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Merck
CN

G4753

Griseofulvin

From Penicillium griseofulvum, 97.0-102.0%, Apoptosis inducer, powder

Synonym(s):

(2S)-trans-7-Chloro-2′,4,6-trimethoxy-6′-methylspiro(benzofuran-2[3H],1′-[2]cyclohexene)-3,4′-dione

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About This Item

Empirical Formula (Hill Notation):
C17H17ClO6
CAS Number:
126-07-8
Molecular Weight:
352.77
NACRES:
NA.77
PubChem Substance ID:
24895185
UNSPSC Code:
12352200
EC Number:
204-767-4
MDL number:
MFCD00082343
Beilstein/REAXYS Number:
95226

Key Documents

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Product Name

Griseofulvin, from Penicillium griseofulvum, 97.0-102.0%

InChI key

DDUHZTYCFQRHIY-RBHXEPJQSA-N

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 string

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

biological source

Penicillium griseofulvum

assay

97.0-102.0%

form

powder

antibiotic activity spectrum

fungi

mode of action

DNA synthesis | interferes

storage temp.

−20°C

Quality Level

100

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Biochem/physiol Actions

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

pictograms

Health hazardExclamation mark
GHS08,GHS07

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

WGK 3

ppe

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT9993
MKCT7975
MKCN0018
MKCD6584
MKBQ4861V

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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
Griseofulvin inhibits fungal mitosis.
K Gull et al.
Nature, 244(5414), 292-294 (1973-07-27)
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
Konstantinos Drosopoulos et al.
Methods in molecular biology (Clifton, N.J.), 1953, 33-42 (2019-03-27)
Cellular models for siRNA and small molecule high-throughput screening have been widely used in the last decade to identify targets for drug discovery. As an example, we present a twofold readout approach based on cell viability and multipolar phenotype. To
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
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