(+)-griseofulvin
7-chloro-4,6,2'-trimethoxy-6'-methylgris-2'-en-3,4'-dione
Identification
| Name | (+)-griseofulvin |
| IUPAC | (2S,5'R)-7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione |
| CAS Number | 126-07-8 |
| EINECS | 204-767-4 |
| FDA UNII | 32HRV3E3D5 |
| Molecular Formula | C17 H17 Cl O6 |
| Molecular Weight | 352.76969000 |
| MDL Number | MFCD00082343 |
| Nikkaji Number | J4.418K |
| Beilstein | 0095226 |
| XlogP3 | 2.20 (est) |
Regulatory
Physical Properties
| Appearance | white to pale cream crystalline powder (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 220.00 °C. @ 760.00 mm Hg |
| Boiling Point | 570.40 °C. @ 760.00 mm Hg (est) |
| Flash Point | 442.00 °F. TCC ( 228.00 °C. ) (est) |
| logP (o/w) | 2.180 |
| Soluble in | water, 81.96 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 200 mg/kg |
| Dermal Toxicity | subcutaneous-mouse LD50 > 12000 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | pharmaceuticals / chemical synthisis |
| Recommendation for (+)-griseofulvin usage levels up to | not for fragrance use. |
| Recommendation for (+)-griseofulvin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
amudane
biogrisin-FP
(1'S,6'R)-7-
chloro-2',4,6-trimethoxy-6'-methylspiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione
(1'S-trans)- 7-
chloro-2',4,6-trimethoxy-6'-methylspiro(benzofuran-2(3H),1'-cyclohex-2'-ene)-3,4'-dione
1'S-trans)- 7-
chloro-2',4,6-trimethoxy-6'-methylspiro(benzofuran-2(3H),1'-cyclohex-2'-ene)-3,4'-dione
7-
chloro-2',4,6-trimethoxy-6'beta-methylspiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione
(2S,5'R)-7-
chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione
7-
chloro-4,6-dimethoxycoumaran-3-one-2-spiro-1'-(2'-methoxy-6'-methylcyclohex-2'-en-4'-one)
7-
chloro-4,6,2'-trimethoxy-6'-methylgris-2'-en-3,4'-dione
delmofulvina
fulcin
fulcine
fulvican grisactin
fulvicin
fulvicin bolus
fulvicin P/G
fulvicin P/G 165
fulvicin P/G 330
fulvicin-P/G
fulvicin-U/F
fulvicin-U/F Powder and Tablets
fulvidex
fulvina
fulvinil
fulvistatin
fungivin
greosin
gresfeed
gricin
grifulin
grifulvin
grifulvin V
gris-PEG
grisactin
grisactin ultra
grisactin V
griscofulvin
grisefuline
griseo
griseofulvin
griseofulvin [USP:INN:BAN:JAN]
griseofulvin [USP:INN]
griseofulvin forte
griseofulvin microsize
griseofulvin-forte
griseofulvina
griseofulvine
griseofulvinum
griseomix
grisetin
grisofulvin
grisovin
grizeofulvin
grysio
guservin
lamoryl
likuden
murfulvin
neo-fulcin
poncyl
spiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl-, (1'S-trans)-
spiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl-, (1'S,6'R)-
spiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl-, (2S-trans)-
spirofulvin
ultragris-165
ultragris-330
xuanjing
PubMed:
An in vitro antibacterial and antifungal effects of cadmium(II) complexes of hexamethyltetraazacyclotetradecadiene and isomers of its saturated analogue.
PubMed:
Effects of added surfactant on swelling and molecular transport in drug-loaded tablets based on hydrophobically modified poly(acrylic acid).
PubMed:
Thermal gelation of aqueous hydroxypropylmethylcellulose solutions with SDS and hydrophobic drug particles.
PubMed:
Metabolite profiling using liquid chromatography/quadrupole time-of-flight mass spectrometry for the identification of a suitable marker and target matrix of griseofulvin use in bovines.
PubMed:
Organized polysaccharide fibers as stable drug carriers.
PubMed:
Synthesis of 4'-thiosemicarbazonegriseofulvin and its effects on the control of enzymatic browning and postharvest disease of fruits.
PubMed:
Microscopic fungi recovered from honey and their toxinogenity.
PubMed:
Synthesis and fungicidal activity of novel 3-(substituted/unsubstituted phenylselenonyl)-1-ribosyl/deoxyribosyl-1H-1,2,4-triazole.
PubMed:
Fungal toenail infections.
PubMed:
Fungi on wheat bran and their toxinogenity.
PubMed:
Relative bioavailability of griseofulvin lyophilized dry emulsion tablet vs. immediate release tablet: a single-dose, randomized, open-label, six-period, crossover study in healthy adult volunteers in the fasted and fed states.
PubMed:
Fungal toenail infections.
PubMed:
Improving the high variable bioavailability of griseofulvin by SEDDS.
PubMed:
Modeling gastrointestinal drug absorption requires more in vivo biopharmaceutical data: experience from in vivo dissolution and permeability studies in humans.
PubMed:
The assessment and management of tinea capitis in children.
PubMed:
Fungi recovered from Slovakian poultry feed mixtures and their toxinogenity.
PubMed:
Therapies for onychomycosis: a review.
PubMed:
Mycological survey of ripped service tree fruits (Sorbus domestica L.) with an emphasis on toxinogenic fungi.
PubMed:
Characterization of molds from dry-cured meat products and their metabolites by micellar electrokinetic capillary electrophoresis and random amplified polymorphic DNA PCR.
PubMed:
The systemic treatment of onychomycosis.
PubMed:
Solid-state fermentation for production of griseofulvin on rice bran using Penicillium griseofulvum.
PubMed:
Supercritical carbon dioxide extraction of griseofulvin from the solid matrix obtained after solid-state fermentation.
PubMed:
Determination of Penicillium mycotoxins in foods and feeds using liquid chromatography-mass spectrometry.
PubMed:
Food-drug interactions.
PubMed:
Ciclopirox nail lacquer and podiatric practice.
PubMed:
Oral griseofulvin remains the treatment of choice for tinea capitis in children.
PubMed:
The evolving role of itraconazole, fluconazole and terbinafine in the treatment of tinea capitis.
PubMed:
Use of propolis and ultragriseofulvin to inhibit aflatoxigenic fungi.
PubMed:
[Influence of foods on the absorption of antimicrobial agents].
PubMed:
Current issues in onychomycosis.
PubMed:
Update on the management of onychomycosis: highlights of the Third Annual International Summit on Cutaneous Antifungal Therapy.
PubMed:
Estimation of the increase in solubility of drugs as a function of bile salt concentration.
PubMed:
The systemic treatment of onychomycosis.
PubMed:
Interactions of warfarin with drugs and food.
PubMed:
Management errors leading to unnecessary hospitalization for kerion.
PubMed:
Estrogen dose in oral contraceptives: FDA committee examines safety and utility of 50 mcg estrogen OCs.
PubMed:
Pharmacokinetic optimisation of oral antifungal therapy.
PubMed:
Influence of higher rates of agitation on release patterns of immediate-release drug products.
PubMed:
Mycotoxins and mycotoxigenic moulds in nuts and sunflower seeds for human consumption.
PubMed:
Is a diurnal rhythm in bioavailability caused by a rhythm in intestinal absorption?
PubMed:
Differentiation of Penicillium griseofulvum Dierckx isolates by enzyme assays and by patulin and griseofulvin analyses.
PubMed:
The bioavailability of griseofulvin from microsized and ultramicrosized tablets in nonfasting volunteers.
PubMed:
In vitro dissolution profile of water-insoluble drug dosage forms in the presence of surfactants.
PubMed:
Standardized high-performance liquid chromatography of 182 mycotoxins and other fungal metabolites based on alkylphenone retention indices and UV-VIS spectra (diode array detection).
PubMed:
Cyclopiazonic acid production by cultures of Aspergillus and Penicillium species isolated from dried beans, corn meal, macaroni, and pecans.
PubMed:
Indirect spectrophotometric methods for the determination of antibiotics with iodine or periodate, and metol and sulphanilamide.
PubMed:
Metabolic mechanisms of drug-nutrient interactions.
PubMed:
Bioavailability of griseofulvin plain tablets in stomach-emptying controlled rabbits and the correlation with bioavailability in humans.
PubMed:
Pharmacologic review: a review of the literature of ketoconazole therapy in the treatment of tinea pedis and onychomycosis.
PubMed:
Effect of food on the bioavailability of griseofulvin from microsize and PEG ultramicrosize (GRIS-PEG) plain tablets.
PubMed:
Physiological criteria and mycotoxin production as AIDS in identification of common asymmetric penicillia.
PubMed:
[Carcinogenic fungi (author's transl)].
PubMed:
[Foods as interfering factors in pharmacotherapy--shown by various examples].
PubMed:
Carcinogens occurring naturally in foods.
PubMed:
Mycotoxin-producing potential of mold flora of dried beans.
PubMed:
Brine shrimp (Artemia salina L.) larvae as a screening system for fungal toxins.
PubMed:
NATURAL, METALLIC AND OTHER SUBSTANCES, AS CARCINOGENS.