7-Chlor-2',4,6-trimethoxy-6'-methyl-spiro(benzo-furan-2(3H),1'-(2)cyclohexen)-3,4'-dion

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Achtung

• Gefahrenhinweise

  H317：Kann allergische Hautreaktionen verursachen.

  H351：Kann vermutlich Krebs verursachen.

• Sicherheit

  P202：Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.

  P261：Einatmen von Staub vermeiden.

  P272：Kontaminierte Arbeitskleidung nicht außerhalb des Arbeitsplatzes tragen.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P302+P352：BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.

  P308+P313：BEI Exposition oder falls betroffen: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

(+)-Griseofulvin Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R60:Kann die Fortpflanzungsfähigkeit beeinträchtigen.
  R61:Kann das Kind im Mutterleib schädigen.
  R40:Verdacht auf krebserzeugende Wirkung.
  R43:Sensibilisierung durch Hautkontakt möglich.
  R45:Kann Krebs erzeugen.

• S-Sätze 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 möglich, dieses Etikett vorzeigen).

• Beschreibung

  Griseofulvin (126-07-8) is an antifungal antimitotic agent. Induces apoptosis of human germ cell tumor cells via disruption of connexin 43/tubulin association concomitant with enhanced translocation of connexin 43 from the cytoplasm to the nucleus.1?Inhibits the growth of adrenocortical cancer cells?in vitro.2 Griseofulvin inhibits centrosome clustering, induces spindle multipolarity, mitotic arrest and cell death in multiple tumor cell lines but not in diploid fibroblasts and keratinocytes with normal centrosome content.3

• Chemische Eigenschaften

  Crystalline Solid

• Originator

  Grifulvin,McNeil,US,1959

• Verwenden

  Griseofulvin is a spirobenzofuran produced by a number of Penicillium species, first isolated in the 1930s by Raistrick's group. Griseofulvin is a selective antifungal agent used to treat skin infections in animals and humans. Griseofulvin acts by binding to fungal tubulin and inhibiting the mitotic spindle. Griseofulvin's ability to bind to keratin is considered an important aspect of the metabolite's access to dermatophytic fungi. More recently, griseofulvin has become an important phenotypic marker in Penicillium taxonomy.

• Verwenden

  adrenegic blocker, Ca channel blocker, coronary vasodilator, antiarrhythmic

• Verwenden

  antifungal, inhibits mitosis in metaphase

• Verwenden

  An antifungal and antiproliferative agent that affects microtubules.

• 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 (Gris-PEG, Grifulvin, Grisactin, Fulvicin) is an oral fungistatic agent used in the long-term treatment of dermatophyte infections caused by Epidermophyton, Microsporum, and Trichophyton spp. Produced by the mold Penicillium griseofulvin, this agent inhibits fungal growth by binding to the microtubules responsible for mitotic spindle formation, leading to defective cell wall development.
  Ineffective topically, griseofulvin is administered orally but has poor gastrointestinal absorption; absorption can be improved by microcrystalline processing of the drug and by taking the drug with fatty meals. Peak serum levels occur 4 hours after dosing. Griseofulvin is metabolized in the liver and has a half-life of 24 to 36 hours. The drug binds to keratin precursor cells and newly synthesized keratin in the stratum corneum of the skin, hair, and nails, stopping the progression of dermatophyte infection.

• 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.

• 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.

• Manufacturing Process

  The experiment was carried out on the 1,000 gallon scale. Three impellers 1'8" diameter at 220 rpm were employed. The air rates were 0 to 5 hours, 40 cfm, 5 to 10 hours, 80 cfm and after 10 hours, 125 cfm. The inoculum rate was 10% v/v. It was prepared by the standard inoculum development technique on the following medium:
  This was inoculated with a spore suspension of P. patulurn (1 liter containing 3-5 x 107 spores/ml) and grown at 25°C in 100 gallon tank. The inoculum is transferred at 40 hours or when the mycelial volume (after spinning 10 minutes at 3,000 rpm) exceeds 25%. The fermentation is conducted as near to the ideal pH curve as possible by addition of crude glucose, according to US Patent 3,069,328.

• Trademarks

  Fulvicin Bolus [Veterinary] (Schering-Plough Animal Health); Fulvicin-P/G (Schering); Fulvicin-U/F (Schering); Fulvicin-U/F Powder and Tablets [Veterinary] (Schering-Plough Animal Health); Grifulvin V (Ortho Pharmaceutical); Grisactin (Wyeth- Ayerst); Gris-PEG (Allergan Herbert);B-gf;Delmofluvina;Flugolin;Fulcine-125;Fulcine-s;Fulvicin p/g;Fulvicin u/f;Fulvicina;Gefulvine;Grfulvin v;Grisaltin;Grisefalin;Grisefulvin;Griseomed;Griseostatin;Grisovina fp;Grisovine;Grisovin-fp;Grisowen;Lamoryl-novum;Lamoyl;Likuden m;Microcidal;Neo fulcin;Neo-filcin;Norofluvin;Ocufen;Sulvina.

• Therapeutic Function

  Antifungal

• 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.

• Reaktivität 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

• Clinical Use

  In the treatment of ringworm of the beard, scalp, and other skin surfaces, 4 to 6 weeks of therapy is often required. Therapy failure may be to the result of an incorrect diagnosis; superficial candidiasis, which may resemble a dermatophyte infection, does not respond to griseofulvin treatment. Onychomycosis responds very slowly to griseofulvin (1 year or more of treatment is commonly required) and cure rates are poor; itraconazole and terbinafine hydrochloride are more effective than griseofulvin for onychomycosis.

• Nebenwirkungen

  Griseofulvin is usually well tolerated. Headache is common with initiation of therapy. Hepatotoxicity (especially in patients with acute intermittent porphyria), dermatitis, and gastrointestinal distress also occur. Griseofulvin increases warfarin metabolism, and griseofulvin metabolism is increased by phenobarbital.

• Nebenwirkungen

  Adverse reactions occur in about 15% of patients and include headache, nausea, vomiting, rashes and photosensitivity.

• Synthese

  Griseofulvin, 7-chloro-2
  ,4,6-trimethoxy-6
  -methylspiro[benzofuran- 2(3H),1
  -[2]-cyclohexen]-3
  ,4-dione (35.4.1), is an antibiotic produced by the mycelial fungus Penicillium patulum.

• Veterinary Drugs and Treatments

  In veterinary species, griseofulvin is approved for use in dogs and cats to treat dermatophytic fungal (see below) infections of the skin, hair and claws, and to treat ringworm (caused by T. equinum and M. gypseum) in horses. It has also been used in laboratory animals and ruminants for the same indications. The oral tablets approved for dogs and cats are no longer marketed in the USA, but human dosage forms are available.

• Arzneimittelwechselwirkung

  Potentially hazardous interactions with other drugs
  Anticoagulants: metabolism of coumarins accelerated (reduced anticoagulant effect).
  Ciclosporin: griseofulvin possibly reduces ciclosporin concentration (two reports of such an interaction in literature).
  Oestrogens and progestogens: metabolism of oral contraceptives accelerated (reduced contraceptive effect).
  Ulipristal: possibly reduced contraceptive effect - avoid.

• 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.

• läuterung 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.]

• Dosage forms

  The average treatment time for tinea capitis is 4 to 6 weeks; for tinea corporis, 2 to 4 weeks; and for tinea pedis, 4 to 8 weeks. Because of the low cure rate and length of therapy, griseofulvin is not commonly used for onychomycosis of the fingernails or toenails. Complete blood count (CBC) is monitored every 3 months during long-term therapy.

• Einzelnachweise

  1) Mauro?et al. (2013),?The anti-mitotic drug griseofulvin induces apoptosis of human germ cell tumor cells through a connexin 43-dependent molecular mechanism; Apoptosis,?18?480 2) Bramann?et al. (2013),?Griseofulvin inhibits the growth of adrenocortical cancer cells in vitro; Horm. Metab. Res.,?45?297 3) Rebacz?et al. (2007),?Identification of griseofulvin as an inhibitor of centrosomal clustering in a phenotype-based screen; Cancer Res., 67?6342

(+)-Griseofulvin Upstream-Materialien And Downstream Produkte

7-Chlor-2',4,6-trimethoxy-6'-methyl-spiro(benzo-furan-2(3H),1'-(2)cyclohexen)-3,4'-dion Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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