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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
Structure of SANGUINARINE NITRATE

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

HIDE SMILES / InChI

Description
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

Sources: Konig G. Über Papaveraceen-Alkaloïde. Arch. Pharm. 1893;231:177.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
32.0 µM [IC50]
200.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Antibacterial efficacy and pharmacokinetic evaluation of sanguinarine in common carp (Cyprinus carpio) following a single intraperitoneal administration.
2016 Aug
Patents

Patents

Sample Use Guides

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
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).
Name Type Language
SANGUINARINE NITRATE
Common Name English
SANGUINARINUM NITRICUM [HPUS]
Common Name English
NSC-59270
Code English
SANGUINARINUM NITRICUM
HPUS  
Common Name English
NSC-646663
Code English
NSC-35607
Code English
(1,3)BENZODIOXOLO(5,6-C)-1,3-DIOXOLO(4,5-I)PHENANTHRIDINIUM, 13-METHYL-, NITRATE (1:1)
Systematic Name English
Code System Code Type Description
CAS
4752-86-7
Created by admin on Fri Dec 15 17:20:12 GMT 2023 , Edited by admin on Fri Dec 15 17:20:12 GMT 2023
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NSC
35607
Created by admin on Fri Dec 15 17:20:12 GMT 2023 , Edited by admin on Fri Dec 15 17:20:12 GMT 2023
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PUBCHEM
72619
Created by admin on Fri Dec 15 17:20:12 GMT 2023 , Edited by admin on Fri Dec 15 17:20:12 GMT 2023
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ECHA (EC/EINECS)
225-276-1
Created by admin on Fri Dec 15 17:20:12 GMT 2023 , Edited by admin on Fri Dec 15 17:20:12 GMT 2023
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EPA CompTox
DTXSID80197184
Created by admin on Fri Dec 15 17:20:12 GMT 2023 , Edited by admin on Fri Dec 15 17:20:12 GMT 2023
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DAILYMED
BOP122S791
Created by admin on Fri Dec 15 17:20:12 GMT 2023 , Edited by admin on Fri Dec 15 17:20:12 GMT 2023
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NSC
59270
Created by admin on Fri Dec 15 17:20:12 GMT 2023 , Edited by admin on Fri Dec 15 17:20:12 GMT 2023
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NSC
646663
Created by admin on Fri Dec 15 17:20:12 GMT 2023 , Edited by admin on Fri Dec 15 17:20:12 GMT 2023
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RXCUI
1537754
Created by admin on Fri Dec 15 17:20:12 GMT 2023 , Edited by admin on Fri Dec 15 17:20:12 GMT 2023
PRIMARY RxNorm
FDA UNII
BOP122S791
Created by admin on Fri Dec 15 17:20:12 GMT 2023 , Edited by admin on Fri Dec 15 17:20:12 GMT 2023
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MESH
C005705
Created by admin on Fri Dec 15 17:20:12 GMT 2023 , Edited by admin on Fri Dec 15 17:20:12 GMT 2023
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