GRISEOFULVIN

First approved in 1959

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 Search

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

Molecular Formula	C17H17ClO6
Molecular Weight	352.766
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.drugbank.ca/drugs/DB00400
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050475s057lbl.pdf

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

Targets

Primary Target	Pharmacology	Condition	Potency
Candida albicans growth 2 Target ID: Candida albicans growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/26900659	Inhibitor 8504
Aspergillus fumigatus growth 1 Target ID: Aspergillus fumigatus growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/26900659	Inhibitor 8504
Fungi growth 1 Target ID: Fungi growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/26369643	Inhibitor 8504
Tubulin alpha chain 3 Target ID: P87066 Gene ID: NA Gene Symbol: TUB1 Target Organism: Candida albicans (Yeast) Sources: http://www.drugbank.ca/drugs/DB00400	Inhibitor 8504
Staphylococcus aureus growth 27 Target ID: Staphylococcus aureus growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/25103127	Inhibitor 8504
Tubulin beta chain 8 Target ID: P10875 Gene ID: NA Gene Symbol: TUB2 Target Organism: Candida albicans (Yeast) Sources: http://www.drugbank.ca/drugs/DB00400	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dermatophyte infection 18 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050475s057lbl.pdf	Curative		Approved 8583	GRIS-PEG Approved Use Gris-PEG® (griseofulvin ultramicrosize) is indicated for the treatment of the following ringworm infections; tinea corporis (ringworm of the body), tinea pedis (athlete’s foot), tinea cruris (ringworm of the groin and thigh), tinea barbae (barber’s itch), tinea capitis (ringworm of the scalp), and tinea unguium (onychomycosis, ringworm of the nails), when caused by one or more of the following genera of fungi: Trichophyton rubrum, Trichophyton tonsurans, Trichophyton mentagrophytes, Trichophyton interdigitalis,Trichophyton verrucosum, Trichophyton megnini, Trichophyton gallinae, Trichophyton crateriform, Trichophyton sulphureum, Trichophyton schoenleini, Microsporum audouini, Microsporum canis, Microsporum gypseum and Epidermophyton floccosum Launch Date 1975

C_max

Value	Dose	Analyte	Population
1.25 μg/mL EXPERIMENT https://link.springer.com/article/10.1007/BF00547378	330 mg single, oral dose: 330 mg route of administration: Oral experiment type: SINGLE co-administered:	GRISEOFULVIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
1.39 μg/mL EXPERIMENT https://link.springer.com/article/10.1007/BF00547378	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	GRISEOFULVIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
600.61 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050475s057lbl.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	GRISEOFULVIN unknown	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: FASTED
629.77 ng/mL REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/065200_ORIGINAL%20APPROVAL_PACKAGE.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	GRISEOFULVIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1310.28 ng/mL REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/065200_ORIGINAL%20APPROVAL_PACKAGE.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	GRISEOFULVIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Analyte	Population
21.1 μg × h/mL EXPERIMENT https://link.springer.com/article/10.1007/BF00547378	330 mg single, oral dose: 330 mg route of administration: Oral experiment type: SINGLE co-administered:	GRISEOFULVIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
25.9 ng × h/mL EXPERIMENT https://link.springer.com/article/10.1007/BF00547378	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	GRISEOFULVIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
8618.89 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050475s057lbl.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	GRISEOFULVIN unknown	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: FASTED
18827.7 ng × h/mL REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/065200_ORIGINAL%20APPROVAL_PACKAGE.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	GRISEOFULVIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
20735.2 ng × h/mL REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/065200_ORIGINAL%20APPROVAL_PACKAGE.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	GRISEOFULVIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
10.3 h EXPERIMENT https://link.springer.com/article/10.1007/BF00547378	330 mg single, oral dose: 330 mg route of administration: Oral experiment type: SINGLE co-administered:	GRISEOFULVIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
10.7 h EXPERIMENT https://link.springer.com/article/10.1007/BF00547378	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	GRISEOFULVIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
10.716 h REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/065200_ORIGINAL%20APPROVAL_PACKAGE.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	GRISEOFULVIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
9.043 h REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/065200_ORIGINAL%20APPROVAL_PACKAGE.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	GRISEOFULVIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
16% EXPERIMENT https://link.springer.com/article/10.1007/BF00547378	330 mg single, oral dose: 330 mg route of administration: Oral experiment type: SINGLE co-administered:		GRISEOFULVIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP1A2 832 CYP2C 17 CYP2D 1 CYP3A 142

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inducer 1966 Sources: https://doi.org/10.1080/10837450902891550 Page: 12.0	yes
CYP2C 37	inducer 1966 Sources: https://journals.sagepub.com/doi/pdf/10.1177/030006059902700402#page=7 Page: 7.0	yes
CYP2D 4	inducer 1966 Sources: https://journals.sagepub.com/doi/pdf/10.1177/030006059902700402#page=7 Page: 7.0	yes
CYP3A 317	inducer 1966 Sources: https://journals.sagepub.com/doi/pdf/10.1177/030006059902700402#page=7 Page: 7.0	yes

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B1-01417	http://www.3bsc.com/index/pro_info.php?id=21629
3B Scientific (Wuhan) Corp	3B2-0216	http://www.3bsc.com/index/pro_info.php?id=19572
abcr GmbH	AB131510	http://www.abcr.com/shop/en/AB131510
AbMole Bioscience	M2726	http://www.abmole.com/products/griseofulvin.html
Aceschem	ACS011873	https://www.aceschem.com/catalog/126-07-8.html
Achemtek	0104-001166	http://www.achemtek.com/126-07-8
Acorn PharmaTech	ACN-048200	http://www.acornpharmatech.com/
Acros Organics	AC227450050	https://www.fishersci.com/shop/products/griseofulvin-97-acros-organics/AC227450050
Acros Organics	AC227451000	https://www.fishersci.com/shop/products/griseofulvin-97-acros-organics/AC227451000
AHH Chemical co.,ltd	API-1202	http://www.ahhchemical.com/product/API-1202.html
AK Scientific, Inc. (AKSCI)	J10209	http://www.aksci.com/item_detail.php?cat=J10209
AK Scientific, Inc. (AKSCI)	M542	http://www.aksci.com/item_detail.php?cat=M542
Alfa Aesar	B23521	https://www.alfa.com/en/catalog/B23521/
ApexBio Technology	B3680	http://www.apexbt.com/griseofulvin.html
Aurum Pharmatech LLC	NE11198	http://www.Aurumpharmatech.com/Product/ProductDetails/NE11198
AvaChem Scientific	6370	https://www.avachem.com/productSearch.asp?6370
Avantor Inc	101095-098	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101095-098
BioSynth	Q-201178	https://www.biosynth.com/en/products/life-science/culture-media-additives/products/Q-201178.html
BLD Pharm	BD132396	http://www.bldpharm.com/products/126-07-8.html
Capot Chemical	17619	http://www.capotchem.com/en/17619.htm
Capot Chemical	PubChem17619	http://www.capotchem.com/en/17619.htm
Chem Scene	CS-3426	http://www.chemscene.com/126-07-8.html
Chemenu	CM110396	http://www.chemenu.com/products/CM110396
Chemspace	CSSB00000743911	https://chem-space.com/CSSB00000743911
China MainChem Co., Ltd	126-07-8	https://www.mainchem.com/product/china-griseofulvin-cas-126-07-8-supplier/
Chiralblock Biosciences	CB11571	http://www.chiralblock.com/products/126-07-8.html
Clearsynth	CS-O-30933	http://www.clearsynth.com/en/CSO30933.html
CSNpharm	CSN11119	https://www.csnpharm.com/products/(+)-griseofulvin.html
Enamine	Z1258578352	https://www.enaminestore.com/catalog/Z1258578352
eNovation Chemicals	D544999	http://www.enovationchem.com/productDetails.asp?productID=D544999
Glentham Life Sciences	GA6599	http://www.glentham.com/products/product/GA6599/
iChemical	EBD2197944	http://www.ichemical.com/products/126-07-8.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00839705	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00839705
LGC Standards	DRE-C14056500	https://www.lgcstandards.com/US/en/p/DRE-C14056500
LGC Standards	LGCFOR0582.00	https://www.lgcstandards.com/US/en/p/LGCFOR0582.00
LGC Standards	MM0582.00	https://www.lgcstandards.com/US/en/p/MM0582.00
mcule	MCULE-1983595404	https://mcule.com/MCULE-1983595404/
MedChem Express	HY-17583	https://www.medchemexpress.com/Griseofulvin.html
MuseChem	A000742	https://www.musechem.com/product/A000742.html
Otava	15386069	https://search.otavachemicals.com/#!/search?query=15386069&type=code&base=dbb
R&D Chemicals	8504	http://www.rdchemicals.com/chemicals.php?mode=details&mol_id=7866
Sigma-Aldrich	1299007_USP	https://www.sigmaaldrich.com/catalog/product/usp/1299007?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1299200_USP	https://www.sigmaaldrich.com/catalog/product/usp/1299200?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	46309_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/46309?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	BP180_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/bp180?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	G0600000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/g0600000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S529241	http://www.smolecule.com/products/s529241
Smolecule	S752225	https://www.smolecule.com/products/s752225
TCI (Tokyo Chemical Industry)	G0384	http://www.tcichemicals.com/eshop/en/us/commodity/G0384/index.html
THE BioTek	bt-269850	https://www.thebiotek.com/product/inhibitors/bt-269850
VladaChem	VL279919-25G	https://www.vladachem.com/product.php?products=126-07-8
VladaChem	VL282011-25G	https://www.vladachem.com/product.php?products=126-07-8

PubMed

Title	Date	PubMed
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015-05-18	25811541
Complexity generation in fungal polyketide biosynthesis: a spirocycle-forming P450 in the concise pathway to the antifungal drug griseofulvin.	2013-10-18	23978092
The anti-mitotic drug griseofulvin induces apoptosis of human germ cell tumor cells through a connexin 43-dependent molecular mechanism.	2013-04	23329179
An efficient domino reaction in ionic liquid: synthesis and biological evaluation of some pyrano- and thiopyrano-fused heterocycles.	2013-03-15	23414843
Synthesis and characterization of some new quinoline based derivatives endowed with broad spectrum antimicrobial potency.	2012-11-15	23058887
Green synthesis and anti-infective activities of fluorinated pyrazoline derivatives.	2012-09-01	22832312
Novel insights into changes in biochemical properties of keratins 8 and 18 in griseofulvin-induced toxic liver injury.	2010-10	20643122
Synthesis and the selective antifungal activity of 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine derivatives.	2010-05	20106559
Synthesis, in vitro antibacterial and antifungal evaluations of new alpha-hydroxyphosphonate and new alpha-acetoxyphosphonate derivatives of tetrazolo [1, 5-a] quinoline.	2010-03	20036039
Tinea capitis: diagnostic criteria and treatment options.	2009-10-31	19873694
Tinea capitis: diagnostic criteria and treatment options.	2009-04-22	19378575
Epidermal growth factor receptor ligands in murine models for erythropoietic protoporphyria: potential novel players in the progression of liver injury.	2009-02-16	19267999
Manifestation of psychiatric behaviors in a mouse model of griseofulvin-induced hepatic porphyria.	2008-12	19043281
A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine.	2008-08	18505790
[Antimycotic therapy of Tinea pedis and other foot mycoses].	2008-07	18808073
Synthesis and biological activity of peptide derivatives of iodoquinazolinones/nitroimidazoles.	2008-04-24	18463598
Differential xenobiotic induction of CYP2A5 in mouse liver, kidney, lung, and olfactory mucosa.	1998-08	9698299
Inhibition of PPAR alpha/RXR alpha-mediated direct hyperplasia pathways during griseofulvin-induced hepatocarcinogenesis.	1998-05-01	9548566
Cell wall active antifungal compounds produced by the marine fungus Hypoxylon oceanicum LL-15G256. III. Biological properties of 15G256 gamma.	1998-03	9589067
Griseofulvin and fluvoxamine interactions with the metabolism of theophylline.	1997-02	9029748
Regulation of CYP 2 A 5 induction by porphyrinogenic agents in mouse primary hepatocytes.	1997-01	9007836
Hepatic injury during ketoconazole therapy in patients with onychomycosis: a controlled cohort study.	1997-01	8985273
Susceptibility to hepatotoxicity in transgenic mice that express a dominant-negative human keratin 18 mutant.	1996-08-15	8770877
Experimental Mallory body formation is accompanied by modulation of the expression of multidrug-resistance genes and their products.	1996-07	8707270
Myositis associated with griseofulvin therapy.	1995-10	7572547
Nephrotic syndrome related to systemic lupus erythematosus after griseofulvin therapy.	1995-08	7577414
Up-regulation of CYP2A5 expression by porphyrinogenic agents in mouse liver.	1995-04	7543189
An unusual case of severe griseofulvin-alcohol interaction.	1994-07	8010556
A double blind study of itraconazole vs griseofulvin in patients with tinea pedis and tinea manus.	1994-04-13	8145958
Proximal myopathy associated with griseofulvin therapy.	1994-01	7836265
Disturbance of keratin homeostasis in griseofulvin-intoxicated mouse liver.	1993-11	7504119
Kawasaki-like syndrome associated with griseofulvin treatment.	1993-07	8403486
Serial light and electron microscopic changes in renal glomeruli in mice fed griseofulvin.	1993-05-01	8323253
Isolated erythroid hypoplasia and renal insufficiency induced by long-term griseofulvin therapy.	1990-11	2237566
[A case of mixed connective tissue disease exacerbated by griseofulvin complicating aseptic meningo-encephalitis and disseminated intravascular coagulation].	1990-10	2084866
Griseofulvin-induced neuropathy.	1990-01-27	1967699
Changes in the cytokeratin intermediate filament cytoskeleton associated with Mallory body formation in mouse and human liver.	1987-11-01	2445643
Screening for new compounds with antiherpes activity.	1984-10	6517562
Mallory body formation runs parallel to gamma-glutamyl transferase induction in hepatocytes of griseofulvin-fed mice.	1983-11-01	6138303
Bile secretion and liver microsomal mixed function oxidase system in mice with griseofulvin-induced hepatic protoporphyria.	1983-05	6679936
[Hepatoma after long-term administration of griseofulvin].	1981-05	7285200
Effect of Griseofulvin on 5-aminolevulinate synthase and on ferrochelatase in mouse liver neoplastic nodules.	1981-04	7214331
Thyroid tumours in rats and hepatomas in mice after griseofulvin treatment.	1978-08	698038
[Case of epilepsy caused by griseofulvin].	1977-10	595848
[Central nervous symptoms as side effects of mycosis treatment with griseofulvin].	1974-10-30	4424881
Letter: Psychotic symptoms with griseofulvin.	1974-09-09	4408278
[Studies in 25 patients with progressive systemic scleroderma treated by long-term administration of griseofulvin].	1973-06-20	4579328
Skin temperature changes in Raynaud's disease after griseofulvin.	1970-03	5414890
[Teratogenic effect of griseofulvin-forte on rat fetus].	1969-01	5768794
Hepatocarcinogenicity of griseofulvin following parenteral administration to infant mice.	1967-10	4294321

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:45:23 GMT 2025` Edited by `admin` on `Mon Mar 31 17:45:23 GMT 2025`
Record UNII	32HRV3E3D5
Record Status	`Validated (UNII)`
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Related Record	Type

Name

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GRISEOFULVIN

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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

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GRISEOFULVIN [MI]

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(1'S,6'R)-7-CHLORO-2',4,6-TRIMETHOXY-6'-METHYLSPIRO(BENZOFURAN-2(3H),1'-(2)CYCLOHEXENE)-3,4'-DIONE

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7-CHLORO-2',4,6-TRIMETHOXY-6'.BETA.-METHYLSPIRO(BENZOFURAN-2(3H),1'-(2)CYCLOHEXENE)-3,4'-DIONE

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GRISEOFULVINUM [WHO-IP LATIN]

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GRISEOFULVIN [WHO-IP]

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Classification Tree Code System Code

NCI_THESAURUS

C514