Griseofulvin

Structural formula
General
Non-proprietary name	Griseofulvin
other names	(2 S , 6 ′ R ) -7-chloro-2 ′, 4,6-trimethoxy-6′-methyl-3 H -spiro [1-benzofuran-2,1′-cyclohexane] -2′-en-3 , 4′-dione;
Molecular formula	C 17 H 17 ClO 6
Brief description	white odorless solid
External identifiers / databases
EC number	204-767-4
ECHA InfoCard	100.004.335
PubChem	441140
ChemSpider	389934
DrugBank	DB00400
Wikidata	Q416096
Drug information
ATC code	D01 AA08 , D01 BA01
Drug class	orally effective antifungal agent
properties
Molar mass	352.77 g mol −1
Physical state	firmly
Melting point	218-220 ° C
solubility	almost insoluble in water (8.64 mg l −1 at 25 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 317-351-360
	P: 201-280-308 + 313
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Griseofulvin is a naturally occurring chemical compound from the group of mold toxins ( mycotoxins ) discovered in 1939 . It is used as a medicinal substance in the treatment of skin infections and fungi and is effective orally .

Occurrence and characteristics

Griseofulvin is secreted by Penicillium griseofulvum and has an antifungal effect on dermatophytes (thread fungi). Against other fungi such as B. mold it is ineffective.

Chemically, griseofulvin is a descendant ( derivative ) of benzofuran .

Mechanism of action

Griseofulvin has an anti- proliferative effect on various cancer cells and inhibits tumor growth in athymic mice . In vitro , the induction of apoptosis in cancer cells is observed, while normal cells are not affected.

unwanted effects

Overdosed griseofulvin can lead to insomnia, dizziness and headache. Also rheumatic side effects have been observed. The effectiveness of other drugs or contraceptives can be reduced (through the induction of various cytochrome P450 isoenzymes).

Trade names

Sanofi: Likuden (D, except trade). Finished preparations are no longer on the market in German-speaking countries.

Individual evidence

↑ ^a ^b Griseofulvin data sheet at AlfaAesar, accessed on March 22, 2010 ( PDF )(JavaScript required) .

↑ Entry on griseofulvin in the ChemIDplus database of the United States National Library of Medicine (NLM) .

↑ ^a ^b Data sheet Griseofulvin from Penicillium griseofulvum at Sigma-Aldrich , accessed on April 3, 2011 ( PDF ).

↑ Karl Wurm, AM Walter: Infectious Diseases. In: Ludwig Heilmeyer (ed.): Textbook of internal medicine. Springer-Verlag, Berlin / Göttingen / Heidelberg 1955; 2nd edition, ibid. 1961, pp. 9–223, here: p. 55.

↑ YH Uen et al .: NF-kappaB pathway is involved in griseofulvin-induced G2 / M arrest and apoptosis in HL-60 cells. In: J Cell Biochem 101, 2007, pp. 1165-1175, PMID 17226769 .

↑ B. Rebacz et al .: Identification of griseofulvin as an inhibitor of centrosomal clustering in a phenotype-based screen. In: Cancer Res 67, 2007, pp. 6342-6350, PMID 17616693 .

↑ YS Ho et al: Griseofulvin potentiates antitumorigenesis effects of nocodazole through induction of apoptosis and G2 / M cell cycle arrest in human colorectal cancer cells. In: Int J Cancer 91, 2001, pp. 393-401, PMID 11169965 .

↑ D. Panda et al .: Kinetic suppression of microtubule dynamic instability by griseofulvin: implications for its possible use in the treatment of cancer. In: PNAS 102, 2005, pp. 9878-9883, PMID 15985553 ; PMC 1174985 (free full text).

↑ P. Singh et al.: Microtubule assembly dynamics: An attractive target for anticancer drugs. In: IUBMB Life 60, 2008, pp. 368-375, PMID 18384115 .

↑ K. Rathinasamy et al .: Griseofulvin stabilizes microtubule dynamics, activates p53 and inhibits the proliferation of MCF-7 cells synergistically with vinblastine. (PDF; 1.7 MB) In: BMC Cancer 10, 2010, 213, doi : 10.1186 / 1471-2407-10-213 .

↑ Torsten Kratz, Albert Diefenbacher: Psychopharmacotherapy in old age. Avoidance of drug interactions and polypharmacy. In: Deutsches Ärzteblatt. Volume 116, Issue 29 f. (July 22) 2019, pp. 508-517, p. 510.

↑ Likuden M 500 mg - patient information, description, dosage and directions. Retrieved June 19, 2018 .

[alfa-1] Griseofulvin data sheet at AlfaAesar, accessed on March 22, 2010 ( PDF )(JavaScript required) .

[2] Entry on griseofulvin in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[Sigma-3] Data sheet Griseofulvin from Penicillium griseofulvum at Sigma-Aldrich , accessed on April 3, 2011 ( PDF ).

[4] Karl Wurm, AM Walter: Infectious Diseases. In: Ludwig Heilmeyer (ed.): Textbook of internal medicine. Springer-Verlag, Berlin / Göttingen / Heidelberg 1955; 2nd edition, ibid. 1961, pp. 9–223, here: p. 55.

[5] YH Uen et al .: NF-kappaB pathway is involved in griseofulvin-induced G2 / M arrest and apoptosis in HL-60 cells. In: J Cell Biochem 101, 2007, pp. 1165-1175, PMID 17226769 .

[6] B. Rebacz et al .: Identification of griseofulvin as an inhibitor of centrosomal clustering in a phenotype-based screen. In: Cancer Res 67, 2007, pp. 6342-6350, PMID 17616693 .

[7] YS Ho et al: Griseofulvin potentiates antitumorigenesis effects of nocodazole through induction of apoptosis and G2 / M cell cycle arrest in human colorectal cancer cells. In: Int J Cancer 91, 2001, pp. 393-401, PMID 11169965 .

[8] D. Panda et al .: Kinetic suppression of microtubule dynamic instability by griseofulvin: implications for its possible use in the treatment of cancer. In: PNAS 102, 2005, pp. 9878-9883, PMID 15985553 ; PMC 1174985 (free full text).

[9] P. Singh et al.: Microtubule assembly dynamics: An attractive target for anticancer drugs. In: IUBMB Life 60, 2008, pp. 368-375, PMID 18384115 .

[10] K. Rathinasamy et al .: Griseofulvin stabilizes microtubule dynamics, activates p53 and inhibits the proliferation of MCF-7 cells synergistically with vinblastine. (PDF; 1.7 MB) In: BMC Cancer 10, 2010, 213, doi : 10.1186 / 1471-2407-10-213 .

[11] Torsten Kratz, Albert Diefenbacher: Psychopharmacotherapy in old age. Avoidance of drug interactions and polypharmacy. In: Deutsches Ärzteblatt. Volume 116, Issue 29 f. (July 22) 2019, pp. 508-517, p. 510.

[12] Likuden M 500 mg - patient information, description, dosage and directions. Retrieved June 19, 2018 .