Identification

Name
Griseofulvin
Accession Number
DB00400  (APRD01004)
Type
Small Molecule
Groups
Approved, 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
  • Griseofulvin
  • Griseofulvin, microcrystalline
  • Griseofulvin, ultramicrosize
  • Griseofulvina
  • Griseofulvine
  • Griseofulvinum
  • Grisovin
  • Grysio
  • Lamoryl
  • Likuden
  • Poncyl
  • Spirofulvin
  • Sporostatin
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fulvicin Pg Tab 330mgTablet330 mgOralSchering Plough1982-12-311998-11-17Canada
Fulvicin U/f Tab 250mgTablet250 mgOralSchering Plough1966-12-312004-07-21Canada
Fulvicin Uf Tab 500mgTablet500 mgOralSchering Plough1966-12-312004-07-21Canada
Gris-PEGTablet, film coated250 mg/1OralRemedy Repack2013-02-222017-02-22Us00884 0773 04 nlmimage10 a715d3be
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/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
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Griseofulviin (microsize)Suspension125 mg/5mLOralRebel Distributors2007-07-26Not applicableUs
GriseofulvinSuspension125 mg/5mLOralActavis Pharma Company2007-07-26Not applicableUs
GriseofulvinTablet125 mg/1OralRising Pharmaceuticals2012-10-23Not applicableUs
GriseofulvinTablet500 mg/1OralSandoz2013-08-07Not applicableUs00781 5515 01 nlmimage10 ac49566a
GriseofulvinSuspension125 mg/5mLOralTeva2008-02-122017-07-31Us
GriseofulvinSuspension125 mg/5mLOralPerrigo New York Inc.2008-07-162017-10-11Us
GriseofulvinSuspension125 mg/5mLOralQualitest2010-10-082018-02-28Us
GriseofulvinTablet250 mg/1OralRising Pharmaceuticals2012-10-23Not applicableUs
GriseofulvinSuspension125 mg/5mLOralPhysicians Total Care, Inc.2006-01-16Not applicableUs
GriseofulvinTablet250 mg/1OralSandoz2013-08-07Not applicableUs
International/Other Brands
Crivicin / Fulcin (Cepharma) / Fulvicin (Schering-Plough) / Grifulvin (McNeil) / Grifulvin V (Orthoneutrogena Labs) / Grisactin / Grison-250 / Grisovin (Fujisawa) / Lamoryl (Lovens) / Likuden (Sanofi) / Poncyl (Takeda) / S-Fulvin / Spirofulvin / Sporostatin (Schering)
Categories
UNII
32HRV3E3D5
CAS number
126-07-8
Weight
Average: 352.766
Monoisotopic: 352.071365983
Chemical Formula
C17H17ClO6
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)[[email protected]]1(O2)[[email protected]](C)CC(=O)C=C1OC

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.

Structured Indications
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
Yeast
ATubulin alpha chain
inhibitor
Yeast
UKeratin, type I cytoskeletal 12
other/unknown
Human
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.

Route of elimination
Not Available
Half life

9-21 hours

Clearance
Not Available
Toxicity

Side 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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcenocoumarolThe serum concentration of Acenocoumarol can be decreased when it is combined with Griseofulvin.Approved
AmlodipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Amlodipine.Approved
AmobarbitalThe serum concentration of Griseofulvin can be decreased when it is combined with Amobarbital.Approved, Illicit
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Griseofulvin.Approved, Investigational
AmrinoneThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Amrinone.Approved
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Griseofulvin.Approved, Investigational
AzelnidipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Azelnidipine.Approved, Investigational
AzimilideThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Azimilide.Investigational
BarbexacloneThe serum concentration of Griseofulvin can be decreased when it is combined with Barbexaclone.Experimental
BarbitalThe serum concentration of Griseofulvin can be decreased when it is combined with Barbital.Illicit
BarnidipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Barnidipine.Approved
BencyclaneThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Bencyclane.Experimental
BenidipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Benidipine.Approved, Investigational
BepridilThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Bepridil.Approved, Withdrawn
BuspironeThe metabolism of Buspirone can be decreased when combined with Griseofulvin.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Griseofulvin.Approved, Investigational
CarbocisteineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Carbocisteine.Approved, Investigational
CarboxyamidotriazoleThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Carboxyamidotriazole.Investigational
CaroverineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Caroverine.Experimental
ChlorotrianiseneThe metabolism of Chlorotrianisene can be increased when combined with Griseofulvin.Investigational, Withdrawn
CilnidipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Cilnidipine.Approved, Investigational
CinnarizineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Griseofulvin.Approved, Investigational, Withdrawn
ClevidipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Clevidipine.Approved
ClorindioneThe serum concentration of Clorindione can be decreased when it is combined with Griseofulvin.Experimental
ConivaptanThe metabolism of Conivaptan can be decreased when combined with Griseofulvin.Approved, Investigational
Conjugated estrogensThe metabolism of Conjugated estrogens can be increased when combined with Griseofulvin.Approved
CyclosporineThe serum concentration of Cyclosporine can be decreased when it is combined with Griseofulvin.Approved, Investigational, Vet Approved
DarodipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Darodipine.Experimental
DesogestrelThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Griseofulvin.Approved
DicoumarolThe serum concentration of Dicoumarol can be decreased when it is combined with Griseofulvin.Approved
DidanosineDidanosine can cause a decrease in the absorption of Griseofulvin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DienestrolThe metabolism of Dienestrol can be increased when combined with Griseofulvin.Approved, Investigational
DienogestThe therapeutic efficacy of Dienogest can be decreased when used in combination with Griseofulvin.Approved
DiethylstilbestrolThe metabolism of Diethylstilbestrol can be increased when combined with Griseofulvin.Approved, Investigational
DiltiazemThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Diltiazem.Approved
DiphenadioneThe serum concentration of Diphenadione can be decreased when it is combined with Griseofulvin.Experimental
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Griseofulvin.Approved, Investigational
DofetilideThe metabolism of Dofetilide can be decreased when combined with Griseofulvin.Approved
DotarizineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Dotarizine.Investigational
DrospirenoneThe therapeutic efficacy of Drospirenone can be decreased when used in combination with Griseofulvin.Approved
EfonidipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Efonidipine.Approved
EperisoneThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Eperisone.Approved, Investigational
EstradiolThe metabolism of Estradiol can be increased when combined with Griseofulvin.Approved, Investigational, Vet Approved
EstramustineThe metabolism of Estramustine can be increased when combined with Griseofulvin.Approved
Estrogens, esterifiedThe metabolism of Estrogens, esterified can be increased when combined with Griseofulvin.Approved
Estrone sulfateThe metabolism of Estrone sulfate can be increased when combined with Griseofulvin.Approved
EthanolThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Ethanol.Approved
Ethinyl EstradiolThe metabolism of Ethinyl Estradiol can be increased when combined with Griseofulvin.Approved
Ethyl biscoumacetateThe serum concentration of Ethyl biscoumacetate can be decreased when it is combined with Griseofulvin.Withdrawn
Ethynodiol diacetateThe therapeutic efficacy of Ethynodiol diacetate can be decreased when used in combination with Griseofulvin.Approved
EtonogestrelThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Griseofulvin.Approved, Investigational
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Griseofulvin.Approved
FelodipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Felodipine.Approved, Investigational
FendilineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Fendiline.Withdrawn
FluindioneThe serum concentration of Fluindione can be decreased when it is combined with Griseofulvin.Investigational
FlunarizineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Flunarizine.Approved
FosphenytoinThe serum concentration of Griseofulvin can be decreased when it is combined with Fosphenytoin.Approved
GabapentinThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Gabapentin.Approved, Investigational
GallopamilThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Gallopamil.Investigational
GestodeneThe therapeutic efficacy of Gestodene can be decreased when used in combination with Griseofulvin.Approved, Investigational
HexestrolThe metabolism of Hexestrol can be increased when combined with Griseofulvin.Withdrawn
HexobarbitalThe serum concentration of Griseofulvin can be decreased when it is combined with Hexobarbital.Approved
IsradipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Isradipine.Approved
LacidipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Lacidipine.Approved, Investigational
LamotrigineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Lamotrigine.Approved, Investigational
LercanidipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Lercanidipine.Approved, Investigational
LevonorgestrelThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Griseofulvin.Approved, Investigational
LidoflazineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Lidoflazine.Experimental
LosartanThe metabolism of Losartan can be decreased when combined with Griseofulvin.Approved
LynestrenolThe therapeutic efficacy of Lynestrenol can be decreased when used in combination with Griseofulvin.Investigational
Magnesium SulfateThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Magnesium Sulfate.Approved, Vet Approved
ManidipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Manidipine.Approved, Investigational
Medroxyprogesterone acetateThe therapeutic efficacy of Medroxyprogesterone acetate can be decreased when used in combination with Griseofulvin.Approved, Investigational
MestranolThe metabolism of Mestranol can be increased when combined with Griseofulvin.Approved
MethallenestrilThe metabolism of Methallenestril can be increased when combined with Griseofulvin.Experimental
MethohexitalThe serum concentration of Griseofulvin can be decreased when it is combined with Methohexital.Approved
MethylphenobarbitalThe serum concentration of Griseofulvin can be decreased when it is combined with Methylphenobarbital.Approved
MibefradilThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Mibefradil.Investigational, Withdrawn
NaftopidilThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Naftopidil.Investigational
NicardipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Nicardipine.Approved
NifedipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Nifedipine.Approved
NiguldipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Niguldipine.Experimental
NiludipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Niludipine.Experimental
NilvadipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Nilvadipine.Approved, Investigational
NimesulideThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Nimesulide.Approved, Investigational, Withdrawn
NisoldipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Nisoldipine.Approved
NitrendipineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Nitrendipine.Approved, Investigational
NorelgestrominThe therapeutic efficacy of Norelgestromin can be decreased when used in combination with Griseofulvin.Approved
NorgestimateThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Griseofulvin.Approved
NorgestrelThe therapeutic efficacy of Norgestrel can be decreased when used in combination with Griseofulvin.Approved
OtiloniumThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Otilonium.Experimental, Investigational
PentobarbitalThe serum concentration of Griseofulvin can be decreased when it is combined with Pentobarbital.Approved, Vet Approved
PerhexilineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Perhexiline.Approved, Investigational
PhenindioneThe serum concentration of Phenindione can be decreased when it is combined with Griseofulvin.Approved, Investigational
PhenobarbitalThe serum concentration of Griseofulvin can be decreased when it is combined with Phenobarbital.Approved
PhenprocoumonThe serum concentration of Phenprocoumon can be decreased when it is combined with Griseofulvin.Approved, Investigational
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Griseofulvin.Approved, Vet Approved
PimozideGriseofulvin may increase the arrhythmogenic activities of Pimozide.Approved
PinaveriumThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Pinaverium.Approved
PregabalinThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Pregabalin.Approved, Illicit, Investigational
PrenylamineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Prenylamine.Withdrawn
PrimidoneThe serum concentration of Griseofulvin can be decreased when it is combined with Primidone.Approved, Vet Approved
ProgesteroneThe therapeutic efficacy of Progesterone can be decreased when used in combination with Griseofulvin.Approved, Vet Approved
QuinidineThe metabolism of Quinidine can be decreased when combined with Griseofulvin.Approved
RanolazineThe metabolism of Ranolazine can be decreased when combined with Griseofulvin.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Griseofulvin.Approved
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Griseofulvin.Approved
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Griseofulvin.Approved
RisedronateThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Risedronate.Approved, Investigational
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Griseofulvin.Approved
SecobarbitalThe serum concentration of Griseofulvin can be decreased when it is combined with Secobarbital.Approved, Vet Approved
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Griseofulvin.Approved
SucralfateSucralfate can cause a decrease in the absorption of Griseofulvin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Griseofulvin.Approved, Investigational
Synthetic Conjugated Estrogens, AThe metabolism of Synthetic Conjugated Estrogens, A can be increased when combined with Griseofulvin.Approved
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Griseofulvin.Approved, Investigational
TerodilineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Terodiline.Experimental
TetrahydropalmatineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Tetrahydropalmatine.Investigational
ThiamylalThe serum concentration of Griseofulvin can be decreased when it is combined with Thiamylal.Approved, Vet Approved
ThiopentalThe serum concentration of Griseofulvin can be decreased when it is combined with Thiopental.Approved, Vet Approved
TioclomarolThe serum concentration of Tioclomarol can be decreased when it is combined with Griseofulvin.Experimental
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Tolfenamic Acid.Approved
TranilastThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Tranilast.Approved, Investigational
UlipristalThe serum concentration of Ulipristal can be decreased when it is combined with Griseofulvin.Approved
VerapamilThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Verapamil.Approved
VinpocetineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Vinpocetine.Investigational
WarfarinThe serum concentration of Warfarin can be decreased when it is combined with Griseofulvin.Approved
XylometazolineThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Xylometazoline.Approved
ZiconotideThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Griseofulvin.Approved
Food Interactions
  • Avoid alcohol.
  • Take this medication with a high fat meal, fatty foods increase bioavailability.

References

Synthesis Reference

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

US20070098805
General References
Not Available
External Links
Human Metabolome Database
HMDB14544
KEGG Drug
D00209
KEGG Compound
C06686
PubChem Compound
441140
PubChem Substance
46508437
ChemSpider
389934
BindingDB
31775
ChEBI
27779
ChEMBL
CHEMBL562
Therapeutic Targets Database
DAP000539
PharmGKB
PA449814
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Griseofulvin
ATC Codes
D01AA08 — GriseofulvinD01BA01 — Griseofulvin
FDA label
Download (131 KB)
MSDS
Download (75.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers2
1CompletedTreatmentDiabetes / Healthy Volunteers1
3CompletedTreatmentTinea 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
Dosage forms
FormRouteStrength
TabletOral330 mg
Tablet, film coatedOral250 mg/1
SuspensionOral125 mg/5mL
TabletOral125 mg/1
TabletOral250 mg/1
TabletOral500 mg/1
Tablet, film coatedOral125 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.
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)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 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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
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

Taxonomy

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
Coumaran / Benzofuran / Anisole / Aryl alkyl ketone / Aryl ketone / Alkyl aryl ether / Cyclohexenone / Aryl chloride / Aryl halide / Benzenoid
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)

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
Uniprot Name
Tubulin beta chain
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
Uniprot Name
Tubulin alpha chain
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
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. [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 un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
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 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. [PubMed:18505790]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:37