ipriflavone

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 457127710

| IUPAC_name = 7-Isopropoxy-3-phenyl-4H-chromen-4-one

| image = Ipriflavone.png

| width = 250

| tradename = Yambolap

| Drugs.com = {{drugs.com|international|ipriflavone}}

| pregnancy_AU =

| pregnancy_US =

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| legal_AU =

| legal_CA =

| legal_UK =

| legal_US = Not FDA approved

| legal_status = Rx-only in Japan

| routes_of_administration =

| bioavailability =

| protein_bound =

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| elimination_half-life =

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| 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

}}

Ipriflavone (INN, JAN; brand name Yambolap) is a synthetic isoflavone which may be used to inhibit bone resorption,{{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 }} maintain bone density and to prevent osteoporosis in postmenopausal women.{{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–}} It is not used to treat osteoporosis. It slows down the action of the osteoclasts (bone-eroding cells), possibly allowing the osteoblasts (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.{{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 }}

A double-blind study reveals that ipriflavone might be effective on reducing tinnitus on otosclerosis sufferers.{{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 }}

Ipriflavone has been described as a phytoestrogen.{{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 }} However, this is incorrect, as the drug does not bind to or activate the estrogen receptor and shows no estrogenic effects in postmenopausal women.{{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 }}{{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 }} The drug prevents bone loss via mechanisms that are distinct from those of estrogens.