Griseofulvin (CHEM003654)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (2)XML
Record Information
Version1.0
Creation Date2014-09-11 02:05:24 UTC
Update Date2026-05-14 16:37:36 UTC
Accession NumberCHEM003654
Identification
Common NameGriseofulvin
ClassSmall Molecule
DescriptionGriseofulvin is only found in individuals that have used or taken this drug. It is an antifungal antibiotic. Griseofulvin may be given by mouth in the treatment of tinea infections. 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 2B
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Anti-Bacterial Agent
  • Antifungal Agent
  • Drug
  • Ester
  • Ether
  • Human Neurotoxin
  • Metabolite
  • Mycotoxin
  • Organic Compound
  • Organochloride
  • PFAS
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(+)-GriseofulvinChEBI
AmudaneChEBI
Curling factorChEBI
FulcinChEBI
FulvicinChEBI
GrifulvinChEBI
GrisactinChEBI
GriseofulvinaChEBI
GriseofulvineChEBI
GriseofulvinumChEBI
GrisovinChEBI
GrysioChEBI
LamorylChEBI
LikudenChEBI
PoncylChEBI
SpirofulvinChEBI
SporostatinChEBI
GREKegg
Gris-pegKegg
Grisactin VKegg
Fulvicin u FHMDB
Fulvicin-u-FHMDB
GrisPEGHMDB
Grifulvin VHMDB
Gris pegHMDB
GrisefulineHMDB
V, GrifulvinHMDB
FulvicinUFHMDB
Chemical FormulaC17H17ClO6
Average Molecular Mass352.766 g/mol
Monoisotopic Mass352.071 g/mol
CAS Registry Number126-07-8
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
Traditional Namegriseofulvin
SMILESCOC1=CC(OC)=C(Cl)C2=C1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1OC
InChI IdentifierInChI=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
InChI KeyDDUHZTYCFQRHIY-RBHXEPJQSA-N
Chemical Taxonomy
Description 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
  • Coumaran
  • Benzofuran
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Cyclohexenone
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Vinylogous ester
  • Ketone
  • Cyclic ketone
  • Ether
  • Oxacycle
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point220°C
Boiling PointNot Available
Solubility8.64 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility0.05 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity87.85 m³·mol⁻¹ChemAxon
Polarizability34.25 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i1-9208000000-bc69e8498dfe1365cbf9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0uxr-0589000000-f8705acff560aebbf057Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0uxr-0469000000-196c982b619369269fc4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-2960000000-3f14b9f983cc6e713b6aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014r-0291000000-6f003312919e202ee091Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0uxr-0589000000-f8705acff560aebbf057Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0uxr-0469000000-196c982b619369269fc4Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-2960000000-3f14b9f983cc6e713b6aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014i-0491000000-79844b907995e8371fbaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0239000000-7cd02bae189372507c96Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-0940000000-979db7ec6757627784a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-6e8e872e3063f2013216Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-6359000000-b8b346f6cfebc0766adfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-7940000000-96dddca714f878c4694cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-dc216555ed72b685bd2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0019000000-ff656557d1783726dcf2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6293000000-1552e154d793f60c7d3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-ccd58a14a68a0a179df4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0239000000-8bf9c021181f8ddf16e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pc0-9351000000-0e6d75fc00dc250731f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-da99c723afce93a9bc57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0159000000-e96870a8def0c72a7f50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052k-3092000000-e5a2facca3e774b65248Spectrum
Toxicity Profile
Route of ExposurePoorly absorbed from GI ranging from 25 to 70% of an oral dose. Absorption is significantly enhanced by administration with or after a fatty meal.
Mechanism of ToxicityGriseofulvin 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.
MetabolismPrimarily hepatic with major metabolites being 6-methyl-griseofulvin and its glucuronide conjugate. Half Life: 9-21 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (1)
Uses/SourcesGriseofulvin is used both in animals and in humans, to treat fungal infections of the skin (commonly known as ringworm) and nails. Griseofulvin is used orally only for dermatophytosis. It is ineffective topically. Griseofulvin is reserved for cases with nail, hair or large body surface involvement. (Wikipedia)
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSide effects are minor: headaches, gastrointestinal reactions and cutaneous eruptions
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00400
HMDB IDHMDB0014544
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00002398
BiGG IDNot Available
BioCyc IDCPD-17786
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGriseofulvin
Chemspider ID389934
ChEBI ID27779
PubChem Compound ID441140
Kegg Compound IDC06686
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

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

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14407521
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15078340
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16922553
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23111828
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25476923
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=3277037