Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H14NO4.NO3 |
Molecular Weight | 394.3344 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[O-][N+]([O-])=O.C[N+]1=C2C3=C(C=CC2=C4C=CC5=C(OCO5)C4=C1)C=C6OCOC6=C3
InChI
InChIKey=RBKBIPRGKKUAFZ-UHFFFAOYSA-N
InChI=1S/C20H14NO4.NO3/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21;2-1(3)4/h2-8H,9-10H2,1H3;/q+1;-1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/27618894Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/9058327 | https://www.ncbi.nlm.nih.gov/pubmed/19716293 | https://www.ncbi.nlm.nih.gov/pubmed/24794108 | https://www.ncbi.nlm.nih.gov/pubmed/27957827
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27618894
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/9058327 | https://www.ncbi.nlm.nih.gov/pubmed/19716293 | https://www.ncbi.nlm.nih.gov/pubmed/24794108 | https://www.ncbi.nlm.nih.gov/pubmed/27957827
Sanguinarine is a toxic polycyclic quaternary ammonium salt. It is extracted from some plants, including bloodroot (Sanguinaria canadensis), Mexican prickly poppy Argemone mexicana, Chelidonium majus and Macleaya cordata. Sanguinarine is a toxin that kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. If applied to the skin, sanguinarine may cause a massive scab of dead flesh, called an eschar. For this reason, sanguinarine is termed an escharotic. Preliminary pre-clinical in vitro and in vivo studies have demonstrated that sanguinarine causes apoptosis in human cancer cells, and recommend study of sanguinarine as a potential cancer treatment. Sanguinarine has been the subject of other medical fields as well. For instance, it has garnered interest as a chemical defense against microorganisms and viruses. Notably, experiments on human plaque accumulation in the presence of sanguinarine suggest the toxin may be effective against oral microbial isolates. However, no products containing sanguinarine are currently approved by the FDA for the treatment of cancer; the FDA warns that unapproved bloodroot preparations are ineffective and dangerous.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL6088 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19716293 |
32.0 µM [IC50] | ||
Target ID: CHEMBL1843 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24794108 |
200.0 µM [IC50] | ||
Target ID: CHEMBL6094 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19716293 |
58.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9058327
Test article (containing 5% sanguinarium chloride) were supplied in 1 cc polypropylene syringesn containing 300 mg of test formulation. The syringes were fitted with a 23-gauge cannula bent to resemble a periodontal probe. For commercialization, the syringe-cannula was connected by means of an adapter to a foot-activated compressed air delivery system. Alternatively, the product could be expressed into the pockets by hand
Route of Administration:
Dental
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27957827
Human GC cells (SGC-7901, BGC-823, HGC-27, AGS and MGC-803) (2 9 103/100 ll/well) were seeded in 96-well plates and incubated for 15 hrs (37°C, 5% CO2). Then, sanguinarine diluted by complete medium (100 ll/well) at serial concentrations (0/5/10/30 mkmol/l) was added to each well. After treating for 24, 48, 72 or 96 hrs, CCK-8 solution (10 ll) was added into each well, followed by incubation for 1 hr. The optical densities at 450 nm were measured using a Microplate Reader (Molecular Devices Sunnyvale, CA, USA).
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C005705
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD