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G2664

Sigma-Aldrich

Griseofulvin

meets USP testing specifications, from Penicillium griseofulvum

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/REAXYS Number:
95226
EC Number:
204-767-4
MDL number:
MFCD00082343
UNSPSC Code:
12352200
PubChem Substance ID:
24895099

biological source

Penicillium griseofulvum

agency

meets USP testing specifications

antibiotic activity spectrum

fungi

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

Griseofulvin disrupts microtubule assembly and mitotic spindle stucture possibly via tubulin aggregation.

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_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
028K1105
014K0758
125K1344
120K1119
098H1166

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Nidhi Aggarwal et al.
Colloids and surfaces. B, Biointerfaces, 105, 158-166 (2013-01-30)
The main objective of the study was to develop a microemulsion (ME) formulation of griseofulvin for the treatment of dermatophytosis (Indian Patent Application 208/DEL/2009). The oil phase was selected on the basis of drug solubility whereas the surfactant and cosurfactant
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
L De Carli et al.
Mutation research, 195(2), 91-126 (1988-03-01)
Griseofulvin (GF) is a mycotoxin produced by various species of Penicillium including P. griseofulvum Dierckx, P. janczewski (P. nigricans) and P. patulum. It is active against dermatophytic fungi of different species in the genera Microsporum, Trychophyton and Epidermophyton. Because of
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
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
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