ContaminantDB: Griseofulvin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-09-11 02:05:24 UTC

Update Date

2016-11-09 01:09:11 UTC

Accession Number

CHEM003654

Identification

Common Name

Griseofulvin

Class

Small Molecule

Description

Griseofulvin 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
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(+)-Griseofulvin	ChEBI
Amudane	ChEBI
Curling factor	ChEBI
Fulcin	ChEBI
Fulvicin	ChEBI
Grifulvin	ChEBI
Grisactin	ChEBI
Griseofulvina	ChEBI
Griseofulvine	ChEBI
Griseofulvinum	ChEBI
Grisovin	ChEBI
Grysio	ChEBI
Lamoryl	ChEBI
Likuden	ChEBI
Poncyl	ChEBI
Spirofulvin	ChEBI
Sporostatin	ChEBI
GRE	Kegg
Gris-peg	Kegg
Grisactin V	Kegg
Fulvicin u F	HMDB
Fulvicin-u-F	HMDB
GrisPEG	HMDB
Grifulvin V	HMDB
Gris peg	HMDB
Grisefuline	HMDB
V, Grifulvin	HMDB
FulvicinUF	HMDB

Chemical Formula

C₁₇H₁₇ClO₆

Average Molecular Mass

352.766 g/mol

Monoisotopic Mass

352.071 g/mol

CAS Registry Number

126-07-8

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 Name

griseofulvin

SMILES

COC1=CC(OC)=C(Cl)C2=C1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1OC

InChI Identifier

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

InChI Key

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

antibiotic antifungal drug (CHEBI:27779 )
organochlorine compound (CHEBI:27779 )
1-benzofurans (CHEBI:27779 )
oxaspiro compound (CHEBI:27779 )
benzofuran antifungal drug (CHEBI:27779 )
Other Polyketides (C06686 )
Dibenzofurans, griseofulvins, dibenzopyrans and xanthones (C06686 )
Antibiotic fungicides (C06686 )
Dibenzofurans, griseofulvins, dibenzopyrans and xanthones (LMPK13060001 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	220°C
Boiling Point	Not Available
Solubility	8.64 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.05 g/L	ALOGPS
logP	2.71	ALOGPS
logP	2.17	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	17.69	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	71.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	87.85 m³·mol⁻¹	ChemAxon
Polarizability	34.25 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05i1-9208000000-bc69e8498dfe1365cbf9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0uxr-0589000000-f8705acff560aebbf057	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0uxr-0469000000-196c982b619369269fc4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-014i-2960000000-3f14b9f983cc6e713b6a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-014r-0291000000-6f003312919e202ee091	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0uxr-0589000000-f8705acff560aebbf057	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0uxr-0469000000-196c982b619369269fc4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-2960000000-3f14b9f983cc6e713b6a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0491000000-79844b907995e8371fba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0239000000-7cd02bae189372507c96	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0940000000-979db7ec6757627784a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0019000000-6e8e872e3063f2013216	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gb9-6359000000-b8b346f6cfebc0766adf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052r-7940000000-96dddca714f878c4694c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-dc216555ed72b685bd2b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udr-0019000000-ff656557d1783726dcf2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-6293000000-1552e154d793f60c7d3e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-ccd58a14a68a0a179df4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0239000000-8bf9c021181f8ddf16e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pc0-9351000000-0e6d75fc00dc250731f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-da99c723afce93a9bc57	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0159000000-e96870a8def0c72a7f50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052k-3092000000-e5a2facca3e774b65248	Spectrum

Toxicity Profile

Route of Exposure

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.

Mechanism of Toxicity

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.

Metabolism

Primarily hepatic with major metabolites being 6-methyl-griseofulvin and its glucuronide conjugate. Half Life: 9-21 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (1)

Uses/Sources

Griseofulvin 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 Level

Not Available

Health Effects

Not Available

Symptoms

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

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID