FISETIN

Possibly Marketed Outside US

First approved in 2023

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H10O6
Molecular Weight	286.2363
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC2=C(C=C1)C(=O)C(O)=C(O2)C3=CC(O)=C(O)C=C3

InChI

InChIKey=XHEFDIBZLJXQHF-UHFFFAOYSA-N

InChI=1S/C15H10O6/c16-8-2-3-9-12(6-8)21-15(14(20)13(9)19)7-1-4-10(17)11(18)5-7/h1-6,16-18,20H

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29383865 | https://www.ncbi.nlm.nih.gov/pubmed/29396047 | https://www.ncbi.nlm.nih.gov/pubmed/24923846

Fisetin, a natural flavonoid found in various fruits, vegetables, and nuts, has various biological properties, including anti-inflammatory, anti-oxidant, neuroprotective in cell culture and in animal models relevant to human diseases. Fisetin can be also a promising agent for the treatment of uveal melanoma. Besides, it is a therapeutic agent for respiratory inflammatory diseases such as chronic obstructive pulmonary disease (COPD), where fisetin inhibits the TNF-α-activated IKK/NF-κB cascade by targeting PKCδ. In vitro and in vivo experiments have revealed that fisetin possesses significant therapeutic effects against diabetic complications and atherosclerosis, where it can suppress vascular inflammatory processes.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Protein kinase C delta type 2 Target ID: Q05655 Gene ID: 5580.0 Gene Symbol: PRKCD Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/29396047	Binding Agent 1064

Conditions

Condition	Modality	Highest Phase	Product
Chronic obstructive pulmonary disease 174 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29396047	Primary	Basic research	Unknown Approved Use Unknown
Uveal melanoma 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29383865	Primary	Basic research	Unknown Approved Use Unknown
Diabetic complications 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24923846	Primary	Preclinical	Unknown Approved Use Unknown
Atherosclerosis 74 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24923846	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Flavones are inhibitors of HIV-1 proteinase.	1992 Oct 30	1445308
Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.	2000 Jul-Aug	10953322
Hydroxylations and methylations of quercetin, fisetin, and catechin by Streptomyces griseus.	2001 Apr	11325228
Wogonin and fisetin induction of apoptosis through activation of caspase 3 cascade and alternative expression of p21 protein in hepatocellular carcinoma cells SK-HEP-1.	2002 Jun	12107653
Structure-activity relationships for inhibition of human 5alpha-reductases by polyphenols.	2002 Mar 15	11931850
Rutin-enhanced antibacterial activities of flavonoids against Bacillus cereus and Salmonella enteritidis.	2002 May	12092809
Methylation of quercetin and fisetin, flavonoids widely distributed in edible vegetables, fruits and wine, by human liver.	2002 May	12051572
Effects of flavonoids on vascular smooth muscle of the isolated rat thoracic aorta.	2003 Dec 19	14623031
Bioflavonoids attenuate renal proximal tubular cell injury during cold preservation in Euro-Collins and University of Wisconsin solutions.	2003 Feb	12631120
Fisetin, a flavonol, inhibits TH2-type cytokine production by activated human basophils.	2003 Jun	12789233
Inhibitory effects of plant-derived flavonoids and phenolic acids on malonaldehyde formation from ethyl arachidonate.	2003 Nov 19	14611194
Different antioxidant effects of polyphenols on lipid peroxidation and hydroxyl radicals in the NADPH-, Fe-ascorbate- and Fe-microsomal systems.	2003 Oct 1	14505792
Some aspects of the in vivo neuroprotective capacity of flavonoids: bioavailability and structure-activity relationship.	2004	15639786
Flavonoids induce apoptosis in human leukemia U937 cells through caspase- and caspase-calpain-dependent pathways.	2004	15572302
Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake.	2004 Jan 9	14557274
Flavonoids such as luteolin, fisetin and apigenin are inhibitors of interleukin-4 and interleukin-13 production by activated human basophils.	2004 Jun	15153793
Strong inhibitory effects of common tea catechins and bioflavonoids on the O-methylation of catechol estrogens catalyzed by human liver cytosolic catechol-O-methyltransferase.	2004 May	15100171
Vascular and anti-oxidant actions of flavonols and flavones.	2004 Nov	15566394
Oxidation products of quercetin catalyzed by mushroom tyrosinase.	2004 Oct 15	15388161
Extract from Rhus verniciflua Stokes is capable of inhibiting the growth of human lymphoma cells.	2004 Sep	15234068
Interactions of the plant flavonoid fisetin with macromolecular targets: insights from fluorescence spectroscopic studies.	2005 Aug 1	16038806
Crystal structure of a human cyclin-dependent kinase 6 complex with a flavonol inhibitor, fisetin.	2005 Feb 10	15689157
Evaluation of the antioxidant activity of flavonoids by "ferric reducing antioxidant power" assay and cyclic voltammetry.	2005 Jan 18	15652192
A blend of polyphenolic compounds explains the stimulatory effect of red wine on human endothelial NO synthase.	2005 Mar	15740983
Distinctive antioxidant and antiinflammatory effects of flavonols.	2006 Dec 27	17177504
Anti-platelet effects of bioactive compounds isolated from the bark of Rhus verniciflua Stokes.	2006 Jun 15	16431050
Effect of different flavonoids on collagen synthesis in human fibroblasts.	2006 Mar	16642409
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Inhibition of the intestinal glucose transporter GLUT2 by flavonoids.	2007 Feb	17172639
Determination of flavonoid aglycones in several food samples by mixed micellar electrokinetic chromatography.	2007 Oct	17654618

Patents

Sample Use Guides

In Vivo Use Guide

hepatocellular carcinoma group rats: 20 mg/kg b.w.

Route of Administration: Oral

In Vitro Use Guide

It was investigated the antiangiogenic efficacy and associated mechanisms of fisetin in human umbilical vein endothelial cells (HUVECs). Fisetin (10-50 μM) strongly inhibited the regular serum plus growth supplement- and vascular endothelial growth factor (VEGF)-induced growth (up to 92%, P < 0.001) and survival (up to 16%, P < 0.001) of HUVEC in a dose- and time-dependent manner. Fisetin also caused cell cycle arrest at G(1) (strong) and G(2)/M (moderate) phases together with a decrease in cyclin D1 and an increase in p53 levels. Fisetin-caused cell death was accompanied by decreased expression of survivin and an increase in cleaved levels of caspases-3 and -7 and poly-(ADP-ribose) polymerase along with an increased ratio of Bax to Bcl-2.

Name

Type

Language

FISETIN

Official Name

English

Fisetin [WHO-DD]

Common Name

English

5-DESOXYQUERCETIN

Common Name

English

FISETIN [MI]

Common Name

English

FISIDENOLON 1521

Common Name

English

FISETIN [INCI]

Common Name

English

3,3',4',7-TETRAHYDROXYFLAVONE

Systematic Name

English

C.I. NATURAL BROWN 1

Common Name

English

NSC-407010

Code

English

NSC-656275

Code

English

2-(3,4-DIHYDROXYPHENYL)-3,7-DIHYDROXY-4H-1-BENZOPYRAN-4-ONE

Systematic Name

English

C.I. 75620

Common Name

English

Classification Tree Code System Code

DSLD

2651 (Number of products:20)