7-Chlor-2',4,6-trimethoxy-6'-methyl-spiro(benzo-furan-2(3H),1'-(2)cyclohexen)-3,4'-dion Chemische Eigenschaften,Einsatz,Produktion Methoden
R-S?tze Betriebsanweisung:
R60:Kann die Fortpflanzungsf?higkeit beeintr?chtigen.
R61:Kann das Kind im Mutterleib sch?digen.
R40:Verdacht auf krebserzeugende Wirkung.
R43:Sensibilisierung durch Hautkontakt m?glich.
R45:Kann Krebs erzeugen.
S-S?tze Betriebsanweisung:
S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
S22:Staub nicht einatmen.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).
Chemische Eigenschaften
Crystalline Solid
Verwenden
It is an antifungal drug. It is used both in animal and in humans, to treat rigworm infections of the skin and nails. It is derived from the mold Penicillium griseofulvum.Environmental contaminants; Food contaminants.
Indications
Griseofulvin (Fulvicin, Grifulvin V) has been used
safely and effectively for decades for dermatophyte infections
of scalp and nails and for more widespread skin
eruptions. However, infections in certain sites (e.g.. toenails)
respond poorly. The drug is generally well tolerated,
even in the long-term courses necessary for nail
disease.
Definition
ChEBI: An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment.
Weltgesundheitsorganisation (WHO)
Griseofulvin, isolated from a penicillin producing mould, has
been widely used as a systemically administered antifungal agent in man for over
20 years. It is effective in dermatophyte infections (including tinea barbae and tinea
capitis) but it is inactive against yeasts and bacteria. Evidence that very high doses
of griseofulvin are carcinogenic, teratogenic and fetotoxic in laboratory animals
has led to an acceptance that it should not be used to treat trivial infections that respond to topical therapy. Oral formulations of griseofulvin are included in the
WHO Model List of Essential Drugs.
(Reference: (WHTAC1) The Use of Essential Drugs, 2nd Report of the WHO Expert
Committee, 722, , 1985)
Antimicrobial activity
The spectrum of useful activity is restricted to dermatophytes
causing skin, nail and hair infections (Epidermophyton,
Microsporum and Trichophyton spp.). Resistance has seldom
been reported.
Allgemeine Beschreibung
White to pale cream-colored crystalline powder. Odorless or almost odorless. Tasteless. Sublimes without decomposition at 410°F.
Air & Water Reaktionen
Insoluble in water.
Reaktivit?t anzeigen
(+)-Griseofulvin is incompatible with strong oxidizing agents. .
Hazard
Possible carcinogen.
Brandgefahr
Flash point data for (+)-Griseofulvin are not available. (+)-Griseofulvin is probably combustible.
Pharmazeutische Anwendungen
A fermentation product of various species of Penicillium,
including Pen. griseofulvum. Available as fine-particle or ultrafine-
particle formulations for oral use.
Mechanism of action
The mechanism of action of griseofulvin is through binding to the protein tubulin, which interferes with the function of the mitotic spindle and, thereby, inhibits cell division. Griseofulvin also may interfere directly with DNA replication. Griseofulvin is gradually being replaced by newer agents .
Pharmakokinetik
Absorption from the gastrointestinal tract is dependent on drug
formulation. Administration with a high-fat meal will increase
the rate and extent of absorption, but individuals tend to achieve
consistently high or low blood concentrations. It appears in the
stratum corneum within 4–8 h as a result of secretion in perspiration.
However, levels begin to fall soon after the drug is
discontinued, and within 48–72 h it can no longer be detected.
It is metabolized in the liver, the metabolites being excreted in
the urine. The elimination half-life is 9–21 h.
Clinical Use
Dermatophyte infections of hair, skin and nail
Nebenwirkungen
Adverse reactions occur in about 15% of patients and include
headache, nausea, vomiting, rashes and photosensitivity.
Stoffwechsel
Griseofulvin is metabolized by the liver, and its metabolites are excreted
in the urine. It is highly protein bound and, therefore, may have high tissue
levels. However, tissue levels decrease and fall as soon as griseofulvin is
discontinued such that its presence is no longer detectable 2 to 3 days after
cessation of therapy.
l?uterung methode
Crystallise it from *benzene or EtOH. Purify 2g of griseofulvin by chromatography on Alumina (40 x 1.5cm) and elute with *C6H6/MeOH (199:1) and follow the UV blue fluorescent band. [MacMillan J Chem Soc 1823 1959, Beilstein 18 III/IV 3160, 18/5 V 150.]
7-Chlor-2',4,6-trimethoxy-6'-methyl-spiro(benzo-furan-2(3H),1'-(2)cyclohexen)-3,4'-dion Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Oxals?ure
Strke
Getreide, Quellflüssigkeit
Spiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione, 7-chloro-2'-hydroxy-4,6-dimethoxy-6'-methyl-, (1'S,6'S)-
Ethanone, 1-(3-chloro-2-hydroxy-4,6-dimethoxyphenyl)-
Spiro[benzofuran-2(3H),1'-[2,5]cyclohexadiene]-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl-
2-chloro-3,5-dimethoxyphenol(WXC05665)
Downstream Produkte
