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G4753

Sigma-Aldrich

Griseofulvin

from Penicillium griseofulvum, 97.0-102.0%

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

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

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

Certificates of Analysis (COA)

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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
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
S Knasmüller et al.
Critical reviews in toxicology, 27(5), 495-537 (1997-11-05)
Griseofulvin (GF) has been in use for more than 30 years as a pharmaceutical drug in humans for the treatment of dermatomycoses. Animal studies give clear evidence that it causes a variety of acute and chronic toxic effects, including liver
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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