(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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 126-07-8
• EC Number: 204-767-4
• MDL Number: MFCD00082343
• Beilstein Number: 95226
• Merck Index: 144549
• PubChem SID: 24895099; 46508437; 24895185; 24869893; 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

JChem

• Acid pKa: 17.688671
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 2.1721375
• LogD (pH = 7.4): 2.1721375
• Log P: 2.1721375
• Molar Refractivity: 87.8459 cm^3
• Polarizability: 33.75892 Å^3
• Polar Surface Area: 71.06 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.71
• LOG S: -3.84
• Solubility (Water): 5.04e-02 g/l

PROPERTIES

Physical Property

• Solubility: 8.64 mg/L; Acetone; Benzene; Ethanol; Ethyl Acetate; Methanol
• Apperance: Crystalline Solid
• Melting Point: 216-220 °C; 218 - 220°C; 218-220 °C(lit.); 218-220°C; 220°C
• Optical Rotation: [α]17/D +370°, c = 1 in chloroform; [α]20/D +355±5°, c = 1% in DMF(lit.)
• Hydrophobicity(logP): 2; 2.053

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: WG9800000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 60-61-40-43; 61-40-43
• Safety Statements: 22-36/37/39-45; 53-45
• TSCA Listed: 否
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H351-H360; H360-H351-H317
• GHS Precautionary statements: P201-P280-P308 + P313; P261-P280-P302+P352-P321-P405-P501A
• 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; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• Storage Temperature: -20°C

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: Highly variable (25 to 70%)
• Half Life: 9-21 hours
• Metabolism: Hepatic demethylation and glucuronidation
• Legal Status: POM (UK), ?-only (U.S.)
• Pregnancy Category: B3 (Australia), C (United States)
• Mechanism of Action: Binds tightly to new keratin which becomes highly resistant to fungal invasions

Product Information

• Purity: ≥95% (HPLC); 95%; 97%; 97.0-102.0%
• Grade: VETRANAL™, analytical standard
• Suitability: meets USP testing specifications
• Biological Source: from Penicillium griseofulvum; Metab. of Penicillium griseofulvum
• Application(s): activity against: Trichophyton rubrum; Antifungal agent against; Epidermophyton floccosum.; Microsporum audouini; Microsporum canis; Microsporum gypseum; Trichophyton crateriform; Trichophyton gallinae; Trichophyton interdigitalis; Trichophyton megnini; Trichophyton mentagrophytes; Trichophyton schoenleini; Trichophyton sulphureum; Trichophyton tonsurans; Trichophyton verrucosum
• Empirical Formula (Hill Notation): C17H17ClO6

DETAILS

DrugBank - DB00400

• 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

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

Features and Benefits
Antimitotic.

Sigma Aldrich - 46309

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - G2664

Biochem/physiol Actions
Griseofulvin disrupts microtubule assembly and mitotic spindle stucture possibly via tubulin aggregation.

Toronto Research Chemicals - G787500

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

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