Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H28O11 |
Molecular Weight | 480.4618 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 11 / 11 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12C[C@@]4(O[C@]3([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@]1(COC(=O)C5=CC=CC=C5)[C@@]6([H])O[C@]2(O)C[C@]4(C)O6
InChI
InChIKey=YKRGDOXKVOZESV-WRJNSLSBSA-N
InChI=1S/C23H28O11/c1-20-9-22(29)13-7-23(20,32-18-16(27)15(26)14(25)12(8-24)31-18)21(13,19(33-20)34-22)10-30-17(28)11-5-3-2-4-6-11/h2-6,12-16,18-19,24-27,29H,7-10H2,1H3/t12-,13-,14-,15+,16-,18+,19-,20+,21+,22-,23+/m1/s1
Molecular Formula | C23H28O11 |
Molecular Weight | 480.4618 |
Charge | 0 |
Count |
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Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 11 / 11 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26514553
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26514553
Peoniflorin (PF) is the chief active component of paeonia, with diverse pharmacological actions and wide application. According to current study findings, PF can ameliorate the decline of memory and learning capacities in many dementia model animals, and have effect in protecting the cerebral ischemia injury, treating Parkinson's disease, reliving pain and improving neural synapse plasticity. Peoniflorin is an Adenosine A1 receptor activator with neuroprotective and antidepressant effects. Upregulates serotonergic systems in vivo. Blood brain barrier permeable. Preclinical studies show that peoniflorin is able to diminish pain, joint swelling, synovial hypertrophy, and the severity of bone erosion and cartilage degradation in experimental arthritis. In China, Korea, and Japan, a decoction of the dried root without bark of Paeonia lactiflora Pall. has been used in the treatment of rheumatoid arthritis, systemic lupus erythematosus, hepatitis, dysmenorrhea, muscle cramping and spasms, and fever for more than 1200 years. A water/ethanol extract of the root is now known as total glucosides of peony (TGP), which contains more than 15 components. Peoniflorin is the most abundant ingredient and accounts for the pharmacological effects observed with TGP in both in vitro and in vivo studies.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0006954 |
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Target ID: GO:0051402 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25967667 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
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moderate | ||||
weak | ||||
weak | ||||
yes [Inhibition 10 uM] | ||||
yes [Inhibition 10 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/22040564/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/22040564/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/22040564/ |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
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PubMed
Title | Date | PubMed |
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Effects of paeoniflorin derivatives on scopolamine-induced amnesia using a passive avoidance task in mice; structure-activity relationship. | 1998 Nov |
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Paeoniflorin reverses guanethidine-induced hypotension via activation of central adenosine A1 receptors in Wistar rats. | 1999 Oct |
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Role of four major components in the effect of Si-Ni-San, a traditional Chinese prescription, against contact sensitivity in mice. | 2006 Sep |
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Protective effects of paeoniflorin against cobalt chloride-induced apoptosis of endothelial cells via HIF-1α pathway. | 2012 Apr |
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Paeoniflorin protects human EA.hy926 endothelial cells against gamma-radiation induced oxidative injury by activating the NF-E2-related factor 2/heme oxygenase-1 pathway. | 2013 Apr 26 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02878863
Peoniflorin tablets (600mg, tid) combination of phosphatidylcholine or silymarin
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25661317
Peoniflorin (10 nmol/L to 1 umol/L) increased the survival of cultured rat cortical neurons subjected to OGD/R. Peoniflorin increased the phosphorylation of Akt and ERK1/2 in these neurons. Peoniflorin (100 nmol/L) treatment of HEK293/A1R cells for 5 min enhanced the co-localization of A1R and EGFR on the cell surface.
Substance Class |
Chemical
Created
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Record UNII |
21AIQ4EV64
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Record Status |
Validated (UNII)
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Record Version |
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DSLD |
3250 (Number of products:2)
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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CONSTITUENT ALWAYS PRESENT -> PARENT |
Compound tested and showed no antiproliferative effects against two human cancer cell lines, OVCA 429 ovarian cancer cells and BT 483 breast cancer cells (IC50 N 100 μM) by MTT assay.
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CONSTITUENT ALWAYS PRESENT -> PARENT |
26.5 ? 3.9% neuroprotective activity of compound against 10.0 uM H2O2-induced neurotoxicity in primary cultures of rat cortical cells.
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CONSTITUENT ALWAYS PRESENT -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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CONSTITUENT ALWAYS PRESENT -> PARENT |
Effect of PL, paeoniflorin and paeonol on degranulation of rat peritoneal mast cells (IC50 = >100 uM) and RBL-2H3 (IC50 = >100 uM) cells.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Compound was tested for anticomplement activity through the Classical Pathway (CP) and Alternative Pathway (AP).
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CONSTITUENT ALWAYS PRESENT -> PARENT |