Berberine
From DrugPedia: A Wikipedia for Drug discovery
| Berberine
| |
| Systematic (IUPAC) name | |
| N/A | |
| Identifiers | |
| CAS number | ? |
| ATC code | ? |
| PubChem | |
| Chemical data | |
| Formula | C20H18NO4+ |
| Mol. mass | 338.369329 |
| SMILES | & |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | ? |
[edit] Description
An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal.
Berberine is a quaternary ammonium salt from the group of isoquinoline alkaloids. It is found in such plants as Berberis, goldenseal (Hydrastis canadensis), and Coptis chinensis, usually in the roots, rhizomes, stems, and bark. Berberine is strongly yellow colored, which is why in earlier times berberis species were used to dye wool, leather and wood. Wool is still today dyed with berberine in Northern India. Under ultraviolet light, berberine shows a strong yellow fluorescence. Because of this it is used in histology for staining heparin in mast cells. As a natural dye berberin has a Colour Index (CI) of 75160.
As a drug, berberine has showed some activity against fungal infections, candida, yeast, parasites, and bacterial/viral infections. Some research has been undertaken into possible use against MRSA infection. Although berberine has been tested and used in diabetes, prostate cancer cell lines, liver and leukaemia cancers, cardiac arrhythmia, and leukemia, it has not been researched thoroughly with humans. Berberine is considered an ineffective antibiotic, but a minority claim that when not tested in isolation but in conjunction with the other biochemical substances from the barberry plant, berberine might then be effective.
Berberine is a component of some eye drops formulations. There is some evidence that it is useful in the treatment of trachoma, and it has been a standard treatment for leishmaniasis.
[edit] General Properties
*Molecular Weight
338.369329
*Molecular Formula
C20H18NO4+
*IUPAC NAME
N/A
*Canonical Smiles
COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC
*Isomeric Smiles
[3H]C1OC2=C(O1)C=C3C(=C2)CC[N+]4=C3C=C5C=CC(=C(C5=C4)OC)OC
*XLogP
N/A
*Topological Polar Surface Area
40.8
