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Details

Stereochemistry ACHIRAL
Molecular Formula C18H16O3
Molecular Weight 280.3178
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IPRIFLAVONE

SMILES

CC(C)OC1=CC=C2C(=O)C(=COC2=C1)C3=CC=CC=C3

InChI

InChIKey=SFBODOKJTYAUCM-UHFFFAOYSA-N
InChI=1S/C18H16O3/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

HIDE SMILES / InChI

Molecular Formula C18H16O3
Molecular Weight 280.3178
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta.
1998 Oct
Effects of ipriflavone on bone augmentation within a titanium cap in rabbit calvaria.
2002 Mar
Effects of methoxyisoflavone, ecdysterone, and sulfo-polysaccharide supplementation on training adaptations in resistance-trained males.
2006 Dec 13
Identification of Hedgehog signaling inhibitors with relevant human exposure by small molecule screening.
2010 Aug
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:44:34 GMT 2023
Edited
by admin
on Fri Dec 15 15:44:34 GMT 2023
Record UNII
80BJ7WN25Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IPRIFLAVONE
INN   JAN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
7-ISOPROPOXYISOFLAVONE
Common Name English
IPRIFLAVONE [MART.]
Common Name English
IPRIFLAVONE [VANDF]
Common Name English
OSTIVONE
Brand Name English
NSC-755888
Code English
OSTEN
Brand Name English
IPRIFLAVONE [MI]
Common Name English
ipriflavone [INN]
Common Name English
IPRIFLAVONE [JAN]
Common Name English
Ipriflavone [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QM05BX01
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
NCI_THESAURUS C1745
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
WHO-ATC M05BX01
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
DSLD 479 (Number of products:64)
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
Code System Code Type Description
RXCUI
51487
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY RxNorm
EVMPD
SUB08278MIG
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
FDA UNII
80BJ7WN25Z
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
DAILYMED
80BJ7WN25Z
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
PUBCHEM
3747
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
INN
3521
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PRIMARY
DRUG BANK
DB13618
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PRIMARY
ChEMBL
CHEMBL165790
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID5040679
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
SMS_ID
100000083142
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
MERCK INDEX
m6388
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY Merck Index
NSC
755888
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
CAS
35212-22-7
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
NCI_THESAURUS
C1505
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
CONCEPT Dietary Supplement
DRUG CENTRAL
1477
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PRIMARY
CHEBI
31719
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
MESH
C018986
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
WIKIPEDIA
IPRIFLAVONE
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
NCI_THESAURUS
C63694
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY