Structure Database (LMSD)

Common Name
Griseofulvin
Systematic Name
(2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H,4'H-spiro[1-benzofuran-2,1'-cyclohex[2]ene]-3,4'-dione
Synonyms
LM ID
LMPK13060001
Formula
C17H17O6Cl
Exact Mass
Calculate m/z
352.071368
Status
Curated


Classification

Biological Context

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.

This information has been provided by Cayman Chemical

References

2. Ho, Y.-S., Duh, J.-S., Jeng, J.-H., et al. Griseofulvin 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).
3. Cacho, R.A., Chooi, Y.-H., Zhou, H., et al. Complexity 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).
4. Roobol, A., Gull, K., and Pogson, C.I. Inhibition by griseofulvin of microtubule assembly in vitro. FEBS Lett. 67(3), 248-251 (1976).
5. Roth, F.J., Jr., Sallman, B., and Blank, H. In vitro studies of the antifungal antibiotic griseofulvin. J. Invest. Dermatol. 33, 403-418 (1959).
6. Gentles, J.C. Experimental ringworm in guinea pigs: Oral treatment with griseofulvin. Nature 182(4633), 476-477 (1958).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Penicillium griseofulvum (#5078)
Eurotiomycetes (#147545)
Griseofulvin, a new oral antibiotic for the treatment of fungous infections of the skin.,
Can Med Assoc J, 1959
Pubmed ID: 13671398

String Representations

InChiKey (Click to copy)
DDUHZTYCFQRHIY-RBHXEPJQSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
[C@]12([C@H](C)CC(=O)C=C1OC)OC1=C(C(OC)=CC(OC)=C1Cl)C2=O

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 3
Aromatic Rings 1
Rotatable Bonds 3
Van der Waals Molecular Volume 306.79
Topological Polar Surface Area 73.13
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 6
logP 3.10
Molar Refractivity 86.64

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Created at
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Updated at
12th Dec 2023