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G4753

Sigma-Aldrich

Griseofulvin

from Penicillium griseofulvum, 97.0-102.0%

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Synonym(s):
(2S)-trans-7-Chloro-2′,4,6-trimethoxy-6′-methylspiro(benzofuran-2[3H],1′-[2]cyclohexene)-3,4′-dione
Empirical Formula (Hill Notation):
C17H17ClO6
CAS Number:
Molecular Weight:
352.77
Beilstein/REAXYS Number:
95226
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

Penicillium griseofulvum

Quality Level

assay

97.0-102.0%

form

powder

antibiotic activity spectrum

fungi

mode of action

DNA synthesis | interferes

storage temp.

−20°C

SMILES string

ClC1=C(O[C@@]2(C(OC)=CC(C[C@H]2C)=O)C3=O)C3=C(OC)C=C1OC

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

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1 of 4

This Item
PHR153412990071299200
vibrant-m

G4753

Griseofulvin

vibrant-m

PHR1534

Griseofulvin

vibrant-m

1299007

Griseofulvin

assay

97.0-102.0%

assay

-

assay

-

assay

-

Quality Level

100

Quality Level

300

Quality Level

-

Quality Level

-

storage temp.

−20°C

storage temp.

-10 to -25°C

storage temp.

2-8°C

storage temp.

2-8°C

biological source

Penicillium griseofulvum

biological source

-

biological source

-

biological source

-

antibiotic activity spectrum

fungi

antibiotic activity spectrum

-

antibiotic activity spectrum

-

antibiotic activity spectrum

-

Biochem/physiol Actions

Antifungal. Mode of action: Disrupts the mitotic spindle structure and inhibits nuclear division. Induces apoptosis in human tumor cell lines.

pictograms

Exclamation markHealth hazard

signalword

Danger

Hazard Classifications

Carc. 2 - Repr. 1B - Skin Sens. 1

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Griseofulvin inhibits fungal mitosis.
K Gull et al.
Nature, 244(5414), 292-294 (1973-07-27)
Xing Wang et al.
Molecular cancer therapeutics, 22(4), 519-528 (2023-02-09)
Extra copies of centrosomes are frequently observed in cancer cells. To survive and proliferate, cancer cells have developed strategies to cluster extra-centrosomes to form bipolar mitotic spindles. The aim of this study was to investigate whether centrosome clustering (CC) inhibition
Dulal Panda et al.
Proceedings of the National Academy of Sciences of the United States of America, 102(28), 9878-9883 (2005-06-30)
The antifungal drug griseofulvin inhibits mitosis strongly in fungal cells and weakly in mammalian cells by affecting mitotic spindle microtubule (MT) function. Griseofulvin also blocks cell-cycle progression at G(2)/M and induces apoptosis in human tumor cell lines. Despite extensive study
Marc S Raab et al.
Cancer research, 72(20), 5374-5385 (2012-09-04)
In contrast to normal cells, malignant cells are frequently aneuploid and contain multiple centrosomes. To allow for bipolar mitotic division, supernumerary centrosomes are clustered into two functional spindle poles in many cancer cells. Recently, we have shown that griseofulvin forces
Aditya K Gupta et al.
Pediatric dermatology, 30(1), 1-6 (2012-09-22)
Two oral antifungal agents, griseofulvin and terbinafine, have regulatory approval in the United States, but it is unknown whether one has superior overall efficacy. Genus-specific differences in efficacy are believed to exist for the two agents. It is not clear

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