A fungal metabolite with antifungal and anticancer activities
Related Products
Active Metabolite(s)
33086Griseofulvic Acid
Labeled Version(s)
33366Griseofulvin-d3
Metabolite(s)
331186-O-Demethyl Griseofulvin
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

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Griseofulvin

Item No. 19461

Technical Information
Formal Name
7-chloro-2',4,6-trimethoxy-6'R-methyl-spiro[benzofuran-2(3H)-1'S-[2]cyclohexene]-3,4'-dione
CAS Number
126-07-8
Synonyms
  • (+)-Griseofulvin
Molecular Formula
C17H17ClO6
Formula Weight
Purity
≥98%
A crystalline solid
λmax
210, 291 nm
SMILES
COC1=C2C(O[C@@]3(C(OC)=CC(C[C@H]3C)=O)C2=O)=C(Cl)C(OC)=C1
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
InChi Key
DDUHZTYCFQRHIY-RBHXEPJQSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    Product Description

    Griseofulvin is a polyketide synthase-derived fungal metabolite originally isolated from P. griseofulvum with antifungal and anticancer activities.1,2 It inhibits microtubule assembly when used at concentrations ranging from 20 to 200 µM.3 Griseofulvin is active against a variety of dermatophytes (MICs = 0.14-0.42 µg/ml) and reduces the number of infected hair follicles in a guinea pig model of M. canis infection when administered at a dose of 60 mg/kg.4,5 It also reduces viability of a variety of human colorectal cancer cells in vitro and induces abnormal mitotic spindle formation and cell cycle arrest at the G2/M phase in HT-29 cells when used at a concentration of 20 µM.6 Griseofulvin (50 mg/kg) reduces tumor growth in a COLO 205 mouse xenograft model. Formulations containing griseofulvin have been used in the treatment of dermatophyte infections of the skin and nails.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cacho, R.A., Chooi, Y.-H., Zhou, H., et alComplexity generation in fungal polyketide biosynthesis: A spirocycle-forming P450 in the concise pathway to the antifungal drug griseofulvin. ACS Chem. Biol. 8(10), 2322-2330 (2013).

    2. Flint, A., Forsey, R.R., and Usher, B. Griseofulvin, a new oral antibiotic for the treatment of fungous infections of the skin. Can. Med. Assoc. J. 81(3), 173-175 (1959).

    3. Roobol, A., Gull, K., and Pogson, C.I. Inhibition by griseofulvin of microtubule assembly in vitro. FEBS Lett. 67(3), 248-251 (1976).

    4. Roth, F.J., Jr., Sallman, B., and Blank, H. In vitro studies of the antifungal antibiotic griseofulvin. J. Invest. Dermatol. 33, 403-418 (1959).

    5. Gentles, J.C. Experimental ringworm in guinea pigs: Oral treatment with griseofulvin. Nature 182(4633), 476-477 (1958).

    6. Ho, Y.-S., Duh, J.-S., Jeng, J.-H., et alGriseofulvin potentiates antitumorigenesis effects of nocodazole through induction of apoptosis and G2/M cell cycle arrest in human colorectal cancer cells. Int. J. Cancer 91(3), 393-401 (2001).