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Merck
CN

G4753

Sigma-Aldrich

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
Beilstein:
95226
EC Number:
204-767-4
MDL number:
MFCD00082343
UNSPSC Code:
12352200
PubChem Substance ID:
24895185
NACRES:
NA.77

Key Documents

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Product Name

Griseofulvin, from Penicillium griseofulvum, 97.0-102.0%

biological source

Penicillium griseofulvum

Quality Level

100

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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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

Signal Word

Danger

Hazard Statements

H317,H351,H360FD

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT9993
MKCT7975
MKCN0018
MKCD6584
MKBQ4861V

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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
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)
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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