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Identification
NameGriseofulvin
Accession NumberDB00400  (APRD01004)
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

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

Structure
Thumb
Synonyms
(+)-griseofulvin
Amudane
Curling factor
Fulcin
Fulvicin
Grifulvin
Grisactin
Griseofulvin
Griseofulvin, microcrystalline
Griseofulvin, ultramicrosize
Griseofulvina
Griseofulvine
Griseofulvinum
Grisovin
Grysio
Lamoryl
Likuden
Poncyl
Spirofulvin
Sporostatin
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fulvicin Pg Tab 330mgtablet330 mgoralSchering Plough Canada Inc1982-12-311998-11-17Canada
Fulvicin U/f Tab 250mgtablet250 mgoralSchering Plough Canada Inc1966-12-312004-07-21Canada
Fulvicin Uf Tab 500mgtablet500 mgoralSchering Plough Canada Inc1966-12-312004-07-21Canada
Gris-pegtablet, film coated125 mg/1oralPEDINOL PHARMACAL INC.1975-04-16Not applicableUs
Gris-pegtablet, film coated250 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Gris-pegtablet, film coated250 mg/1oralREMEDYREPACK INC.2013-02-22Not applicableUs
Gris-pegtablet, film coated250 mg/1oralPEDINOL PHARMACAL INC.1975-04-16Not applicableUs
Griseofulvintablet, film coated250 mg/1oralOceanside Pharmaceuticals2012-12-03Not applicableUs
Griseofulvintablet, film coated125 mg/1oralOceanside Pharmaceuticals2012-12-03Not applicableUs
Grisovin Fp Tab 125mgtablet125 mgoralGlaxo Canada Inc1964-12-311996-09-10Canada
Grisovin Fp Tab 250mgtablet250 mgoralGlaxo Canada Inc1962-12-311996-09-10Canada
Grisovin Fp Tab 500mgtablet500 mgoralGlaxo Canada Inc1967-12-311996-09-10Canada
Grisovin-FP 125mg Tabtablet125 mgoralRoberts Pharmaceutical Canada Inc.1995-12-311997-04-14Canada
Grisovin-FP 250mg Tabtablet250 mgoralRoberts Pharmaceutical Canada Inc.1996-07-301999-08-11Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Griseofulviin (microsize)suspension125 mg/5mLoralRebel Distributors Corp2007-07-26Not applicableUs
Griseofulvintablet125 mg/1oralRising Pharmaceuticals, Inc2012-10-23Not applicableUs
Griseofulvinsuspension125 mg/5mLoralTeva Pharmaceuticals USA Inc2008-02-12Not applicableUs
Griseofulvinsuspension125 mg/5mLoralPerrigo New York Inc2008-07-16Not applicableUs
Griseofulvintablet500 mg/1oralRising Pharmaceuticals Inc.2012-10-23Not applicableUs
Griseofulvintablet500 mg/1oralSandoz Inc2013-08-07Not applicableUs
Griseofulvintablet250 mg/1oralSandoz Inc2013-08-07Not applicableUs
Griseofulvinsuspension125 mg/5mLoralPhysicians Total Care, Inc.2006-01-16Not applicableUs
Griseofulvinsuspension125 mg/5mLoralQualitest Pharmaceuticals2010-10-08Not applicableUs
Griseofulvintablet250 mg/1oralRising Pharmaceuticals, Inc2012-10-23Not applicableUs
Griseofulvinsuspension125 mg/5mLoralActavis Mid Atlantic LLC2007-07-26Not applicableUs
Ultramicrosize Griseofulvintablet, coated250 mg/1oralCore Pharma, Llc2014-09-29Not applicableUs
Ultramicrosize Griseofulvintablet, coated125 mg/1oralCore Pharma, Llc2014-09-29Not applicableUs
Ultramicrosize Griseofulvintablet, coated250 mg/1oralRicon Pharma Llc.2014-01-09Not applicableUs
Ultramicrosize Griseofulvintablet, coated125 mg/1oralRicon Pharma Llc.2014-01-09Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CrivicinNot Available
FulcinCepharma
FulvicinSchering-Plough
GrifulvinMcNeil
Grifulvin VOrthoneutrogena Labs
GrisactinNot Available
Grison-250Not Available
GrisovinFujisawa
LamorylLovens
LikudenSanofi
PoncylTakeda
S-FulvinNot Available
SpirofulvinNot Available
SporostatinSchering
Brand mixturesNot Available
SaltsNot Available
Categories
UNII32HRV3E3D5
CAS number126-07-8
WeightAverage: 352.766
Monoisotopic: 352.071365983
Chemical FormulaC17H17ClO6
InChI KeyInChIKey=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)[[email protected]](C)CC(=O)C=C1OC
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassNot Available
Direct ParentBenzofurans
Alternative Parents
Substituents
  • Benzofuran
  • Aryl alkyl ketone
  • Aryl ketone
  • Anisole
  • Chlorobenzene
  • Alkyl aryl ether
  • Benzenoid
  • Aryl halide
  • Aryl chloride
  • Vinylogous ester
  • Cyclic ketone
  • Ketone
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor 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.
PharmacodynamicsGriseofulvin 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 actionGriseofulvin 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.
Related Articles
AbsorptionPoorly 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 distributionNot Available
Protein bindingNot Available
Metabolism

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

SubstrateEnzymesProduct
Griseofulvin
Not Available
6-methyl-griseofulvinDetails
Route of eliminationNot Available
Half life9-21 hours
ClearanceNot Available
ToxicitySide effects are minor: headaches, gastrointestinal reactions and cutaneous eruptions
Affected organisms
  • Yeast and other Trichophyton or Microsporum fungi
  • Dermatophytic fungi including Trichophyton, Microsporum and Epidermophyton
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
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
Dosage forms
FormRouteStrength
Tabletoral330 mg
Tablet, film coatedoral125 mg/1
Tablet, film coatedoral250 mg/1
Suspensionoral125 mg/5mL
Tabletoral125 mg/1
Tabletoral250 mg/1
Tabletoral500 mg/1
Tabletoral125 mg
Tabletoral250 mg
Tabletoral500 mg
Tablet, coatedoral125 mg/1
Tablet, coatedoral250 mg/1
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point220 °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)17.69ChemAxon
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

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

US20070098805
General ReferencesNot Available
External Links
ATC CodesD01AA08D01BA01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (131 KB)
MSDSDownload (75.7 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolThe serum concentration of Acenocoumarol can be decreased when it is combined with Griseofulvin.
AmobarbitalThe serum concentration of Griseofulvin can be decreased when it is combined with Amobarbital.
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Griseofulvin.
ButabarbitalThe serum concentration of Griseofulvin can be decreased when it is combined with Butabarbital.
ButethalThe serum concentration of Griseofulvin can be decreased when it is combined with Butethal.
CarbocisteineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Carbocisteine.
ChlorotrianiseneThe metabolism of Chlorotrianisene can be increased when combined with Griseofulvin.
CyclosporineThe serum concentration of Cyclosporine can be decreased when it is combined with Griseofulvin.
DicoumarolThe serum concentration of Dicoumarol can be decreased when it is combined with Griseofulvin.
DienogestThe therapeutic efficacy of Dienogest can be decreased when used in combination with Griseofulvin.
EthanolThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Ethanol.
EtonogestrelThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Griseofulvin.
HeptabarbitalThe serum concentration of Griseofulvin can be decreased when it is combined with Heptabarbital.
HexobarbitalThe serum concentration of Griseofulvin can be decreased when it is combined with Hexobarbital.
HydrocodoneThe serum concentration of Hydrocodone can be decreased when it is combined with Griseofulvin.
LevonorgestrelThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Griseofulvin.
Medroxyprogesterone acetateThe therapeutic efficacy of Medroxyprogesterone Acetate can be decreased when used in combination with Griseofulvin.
MethohexitalThe serum concentration of Griseofulvin can be decreased when it is combined with Methohexital.
NimodipineThe serum concentration of Nimodipine can be decreased when it is combined with Griseofulvin.
NorethisteroneThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Griseofulvin.
PentobarbitalThe serum concentration of Griseofulvin can be decreased when it is combined with Pentobarbital.
PhenobarbitalThe serum concentration of Griseofulvin can be decreased when it is combined with Phenobarbital.
PorfimerGriseofulvin may increase the photosensitizing activities of Porfimer.
PrimidoneThe serum concentration of Griseofulvin can be decreased when it is combined with Primidone.
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Griseofulvin.
SecobarbitalThe serum concentration of Griseofulvin can be decreased when it is combined with Secobarbital.
UlipristalThe serum concentration of Ulipristal can be decreased when it is combined with Griseofulvin.
VerteporfinGriseofulvin may increase the photosensitizing activities of Verteporfin.
WarfarinThe serum concentration of Warfarin can be decreased when it is combined with Griseofulvin.
Food Interactions
  • Avoid alcohol.
  • Take this medication with a high fat meal, fatty foods increase bioavailability.

Targets

Kind
Protein
Organism
Yeast
Pharmacological action
yes
Actions
inhibitor
General Function:
Structural constituent of cytoskeleton
Specific Function:
Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
Gene Name:
TUB2
Uniprot ID:
P10875
Molecular Weight:
49941.65 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Czymmek KJ, Bourett TM, Shao Y, DeZwaan TM, Sweigard JA, Howard RJ: Live-cell imaging of tubulin in the filamentous fungus Magnaporthe grisea treated with anti-microtubule and anti-microfilament agents. Protoplasma. 2005 Apr;225(1-2):23-32. Epub 2005 May 4. [PubMed:15868210 ]
  4. Kiso T, Fujita K, Ping X, Tanaka T, Taniguchi M: Screening for microtubule-disrupting antifungal agents by using a mitotic-arrest mutant of Aspergillus nidulans and novel action of phenylalanine derivatives accompanying tubulin loss. Antimicrob Agents Chemother. 2004 May;48(5):1739-48. [PubMed:15105129 ]
  5. Wang L, Zhou HB, Frisvad JC, Samson RA: Penicillium persicinum, a new griseofulvin, chrysogine and roquefortine C producing species from Qinghai Province, China. Antonie Van Leeuwenhoek. 2004 Aug;86(2):173-9. [PubMed:15280651 ]
Kind
Protein
Organism
Yeast
Pharmacological action
yes
Actions
inhibitor
General Function:
Structural constituent of cytoskeleton
Specific Function:
Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
Gene Name:
TUB1
Uniprot ID:
P87066
Molecular Weight:
49967.725 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
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
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. [PubMed:12388748 ]
  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. [PubMed:14693542 ]

Enzymes

Kind
Protein
Organism
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. 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. [PubMed:9029748 ]
Kind
Protein
Organism
Human
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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. [PubMed:18505790 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23