GENISTEIN

Possibly Marketed Outside US

First approved in 2007

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H10O5
Molecular Weight	270.2375
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1cc(ccc1-c2coc3cc(cc(c3c2=O)O)O)O

InChI

InChIKey=TZBJGXHYKVUXJN-UHFFFAOYSA-N

InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H

HIDE SMILES / InChI

Molecular Formula	C15H10O5
Molecular Weight	270.2375
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugbank.ca/drugs/DB01645
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15909536 | https://www.ncbi.nlm.nih.gov/pubmed/28265354 | https://www.ncbi.nlm.nih.gov/pubmed/25996650 | https://clinicaltrials.gov/ct2/show/NCT01664650

GENISTEIN is an isoflavonoid derived from soy products. It inhibits protein-tyrosine kinase and topoisomerase-II (DNA topoisomerases, type II) activity and is used as an antineoplastic and antitumor agent. Experimentally, it has been shown to induce G2 phase arrest in human and murine cell lines. Additionally, genistein has antihelmintic activity. It has been determined to be the active ingredient in Felmingia vestita, which is a plant traditionally used against worms. It has also been demonstrated to be effective against intestinal parasites such as the common liver fluke, pork trematode and poultry cestode. Further, genistein is a phytoestrogen which has selective estrogen receptor modulator properties. It has been investigated in clinical trials as an alternative to classical hormone therapy to help prevent cardiovascular disease in postmenopausal women. Genistein can be found in food sources such as tofu, fava beans, soybeans, kudzu, and lupin. It is also present in certain cell cultures and medicinal plants.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase II alpha 34 Target ID: CHEMBL1806 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7769390	Inhibitor 7728		0.11 µM [IC50]
Estrogen receptor beta 106 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17574424	Modulator 780		6.8 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Metabolic syndrome 30 Sources: https://clinicaltrials.gov/ct2/show/NCT01664650	Primary	Phase III 643	Unknown Approved Use Unknown
Cystic fibrosis 138 Sources: https://clinicaltrials.gov/ct2/show/NCT00590538	Primary	Phase II 1101	Unknown Approved Use Unknown
Colorectal cancer 94 Sources: https://clinicaltrials.gov/ct2/show/NCT01985763	Primary	Phase II 1101	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Differential estrogen receptor binding of estrogenic substances: a species comparison.	2000 Nov 15	11162928
FAK induction in keratinocytes in an in vitro model of reepithelialization.	2001 Apr	11266269
Mitogenic effect of oxidized low-density lipoprotein on vascular smooth muscle cells mediated by activation of Ras/Raf/MEK/MAPK pathway.	2001 Apr	11264247
Characterization of the serotonin receptor mediating contraction in the mouse thoracic aorta and signal pathway coupling.	2001 Apr	11259531
Differential effects of flavonoids on 3T3-L1 adipogenesis and lipolysis.	2001 Apr	11245597
Excitation-contraction coupling in pulmonary vascular smooth muscle involves tyrosine kinase and Rho kinase.	2001 Apr	11238006
PTH stimulates PLCbeta and PLCgamma isoenzymes in rat enterocytes: influence of ageing.	2001 Feb	11257458
Genistein potentiates the radiation effect on prostate carcinoma cells.	2001 Feb	11234894
Involvement of ErbB-2 in rheumatoid synovial cell growth.	2001 Feb	11229455
Effects of genistein on the periovulatory expression of messenger ribonucleic acid for matrix metalloproteinases and tissue inhibitors of metalloproteinases in the rat ovary.	2001 Feb	11226050
Involvement of erythropoietin-induced cytosolic free calcium mobilization in activation of mitogen-activated protein kinase and DNA synthesis in vascular smooth muscle cells.	2001 Feb	11212961
Effect of genistein-enriched diets on the endocrine process of gametogenesis and on reproduction efficiency of the rainbow trout Oncorhynchus mykiss.	2001 Feb	11178883
A common mechanism for cystic fibrosis transmembrane conductance regulator protein activation by genistein and benzimidazolone analogs.	2001 Feb	11160632
Assessment of CFTR chloride channel openers in intact normal and cystic fibrosis murine epithelia.	2001 Feb	11159718
Signaling events following chemokine receptor ligation in human dendritic cells at different developmental stages.	2001 Feb	11157850
Detrimental effect of cancer preventive phytochemicals silymarin, genistein and epigallocatechin 3-gallate on epigenetic events in human prostate carcinoma DU145 cells.	2001 Feb 1	11170137
Cytokine regulation of the expression of estrogenic biosynthetic enzymes in cultured rat granulosa cells.	2001 Feb 14	11165036
Overexpression of BCL-X(L) underlies the molecular basis for resistance to staurosporine-induced apoptosis in PC-3 cells.	2001 Feb 15	11245486
Regulation of p42/p44 MAPK and p38 MAPK by the adenosine A(1) receptor in DDT(1)MF-2 cells.	2001 Feb 16	11226388
Molecular biology of transplant arteriosclerosis and sites of therapeutic intervention.	2001 Feb-Mar	11266824
The mechanism of maitotoxin-induced elevation of the cytosolic free calcium level in rat cerebrocortical synaptosomes.	2001 Jan	11243582
Genistein prevents the glucose autoxidation mediated atherogenic modification of low density lipoprotein.	2001 Jan	11234992
Modulation of noradrenaline-induced microvascular constriction by protein kinase inhibitors.	2001 Jan	11191837
Contractile actions of proteinase-activated receptor-derived polypeptides in guinea-pig gastric and lung parenchymal strips: evidence for distinct receptor systems.	2001 Jan	11159706
Leukotriene C(4) enhances the contraction of porcine tracheal smooth muscle through the activation of Y-27632, a rho kinase inhibitor, sensitive pathway.	2001 Jan	11156567
Growth hormone- and prolactin-induced proliferation of insulinoma cells, INS-1, depends on activation of STAT5 (signal transducer and activator of transcription 5).	2001 Jan	11145745
Activation of human neutrophils by technical toxaphene.	2001 Jan	11141326
Genistein inhibits nonoxidative ribose synthesis in MIA pancreatic adenocarcinoma cells: a new mechanism of controlling tumor growth.	2001 Jan	11138960
Agents that increase tyrosine phosphorylation activate a non-selective cation current in single rabbit portal vein smooth muscle cells.	2001 Jan 15	11208969
Salicylates inhibit T cell adhesion on endothelium under nonstatic conditions: induction of L-selectin shedding by a tyrosine kinase-dependent mechanism.	2001 Jan 15	11145657
The phytoestrogen genistein produces acute nitric oxide-dependent dilation of human forearm vasculature with similar potency to 17beta-estradiol.	2001 Jan 16	11208686
Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5.	2001 Jan 22	11165023
Effect of intraovarian factors on porcine follicular cells: cumulus expansion, granulosa and cumulus cell progesterone production.	2001 Jan 31	11182513
Differential effects of protein tyrosine kinase inhibitors on interferon-gamma-induction of major histocompatibility complex class II and intercellular adhesion molecule-1 expression in human corneal epithelial cells.	2001 Jan-Feb	11163041
Novel CFTR chloride channel activators identified by screening of combinatorial libraries based on flavone and benzoquinolizinium lead compounds.	2001 Jun 8	11262417
Interleukin-6 up-regulates the oxytocin receptor in cultured uterine smooth muscle cells.	2001 Mar	11270639
Differences in signal transduction pathways by which platelet-derived and fibroblast growth factors activate extracellular signal-regulated kinase in differentiating oligodendrocytes.	2001 Mar	11259511
Effects of estrogens in vitro and in vivo on cartilage growth in the tilapia (Oreochromis mossambicus).	2001 Mar	11254371
Vascular endothelial growth factor and the in vivo increase in plasma extravasation in the hamster cheek pouch.	2001 Mar	11250886
Src tyrosine kinases and extracellular signal-regulated kinase 1/2 mitogen-activated protein kinases mediate pressure-induced c-fos expression in cannulated rat mesenteric small arteries.	2001 Mar	11244024
Bile acids induce eosinophil degranulation by two different mechanisms.	2001 Mar	11230738
Protein tyrosine kinase inhibitors alter human dopamine transporter activity in Xenopus oocytes.	2001 Mar	11181926
Phytoestrogens and gonadotropin-releasing hormone pulse generator activity and pituitary luteinizing hormone release in the rat.	2001 Mar	11181536
Ca(2+)-dependent production of reactive oxygen metabolites by human neutrophils in response to fluorinated propranolol analogues.	2001 Mar 1	11239494
Initiation of polyoma virus origin-dependent DNA replication through STAT5 activation by human granulocyte-macrophage colony-stimulating factor.	2001 Mar 1	11222369
Paclitaxel sensitization of multidrug-resistant cells to chemotherapy is independent of the cell cycle.	2001 Mar 1	11170102
Corticosterone-induced rapid phosphorylation of p38 and JNK mitogen-activated protein kinases in PC12 cells.	2001 Mar 16	11257496
Dihydropyridine calcium channel blockers inhibit ascorbic acid accumulation in human intestinal Caco-2 cells.	2001 Mar 2	11270621
Effects of simple aromatic compounds and flavonoids on Ca2+ fluxes in rat pituitary GH(4)C(1) cells.	2001 Mar 2	11239912
The "in vivo" and "ex vivo" roles of cylcooxygenase-2, nuclear factor-kappaB and protein kinases pathways in the up-regulation of B1 receptor-mediated contraction of the rabbit aorta.	2001 Mar 2	11164947

Patents

Sample Use Guides

In Vivo Use Guide

54 mg/day in 2 tablets for 12 months.

Route of Administration: Oral

In Vitro Use Guide

Cells were cultured in Dulbecco’s modified Eagle’s medium (U2OS, HCT116) media containing fetal calf serum, penicillin, streptomycin, glutamine, nonessential amino acids (Hyclone). The long-term growth curves of both 10 μmol/L genistein-treated U2OS and HCT116 cells were then determined by MTS assay. The experiment was conducted for 60 days with measuring the population doublings (PD) every 2–4 days after each dilution.

Substance Class	Chemical Created by `admin` on `Sat Jun 26 02:43:51 UTC 2021` Edited by `admin` on `Sat Jun 26 02:43:51 UTC 2021`
Record UNII	DH2M523P0H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GENISTEIN

Official Name

English

4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-3-(4-HYDROXYPHENYL)-

Systematic Name

English

GENISTEIN [INCI]

Common Name

English

BIO-300

Code

English

GENISTEIN [HSDB]

Common Name

English

SOPHORICOL

Common Name

English

GENISTEIN [MART.]

Common Name

English

GENISTEIN [INN]

Common Name

English

GENISTEIN (CONSTITUENT OF RED CLOVER) [DSC]

Common Name

English

4',5,7-TRIHYDROXYISOFLAVONE

Common Name

English

NSC-36586

Code

English

GENISTEIN [MI]

Common Name

English

5,7-DIHYDROXY-3-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE

Systematic Name

English

GENISTEIN (CONSTITUENT OF SOY ISOFLAVONES) [DSC]

Common Name

English

GENISTEIN [WHO-DD]

Common Name

English

GENISTEIN [USAN]

Common Name

English

GENISTEIN [USP-RS]

Common Name

English

FW-635I-2

Code

English

5,7-DIHYDROXY-3-(4-HYDROXYPHENYL)-CHROMEN-4-ONE

Systematic Name

English

SIPI-807-1

Code

English

NPI-031L

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1967