Ipriflavone

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
IUPAC name
  • 7-Isopropoxy-3-phenyl-4H-chromen-4-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.125.854
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Chemical and physical data
FormulaC18H16O3
Molar mass280.323 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)OC1=CC2=C(C=C1)C(=O)C(=CO2)C3=CC=CC=C3
InChI
  • 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
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Ipriflavone (INN, JAN; brand name Yambolap) is a synthetic isoflavone which may be used to inhibit bone resorption,[2] maintain bone density and to prevent osteoporosis in postmenopausal women.[1] 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.[3]

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

Ipriflavone has been described as a phytoestrogen.[5] However, this is incorrect, as the drug does not bind to or activate the estrogen receptor and shows no estrogenic effects in postmenopausal women.[6][7] The drug prevents bone loss via mechanisms that are distinct from those of estrogens.[5]

References

  1. 1 2 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 651–. ISBN 978-1-4757-2085-3.
  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. PMID 9263610. S2CID 21565791.
  3. Alexandersen P, Toussaint A, Christiansen C, Devogelaer JP, Roux C, Fechtenbaum J, et al. (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. PMID 11255425.
  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. PMID 1343452.
  5. 1 2 Arjmandi 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. PMID 10602847. S2CID 31022310.
  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. PMID 7736326. S2CID 24212438.
  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. PMID 1491124. S2CID 32186052.
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