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126-07-8 molecular structure
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(2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

ChemBase ID: 283
Molecular Formular: C17H17ClO6
Molecular Mass: 352.76628
Monoisotopic Mass: 352.07136594
SMILES and InChIs

SMILES:
Clc1c2O[C@]3([C@@H](CC(=O)C=C3OC)C)C(=O)c2c(OC)cc1OC
Canonical SMILES:
COC1=CC(=O)C[C@H]([C@@]21Oc1c(C2=O)c(OC)cc(c1Cl)OC)C
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
InChIKey:
DDUHZTYCFQRHIY-RBHXEPJQSA-N

Cite this record

CBID:283 http://www.chembase.cn/molecule-283.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
IUPAC Traditional name
griseofulvin
(2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione
Brand Name
Amudane
Biogrisin-fp
Curling factor
Delmofulvina
Fulcin
Fulcine
Fulvican grisactin
Fulvicin
Fulvicin P/G
Fulvicin U/F
Fulvicin-P/G
Fulvicin-U/F
Fulvina
Fulvinil
Fulvistatin
Fungivin
Greosin
Gresfeed
Gricin
Grifulin
Grifulvin
Grifulvin V
Gris-PEG
Grisactin
Grisactin Ultra
Griscofulvin
Grisefuline
Griseo
Griseofulvin forte
Griseofulvin-forte
Griseomix
Grisetin
Grisofulvin
Grisovin
Grisovin FP
Grizeofulvin
Grysio
Guservin
Lamoryl
Likuden
Likunden
Murfulvin
Neo-Fulcin
Neocid
Poncyl
Spirofulvin
Sporostatin
Sporostatin xan
Xuanjing
Synonyms
Griseofulvin
(+)-Griseofulvin
Griseofulvina [INN-Spanish]
Griseofulvine [INN-French]
Griseofulvinum [INN-Latin]
Griseofulvin
(2S)-trans-7-Chloro-2′,4,6-trimethoxy-6′-methylspiro(benzofuran-2[3H],1′-[2]cyclohexene)-3,4′-dione
Griseofulvin
(1'S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohex[2]ene]-3,4'-dione
Grisovin
Fulvicin
Curling factor
Gricin
Grifulvin
Grisactin
Norofulvin
Likuden
Idifulvin
(1'S,6'R)-7-Chloro-2',4,6-trimethoxy-6'-methyl-spiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione
Amudane
Fulcin
Grisovi
(+)-Griseofulvin
Spirofulvin
Sporostatin
Xuanjing
(2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione
(2S)-反式-7-氯-2′,4,6-三甲氧基-6′-甲基螺(苯并呋喃-2[3H],1′-[2]环己烯)-3,4′-二酮
灰黄霉素
(+)-灰黄霉素
灰黄霉素
CAS Number
126-07-8
EC Number
204-767-4
MDL Number
MFCD00082343
Beilstein Number
95226
Merck Index
144549
PubChem SID
24895099
24869893
46508437
24895185
160963746
PubChem CID
441140
CHEBI ID
27779
ATC CODE
D01BA01
D01AA08
CHEMBL
562
Chemspider ID
389934
DrugBank ID
DB00400
KEGG ID
D00209
Unique Ingredient Identifier
32HRV3E3D5
Wikipedia Title
Griseofulvin
Medline Plus
a682295

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 17.688671  H Acceptors
H Donor LogD (pH = 5.5) 2.1721375 
LogD (pH = 7.4) 2.1721375  Log P 2.1721375 
Molar Refractivity 87.8459 cm3 Polarizability 33.75892 Å3
Polar Surface Area 71.06 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.71  LOG S -3.84 
Solubility (Water) 5.04e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
8.64 mg/L expand Show data source
Acetone expand Show data source
Benzene expand Show data source
Ethanol expand Show data source
Ethyl Acetate expand Show data source
Methanol expand Show data source
Apperance
Crystalline Solid expand Show data source
Melting Point
216-220 °C expand Show data source
218 - 220°C expand Show data source
218-220 °C(lit.) expand Show data source
218-220°C expand Show data source
220°C expand Show data source
Optical Rotation
[α]17/D +370°, c = 1 in chloroform expand Show data source
[α]20/D +355±5°, c = 1% in DMF(lit.) expand Show data source
Hydrophobicity(logP)
2 expand Show data source
2.053 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
RTECS
WG9800000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
60-61-40-43 expand Show data source
61-40-43 expand Show data source
Safety Statements
22-36/37/39-45 expand Show data source
53-45 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H317-H351-H360 expand Show data source
H360-H351-H317 expand Show data source
GHS Precautionary statements
P201-P280-P308 + P313 expand Show data source
P261-P280-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
Storage Temperature
-20°C expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
Highly variable (25 to 70%) expand Show data source
Half Life
9-21 hours expand Show data source
Metabolism
Hepatic demethylation and glucuronidation expand Show data source
Legal Status
POM (UK), ?-only (U.S.) expand Show data source
Pregnancy Category
B3 (Australia), C (United States) expand Show data source
Mechanism of Action
Binds tightly to new keratin which becomes highly resistant to fungal invasions expand Show data source
Purity
≥95% (HPLC) expand Show data source
95% expand Show data source
97% expand Show data source
97.0-102.0% expand Show data source
Grade
VETRANAL™, analytical standard expand Show data source
Certificate of Analysis
Download expand Show data source
Suitability
meets USP testing specifications expand Show data source
Biological Source
from Penicillium griseofulvum expand Show data source
Metab. of Penicillium griseofulvum expand Show data source
Application(s)
activity against: Trichophyton rubrum expand Show data source
Antifungal agent against expand Show data source
Epidermophyton floccosum. expand Show data source
Microsporum audouini expand Show data source
Microsporum canis expand Show data source
Microsporum gypseum expand Show data source
Trichophyton crateriform expand Show data source
Trichophyton gallinae expand Show data source
Trichophyton interdigitalis expand Show data source
Trichophyton megnini expand Show data source
Trichophyton mentagrophytes expand Show data source
Trichophyton schoenleini expand Show data source
Trichophyton sulphureum expand Show data source
Trichophyton tonsurans expand Show data source
Trichophyton verrucosum expand Show data source
Empirical Formula (Hill Notation)
C17H17ClO6 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00400 external link
Item Information
Drug Groups approved
Description An antifungal antibiotic. Griseofulvin may be given by mouth in the treatment of tinea infections. [PubChem]
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.
Pharmacology 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.
Toxicity Side effects are minor: headaches, gastrointestinal reactions and cutaneous eruptions
Affected Organisms
Yeast and other Trichophyton or Microsporum fungi
Biotransformation Primarily hepatic with major metabolites being 6-methyl-griseofulvin and its glucuronide conjugate.
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.
Half Life 9-21 hours
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Sigma Aldrich - G4753 external link
Biochem/physiol Actions
Antifungal. Mode of action: Disrupts the mitotic spindle structure and inhibits nuclear division.1 Induces apoptosis in human tumor cell lines.2
包装
5, 25, 50 g in poly bottle
Sigma Aldrich - 856444 external link
Features and Benefits
Antimitotic.
Sigma Aldrich - 46309 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Sigma Aldrich - G2664 external link
Biochem/physiol Actions
Griseofulvin disrupts microtubule assembly and mitotic spindle stucture possibly via tubulin aggregation.
Toronto Research Chemicals - G787500 external link
It is an antifungal drug. It is used both in animal and in humans, to treat rigworm infections of the skin and nails. It is derived from the mold Penicillium griseofulvum.

REFERENCES

REFERENCES

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