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
3D model of Griseofulvin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
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
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