GENISTEIN

Possibly Marketed Outside US

First approved in 2007

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H10O5
Molecular Weight	270.2369
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(C=C1)C2=COC3=C(C(O)=CC(O)=C3)C2=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	270.2369
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 37 Target ID: CHEMBL1806 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7769390	Inhibitor 8504		0.11 µM [IC50]
Estrogen receptor beta 113 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17574424	Modulator 846		6.8 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Metabolic syndrome 34 Sources: https://clinicaltrials.gov/ct2/show/NCT01664650	Primary	Phase III 665	Unknown Approved Use Unknown
Cystic fibrosis 120 Sources: https://clinicaltrials.gov/ct2/show/NCT00590538	Primary	Phase II 1147	Unknown Approved Use Unknown
Colorectal cancer 102 Sources: https://clinicaltrials.gov/ct2/show/NCT01985763	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
341 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11285356/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
0.48 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12540402/	0.4 mg/kg bw single, oral dose: 0.4 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
0.43 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12540402/	0.4 mg/kg bw single, oral dose: 0.4 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED
0.87 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12540402/	0.8 mg/kg bw single, oral dose: 0.8 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
241.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15943224/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
550.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15943224/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1484.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15943224/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1773.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15943224/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
4.54 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11285356/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
6.33 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12540402/	0.4 mg/kg bw single, oral dose: 0.4 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
5.35 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12540402/	0.4 mg/kg bw single, oral dose: 0.4 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED
9.77 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12540402/	0.8 mg/kg bw single, oral dose: 0.8 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
2637.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15943224/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6562.2 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15943224/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
19782.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15943224/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
26132.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15943224/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
6.78 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11285356/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
7.68 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12540402/	0.4 mg/kg bw single, oral dose: 0.4 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
8.31 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12540402/	0.4 mg/kg bw single, oral dose: 0.4 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED
7.41 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12540402/	0.8 mg/kg bw single, oral dose: 0.8 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
7.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15943224/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
7.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15943224/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15943224/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
9.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15943224/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	GENISTEIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
300 mg single, oral Highest studied dose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: https://pubmed.ncbi.nlm.nih.gov/24692809/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/24692809/	Sources: https://pubmed.ncbi.nlm.nih.gov/24692809/
600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15231450/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15231450/	Sources: https://pubmed.ncbi.nlm.nih.gov/15231450/

PubMed

Title	Date	PubMed
Novel CFTR chloride channel activators identified by screening of combinatorial libraries based on flavone and benzoquinolizinium lead compounds.	2001-06-08	11262417
FAK induction in keratinocytes in an in vitro model of reepithelialization.	2001-04	11266269
Mitogenic effect of oxidized low-density lipoprotein on vascular smooth muscle cells mediated by activation of Ras/Raf/MEK/MAPK pathway.	2001-04	11264247
Characterization of the serotonin receptor mediating contraction in the mouse thoracic aorta and signal pathway coupling.	2001-04	11259531
Differential effects of flavonoids on 3T3-L1 adipogenesis and lipolysis.	2001-04	11245597
Excitation-contraction coupling in pulmonary vascular smooth muscle involves tyrosine kinase and Rho kinase.	2001-04	11238006
Molecular biology of transplant arteriosclerosis and sites of therapeutic intervention.	2001-03-27	11266824
Corticosterone-induced rapid phosphorylation of p38 and JNK mitogen-activated protein kinases in PC12 cells.	2001-03-16	11257496
Effect of phytoestrogen and antioxidant supplementation on oxidative DNA damage assessed using the comet assay.	2001-03-07	11182547
Dihydropyridine calcium channel blockers inhibit ascorbic acid accumulation in human intestinal Caco-2 cells.	2001-03-02	11270621
Effects of simple aromatic compounds and flavonoids on Ca2+ fluxes in rat pituitary GH(4)C(1) cells.	2001-03-02	11239912
Ca(2+)-dependent production of reactive oxygen metabolites by human neutrophils in response to fluorinated propranolol analogues.	2001-03-01	11239494
Initiation of polyoma virus origin-dependent DNA replication through STAT5 activation by human granulocyte-macrophage colony-stimulating factor.	2001-03-01	11222369
Paclitaxel sensitization of multidrug-resistant cells to chemotherapy is independent of the cell cycle.	2001-03-01	11170102
Interleukin-6 up-regulates the oxytocin receptor in cultured uterine smooth muscle cells.	2001-03	11270639
Differences in signal transduction pathways by which platelet-derived and fibroblast growth factors activate extracellular signal-regulated kinase in differentiating oligodendrocytes.	2001-03	11259511
Effects of estrogens in vitro and in vivo on cartilage growth in the tilapia (Oreochromis mossambicus).	2001-03	11254371
Vascular endothelial growth factor and the in vivo increase in plasma extravasation in the hamster cheek pouch.	2001-03	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.	2001-03	11244024
Bile acids induce eosinophil degranulation by two different mechanisms.	2001-03	11230738
Protein tyrosine kinase inhibitors alter human dopamine transporter activity in Xenopus oocytes.	2001-03	11181926
Phytoestrogens and gonadotropin-releasing hormone pulse generator activity and pituitary luteinizing hormone release in the rat.	2001-03	11181536
Adenosine-induced late preconditioning in mouse hearts: role of p38 MAP kinase and mitochondrial K(ATP) channels.	2001-03	11179074
Sex steroid receptor regulation by genistein in the prepubertal rat uterus.	2001-02-28	11223185
Regulation of p42/p44 MAPK and p38 MAPK by the adenosine A(1) receptor in DDT(1)MF-2 cells.	2001-02-16	11226388
Overexpression of BCL-X(L) underlies the molecular basis for resistance to staurosporine-induced apoptosis in PC-3 cells.	2001-02-15	11245486
Heparin-binding epidermal-growth-factor-like growth factor gene expression is induced by scrape-wounding epithelial cell monolayers: involvement of mitogen-activated protein kinase cascades.	2001-02-15	11171084
Regulation of acetylcholine release by extracellular matrix proteins at developing motoneurons in Xenopus cell cultures.	2001-02-15	11170182
Detrimental effect of cancer preventive phytochemicals silymarin, genistein and epigallocatechin 3-gallate on epigenetic events in human prostate carcinoma DU145 cells.	2001-02-01	11170137
PTH stimulates PLCbeta and PLCgamma isoenzymes in rat enterocytes: influence of ageing.	2001-02	11257458
Genistein potentiates the radiation effect on prostate carcinoma cells.	2001-02	11234894
Involvement of ErbB-2 in rheumatoid synovial cell growth.	2001-02	11229455
Effects of genistein on the periovulatory expression of messenger ribonucleic acid for matrix metalloproteinases and tissue inhibitors of metalloproteinases in the rat ovary.	2001-02	11226050
Differences in electromechanical coupling between bradykinin and the nonpeptide kinin B2 receptor agonist, FR 190997, in the circular muscle of guinea-pig colon.	2001-02	11218070
Involvement of erythropoietin-induced cytosolic free calcium mobilization in activation of mitogen-activated protein kinase and DNA synthesis in vascular smooth muscle cells.	2001-02	11212961
Regulation of MAP kinase by calcium-sensing receptor in bovine parathyroid and CaR-transfected HEK293 cells.	2001-02	11208605
Effect of genistein-enriched diets on the endocrine process of gametogenesis and on reproduction efficiency of the rainbow trout Oncorhynchus mykiss.	2001-02	11178883
Effect of intraovarian factors on porcine follicular cells: cumulus expansion, granulosa and cumulus cell progesterone production.	2001-01-31	11182513
Direct inhibition of the hexose transporter GLUT1 by tyrosine kinase inhibitors.	2001-01-23	11170395
Leflunomide inhibits activation of inducible nitric oxide synthase in rat astrocytes.	2001-01-19	11166726
The phytoestrogen genistein produces acute nitric oxide-dependent dilation of human forearm vasculature with similar potency to 17beta-estradiol.	2001-01-16	11208686
Agents that increase tyrosine phosphorylation activate a non-selective cation current in single rabbit portal vein smooth muscle cells.	2001-01-15	11208969
The mechanism of maitotoxin-induced elevation of the cytosolic free calcium level in rat cerebrocortical synaptosomes.	2001-01	11243582
Genistein prevents the glucose autoxidation mediated atherogenic modification of low density lipoprotein.	2001-01	11234992
Comparative assessment of endocrine modulators with oestrogenic activity: I. Definition of a hygiene-based margin of safety (HBMOS) for xeno-oestrogens against the background of European developments.	2001-01	11218041
Secretory transport of p-aminohippuric acid across intestinal epithelial cells in Caco-2 cells and isolated intestinal tissue.	2001-01	11206195
[In vitro and in vivo study of regulation mechanisms of type I interleukin-1 receptor].	2001-01	11201166
Modulation of noradrenaline-induced microvascular constriction by protein kinase inhibitors.	2001-01	11191837
Constitutive activation of Lck and Fyn tyrosine kinases in large granular lymphocytes infected with the gamma-herpesvirus agents of malignant catarrhal fever.	2001-01	11168636
Tyrosine kinase inhibitors against EGF receptor-positive malignancies.	2001	11217368

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 `Mon Mar 31 18:12:23 GMT 2025` Edited by `admin` on `Mon Mar 31 18:12:23 GMT 2025`
Record UNII	DH2M523P0H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GENISTEIN

Official Name

English

FW-635I-2

Preferred Name

English

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

Systematic 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

Genistein [WHO-DD]

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 [USAN]

Common Name

English

GENISTEIN [USP-RS]

Common Name

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