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Ipriflavone

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Ipriflavone
Clinical data
Trade namesYambolap
Other namesFLI13; 7-Isopropoxyisoflavone[1]
AHFS/Drugs.comInternational Drug Names
ATC code
Legal status
Legal status
  • US:Not FDA approved
  • Rx-only in Japan
Identifiers
  • 7-Isopropoxy-3-phenyl-4H-chromen-4-one
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.125.854Edit this at Wikidata
Chemical and physical data
FormulaC18H16O3
Molar mass280.323g·mol−1
3D model (JSmol)
  • CC(C)OC1=CC2=C(C=C1)C(=O)C(=CO2)C3=CC=CC=C3
  • 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☒N
  • Key:SFBODOKJTYAUCM-UHFFFAOYSA-N☒N
☒NcheckY(what is this?)(verify)

Ipriflavone(INN,JAN;brand nameYambolap) is asyntheticisoflavonewhich may be used to inhibit bone resorption,[2]maintain bone density and to preventosteoporosisin postmenopausal women.[1]It is not used to treat osteoporosis. It slows down the action of theosteoclasts(bone-eroding cells), possibly allowing theosteoblasts(bone-building cells) to build up bone mass.

A clinical trial reported in 2001 that it wasnoteffective in prevention or treatment of osteoporosis.[3]

A double-blind study reveals that ipriflavone might be effective on reducing tinnitus onotosclerosissufferers.[4]

Ipriflavone has been described as aphytoestrogen.[5]However, this is incorrect, as the drug does not bind to or activate theestrogen receptorand shows noestrogeniceffects inpostmenopausalwomen.[6][7]The drug preventsbone lossvia mechanisms that are distinct from those ofestrogens.[5]

References

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  1. ^abElks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies.Springer. pp. 651–.ISBN978-1-4757-2085-3.
  2. ^Civitelli R (1997). "In vitro and in vivo effects of ipriflavone on bone formation and bone biomechanics".Calcified Tissue International.61 Suppl 1: S12-4.doi:10.1007/s002239900378.PMID9263610.S2CID21565791.
  3. ^Alexandersen P, Toussaint A, Christiansen C, Devogelaer JP, Roux C, Fechtenbaum J, et al. (Ipriflavone Multicenter European Fracture Study) (March 2001). "Ipriflavone in the treatment of postmenopausal osteoporosis: a randomized controlled trial".JAMA.285(11): 1482–8.doi:10.1001/jama.285.11.1482.PMID11255425.
  4. ^Sziklai I, Komora V, Ribári O (1992). "Double-blind study on the effectiveness of a bioflavonoid in the control of tinnitus in otosclerosis".Acta Chirurgica Hungarica.33(1–2): 101–7.PMID1343452.
  5. ^abArjmandi BH, Birnbaum RS, Juma S, Barengolts E, Kukreja SC (January 2000). "The synthetic phytoestrogen, ipriflavone, and estrogen prevent bone loss by different mechanisms".Calcified Tissue International.66(1): 61–5.doi:10.1007/s002230050012.PMID10602847.S2CID31022310.
  6. ^Petilli M, Fiorelli G, Benvenuti S, Frediani U, Gori F, Brandi ML (February 1995). "Interactions between ipriflavone and the estrogen receptor".Calcified Tissue International.56(2): 160–5.doi:10.1007/BF00296349.PMID7736326.S2CID24212438.
  7. ^Melis GB, Paoletti AM, Cagnacci A, Bufalino L, Spinetti A, Gambacciani M, Fioretti P (November 1992). "Lack of any estrogenic effect of ipriflavone in postmenopausal women".Journal of Endocrinological Investigation.15(10): 755–61.doi:10.1007/BF03347647.PMID1491124.S2CID32186052.
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