Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H14NO4.Cl |
| Molecular Weight | 367.782 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Cl-].C[N+]1=CC2=C(C=CC3=C2OCO3)C4=C1C5=CC6=C(OCO6)C=C5C=C4
InChI
InChIKey=GIZKAXHWLRYMLE-UHFFFAOYSA-M
InChI=1S/C20H14NO4.ClH/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;1H/q+1;/p-1
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C20H14NO4 |
| Molecular Weight | 332.3295 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/18466423Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/28123499 | https://www.ncbi.nlm.nih.gov/pubmed/15753082 | https://www.ncbi.nlm.nih.gov/pubmed/2689627
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18466423
Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/28123499 | https://www.ncbi.nlm.nih.gov/pubmed/15753082 | https://www.ncbi.nlm.nih.gov/pubmed/2689627
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 Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P62139 Gene ID: 1.00009296E8 Gene Symbol: PPP1CA Target Organism: Oryctolagus cuniculus (Rabbit) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20208361 |
42.54 µM [IC50] | ||
Target ID: CHEMBL2437 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20208361 |
2.5 µM [IC50] | ||
Target ID: Calcineurin (bovine) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20208361 |
77.04 µM [IC50] | ||
Target ID: CHEMBL6026 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15753082 |
17.3 µM [IC50] | ||
Target ID: CHEMBL1764941 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15753082 |
12.5 µM [IC50] | ||
Target ID: CHEMBL4804 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15753082 |
57.8 µM [IC50] | ||
Target ID: CHEMBL335 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15753082 |
67.9 µM [IC50] | ||
Target ID: CHEMBL2635 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15753082 |
74.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
30.16 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31943246 |
0.1 mg/kg single, intramuscular dose: 0.1 mg/kg route of administration: Intramuscular experiment type: SINGLE co-administered: |
SANGUINARIUM plasma | Sus scrofa population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
3.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31943246 |
0.1 mg/kg single, oral dose: 0.1 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
SANGUINARIUM plasma | Sus scrofa population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
5.86 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31943246 |
0.1 mg/kg 3 times / day multiple, oral dose: 0.1 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
SANGUINARIUM plasma | Sus scrofa population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
35.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31943246 |
0.1 mg/kg single, intramuscular dose: 0.1 mg/kg route of administration: Intramuscular experiment type: SINGLE co-administered: |
SANGUINARIUM plasma | Sus scrofa population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
15.62 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31943246 |
0.1 mg/kg single, oral dose: 0.1 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
SANGUINARIUM plasma | Sus scrofa population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
31.06 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31943246 |
0.1 mg/kg 3 times / day multiple, oral dose: 0.1 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
SANGUINARIUM plasma | Sus scrofa population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.29 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31943246 |
0.1 mg/kg single, intramuscular dose: 0.1 mg/kg route of administration: Intramuscular experiment type: SINGLE co-administered: |
SANGUINARIUM plasma | Sus scrofa population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
2.33 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31943246 |
0.1 mg/kg single, oral dose: 0.1 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
SANGUINARIUM plasma | Sus scrofa population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
3.17 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31943246 |
0.1 mg/kg 3 times / day multiple, oral dose: 0.1 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
SANGUINARIUM plasma | Sus scrofa population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15993743/ |
likely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15993743/ |
likely | |||
| no | ||||
| no | ||||
| weak [IC50 144 uM] | ||||
| weak | ||||
| weak | ||||
| weak | ||||
| weak | ||||
| yes [IC50 2.1 uM] | ||||
| yes [Ki 2 uM] | ||||
| yes [Ki 2 uM] | ||||
| yes [Ki 3.8 uM] | ||||
| yes [Ki 8.9 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/15993743/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15993743/ |
yes | |||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Protective effect of bioantioxidants on argemone oil/sanguinarine alkaloid induced genotoxicity in mice. | 2006-11-28 |
|
| Simultaneous analysis of alkaloids from Zanthoxylum nitidum by high performance liquid chromatography-diode array detector-electrospray tandem mass spectrometry. | 2006-09-18 |
|
| Safety evaluation studies on argemone oil through dietary exposure for 90days in rats. | 2006-07 |
|
| Apoptotic response of uveal melanoma cells upon treatment with chelidonine, sanguinarine and chelerythrine. | 2006-06-08 |
|
| The benzophenanthridine alkaloid sanguinarine perturbs microtubule assembly dynamics through tubulin binding. A possible mechanism for its antiproliferative activity. | 2006-05 |
|
| Cyclooxygenase 2 rescues LNCaP prostate cancer cells from sanguinarine-induced apoptosis by a mechanism involving inhibition of nitric oxide synthase activity. | 2006-04-01 |
|
| Development of a kinetic metabolic model: application to Catharanthus roseus hairy root. | 2006-04 |
|
| The plant alkaloid Sanguinarine affects swine granulosa cell activity. | 2006-04 |
|
| Disruption of nucleocytoplasmic trafficking of cyclin D1 and topoisomerase II by sanguinarine. | 2006-03-02 |
|
| Anticariogenic activity of macelignan isolated from Myristica fragrans (nutmeg) against Streptococcus mutans. | 2006-03 |
|
| Differential effects of selected natural compounds with anti-inflammatory activity on the glucocorticoid receptor and NF-kappaB in HeLa cells. | 2006-02-01 |
|
| Enhancement of UVB radiation-mediated apoptosis by sanguinarine in HaCaT human immortalized keratinocytes. | 2006-02 |
|
| Investigation of sanguinarine and chelerythrine effects on CYP1A1 expression and activity in human hepatoma cells. | 2006-02 |
|
| Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway. | 2006-01-17 |
|
| A liquid chromatographic-mass spectrometric evidence of dihydrosanguinarine as a first metabolite of sanguinarine transformation in rat. | 2006-01-02 |
|
| Sanguinarine blocks cytokinesis in bacteria by inhibiting FtsZ assembly and bundling. | 2005-12-20 |
|
| [Effect of some isoquinoline alkaloids on enzymatic activity of acetylcholinesterase and monoamine oxidase]. | 2005-12-13 |
|
| Correlation of DNA damage in epidemic dropsy patients to carcinogenic potential of argemone oil and isolated sanguinarine alkaloid in mice. | 2005-12-10 |
|
| Randomized controlled clinical trials on agents used for chemical plaque control. | 2005-11 |
|
| A rapid and reliable solid-phase extraction method for high-performance liquid chromatographic analysis of opium alkaloids from papaver plants. | 2005-11 |
|
| Effects of the limited analyte solubility on its mobility and zone shape: electrophoretic behavior of sanguinarine and chelerythrine around pH 7. | 2005-09 |
|
| [Biosynthesis of poppy isoquinoline alkaloids in nature and in vitro culture. 2. Bracteum poppy (Papaver bracteatum Lindl.)]. | 2005-08-17 |
|
| Sanguinarine activates polycyclic aromatic hydrocarbon associated metabolic pathways in human oral keratinocytes and tissues. | 2005-08-14 |
|
| Sanguinarine activates polycyclic aromatic hydrocarbon associated metabolic pathways in human oral keratinocytes and tissues. | 2005-07-28 |
|
| Study of the inhibition of alpha-amylase by the benzo[c]phenanthridine alkaloids sanguinarine and chelerythrine. | 2005-06 |
|
| Effects of sanguinaria in fluoride-containing dentifrices on the remineralisation of subsurface carious lesion in vitro. | 2005-06 |
|
| The benzo[c]phenanthridine alkaloid, sanguinarine, is a selective, cell-active inhibitor of mitogen-activated protein kinase phosphatase-1. | 2005-05-13 |
|
| Sanguinarine biosynthesis is associated with the endoplasmic reticulum in cultured opium poppy cells after elicitor treatment. | 2005-05 |
|
| Capillary zone electrophoretic studies of interactions of some quaternary isoquinoline alkaloids with DNA constituents and DNA. | 2005-05 |
|
| In situ extraction strategy affects benzophenanthridine alkaloid production fluxes in suspension cultures of Eschscholtzia californica. | 2005-02-05 |
|
| Immunohistochemical assessment of Viadent-associated leukoplakia. | 2005-02 |
|
| Reversal of a full-length mutant huntingtin neuronal cell phenotype by chemical inhibitors of polyglutamine-mediated aggregation. | 2005-01-13 |
|
| In vivo DNA damaging potential of sanguinarine alkaloid, isolated from argemone oil, using alkaline Comet assay in mice. | 2005-01 |
|
| [Effect of alkaloid sanguinarine and a pharmaceutical preparation ukrain on modulation of vesicular membrane fusion and actin cytoskeleton of macrophages]. | 2005 |
|
| Induction of contracture and extracellular Ca2+ influx in cardiac muscle by sanguinarine: a study on cardiotoxicity of sanguinarine. | 2005 |
|
| Unequivocal evidence of genotoxic potential of argemone oil in mice. | 2004-12-10 |
|
| Aggregation and other intermolecular interactions of biological buffers observed by capillary electrophoresis and UV photometry. | 2004-10-08 |
|
| Molecular cloning and characterization of norcoclaurine synthase, an enzyme catalyzing the first committed step in benzylisoquinoline alkaloid biosynthesis. | 2004-10 |
|
| Effect of chemopreventive agents on glutathione S-transferase P1-1 gene expression mechanisms via activating protein 1 and nuclear factor kappaB inhibition. | 2004-09-15 |
|
| Sanguinarine: an evaluation of in vivo cytogenetic activity. | 2004-09-12 |
|
| Sanguinarine causes cell cycle blockade and apoptosis of human prostate carcinoma cells via modulation of cyclin kinase inhibitor-cyclin-cyclin-dependent kinase machinery. | 2004-08 |
|
| Involvement of cytochrome P450 1A in sanguinarine detoxication. | 2004-07-15 |
|
| Chelerythrine and other benzophenanthridine alkaloids block the human P2X7 receptor. | 2004-07 |
|
| Capillary electrophoretic studies of acid-base properties of sanguinarine and chelerythrine alkaloids. | 2004-06-18 |
|
| Suppression of angiogenesis by the plant alkaloid, sanguinarine. | 2004-04-30 |
|
| Natural antimycobacterial metabolites: current status. | 2004-04 |
|
| Isopanduratin A from Kaempferia pandurata as an active antibacterial agent against cariogenic Streptococcus mutans. | 2004-04 |
|
| Hairy root induction of Papaver somniferum var. album, a difficult-to-transform plant, by A rhizogenes LBA 9402. | 2004-03 |
|
| Local anti-infective therapy: pharmacological agents. A systematic review. | 2003-12 |
|
| [Inhibition of liver mitochondrial monoamine oxidase activity by alkaloids isolated from Chelidonium and Macleaya and by their derivative drugs]. | 2003 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2689627
15 ml (0.03%) bid for two consecutive rinses of 15 seconds each
Route of Administration:
Dental
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20208361
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 09:16:35 GMT 2025
by
admin
on
Wed Apr 02 09:16:35 GMT 2025
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| Record UNII |
B8Z8J4400H
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| Record Status |
Validated (UNII)
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| Record Version |
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Download
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Preferred Name | English | ||
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Official Name | English | ||
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Common Name | English | ||
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Systematic Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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NCI_THESAURUS |
C28394
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EE-15
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5578-73-4
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100000084072
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B8Z8J4400H
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CHEMBL417799
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m9763
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68635
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sanguinarine chloride
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7030
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C005705
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DTXSID30971158
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SUB10442MIG
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C80864
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| Related Record | Type | Details | ||
|---|---|---|---|---|
|
SOLVATE->ANHYDROUS | |||
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PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |