U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C20H14NO4
Molecular Weight 332.3295
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of SANGUINARIUM

SMILES

C[N+]1=CC2=C3OCOC3=CC=C2C4=C1C5=CC6=C(OCO6)C=C5C=C4

InChI

InChIKey=INVGWHRKADIJHF-UHFFFAOYSA-N
InChI=1S/C20H14NO4/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/h2-8H,9-10H2,1H3/q+1

HIDE SMILES / InChI

Description

Sanguinarine is an extract of the bloodroot plant Sanguinaria canadensis, a member of the poppy family. It is an inhibitor of protein phosphatases PP1, PP2C and PP2B in vitro. Also inhibits mitogen-activated protein kinase phosphatase-1 (MKP-1) and other enzymes. Sanguinarine exerts a protective effect in cerebral ischemia, and this effect is associated with its anti-inflammatory and anti-apoptotic properties. It was clinically tested as an agent against gingivitis and tooth plaques.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
42.54 µM [IC50]
2.5 µM [IC50]
77.04 µM [IC50]
17.3 µM [IC50]
12.5 µM [IC50]
57.8 µM [IC50]
67.9 µM [IC50]
74.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
30.16 ng/mL
0.1 mg/kg single, intramuscular
SANGUINARIUM plasma
Sus scrofa
3.4 ng/mL
0.1 mg/kg single, oral
SANGUINARIUM plasma
Sus scrofa
5.86 ng/mL
0.1 mg/kg 3 times / day multiple, oral
SANGUINARIUM plasma
Sus scrofa

AUC

ValueDoseCo-administeredAnalytePopulation
35.4 ng × h/mL
0.1 mg/kg single, intramuscular
SANGUINARIUM plasma
Sus scrofa
15.62 ng × h/mL
0.1 mg/kg single, oral
SANGUINARIUM plasma
Sus scrofa
31.06 ng × h/mL
0.1 mg/kg 3 times / day multiple, oral
SANGUINARIUM plasma
Sus scrofa

T1/2

ValueDoseCo-administeredAnalytePopulation
1.29 h
0.1 mg/kg single, intramuscular
SANGUINARIUM plasma
Sus scrofa
2.33 h
0.1 mg/kg single, oral
SANGUINARIUM plasma
Sus scrofa
3.17 h
0.1 mg/kg 3 times / day multiple, oral
SANGUINARIUM plasma
Sus scrofa

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
15 ml (0.03%) bid for two consecutive rinses of 15 seconds each
Route of Administration: Dental
In Vitro Use Guide
Sanguinarine showed cytotoxicity toward HL60 cells with an IC50 value of 0.37 uM. Fluorescence microscope observation allowed the visualization of apoptotic cells with condensed and fragmented nuclei in HL60 cells. They were observed in HL60 cells treated for 6h with 1 uM sanguinarine.