U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C18H16O3.FH
Molecular Weight 300.3242
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 7-(1-Methylethoxy)-3-phenyl-4H-1-benzopyran-4-one hydrofluoride

SMILES

F.CC(C)OC1=CC2=C(C=C1)C(=O)C(=CO2)C3=CC=CC=C3

InChI

InChIKey=BUJJBYFEAVKPKG-UHFFFAOYSA-N
InChI=1S/C18H16O3.FH/c1-12(2)21-14-8-9-15-17(10-14)20-11-16(18(15)19)13-6-4-3-5-7-13;/h3-12H,1-2H3;1H

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://www.houseofnutrition.com/ipriflavone.html http://www.anaturalhealingcenter.com/documents/Thorne/monos/IpriflavoneMono.pdf

Ipriflavone (chemical structure: 7-isopropoxyisoflavone), derived from the soy isoflavone, daidzein, holds great promise for osteoporosis prevention and treatment. Ipriflavone (IP) was discovered in the 1930s but has only recently begun to be embraced by the medical community in this country. Over 150 studies on safety and effectiveness, both animal and human, have been conducted in Italy, Hungary, and Japan. As of 1997, 2,769 patients had been treated a total of 3,132 patient years. Preliminary studies have pointed to its effectiveness in the treatment of other conditions involving bone pathology, including Paget’s disease, hyperparathyroidism, renal osteodystrophy, and tinnitus due to otosclerosis. Ipriflavone appears to have several mechanisms of action, all of which enhance bone density, making them seemingly superior to many of the other treatments available for osteoporosis prevention and treatment. IP also inhibits osteoclastic activity (motility and resorptive activity) by modulating intracellular free calcium. IP’s bone-forming mechanisms include stimulation of cell proliferation and maturation of osteoblasts by inhibiting calcium influx into osteoblasts and phosphoinositide hydrolysis. Despite similarities to estrogen, IP possesses no intrinsic estrogenic activity, but does potentiate estrogen. Importantly, IP does not change bone mineral composition or crystalline structure. A clinical trial reported in 2001 that it was not effective in prevention or treatment of osteoporosis.

Originator

Curator's Comment: Over 150 studies on safety and effectiveness, both animal and human, have been conducted in Italy, Hungary, and Japan. As of 1997, 2,769 patients had been treated a total of 3,132 patient years

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Identification of Hedgehog signaling inhibitors with relevant human exposure by small molecule screening.
2010-08
Effects of methoxyisoflavone, ecdysterone, and sulfo-polysaccharide supplementation on training adaptations in resistance-trained males.
2006-12-13
Effects of ipriflavone on bone augmentation within a titanium cap in rabbit calvaria.
2002-03
Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta.
1998-10
Patents

Patents

Sample Use Guides

Paget's disease of bone: 600 mg/day and 1200 mg/day during 30 days
Route of Administration: Oral
In the cytokinesis-blocked micronucleus assay, the concentration of Ipriflavone (10 μg/mL) induced a statistically significant increase in micronucleus assay formation and decreased cell proliferation, demonstrating to be mutagenic and cytotoxic at this concentration.
Name Type Language
7-(1-Methylethoxy)-3-phenyl-4H-1-benzopyran-4-one hydrofluoride
Systematic Name English
4H-1-Benzopyran-4-one, 7-(1-methylethoxy)-3-phenyl-, hydrofluoride
Preferred Name English
Code System Code Type Description
CAS
1532511-88-8
Created by admin on Wed Apr 02 10:33:53 GMT 2025 , Edited by admin on Wed Apr 02 10:33:53 GMT 2025
PRIMARY
FDA UNII
QMY8UPG2Q9
Created by admin on Wed Apr 02 10:33:53 GMT 2025 , Edited by admin on Wed Apr 02 10:33:53 GMT 2025
PRIMARY