Griseofulvin

Identification

Summary

Griseofulvin is an antifungal agent used to treat a variety of superficial tinea infections and fungal infections of the fingernails and toes.

Brand Names
Gris-peg
Generic Name
Griseofulvin
DrugBank Accession Number
DB00400
Background

An antifungal antibiotic. Griseofulvin may be given by mouth in the treatment of tinea infections.

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Weight
Average: 352.766
Monoisotopic: 352.071365983
Chemical Formula
C17H17ClO6
Synonyms
  • (+)-griseofulvin
  • Amudane
  • Griseofulvin
  • Griseofulvin, microcrystalline
  • Griseofulvin, ultramicrosize
  • Griseofulvina
  • Griséofulvine
  • Griseofulvinum

Pharmacology

Indication

For the treatment of ringworm infections of the skin, hair, and nails, namely: tinea corporis, tinea pedis, tinea cruris, tinea barbae, cradle cap or other conditions caused by Trichophyton or Microsporum fungi.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofTinea capitis••••••••••••••••••••••• ••••••
Treatment ofTinea corporis••••••••••••••••••••••• ••••••
Treatment ofTinea cruris••••••••••••••••••••••• ••••••
Treatment ofTinea pedis••••••••••••••••••••••• ••••••
Treatment ofTinea unguium••••••••••••••••••••••• ••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

Mechanism of action

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.

TargetActionsOrganism
ATubulin beta chain
inhibitor
Trichophyton rubrum
UKeratin, type I cytoskeletal 12
other/unknown
Humans
Absorption

Poorly absorbed from GI ranging from 25 to 70% of an oral dose. Absorption is significantly enhanced by administration with or after a fatty meal.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Primarily hepatic with major metabolites being 6-methyl-griseofulvin and its glucuronide conjugate.

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

9-21 hours

Clearance

Not Available

Adverse Effects
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Toxicity

Side effects are minor: headaches, gastrointestinal reactions and cutaneous eruptions.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Griseofulvin.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Griseofulvin.
AcenocoumarolThe metabolism of Acenocoumarol can be increased when combined with Griseofulvin.
AlbendazoleThe metabolism of Albendazole can be increased when combined with Griseofulvin.
AlectinibThe metabolism of Alectinib can be increased when combined with Griseofulvin.
Food Interactions
  • Avoid alcohol.
  • Take with a high fat meal.

Products

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Product Images
International/Other Brands
Crivicin / Curling factor / Fulcin (Cepharma) / Fulvicin (Schering-Plough) / Grifulvin (McNeil) / Grisactin / Grison-250 / Grisovin (Fujisawa) / Lamoryl (Lovens) / Likuden (Sanofi) / Poncyl (Takeda) / S-Fulvin / Spirofulvin / Sporostatin (Schering)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Fulvicin Pg Tab 330mgTablet330 mg / tabOralSchering Plough1982-12-311998-11-17Canada flag
Fulvicin U/f Tab 250mgTablet250 mgOralSchering Plough1966-12-312004-07-21Canada flag
Fulvicin Uf Tab 500mgTablet500 mgOralSchering Plough1966-12-312004-07-21Canada flag
Gris-PEGTablet, film coated250 mg/1OralRemedy Repack2012-08-072013-09-04US flag
Gris-PEGTablet, film coated125 mg/1OralPedinol Pharmacal, Inc.2016-07-26Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Grifulvin VTablet500 mg/1OralPhysicians Total Care, Inc.2005-09-012011-06-30US flag
Grifulvin VTablet500 mg/1OralOrtho Mc Neil Pharmaceuticals1980-06-022014-05-31US flag
Griseofulviin (microsize)Suspension125 mg/5mLOralRebel Distributors2007-07-26Not applicableUS flag
GriseofulvinSuspension125 mg/5mLOralActavis Pharma, Inc.2007-07-26Not applicableUS flag
GriseofulvinSuspension125 mg/5mLOralCosette Pharmaceuticals, Inc.2022-11-01Not applicableUS flag

Categories

ATC Codes
D01BA01 — GriseofulvinD01AA08 — Griseofulvin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzofurans
Sub Class
Not Available
Direct Parent
Benzofurans
Alternative Parents
Coumarans / Aryl alkyl ketones / Anisoles / Cyclohexenones / Alkyl aryl ethers / Aryl chlorides / Vinylogous esters / Oxacyclic compounds / Organochlorides / Organic oxides
show 1 more
Substituents
Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl chloride / Aryl halide / Aryl ketone / Benzenoid / Benzofuran / Carbonyl group
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
antibiotic antifungal drug, organochlorine compound, 1-benzofurans, oxaspiro compound, benzofuran antifungal drug (CHEBI:27779) / Other Polyketides, Dibenzofurans, griseofulvins, dibenzopyrans and xanthones, Antibiotic fungicides (C06686) / Dibenzofurans, griseofulvins, dibenzopyrans and xanthones (LMPK13060001)
Affected organisms
  • Yeast and other Trichophyton or Microsporum fungi
  • Dermatophytic fungi including Trichophyton, Microsporum and Epidermophyton

Chemical Identifiers

UNII
32HRV3E3D5
CAS number
126-07-8
InChI Key
DDUHZTYCFQRHIY-RBHXEPJQSA-N
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
IUPAC Name
(2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione
SMILES
COC1=CC(OC)=C(Cl)C2=C1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1OC

References

Synthesis Reference

Gary Liversidge, "Methods of making and using novel griseofulvin compositions." U.S. Patent US20070098805, issued May 03, 2007.

US20070098805
General References
  1. FDA Approved Drug Products: Gris-Peg (ultramicrosize griseofulvin) tablets for oral use [Link]
Human Metabolome Database
HMDB0014544
KEGG Drug
D00209
KEGG Compound
C06686
PubChem Compound
441140
PubChem Substance
46508437
ChemSpider
389934
BindingDB
31775
RxNav
5021
ChEBI
27779
ChEMBL
CHEMBL562
ZINC
ZINC000000622123
Therapeutic Targets Database
DAP000539
PharmGKB
PA449814
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Griseofulvin
FDA label
Download (131 KB)
MSDS
Download (75.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentTinea Capitis1
1CompletedNot AvailableHealthy Volunteers (HV)2
1CompletedTreatmentAntifungal Agents1
1CompletedTreatmentDiabetes / Healthy Volunteers (HV)1
Not AvailableCompletedTreatmentTinea Capitis1

Pharmacoeconomics

Manufacturers
  • Wyeth ayerst laboratories
  • Johnson and johnson consumer companies inc
  • Orthoneutrogena
  • Actavis mid atlantic llc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Perrigo co tennessee inc
  • Elorac inc
  • Johnson and johnson consumer products inc
  • Schering corp sub schering plough corp
  • Pedinol pharmacal inc
  • Pliva inc
Packagers
  • Actavis Group
  • Amerisource Health Services Corp.
  • Cipla Ltd.
  • Dept Health Central Pharmacy
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Novartis AG
  • Nucare Pharmaceuticals Inc.
  • Ortho Mcneil Janssen Pharmaceutical Inc.
  • Ortho-McNeil-Janssen Pharmaceuticals Inc.
  • Patriot Pharmaceuticals
  • PD-Rx Pharmaceuticals Inc.
  • PEDiNOL
  • Perrigo Co.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Pliva Inc.
  • Remedy Repack
  • Teva Pharmaceutical Industries Ltd.
Dosage Forms
FormRouteStrength
TabletOral330 mg / tab
Tablet, film coatedOral500 MG
TabletOral500 mg/1
Tablet, film coatedOral125 mg/1
Tablet, film coatedOral250 mg/1
PowderNot applicable1 g/1g
SuspensionOral125 mg/5mL
TabletOral125 mg/1
TabletOral250 mg/1
TabletOral125 mg / tab
TabletOral250 mg / tab
TabletOral500 mg / tab
Tablet, film coatedOral500.00 mg
TabletOral500 MG
TabletOral
Tablet, coatedOral125 mg/1
Tablet, coatedOral250 mg/1
Tablet, coatedOral500 mg
TabletOral250 mg
TabletOral125 mg
Prices
Unit descriptionCostUnit
Griseofulvin Microsize 125 mg/5ml Suspension 120ml Bottle43.0USD bottle
Grifulvin v 500 mg tablet4.78USD tablet
Gris-peg 250 mg tablet2.75USD tablet
Gris-peg 125 mg tablet2.24USD tablet
Griseofulvin powder2.2USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)220 °CPhysProp
water solubility8.64 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.18HANSCH,C ET AL. (1995)
logS-4.61ADME Research, USCD
Caco2 permeability-4.44ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.0504 mg/mLALOGPS
logP2.71ALOGPS
logP2.17Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)19.62Chemaxon
pKa (Strongest Basic)-4.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area71.06 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity87.85 m3·mol-1Chemaxon
Polarizability34.25 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9208
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.612
P-glycoprotein inhibitor IInhibitor0.8183
P-glycoprotein inhibitor IIInhibitor0.5133
Renal organic cation transporterNon-inhibitor0.882
CYP450 2C9 substrateNon-substrate0.7921
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateSubstrate0.6249
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.7043
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8235
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.8544
BiodegradationNot ready biodegradable0.9964
Rat acute toxicity1.5788 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.938
hERG inhibition (predictor II)Non-inhibitor0.8869
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-05i1-9208000000-bc69e8498dfe1365cbf9
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0uxr-0589000000-f8705acff560aebbf057
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0uxr-0469000000-196c982b619369269fc4
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-014i-2960000000-3f14b9f983cc6e713b6a
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-014r-0291000000-6f003312919e202ee091
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0uxr-0589000000-f8705acff560aebbf057
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0uxr-0469000000-196c982b619369269fc4
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-2960000000-3f14b9f983cc6e713b6a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-8670d53cc318081e77cb
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-764e5f43756b438cdbef
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0094000000-080d99d59e3bd1a4af44
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uxr-2159000000-af51645de3a3776ffb9c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-8559000000-052a71f9375161fe3f53
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-7193000000-b825643f74625eaa197f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-189.3693133
predicted
DarkChem Lite v0.1.0
[M-H]-188.9972133
predicted
DarkChem Lite v0.1.0
[M-H]-188.5803133
predicted
DarkChem Lite v0.1.0
[M-H]-177.21696
predicted
DeepCCS 1.0 (2019)
[M+H]+189.9297133
predicted
DarkChem Lite v0.1.0
[M+H]+190.2279133
predicted
DarkChem Lite v0.1.0
[M+H]+189.1893133
predicted
DarkChem Lite v0.1.0
[M+H]+179.61253
predicted
DeepCCS 1.0 (2019)
[M+Na]+189.1258133
predicted
DarkChem Lite v0.1.0
[M+Na]+189.3465133
predicted
DarkChem Lite v0.1.0
[M+Na]+188.9343133
predicted
DarkChem Lite v0.1.0
[M+Na]+185.75139
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Trichophyton rubrum
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Trichophyton rubrum has been chosen as a representative organism susceptible to griseofulvin. It is also active against several other types of dermatophytic fungi, including Trichophyton and Microsporum spp.
General Function
Tubulin is the major constituent of microtubules, a cylinder consisting of laterally associated linear protofilaments composed of alpha- and beta-tubulin heterodimers. Microtubules grow by the addition of GTP-tubulin dimers to the microtubule end, where a stabilizing cap forms. Below the cap, tubulin dimers are in GDP-bound state, owing to GTPase activity of alpha-tubulin.
Specific Function
Gtp binding
Gene Name
Not Available
Uniprot ID
Q5UBX3
Uniprot Name
Tubulin beta chain
Molecular Weight
49669.63 Da
References
  1. S Al-Janabi AAH, Matrood Bashi A: Synthesis and antifungal activity of novel griseofulvin nanoparticles with zinc oxide against dermatophytic fungi: Trichophyton mentagrophytes and Trichophyton verrucosum: A primary study. Curr Med Mycol. 2022 Jun;8(2):40-44. doi: 10.18502/cmm.8.2.10331. [Article]
  2. FDA Approved Drug Products: Gris-Peg (ultramicrosize griseofulvin) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Other/unknown
General Function
Structural molecule activity
Specific Function
May play a unique role in maintaining the normal corneal epithelial function. Together with KRT3, essential for the maintenance of corneal epithelium integrity (By similarity).
Gene Name
KRT12
Uniprot ID
Q99456
Uniprot Name
Keratin, type I cytoskeletal 12
Molecular Weight
53510.935 Da
References
  1. Nakamichi I, Hatakeyama S, Nakayama KI: Formation of Mallory body-like inclusions and cell death induced by deregulated expression of keratin 18. Mol Biol Cell. 2002 Oct;13(10):3441-51. [Article]
  2. Sobue S, Sekiguchi K, Nabeshima T: Intracutaneous distributions of fluconazole, itraconazole, and griseofulvin in Guinea pigs and binding to human stratum corneum. Antimicrob Agents Chemother. 2004 Jan;48(1):216-23. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Rasmussen BB, Jeppesen U, Gaist D, Brosen K: Griseofulvin and fluvoxamine interactions with the metabolism of theophylline. Ther Drug Monit. 1997 Feb;19(1):56-62. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Yasuda K, Ranade A, Venkataramanan R, Strom S, Chupka J, Ekins S, Schuetz E, Bachmann K: A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine. Drug Metab Dispos. 2008 Aug;36(8):1689-97. doi: 10.1124/dmd.108.020701. Epub 2008 May 27. [Article]
  2. Griseofulvin drug summary [Link]

Drug created at June 13, 2005 13:24 / Updated at March 03, 2024 02:25