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(+)-griseofulvin
7-chloro-4,6,2'-trimethoxy-6'-methylgris-2'-en-3,4'-dione

Supplier Sponsors

Name:(2S,5'R)-7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione
CAS Number: 126-07-8Picture of molecule3D/inchi
Other(deleted CASRN):11103-62-1
ECHA EINECS - REACH Pre-Reg:204-767-4
FDA UNII: 32HRV3E3D5
Nikkaji Web:J4.418K
Beilstein Number:0095226
MDL:MFCD00082343
XlogP3:2.20 (est)
Molecular Weight:352.76969000
Formula:C17 H17 Cl O6
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:pharmaceuticals / chemical synthisis
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
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PubMed:Search
NCBI:Search
 
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)
 water, 8.64 mg/L @ 25 °C (exp)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Griseofulvin >99% by HPLC
Odor: characteristic
Use: A spirobenzofuran produced by a number of penicillium species; a selective antifungal agent used to treat skin infections in animals and humans; acts by binding to fungal tubulin and inhibiting the mitotic spindle.
Glentham Life Sciences
Griseofulvin
Santa Cruz Biotechnology
For experimental / research use only.
Griseofulvin ≥99%
Sigma-Aldrich
For experimental / research use only.
Griseofulvin pharmaceutical secondary standard; traceable to USP, PhEur, BP
Sigma-Aldrich: Sigma
For experimental / research use only.
Griseofulvin
from Penicillium griseofulvum, 97.0-102.0%
TCI AMERICA
For experimental / research use only.
(+)-Griseofulvin >97.0%(HPLC)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 200 mg/kg
National Technical Information Service. Vol. AD277-689

intravenous-mouse LD50 280 mg/kg
Toxicology and Applied Pharmacology. Vol. 2, Pg. 44, 1960.

oral-mouse LD50 > 50000 mg/kg
Toxicology and Applied Pharmacology. Vol. 2, Pg. 44, 1960.

intraperitoneal-rat LD50 > 5000 mg/kg
Toxicology and Applied Pharmacology. Vol. 2, Pg. 44, 1960.

intravenous-rat LD50 400 mg/kg
BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE
Nature. Vol. 182, Pg. 1320, 1958.

oral-rat LD50 > 10000 mg/kg
Drugs in Japan Vol. 6, Pg. 215, 1982.

Dermal Toxicity:
subcutaneous-mouse LD50 > 12000 mg/kg
Toxicology and Applied Pharmacology. Vol. 2, Pg. 44, 1960.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
EPA GENetic TOXicology:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :441140
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2S,5'R)-7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione
Chemidplus:0000126078
EPA/NOAA CAMEO:hazardous materials
RTECS:WG9800000 for cas# 126-07-8
 
References:
 (2S,5'R)-7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):441140
Pubchem (sid):134973200
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C06686
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2932.99.7000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
Formulations/Preparations:
•dusts 1.5-3.5% wtwt for use at 75 lbacre. wettable powders, dispersible concentrates (soln in dimethyl formamide with dispersing agent). srp: not approved for use on crops in us. •griseofulvin, usp (fulvicin uf, grifulvin v, grisactin), is marketed in capsules containing 125 or 250 mg & in tablets containing 125, 250, or 500 mg; it is also avail as oral suspension (125 mg5 ml). tablets incorporating ultramicrosized prepn (fulvicin pg, gris-peg) contain 125 or 250 mg of griseofulvin (equivalent to 250 or 500 mg of prepn...above). •bioavailability of a 500 mg microsize formulation was compared to 2 new ultramicrosize formulations. one 330 mg ultramicrosize tablet is bioequivalent to 2 165 mg ultramicrosize tablets & either ultramicrosize dosage regimen is bioequivalent to 500 mg of the microsize formulation.[lin c et al; j int med res 10 (4): 274 (1982)] pubmed abstract •the bioavailability of griseofulvin tablets spray dried with 20% methylcellulose was determined in 10 rabbits. compared to regular tablets, drug absorption was greater in the spray dried prepn. •tablet, 250 mg, 500 mg; suspension, 250 mgml grifulvin v
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
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
 

Articles:

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.
 
Notes:
an antifungal antibiotic. griseofulvin may be given by mouth in the treatment of tinea infections.
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