Griseofulvin
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| Category | Antibiotics |
| Catalog number | BBF-01806 |
| CAS | 126-07-8 |
| Molecular Weight | 352.77 |
| Molecular Formula | C17H17ClO6 |
| Purity | >98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-01806 | 50 g | $199 | In stock |
Online Inquiry
Add to cartDescription
It is produced by the strain of Penicillum griseofulvum. It can inhibit the strains of ClassZygomycetes, Ascomycetes and Deuteromycetes (MIC is 1-20 μg/mL), It can also inhibit the crimping of the spore tube of garlic rot grape (MIC is 1 μg/mL). It has obvious inhibitory effect on metaphase mitosis of bone marrow, small intestine and Walker 256 cancer cells.
Specification
| Synonyms | Curling factor; Fulvicin; Gris PEG; GrisPEG; Gris-PEG; Grisactin; Amudane; 7-Chloro-2',4,6-trimethoxy-6'beta-methylspiro(benzofuran-2(3H), 1'-(2)cyclohexene)-3,4'-dione; (2S-trans)-7-Chloro-2',4,6-trimethoxy-6'-methylspiro(benzofuran-2(3H), 1'-(2)cyclohexene)-3,4'-dione |
| Storage | 2-8 °C |
| IUPAC Name | (2S,5'R)-7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione |
| Canonical SMILES | CC1CC(=O)C=C(C12C(=O)C3=C(O2)C(=C(C=C3OC)OC)Cl)OC |
| 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 |
| InChI Key | DDUHZTYCFQRHIY-RBHXEPJQSA-N |
| Source | Penicillium sp. |
Properties
| Appearance | ColoRed diamond or Acicular Crystal |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Fungi |
| Boiling Point | 469.04 °C (Predicted) |
| Melting Point | 225-226 °C |
| Density | 1.2579 g/cm3 (Predicted) |
| Solubility | Slightly soluble in Chloroform, Ethyl Acetate, Acetone, Benzene, Dioxane |
| LogP | 2.18 |
Toxicity
| Carcinogenicity | 2B, possibly carcinogenic to humans. |
| 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. |
Reference Reading
1.Strategies for improving the solubility and metabolic stability of griseofulvin analogues.
Petersen AB1, Konotop G2, Hanafiah NH2, Hammershøj P1, Raab MS2, Krämer A3, Clausen MH4. Eur J Med Chem. 2016 Mar 28;116:210-215. doi: 10.1016/j.ejmech.2016.03.071. [Epub ahead of print]
We report two types of modifications to the natural product griseofulvin as strategies to improve solubility and metabolic stability: the conversion of aryl methyl ethers into aryl difluoromethyl ethers at metabolic hotspots and the conversion of the C-ring ketone into polar oximes. The syntheses of the analogues are described together with their solubility, metabolic half-life in vitro and antiproliferative effect in two cancer cell lines. We conclude that on balance, the formation of polar oximes is the most promising strategy for improving the properties of the analogues.
2.Influence of spray drying and dispersing agent on surface and dissolution properties of griseofulvin micro and nanocrystals.
Shah DA1, Patel M1, Murdande SB2, Dave RH1. Drug Dev Ind Pharm. 2016 May 4:1-9. [Epub ahead of print]
The purpose for the current research is to compare and evaluate physiochemical properties of spray-dried (SD) microcrystals (MCs), nanocrystals (NCs), and nanocrystals with a dispersion agent (NCm) from a poorly soluble compound. The characterization was carried out by performing size and surface analysis, interfacial tension (at particle moisture interface), and in-vitro drug dissolution rate experiments. Nanosuspensions were prepared by media milling and were spray-dried. The SD powders that were obtained were characterized morphologically using scanning electron microscopy (SEM), polarized light microscopy (PLM), and Flowchem. Solid-state characterization was performed using X-ray powder diffraction (XRPD), Fourier transfer infrared spectroscopy (FT-IR), and differential scanning calorimetry (DSC) for the identification of the crystalline nature of all the SD powders. The powders were characterized for their redispersion tendency in the water and in pH 1.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C17H17ClO6
Molecular Weight (Monoisotopic Mass): 352.0714 Da
Molecular Weight (Avergae Mass): 352.766 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C17H17ClO6
Molecular Weight (Monoisotopic Mass): 352.0714 Da
Molecular Weight (Avergae Mass): 352.766 Da
LC-MS/MS Spectrum - LC-ESI-qTof , Positive
Experimental Conditions
Instrument Type: LC-ESI-qTof
Ionization Mode: Positive
Ionization Mode: Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C17H17ClO6
Molecular Weight (Monoisotopic Mass): 352.0714 Da
Molecular Weight (Avergae Mass): 352.766 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C17H17ClO6
Molecular Weight (Monoisotopic Mass): 352.0714 Da
Molecular Weight (Avergae Mass): 352.766 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
