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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H17ClO6
Molecular Weight 352.766
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GRISEOFULVIN

SMILES

COC1=CC(OC)=C(Cl)C2=C1C(=O)[C@]3(O2)[C@H](C)CC(=O)C=C3OC

InChI

InChIKey=DDUHZTYCFQRHIY-RBHXEPJQSA-N
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

HIDE SMILES / InChI

Description

Griseofulvin is a mycotoxic metabolic product of Penicillium spp. It was the first available oral agent for the treatment of dermatophytoses and has now been used for more than forty years. Griseofulvin is fungistatic with in vitro activity against various species of Microsporum Epidermophyton, and Trichophyton. It has no effect on bacteria or on other genera of fungi. Following oral administration, griseofulvin is deposited in the keratin precursor cells and has a greater affinity for diseased tissue. The drug is tightly bound to the new keratin which becomes highly resistant to fungal invasions. Once the keratin-Griseofulvin complex reaches the skin site of action, it binds to fungal microtubules (tubulin) thus altering fungal mitosis. Griseofulvin is fungistatic, however the exact mechanism by which it inhibits the growth of dermatophytes is not clear. It is thought to inhibit fungal cell mitosis and nuclear acid synthesis. It also binds to and interferes with the function of spindle and cytoplasmic microtubules by binding to alpha and beta tubulin. It binds to keratin in human cells, then once it reaches the fungal site of action, it binds to fungal microtubes thus altering the fungal process of mitosis.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
Kawasaki-like syndrome associated with griseofulvin treatment.
1993 Jul
Serial light and electron microscopic changes in renal glomeruli in mice fed griseofulvin.
1993 May-Jun
Susceptibility to hepatotoxicity in transgenic mice that express a dominant-negative human keratin 18 mutant.
1996 Aug 15
Experimental Mallory body formation is accompanied by modulation of the expression of multidrug-resistance genes and their products.
1996 Jul
Griseofulvin and fluvoxamine interactions with the metabolism of theophylline.
1997 Feb
Regulation of CYP 2 A 5 induction by porphyrinogenic agents in mouse primary hepatocytes.
1997 Jan
Hepatic injury during ketoconazole therapy in patients with onychomycosis: a controlled cohort study.
1997 Jan
Differential xenobiotic induction of CYP2A5 in mouse liver, kidney, lung, and olfactory mucosa.
1998 Aug
Cell wall active antifungal compounds produced by the marine fungus Hypoxylon oceanicum LL-15G256. III. Biological properties of 15G256 gamma.
1998 Mar
Inhibition of PPAR alpha/RXR alpha-mediated direct hyperplasia pathways during griseofulvin-induced hepatocarcinogenesis.
1998 May 1
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Sample Use Guides

In Vivo Use Guide
Adults: Daily administration of 375 mg (as a single dose or in divided doses) will give a satisfactory response in most patients with tinea corporis, tinea cruris, and tinea capitis. For those fungal infections more difficult to eradicate, such as tinea pedis and tinea unguium, a divided dose of 750 mg is recommended. Pediatric Use: Approximately 7.3 mg per kg of body weight per day of ultramicrosize griseofulvin is an effective dose for most pediatric patients. On this basis, the following dosage schedule is suggested: 16-27 kg: 125 mg to 187.5 mg daily. over 27 kg: 187.5 mg to 375 mg daily
Route of Administration: Oral
In Vitro Use Guide
Griseofulvin displayed strong inhibitory effects on the growth of A. solani and S. aureus with MIC of 3.13 uM for each.
Name Type Language
GRISEOFULVIN
EP   GREEN BOOK   HSDB   INN   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
GRISEOFULVIN [HSDB]
Common Name English
SPIRO(BENZOFURAN-2(3H),1'-(2)CYCLOHEXENE)-3,4'-DIONE, 7-CHLORO-2',4,6-TRIMETHOXY-6'-METHYL-, (1'S-TRANS)-
Common Name English
(1'S-TRANS)- 7-CHLORO-2',4,6-TRIMETHOXY-6'-METHYLSPIRO(BENZOFURAN-2(3H),1'-CYCLOHEX-2'-ENE)-3,4'-DIONE
Common Name English
GRISEOFULVIN [MI]
Common Name English
(1'S,6'R)-7-CHLORO-2',4,6-TRIMETHOXY-6'-METHYLSPIRO(BENZOFURAN-2(3H),1'-(2)CYCLOHEXENE)-3,4'-DIONE
Common Name English
GRISEOFULVIN [GREEN BOOK]
Common Name English
GRISEOFULVIN [ORANGE BOOK]
Common Name English
GRISACTIN V
Brand Name English
GRISEOFULVIN [WHO-DD]
Common Name English
GRISEOFULVIN [INN]
Common Name English
GRIS-PEG
Brand Name English
7-CHLORO-2',4,6-TRIMETHOXY-6'.BETA.-METHYLSPIRO(BENZOFURAN-2(3H),1'-(2)CYCLOHEXENE)-3,4'-DIONE
Common Name English
GRISEOFULVIN PERMEABILITY DIAMETER
USP-RS  
Common Name English
GRISEOFULVIN PERMEABILITY DIAMETER [USP-RS]
Common Name English
GRISEOFULVINUM [WHO-IP LATIN]
Common Name English
GRISEOFULVIN [VANDF]
Common Name English
GRISEOFULVIN [MART.]
Common Name English
GRISEOFULVIN [EP]
Common Name English
NSC-34533
Code English
GRISEOFULVIN [USP]
Common Name English
GRISEOFULVIN [WHO-IP]
Common Name English
Classification Tree Code System Code
NDF-RT N0000008732
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
LIVERTOX 471
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
WHO-ATC D01AA08
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
WHO-VATC QD01BA01
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
EPA PESTICIDE CODE 471400
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
WHO-VATC QD01AA08
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
CFR 21 CFR 520.1100
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
WHO-ATC D01BA01
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
NDF-RT N0000175085
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
WHO-ESSENTIAL MEDICINES LIST 6.3
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
NDF-RT N0000175848
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
Code System Code Type Description
RXCUI
91077
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
ALTERNATIVE
NCI_THESAURUS
C65819
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
PRIMARY
WIKIPEDIA
GRISEOFULVIN
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
PRIMARY
INN
875
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
PRIMARY
RXCUI
217398
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
ALTERNATIVE
DRUG BANK
DB00400
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
PRIMARY
CAS
126-07-8
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
PRIMARY
RXCUI
5021
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
PRIMARY
ECHA (EC/EINECS)
204-767-4
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
GRISEOFULVIN
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
PRIMARY Description: White to pale cream powder; almost odourless. Solubility: Very slightly soluble in water; slightly soluble in ethanol (~750 g/l) TS; freely soluble in tetrachloroethane R. Category: Antifungal. Storage: Griseofulvin should be kept in a well-closed container. Additional information: The particles of Griseofulvin are generally up to 5 .MU.m in maximum dimension, although occasionally larger particles may be present that exceed 30 μm.Definition: Griseofulvin contains not less than 97.0% and not more than 102.0% of C17H17ClO6, calculated with reference to the dried substance.
MERCK INDEX
M5854
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
PRIMARY Merck Index
EVMPD
SUB07966MIG
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
PRIMARY
ChEMBL
CHEMBL562
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
PRIMARY
MESH
D006118
Created by admin on Tue Mar 06 16:27:38 UTC 2018 , Edited by admin on Tue Mar 06 16:27:38 UTC 2018
PRIMARY