Ipriflavone

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.

Ipriflavone

Clinical data
Trade names	Yambolap
Other names	FLI13; 7-Isopropoxyisoflavone[1]
AHFS/Drugs.com	International Drug Names
ATC code	M05BX01 (WHO)
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	35212-22-7^N
PubChem CID	3747
ChemSpider	3616^N
UNII	80BJ7WN25Z
KEGG	D01338^Y
ChEMBL	ChEMBL165790^N
CompTox Dashboard (EPA)	DTXSID5040679
ECHA InfoCard	100.125.854
Chemical and physical data
Formula	C18H16O3
Molar mass	280.323 g·mol^−1
3D model (JSmol)	Interactive image
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
^NY (what is this?)  (verify)

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. 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.
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. 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.
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.
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.

External links

• Ipriflavone at PDR Health