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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H28O11
Molecular Weight 480.4627
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PEONIFLORIN

SMILES

C[C@]12C[C@@]3([C@]4([H])C[C@]1([C@]4(COC(=O)c5ccccc5)[C@]([H])(O2)O3)O[C@@]6([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O6)O)O)O)O

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

HIDE SMILES / InChI

Molecular Formula C23H28O11
Molecular Weight 480.4627
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 11 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer









Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Effects of paeoniflorin derivatives on scopolamine-induced amnesia using a passive avoidance task in mice; structure-activity relationship.
1998 Nov
Paeoniflorin reverses guanethidine-induced hypotension via activation of central adenosine A1 receptors in Wistar rats.
1999 Oct
Role of four major components in the effect of Si-Ni-San, a traditional Chinese prescription, against contact sensitivity in mice.
2006 Sep
Protective effects of paeoniflorin against cobalt chloride-induced apoptosis of endothelial cells via HIF-1α pathway.
2012 Apr
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

Patents

Sample Use Guides

Peoniflorin tablets (600mg, tid) combination of phosphatidylcholine or silymarin
Route of Administration: Oral
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
by admin
on Fri Jun 25 23:26:55 UTC 2021
Edited
by admin
on Fri Jun 25 23:26:55 UTC 2021
Record UNII
21AIQ4EV64
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PEONIFLORIN
INCI  
INCI  
Official Name English
.BETA.-D-GLUCOPYRANOSIDE, 5B-((BENZOYLOXY)METHYL)TETRAHYDRO-5-HYDROXY-2-METHYL-2,5-METHANO-1H-3,4-DIOXACYCLOBUTA(CD)PENTALEN-1A(2H)-YL, (1AR-(1A.ALPHA.,2.BETA.,3A.ALPHA.,5.ALPHA.,5A.ALPHA.,5B.ALPHA.))-
Common Name English
PAEONIFLORIN
Common Name English
PAEONIFLORIN [USP-RS]
Common Name English
.BETA.-D-GLUCOPYRANOSIDE, (1AR,2S,3AR,5R,5AR,5BS)-5B-((BENZOYLOXY)METHYL)TETRAHYDRO-5-HYDROXY-2-METHYL-2,5-METHANO-1H-3,4-DIOXACYCLOBUTA(CD)PENTALEN-1A(2H)-YL
Common Name English
PEONIFLORIN [INCI]
Common Name English
NSC-178886
Code English
Classification Tree Code System Code
DSLD 3250 (Number of products:2)
Created by admin on Fri Jun 25 23:26:55 UTC 2021 , Edited by admin on Fri Jun 25 23:26:55 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
245-476-2
Created by admin on Fri Jun 25 23:26:55 UTC 2021 , Edited by admin on Fri Jun 25 23:26:55 UTC 2021
PRIMARY
EPA CompTox
23180-57-6
Created by admin on Fri Jun 25 23:26:55 UTC 2021 , Edited by admin on Fri Jun 25 23:26:55 UTC 2021
PRIMARY
WIKIPEDIA
PAEONIFLORIN
Created by admin on Fri Jun 25 23:26:55 UTC 2021 , Edited by admin on Fri Jun 25 23:26:55 UTC 2021
PRIMARY
PUBCHEM
442534
Created by admin on Fri Jun 25 23:26:55 UTC 2021 , Edited by admin on Fri Jun 25 23:26:55 UTC 2021
PRIMARY
RXCUI
2288155
Created by admin on Fri Jun 25 23:26:55 UTC 2021 , Edited by admin on Fri Jun 25 23:26:55 UTC 2021
PRIMARY
FDA UNII
21AIQ4EV64
Created by admin on Fri Jun 25 23:26:55 UTC 2021 , Edited by admin on Fri Jun 25 23:26:55 UTC 2021
PRIMARY
USP_CATALOG
1491616
Created by admin on Fri Jun 25 23:26:55 UTC 2021 , Edited by admin on Fri Jun 25 23:26:55 UTC 2021
PRIMARY USP-RS
CAS
23180-57-6
Created by admin on Fri Jun 25 23:26:55 UTC 2021 , Edited by admin on Fri Jun 25 23:26:55 UTC 2021
PRIMARY
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