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Ipriflavone (Osteofix)

CAS# 35212-22-7

Ipriflavone (Osteofix)

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Chemical structure

Ipriflavone (Osteofix)

3D structure

Chemical Properties of Ipriflavone (Osteofix)

Cas No. 35212-22-7 SDF Download SDF
PubChem ID 3747 Appearance Powder
Formula C18H16O3 M.Wt 280.32
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : ≥ 29 mg/mL (103.45 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 3-phenyl-7-propan-2-yloxychromen-4-one
SMILES CC(C)OC1=CC2=C(C=C1)C(=O)C(=CO2)C3=CC=CC=C3
Standard InChIKey SFBODOKJTYAUCM-UHFFFAOYSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Protocol

Cell Assay [1]
Ipriflavone is dissolved in absolute ethanol and added to the medium at 1-50 μM. The final ethanol concentrations are <0.5% (v/v). MDA-231 cells are seeded in 35 mm culture dishes in DMEM supplemented with 10% FBS in the presence of ipriflavone (1, 10 or 50 μM) or ethanol. After 48 hr incubation, the medium is changed with fresh medium containing the same concentrations of ipriflavone or ethanol. After incubation for 24, 48, 72 and 96 hr from the initial seeding, cells are treated with trypan blue to estimate the number of viable cells[1].

Animal Administration [1][3]
Rats: To assess the potential impact of ipriflavone on the biomechanical properties and mineral composition of bone, adult male rats are orally administered two doses (200 or 400 mg/kg bw) of ipriflavone for 1 month. Bone biomechanics are evaluated by vibration damping, an index of strain energy loss, and impact strength[3]. Mice: Ipriflavone is suspended in water containing 0.5% (w/v) methylcellulose and given to mice orally at 6 or 12 mg/0.2 mL daily, which is equivalent to 200 or 400 mg/kg body weight. MDA-231 cells are injected s.c. into the interscapular space of nude mice (on day 0), which are then given ipriflavone (6 or 12 mg/mouse) or the methylcellulose solution orally from day 1 to day 27. Tumor growth is analyzed twice a week by measuring the tumor volume[1].

References:
[1]. Iisaki T, et al. Ipriflavone inhibits osteolytic bone metastasis of human breast cancer cells in a nude mouse model. Int J Cancer. 2002 Aug 1;100(4):381-7. [2]. Hagiwara H, et al. Ipriflavone down-regulates endothelin receptor levels during differentiation of rat calvarial osteoblast-like cells. J Biochem. 1999 Jul;126(1):168-73. [3]. Civitelli R, et al. Ipriflavone improves bone density and biomechanical properties of adult male rat bones. Calcif Tissue Int. 1995 Mar;56(3):215-9.

Ipriflavone (Osteofix) Dilution Calculator

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Preparing Stock Solutions of Ipriflavone (Osteofix)

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.5674 mL 17.8368 mL 35.6735 mL 71.347 mL 89.1838 mL
5 mM 0.7135 mL 3.5674 mL 7.1347 mL 14.2694 mL 17.8368 mL
10 mM 0.3567 mL 1.7837 mL 3.5674 mL 7.1347 mL 8.9184 mL
50 mM 0.0713 mL 0.3567 mL 0.7135 mL 1.4269 mL 1.7837 mL
100 mM 0.0357 mL 0.1784 mL 0.3567 mL 0.7135 mL 0.8918 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Ipriflavone (Osteofix)

Ipriflavone is a synthetic isoflavone derivative used to suppress bone resorption.

In Vitro:Ipriflavone inhibits the proliferation and DNA synthesis of MDA-231 cells and blocks the ligand-induced phosphorylation of Tyr(845) of the EGFR. Ipriflavone does not promote apoptosis of MDA-231 cells[1]. Ipriflavone also promotes the deposition of calcium and the formation of mineralized nodules by newborn rat calvarial osteoblast-like cells as well as the activity of alkaline phosphatase[2].

In Vivo:Daily oral administration of ipriflavone at 12 mg/mouse significantly inhibits the development of new osteolytic bone metastases and the progression of established osteolytic lesions, prolonging the life of tumor-bearing mice. Ipriflavone reduces the number of osteoclasts at the bone-cancer interface with no severe adverse effects on the host[1]. 1-month treatment with ipriflavone increases bone density and improves the biomechanical properties of adult rat male bones without altering mineral composition[3]

References:
[1]. Iisaki T, et al. Ipriflavone inhibits osteolytic bone metastasis of human breast cancer cells in a nude mouse model. Int J Cancer. 2002 Aug 1;100(4):381-7. [2]. Hagiwara H, et al. Ipriflavone down-regulates endothelin receptor levels during differentiation of rat calvarial osteoblast-like cells. J Biochem. 1999 Jul;126(1):168-73. [3]. Civitelli R, et al. Ipriflavone improves bone density and biomechanical properties of adult male rat bones. Calcif Tissue Int. 1995 Mar;56(3):215-9.

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References on Ipriflavone (Osteofix)

Pharmacokinetics of ipriflavone and metabolites after oral administration of a corn-oil suspension relative to the Osteofix tablet.[Pubmed:10423615]

Am J Ther. 1997 Jul-Aug;4(7-8):229-38.

Ipriflavone (IP) is a derivative of naturally occurring isoflavones and is marketed as Osteofix for the treatment of osteoporosis in Europe. IP has poor aqueous solubility, and the Osteofix compressed tablet has poor and variable bioavailability (F ). IP is incompletely absorbed after oral administration and is converted to five major metabolites (M1, M2, M3, M4, and M5). It is also further converted to metabolites M6 and M7 to a very small extent. The metabolites, especially M2 and M5, also have activity. A pilot study was conducted in healthy male volunteers that showed an 8- to 20-fold increase in the IP bioavailability after administration of Osteofix tablets in the fed state relative to the fasting state. A four-way crossover study was conducted in 16 healthy male volunteers, receiving Osteofix in fed state and 50, 100, and 200 mg of IP corn-oil suspension in fasted state. All IP administrations were safe and well tolerated. There was a reduction in the IP plasma level variability after 100-mg corn-oil administration as compared with that for the tablet. There was an increased relative F after the suspension, which was such that the 50-mg IP corn-oil suspension yielded similar levels as the 200-mg tablet. M5 was the major metabolite, consistent with earlier reports. The area under the curve to the last measured time point (AUC ( t ) ) levels were lower for M5, M3, and M2; higher for M1 and M2; and similar for IP after 50-mg corn-oil administration, as compared with the values for the tablet. This result may partially be explained by differences in the half-lives. Absorption/formation of M2 was delayed. The metabolite formation, except for M1 and M5, decreased with increased doses, which was accompanied by the prolonged half-life of IP and nonproportional increase in the IP AUC ( t ). This result may be due to autoinhibition of IP metabolism, because IP is an inhibitor of CYP3A4, and the metabolism of IP may be partly CYP3A4 mediated. Osteofix F may be improved by formulations that increase solubility, such as the corn-oil suspension. Although equivalent IP exposure from the tablet may be achieved at much lower overall doses because of the improved F by the corn-oil suspension, higher doses may require reconfirmation of safety and efficacy, given the differences in metabolic profiles obtained at higher doses.

Description

Ipriflavone is a synthetic isoflavone derivative used to suppress bone resorption.

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