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{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 457127710
| IUPAC_name = 7-Isopropoxy-3-phenyl-4''H''-chromen-4-one
| image = Ipriflavone.png
| width = 250


| tradename = Yambolap
| Drugs.com = {{drugs.com|international|ipriflavone}}
| pregnancy_AU = 
| pregnancy_US = 
| pregnancy_category =
| legal_AU = 
| legal_CA = 
| legal_UK = 
| legal_US = Not FDA approved
| legal_status = Rx-only in Japan
| routes_of_administration =


| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =


| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 35212-22-7
| ATC_prefix = M05
| ATC_suffix = BX01
| PubChem = 3747
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 80BJ7WN25Z
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D01338
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 165790
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 3616


| C=18 | H=16 | O=3
| SMILES = CC(C)OC1=CC2=C(C=C1)C(=O)C(=CO2)C3=CC=CC=C3
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = SFBODOKJTYAUCM-UHFFFAOYSA-N
| synonyms = FLI13; 7-Isopropoxyisoflavone<ref name="Elks2014" />
}}

'''Ipriflavone''' ([[International Nonproprietary Name|INN]], [[Japanese Accepted Name|JAN]]; brand name '''Yambolap''') is a [[synthetic compound|synthetic]] [[isoflavone]] which may be used to inhibit bone resorption,<ref name="pmid9263610">{{cite journal | vauthors = Civitelli R | title = In vitro and in vivo effects of ipriflavone on bone formation and bone biomechanics | journal = Calcified Tissue International | volume = 61 Suppl 1 | pages = S12-4 | year = 1997 | pmid = 9263610 | doi = 10.1007/s002239900378 | s2cid = 21565791 }}</ref> maintain bone density and to prevent [[osteoporosis]] in postmenopausal women.<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA651|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=651–}}</ref> It is not used to treat osteoporosis. It slows down the action of the [[osteoclast]]s (bone-eroding cells), possibly allowing the [[osteoblast]]s (bone-building cells) to build up bone mass.

A clinical trial reported in 2001 that it was ''not'' effective in prevention or treatment of osteoporosis.<ref>{{cite journal | vauthors = Alexandersen P, Toussaint A, Christiansen C, Devogelaer JP, Roux C, Fechtenbaum J, Gennari C, Reginster JY | display-authors = 6 | title = Ipriflavone in the treatment of postmenopausal osteoporosis: a randomized controlled trial | journal = JAMA | volume = 285 | issue = 11 | pages = 1482–8 | date = March 2001 | pmid = 11255425 | doi = 10.1001/jama.285.11.1482 | collaboration = Ipriflavone Multicenter European Fracture Study }}</ref>

A double-blind study reveals that ipriflavone might be effective on reducing tinnitus on [[otosclerosis]] sufferers.<ref>{{cite journal | vauthors = Sziklai I, Komora V, Ribári O | title = Double-blind study on the effectiveness of a bioflavonoid in the control of tinnitus in otosclerosis | journal = Acta Chirurgica Hungarica | volume = 33 | issue = 1–2 | pages = 101–7 | year = 1992 | pmid = 1343452 }}</ref>

Ipriflavone has been described as a [[phytoestrogen]].<ref name="ArjmandiBirnbaum2000">{{cite journal | vauthors = Arjmandi BH, Birnbaum RS, Juma S, Barengolts E, Kukreja SC | title = The synthetic phytoestrogen, ipriflavone, and estrogen prevent bone loss by different mechanisms | journal = Calcified Tissue International | volume = 66 | issue = 1 | pages = 61–5 | date = January 2000 | pmid = 10602847 | doi = 10.1007/s002230050012 | s2cid = 31022310 }}</ref> However, this is incorrect, as the drug does not bind to or activate the [[estrogen receptor]] and shows no [[estrogen]]ic effects in [[postmenopausal]] women.<ref name="PetilliFiorelli1995">{{cite journal | vauthors = Petilli M, Fiorelli G, Benvenuti S, Frediani U, Gori F, Brandi ML | title = Interactions between ipriflavone and the estrogen receptor | journal = Calcified Tissue International | volume = 56 | issue = 2 | pages = 160–5 | date = February 1995 | pmid = 7736326 | doi = 10.1007/BF00296349 | s2cid = 24212438 }}</ref><ref name="MelisPaoletti2014">{{cite journal | vauthors = Melis GB, Paoletti AM, Cagnacci A, Bufalino L, Spinetti A, Gambacciani M, Fioretti P | title = Lack of any estrogenic effect of ipriflavone in postmenopausal women | journal = Journal of Endocrinological Investigation | volume = 15 | issue = 10 | pages = 755–61 | date = November 1992 | pmid = 1491124 | doi = 10.1007/BF03347647 | s2cid = 32186052 }}</ref> The drug prevents [[osteoporosis|bone loss]] via mechanisms that are distinct from those of [[estrogen]]s.<ref name="ArjmandiBirnbaum2000" />

== References ==
{{Reflist|2}}

== External links ==
* [http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/ipr_0147.shtml Ipriflavone] at PDR Health

{{Drugs for treatment of bone diseases}}
{{Isoflavones}}

[[Category:Isoflavones]]
[[Category:Phenol ethers]]

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