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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H20O9
Molecular Weight 416.3781
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PUERARIN

SMILES

[H][C@]1(O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C2=C(O)C=CC3=C2OC=C(C3=O)C4=CC=C(O)C=C4

InChI

InChIKey=HKEAFJYKMMKDOR-VPRICQMDSA-N
InChI=1S/C21H20O9/c22-7-14-17(26)18(27)19(28)21(30-14)15-13(24)6-5-11-16(25)12(8-29-20(11)15)9-1-3-10(23)4-2-9/h1-6,8,14,17-19,21-24,26-28H,7H2/t14-,17-,18+,19-,21+/m1/s1

HIDE SMILES / InChI
Puerarin (7, 4’-dihydroxyisolavone-8-β-glucopyranoside) is an active isoflavone extracted from the roots of Pueraria lobata (Willd.) Ohwi. Puerarin is widely used in traditional Chinese medicine, and is clinically used in China for the treatment of coronary artery disease, heart failure, hypertension and myocardial infarction. It has been reported that puerarin had therapeutic effects on diabetes mellitus, arteriosclerosis and myocardial ischemia in animals. Puerarin demonstrated beta-adrenergic receptor blocking effect. On the other hand, puerarin stimulated alpha1-adrenoreceptor to increase glucose uptake into cultured C2C12 cells of mice. Puerarin has been investigated for the treatment (phase II clinical trials) of Alcohol Abuse, Rheumatoid Arthritis and Hypertension.

Originator

Sources: DOI: 10.1248/cpb.7.134

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
11.07 ng/mL
9.984 mg single, oral
dose: 9.984 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PUERARIN blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
85.9 ng × h/mL
9.984 mg single, oral
dose: 9.984 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PUERARIN blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.48 h
9.984 mg single, oral
dose: 9.984 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PUERARIN blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
1200 mg single, oral
Highest studied dose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources: Page: p.6
healthy, 25.8 ± 3.2
n = 10
Health Status: healthy
Age Group: 25.8 ± 3.2
Sex: M+F
Population Size: 10
Sources: Page: p.6
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
[Estrogen-like effects of puerarin and total isoflavones from Pueraria lobata].
2002 Aug
The Neuroprotection of puerarin against cerebral ischemia is associated with the prevention of apoptosis in rats.
2005 Jul
Reversal of chemical-induced liver fibrosis in Wistar rats by puerarin.
2006 Jul
Induction of apoptosis by puerarin in colon cancer HT-29 cells.
2006 Jul 8
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
[Effect of compound Puerarin on the collage IV in streptozotocin-induced diabetic nephropathy rats].
2008 Apr
Phytoestrogens induce differential estrogen receptor beta-mediated responses in transfected MG-63 cells.
2008 Aug-Dec
Effect of puerarin on the expression of extracellular matrix in rats with streptozotocin-induced diabetic nephropathy.
2009 Jan-Feb
[Apoptosis of NB4 cells induced by flavonoids of puerarin in vitro].
2010 Apr
Puerarin suppresses AGEs-induced inflammation in mouse mesangial cells: a possible pathway through the induction of heme oxygenase-1 expression.
2010 Apr 15
Protective role of puerarin on lead-induced alterations of the hepatic glutathione antioxidant system and hyperlipidemia in rats.
2011 Dec
Role of the interaction between puerarin and the erythrocyte membrane in puerarin-induced hemolysis.
2011 Jul 15
Puerarin activates endothelial nitric oxide synthase through estrogen receptor-dependent PI3-kinase and calcium-dependent AMP-activated protein kinase.
2011 Nov 15
Puerarin, a selective oestrogen receptor modulator, disrupts pregnancy in rats at pre-implantation stage.
2012 Nov
UDP-glucuronosyltransferase 1A1 is the principal enzyme responsible for puerarin metabolism in human liver microsomes.
2012 Nov
Protective effects of puerarin on experimental chronic lead nephrotoxicity in immature female rats.
2013 Feb
Puerarin mediates hepatoprotection against CCl4-induced hepatic fibrosis rats through attenuation of inflammation response and amelioration of metabolic function.
2013 Feb
Anti-fibrotic effects of puerarin on CCl4-induced hepatic fibrosis in rats possibly through the regulation of PPAR-γ expression and inhibition of PI3K/Akt pathway.
2013 Jun
Protective effect of puerarin on lead-induced mouse cognitive impairment via altering activities of acetyl cholinesterase, monoamine oxidase and nitric oxide synthase.
2013 May
Anti-diabetic effects of puerarin, isolated from Pueraria lobata (Willd.), on streptozotocin-diabetogenic mice through promoting insulin expression and ameliorating metabolic function.
2013 Oct
Puerarin protects against lead-induced cytotoxicity in cultured primary rat proximal tubular cells.
2014 Oct
Puerarin ameliorates carbon tetrachloride-induced oxidative DNA damage and inflammation in mouse kidney through ERK/Nrf2/ARE pathway.
2014 Sep
Puerarin attenuates learning and memory impairments and inhibits oxidative stress in STZ-induced SAD mice.
2015 Dec
Impact of kudzu and puerarin on sperm function.
2015 Jun
Protective effects of puerarin against tetrabromobisphenol a-induced apoptosis and cardiac developmental toxicity in zebrafish embryo-larvae.
2015 Sep
Puerarin protects mouse liver against nickel-induced oxidative stress and inflammation associated with the TLR4/p38/CREB pathway.
2016 Jan 5
Patents

Patents

Sample Use Guides

400 mg once a day. The treatment course consisted of 2 weeks followed by a 15-day interval for 24 weeks.
Route of Administration: Intravenous
Radioactive glucose (2-DG) uptake was enhanced within 3 min of exposure to 10 uM/l puerarin. This action of puerarin increased gradually with longer incubation times to become half-maximal at 10 min and became maximally stimulated at 30 min.
Name Type Language
PUERARIN
INCI   WHO-DD  
INCI  
Official Name English
4H-1-BENZOPYRAN-4-ONE, 8-.BETA.-D-GLUCOPYRANOSYL-7-HYDROXY-3-(4-HYDROXYPHENYL)-
Common Name English
DAIDZEIN 8-C-GLUCOSIDE
Common Name English
PUERARIN [INCI]
Common Name English
NPI 031G
Code English
NSC-380711
Code English
KAKONEIN
Common Name English
PUERARIN 80 MM
Brand Name English
Puerarin [WHO-DD]
Common Name English
Classification Tree Code System Code
DSLD 3581 (Number of products:1)
Created by admin on Sat Dec 16 01:54:25 GMT 2023 , Edited by admin on Sat Dec 16 01:54:25 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID30958020
Created by admin on Sat Dec 16 01:54:25 GMT 2023 , Edited by admin on Sat Dec 16 01:54:25 GMT 2023
PRIMARY
PUBCHEM
5281807
Created by admin on Sat Dec 16 01:54:25 GMT 2023 , Edited by admin on Sat Dec 16 01:54:25 GMT 2023
PRIMARY
WIKIPEDIA
PUERARIN
Created by admin on Sat Dec 16 01:54:25 GMT 2023 , Edited by admin on Sat Dec 16 01:54:25 GMT 2023
PRIMARY
NSC
380711
Created by admin on Sat Dec 16 01:54:25 GMT 2023 , Edited by admin on Sat Dec 16 01:54:25 GMT 2023
PRIMARY
MESH
C033607
Created by admin on Sat Dec 16 01:54:25 GMT 2023 , Edited by admin on Sat Dec 16 01:54:25 GMT 2023
PRIMARY
FDA UNII
Z9W8997416
Created by admin on Sat Dec 16 01:54:25 GMT 2023 , Edited by admin on Sat Dec 16 01:54:25 GMT 2023
PRIMARY
SMS_ID
100000127786
Created by admin on Sat Dec 16 01:54:25 GMT 2023 , Edited by admin on Sat Dec 16 01:54:25 GMT 2023
PRIMARY
DRUG BANK
DB12290
Created by admin on Sat Dec 16 01:54:25 GMT 2023 , Edited by admin on Sat Dec 16 01:54:25 GMT 2023
PRIMARY
EVMPD
SUB33910
Created by admin on Sat Dec 16 01:54:25 GMT 2023 , Edited by admin on Sat Dec 16 01:54:25 GMT 2023
PRIMARY
CAS
3681-99-0
Created by admin on Sat Dec 16 01:54:25 GMT 2023 , Edited by admin on Sat Dec 16 01:54:25 GMT 2023
PRIMARY