Griseofulvin (T3D4696)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2014-09-11 02:05:24 UTC
Update Date2014-12-24 20:26:55 UTC
Accession NumberT3D4696
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.
Compound Type
  • Anti-Bacterial Agent
  • Antifungal Agent
  • Drug
  • Ester
  • Ether
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
(+)-griseofulvin
Amudane
Crivicin
Curling factor
Fulcin
Fulvicin
Grifulvin
Grifulvin V
Gris-PEG
Grisactin
Griseofulvina
Griseofulvine
Griseofulvinum
Grison-250
Grisovin
Grysio
Lamoryl
Likuden
Poncyl
S-Fulvin
Spirofulvin
Sporostatin
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
SMILES[H][C@@]1(C)CC(=O)C=C(OC)[C@@]11OC2=C(C1=O)C(OC)=CC(OC)=C2Cl
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 KeyInChIKey=DDUHZTYCFQRHIY-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)
LogP2.18
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i1-9208000000-bc69e8498dfe1365cbf92017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0uxr-0589000000-f8705acff560aebbf0572017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0uxr-0469000000-196c982b619369269fc42017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-2960000000-3f14b9f983cc6e713b6a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014r-0291000000-6f003312919e202ee0912017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0uxr-0589000000-f8705acff560aebbf0572017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0uxr-0469000000-196c982b619369269fc42017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-2960000000-3f14b9f983cc6e713b6a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014i-0491000000-79844b907995e8371fba2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0239000000-7cd02bae189372507c962021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-0940000000-979db7ec6757627784a32021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-6e8e872e3063f20132162016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-6359000000-b8b346f6cfebc0766adf2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-7940000000-96dddca714f878c4694c2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-dc216555ed72b685bd2b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0019000000-ff656557d1783726dcf22016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6293000000-1552e154d793f60c7d3e2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-ccd58a14a68a0a179df42021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0239000000-8bf9c021181f8ddf16e12021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pc0-9351000000-0e6d75fc00dc250731f32021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-da99c723afce93a9bc572021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0159000000-e96870a8def0c72a7f502021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052k-3092000000-e5a2facca3e774b652482021-09-23View Spectrum
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00400
HMDB IDHMDB14544
PubChem Compound ID441140
ChEMBL IDCHEMBL562
ChemSpider ID389934
KEGG IDC06686
UniProt IDNot Available
OMIM ID
ChEBI ID27779
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkGriseofulvin
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. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Keratin, type I cytoskeletal 12
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. [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. [14693542 ]