tinea cruris, tinea barbae, cradle cap or other conditions caused by <i>Trichophyton</i> or <i>Microsporum</i> fungi.
Pharmacology:	Griseofulvin is a mycotoxic metabolic product of Penicillium spp. It was the first available oral agent for the treatment of dermatophytoses and has now been used for more than forty years. Griseofulvin is fungistatic with in vitro activity against various species of Microsporum Epidermophyton, and Trichophyton. It has no effect on bacteria ... show more » Griseofulvin is a mycotoxic metabolic product of Penicillium spp. It was the first available oral agent for the treatment of dermatophytoses and has now been used for more than forty years. Griseofulvin is fungistatic with in vitro activity against various species of Microsporum Epidermophyton, and Trichophyton. It has no effect on bacteria or on other genera of fungi. Following oral administration, griseofulvin is deposited in the keratin precursor cells and has a greater affinity for diseased tissue. The drug is tightly bound to the new keratin which becomes highly resistant to fungal invasions. Once the keratin-Griseofulvin complex reaches the skin site of action, it binds to fungal microtubules (tubulin) thus altering fungal mitosis. show less «
Mechanism of Action:	Griseofulvin is fungistatic, however the exact mechanism by which it inhibits the growth of dermatophytes is not clear. It is thought to inhibit fungal cell mitosis and nuclear acid synthesis. It also binds to and interferes with the function of spindle and cytoplasmic microtubules by binding to alpha and beta tubulin. It binds to keratin in human ... show more » Griseofulvin is fungistatic, however the exact mechanism by which it inhibits the growth of dermatophytes is not clear. It is thought to inhibit fungal cell mitosis and nuclear acid synthesis. It also binds to and interferes with the function of spindle and cytoplasmic microtubules by binding to alpha and beta tubulin. It binds to keratin in human cells, then once it reaches the fungal site of action, it binds to fungal microtubes thus altering the fungal process of mitosis. show less «
Absorption:	Poorly absorbed from GI ranging from 25 to 70% of an oral dose. Absorption is significantly enhanced by administration with or after a fatty meal.
Biotransformation:	Primarily hepatic with major metabolites being 6-methyl-griseofulvin and its glucuronide conjugate.
Half Life:	9-21 hours
Toxicity:	Side effects are minor: headaches, gastrointestinal reactions and cutaneous eruptions
Affected organisms:	Yeast and other Trichophyton or Microsporum fungi

Interactions

Food interaction:

Avoid alcohol.

Take this medication with a high fat meal, fatty foods increase bioavailability.

Drug interaction:

Secobarbital	The barbiturate, secobarbital, decreases the effect of griseofulvin.
Hexobarbital	The barbiturate, hexobarbital, decreases the effect of griseofulvin.
Anisindione	Griseofulvin may decrease the anticoagulant effect of anisindione.
Diethylstilbestrol	The enzyme inducer, griseofulvin, decreases the effect of the hormone agent, diethylstilbestrol.
Ethinyl Estradiol	This product may cause a slight decrease of contraceptive effect

Secobarbital	The barbiturate, secobarbital, decreases the effect of griseofulvin.
Hexobarbital	The barbiturate, hexobarbital, decreases the effect of griseofulvin.
Anisindione	Griseofulvin may decrease the anticoagulant effect of anisindione.
Diethylstilbestrol	The enzyme inducer, griseofulvin, decreases the effect of the hormone agent, diethylstilbestrol.
Ethinyl Estradiol	This product may cause a slight decrease of contraceptive effect
Talbutal	The barbiturate, talbutal, decreases the effect of griseofulvin.
Aprobarbital	The barbiturate, aprobarbital, decreases the effect of griseofulvin.
Estradiol	The enzyme inducer, griseofulvin, decreases the effect of the hormone agent, estradiol.
Butalbital	The barbiturate, butalbital, decreases the effect of griseofulvin.
Heptabarbital	The barbiturate, heptabarbital, decreases the effect of griseofulvin.
Quinidine barbiturate	The barbiturate, quinidine barbiturate, decreases the effect of griseofulvin.
Amobarbital	The barbiturate, amobarbital, decreases the effect of griseofulvin.
Acetylsalicylic acid	Griseofulvin may decrease the efficacy of acetylsalicylic acid.
Butabarbital	The barbiturate, butabarbital, decreases the effect of griseofulvin.
Dihydroquinidine barbiturate	The barbiturate, dihydroquinidine barbiturate, decreases the effect of griseofulvin.
Estrone	The enzyme inducer, griseofulvin, decreases the effect of the hormone agent, estrone.
Quinestrol	The enzyme inducer, griseofulvin, decreases the effect of the hormone agent, quinestrol.
Pentobarbital	The barbiturate, pentobarbital, decreases the effect of griseofulvin.
Butethal	The barbiturate, butethal, decreases the effect of griseofulvin.
Estropipate	The enzyme inducer, griseofulvin, decreases the effect of the hormone agent, estropipate.
Methohexital	The barbiturate, methohexital, decreases the effect of griseofulvin.
Methylphenobarbital	The barbiturate, methylphenobarbital, decreases the effect of griseofulvin.
Chlorotrianisene	The enzyme inducer, griseofulvin, decreases the effect of the hormone agent, chlorotrianisene.
Norethindrone	This product may cause a slight decrease of contraceptive effect
Cyclosporine	Griseofulvin decreases the effect of cyclosporine
Conjugated Estrogens	The enzyme inducer, griseofulvin, decreases the effect of the hormone agent, conjugated estrogens.
Medroxyprogesterone	The enzyme inducer, griseofulvin, may decrease the effect of the hormone, medroxyprogesterone.
Acenocoumarol	Griseofulvin may decrease the anticoagulant effect of acenocoumarol.
Warfarin	Griseofulvin may decrease the anticoagulant effect of warfarin.
Phenobarbital	The barbiturate, phenobarbital, decreases the effect of griseofulvin.
Mestranol	This product may cause a slight decrease of contraceptive effect
Clomifene	The enzyme inducer, griseofulvin, decreases the effect of the hormone agent, clomifene.
Megestrol	The enzyme inducer, griseofulvin, may decrease the effect of the hormone, megestrol.
Primidone	The barbiturate, primidone, decreases the effect of griseofulvin.
Estriol	The enzyme inducer, griseofulvin, decreases the effect of the hormone agent, estriol.
Dicumarol	Griseofulvin may decrease the anticoagulant effect of dicumarol.

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Targets

Tubulin beta chain

Tubulin alpha chain

Keratin, type I cytoskeletal 12

Enzymes

Cytochrome P450 1A2

Cytochrome P450 3A4