Griseofulvin

Griseofulvin
Clinical data
Trade names	Gris-peg, Grifulvin V, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682295
Pregnancy; category	AU: D;
Routes of; administration	By mouth
ATC code	D01AA08 (WHO) D01BA01 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	Highly variable (25 to 70%)
Metabolism	Liver (demethylation and glucuronidation)
Elimination half-life	9–21 hours
Identifiers
	IUPAC name (2S,6'R)- 7-chloro- 2',4,6-trimethoxy- 6'-methyl- 3H,4'H-spiro [1-benzofuran- 2,1'-cyclohex[2]ene]- 3,4'-dione;
CAS Number	126-07-8 ;
PubChem CID	441140;
DrugBank	DB00400 ;
ChemSpider	389934 ;
UNII	32HRV3E3D5;
KEGG	D00209 ;
ChEBI	CHEBI:27779 ;
ChEMBL	ChEMBL562 ;
CompTox Dashboard (EPA)	DTXSID8020674 ;
ECHA InfoCard	100.004.335
Chemical and physical data
Formula	C17H17ClO6
Molar mass	352.77 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2c3c(O[C@@]21C(/OC)=C\C(=O)C[C@H]1C)c(Cl)c(OC)cc3OC;
	InChI 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 ; Key:DDUHZTYCFQRHIY-RBHXEPJQSA-N ;
	(verify)

Griseofulvin is an antifungal medication used to treat dermatophytoses (ringworm).^[1]^[2] This includes fungal infections of the nails and scalp, as well as the skin when antifungal creams have not worked.^[3] It is taken by mouth.^[2]

Common side effects include allergic reactions, nausea, diarrhea, headache, trouble sleeping, and feeling tired.^[2] It is not recommended in people with liver failure or porphyria.^[2] Use during or in the months before pregnancy may result in harm to the baby.^[2]^[3] Griseofulvin works by interfering with fungal mitosis.^[1]^[2]

Griseofulvin was discovered in 1939 from the soil fungus Penicillium griseofulvum.^[4]^[5]^[6] It is on the World Health Organization's List of Essential Medicines.^[7]

^ ^a ^b K. Gull, A. P. Trinci (1 August 1973). "Griseofulvin inhibits Fungal Mitosis". Nature. 244 (5414): 292–294. doi:10.1038/244292A0. ISSN 1476-4687. PMID 4583105. Wikidata Q53705508.
^ ^a ^b ^c ^d ^e ^f "Griseofulvin". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
^ ^a ^b World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 149. hdl:10665/44053. ISBN 9789241547659.
^ Block SS (2001). Disinfection, Sterilization, and Preservation. Lippincott Williams & Wilkins. p. 631. ISBN 9780683307405. Archived from the original on 20 December 2016.
^ Ash M, Ash I (2004). Handbook of Preservatives. Synapse Info Resources. p. 406. ISBN 978-1-890595-66-1. Archived from the original on 31 December 2013.
^ Beekman AM, Barrow RA (2014). "Fungal metabolites as pharmaceuticals". Australian Journal of Chemistry. 67 (6): 827–843. doi:10.1071/ch13639.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[gull-1] K. Gull, A. P. Trinci (1 August 1973). "Griseofulvin inhibits Fungal Mitosis". Nature. 244 (5414): 292–294. doi:10.1038/244292A0. ISSN 1476-4687. PMID 4583105. Wikidata Q53705508.

[AHFS2016-2] ^ ^a ^b ^c ^d ^e ^f "Griseofulvin". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.

[WHO2008-3] World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 149. hdl:10665/44053. ISBN 9789241547659.

[4] Block SS (2001). Disinfection, Sterilization, and Preservation. Lippincott Williams & Wilkins. p. 631. ISBN 9780683307405. Archived from the original on 20 December 2016.

[AshAsh2004-5] Ash M, Ash I (2004). Handbook of Preservatives. Synapse Info Resources. p. 406. ISBN 978-1-890595-66-1. Archived from the original on 31 December 2013.

[10.1071/ch13639-6] Beekman AM, Barrow RA (2014). "Fungal metabolites as pharmaceuticals". Australian Journal of Chemistry. 67 (6): 827–843. doi:10.1071/ch13639.

[WHO21st-7] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

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