Griseofulvin (Grifulvin)

Alias:
Cat No.:V1623 Purity: ≥98%
Griseofulvin (Gris-PEG; Grifulvin; Fulvicin, Grisactin, Amudane), a naturally occurring spirocyclic compound isolatedfrom some strains of the mold Penicillium griseofulvumam, is an oral antifungal medication approved for use in the treatment of various dermatophytoses (ringworm) such as fungal infections of the nails and skin when antifungal creams did not work.
Griseofulvin (Grifulvin) Chemical Structure CAS No.: 126-07-8
Product category: Microtubule Associated
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Griseofulvin (Gris-PEG; Grifulvin; Fulvicin, Grisactin, Amudane), a naturally occurring spirocyclic compound isolated from some strains of the mold Penicillium griseofulvumam, is an oral antifungal medication approved for use in the treatment of various dermatophytoses (ringworm) such as fungal infections of the nails and skin when antifungal creams did not work. Griseofulvin is a tubulin/microtubule inhibitor that acts by inhibiting cell mitosis via interfering with microtubule function. Griseofulvin is used orally only for dermatophytosis. It is ineffective topically. It is reserved for cases with nail, hair, or large body surface involvement.

Biological Activity I Assay Protocols (From Reference)
ln Vitro

In vitro activity: Griseofulvin is active against dermatophytes of different species in the genera Microsporum, Trichophyton and Epidermophyton. Other fungi such as Scopulariopsis brevicaulis and Hendersomula toruloidea are insensitive. Griseofulvin has little or no effect against yeasts and bacteria. The minimum inhibitory concentration of Griseofulvin tested in vitro against various dermatophytes ranges between 0.14 and 0.6 μg/mL. Main effect of Griseofulvin on cell mitosis is disorganization of the spindle microtubules. Griseofulvin is also able to induce structural chromosomal aberrations in mammalian cells. Griseofulvin inhibits the viability of human colon adenocarcinoma cells COLO 205 and HT 29, hepatoma cells Hep G2 and Hep 3B, leukemia cells HL 60, and normal keratinocytes (#76 KhGH) with IC50s of ~1 and ~5 μM, 5 and 5 μM, 1 μM, and 50 μM, respectively after a 30 hr incubation,. Griseofulvin (20 μM) induces a marked presence of abnormal mitotic spindle formation with mono-, bi-, and tripolar spindles of varying lengths in HT 29 cells, and causes G2/M cell cycle arrest at 24h through elevation of cyclin B1/cdc2 kinase activity and down-regulation of myt-1 protein expression. Griseofulvin is able to induce apoptosis of HT 29 cells via caspase3 activation, Bcl-2 hyperphosphorylation and inhibition of the normal function of Bcl-2 associated with Bax.


Cell Assay: The cells (5× 103/mL) are incubated in triplicate in a 96-well plate in the presence or absence of indicated concentration of Griseofulvin in a final volume of 0.2 mL for different time intervals at 37 ℃. Thereafter, 20 μL MTT solution (5 mg/mL in PBS) is added to each well. After a 2-hour incubation at 37 ℃, 0.1 mL lysis buffer (20% SDS, 50% dimethylformamide) is added, incubation is continued overnight at 37 ℃, and then the optical density at 570 nm is measured by plate reader.

ln Vivo
Griseofulvin displays potent anti-infection activity in vivo. The minimum effective dose of Griseofulvin given daily per os is 250 mg/kg (6 days) in mice with a cutaneous infection of Trichophyton quinckeanum and 25 mg/kg (12 days) in guinea pigs with a cutaneous infection of Trichophyton mentagrophytes. Griseofulvin (50 mg/kg) is able to suppress COLO 205 tumor xenografts growth. Treatment with Griseofulvin and nocodazole (5 mg/kg) together significantly enhances the efficacy of nocodazole, leading to cessation of tumor growth.
Animal Protocol
Dissolved in DMSO; 50 mg/kg; i.p. injection
Human colon adenocarcinoma xenografts COLO 205
References
Mutat Res.1988 Mar;195(2):91-126;Int J Cancer.2001 Feb 1;91(3):393-401.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H17CLO6
Molecular Weight
352.77
CAS #
126-07-8
Related CAS #
Griseofulvin;126-07-8
SMILES
O=C1[C@]2(C(OC)=CC(C[C@H]2C)=O)OC3=C(Cl)C(OC)=CC(OC)=C13
InChi Key
DDUHZTYCFQRHIY-RBHXEPJQSA-N
InChi Code
InChI=1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3/t8-,17+/m1/s1
Chemical Name
(2S,6R)-7-chloro-2,4,6-trimethoxy-6-methyl-3H-spiro[benzofuran-2,1-cyclohexan]-2-ene-3,4-dione
Synonyms

Gris PEG, Griseofulvin, Fulvicin, Grisactin, GrisPEG, Gris-PEG,Amudane

Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO:50 mg/mL (141.7 mM)
Water:<1 mg/mL
Ethanol:<1 mg/mL
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.8347 mL 14.1735 mL 28.3471 mL
5 mM 0.5669 mL 2.8347 mL 5.6694 mL
10 mM 0.2835 mL 1.4174 mL 2.8347 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

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