Ipriflavone | Yambolap | FL-113 | CAS#35212-22-7 | Osteoclast Inhibitor

MedKoo Cat#: 328711 | Name: Ipriflavone

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ipriflavone, also known as Yambolap and FL-113, is an osteoclast inhibitor and is effective for enhancing osteoblastic bone formation.

Chemical Structure

Ipriflavone

CAS#35212-22-7

Theoretical Analysis

MedKoo Cat#: 328711

Name: Ipriflavone

CAS#: 35212-22-7

Chemical Formula: C18H16O3

Exact Mass: 280.1099

Molecular Weight: 280.32

Elemental Analysis: C, 77.12; H, 5.75; O, 17.12

Price and Availability

Size	Price	Availability	Quantity
5g	USD 250.00	2 Weeks
25g	USD 550.00	2 Weeks

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Synonym

Ipriflavone; FL-113; FL 113; FL113; Yambolap; TC 80; TC-80; TC80

IUPAC/Chemical Name

7-isopropoxy-3-phenyl-4H-chromen-4-one

InChi Key

SFBODOKJTYAUCM-UHFFFAOYSA-N

InChi Code

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

SMILES Code

O=C1C(C2=CC=CC=C2)=COC3=CC(OC(C)C)=CC=C13

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

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

In vitro activity:

Ipriflavone increased the HA accumulation and suppressed the MMP1 and MMP3 expression on TNF-α stimulated FLS. Reference: Int J Mol Sci. 2022 Apr 7;23(8):4089. https://pubmed.ncbi.nlm.nih.gov/35456905/

In vivo activity:

Thus, these results demonstrated that IP (ipriflavone) suppressed NLRP3/ASC/Caspase‐1 in diabetic mice by antagonizing GR. Therefore, all results indicated that IP repressed neuroinflammation in diabetic mice through GR/NF‐κB/NLRP3 /ASC/Caspase‐1 pathway. Reference: Aging Cell. 2022 Mar;21(3):e13572. https://pubmed.ncbi.nlm.nih.gov/35172041/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	71.35
	DMF:PBS (pH 7.2) (1:4)	0.2	0.71
	DMSO	33.1	118.11
	Ethanol	1.5	5.35

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 280.32 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Koike H, Nishida Y, Shinomura T, Ohkawara B, Ohno K, Zhuo L, Kimata K, Ushida T, Imagama S. Possible Repositioning of an Oral Anti-Osteoporotic Drug, Ipriflavone, for Treatment of Inflammatory Arthritis via Inhibitory Activity of KIAA1199, a Novel Potent Hyaluronidase. Int J Mol Sci. 2022 Apr 7;23(8):4089. doi: 10.3390/ijms23084089. PMID: 35456905; PMCID: PMC9030858. 2. Shi X, Zhang Y, Xie X, Pang M, Laster K, Li J, Ma X, Liu K, Dong Z, Kim DJ. Ipriflavone Suppresses Growth of Esophageal Squamous Cell Carcinoma Through Inhibiting mTOR In Vitro and In Vivo. Front Oncol. 2021 Jun 10;11:648809. doi: 10.3389/fonc.2021.648809. PMID: 34178634; PMCID: PMC8222593. 3. Nie R, Lu J, Xu R, Yang J, Shen X, Ouyang X, Zhu D, Huang Y, Zhao T, Zhao X, Lu Y, Qian M, Wang J, Shen X. Ipriflavone as a non-steroidal glucocorticoid receptor antagonist ameliorates diabetic cognitive impairment in mice. Aging Cell. 2022 Mar;21(3):e13572. doi: 10.1111/acel.13572. Epub 2022 Feb 16. PMID: 35172041; PMCID: PMC8920458. 4. Wang X, Zheng A, Xin XZ, Peng LJ, Wang J, Cao LY, Jiang XQ. Osteogenic Induction of Low-dose Ipriflavone on Bone Marrow Mesenchymal Stem Cells Extracted from Osteoporosis Rats. Chin J Dent Res. 2021 Sep 7;24(3):153-158. doi: 10.3290/j.cjdr.b1965039. PMID: 34491009.

In vitro protocol:

In vivo protocol:

1. Nie R, Lu J, Xu R, Yang J, Shen X, Ouyang X, Zhu D, Huang Y, Zhao T, Zhao X, Lu Y, Qian M, Wang J, Shen X. Ipriflavone as a non-steroidal glucocorticoid receptor antagonist ameliorates diabetic cognitive impairment in mice. Aging Cell. 2022 Mar;21(3):e13572. doi: 10.1111/acel.13572. Epub 2022 Feb 16. PMID: 35172041; PMCID: PMC8920458. 2. Wang X, Zheng A, Xin XZ, Peng LJ, Wang J, Cao LY, Jiang XQ. Osteogenic Induction of Low-dose Ipriflavone on Bone Marrow Mesenchymal Stem Cells Extracted from Osteoporosis Rats. Chin J Dent Res. 2021 Sep 7;24(3):153-158. doi: 10.3290/j.cjdr.b1965039. PMID: 34491009.

1: Fujimori M, Kadota K, Kato K, Seto Y, Onoue S, Sato H, Ueda H, Tozuka Y. Low hygroscopic spray-dried powders with trans-glycosylated food additives enhance the solubility and oral bioavailability of ipriflavone. Food Chem. 2016 Jan 1;190:1050-5. doi: 10.1016/j.foodchem.2015.06.081. Epub 2015 Jun 23. PubMed PMID: 26213075. 2: Tanida S, Kurokawa T, Sato H, Kadota K, Tozuka Y. Evaluation of the Micellization Mechanism of an Amphipathic Graft Copolymer with Enhanced Solubility of Ipriflavone. Chem Pharm Bull (Tokyo). 2016;64(1):68-72. doi: 10.1248/cpb.c15-00655. PubMed PMID: 26726747. 3: Patchen B, Koppe T, Cheng A, Seo YA, Wessling-Resnick M, Fraenkel PG. Dietary supplementation with ipriflavone decreases hepatic iron stores in wild type mice. Blood Cells Mol Dis. 2016 Sep;60:36-43. doi: 10.1016/j.bcmd.2016.05.004. Epub 2016 May 8. PubMed PMID: 27519943. 4: Xiao Z, Huang C, Wu J, Sun L, Hao W, Leung LK, Huang J. The neuroprotective effects of ipriflavone against H ₂O ₂ and amyloid beta induced toxicity in human neuroblastoma SH-SY5Y cells. Eur J Pharmacol. 2013 Dec 5;721(1-3):286-93. doi: 10.1016/j.ejphar.2013.09.023. Epub 2013 Sep 29. PubMed PMID: 24084576. 5: Delarmelina JM, Dutra JC, Batitucci Mdo C. Antimutagenic activity of ipriflavone against the DNA-damage induced by cyclophosphamide in mice. Food Chem Toxicol. 2014 Mar;65:140-6. doi: 10.1016/j.fct.2013.12.028. Epub 2013 Dec 31. PubMed PMID: 24389340. 6: Radzki RP, Bieńko M, Filip R, Pierzynowski SG. The Protective and Therapeutic Effect of Exclusive and Combined Treatment with Alpha-ketoglutarate Sodium Salt and Ipriflavone on Bone Loss in Orchidectomized Rats. J Nutr Health Aging. 2016;20(6):628-36. doi: 10.1007/s12603-015-0654-1. PubMed PMID: 27273352. 7: Lv WT, Yang YH, Ma LQ, Wang P, Li K. Ipriflavone reverses the adverse effects of a low-calcium diet on the histology of the tibia in caged layers. Br Poult Sci. 2014;55(2):207-14. doi: 10.1080/00071668.2013.878785. Epub 2014 Apr 24. PubMed PMID: 24404906. 8: Yun C, Ding L, Leng Y, Zhu H, Wen A, Yang L. Determination of ipriflavone in human plasma by LC-MS and its application in a pharmacokinetic study. Biomed Chromatogr. 2012 Jan;26(1):123-8. doi: 10.1002/bmc.1641. Epub 2011 May 19. PubMed PMID: 21594876. 9: Belcavello L, Vencioneck Dutra JC, de Freitas JV, Aranha IP, do Carmo Pimentel Batitucci M. Mutagenicity of ipriflavone in vivo and in vitro. Food Chem Toxicol. 2012 Mar;50(3-4):996-1000. doi: 10.1016/j.fct.2011.12.013. Epub 2011 Dec 17. PubMed PMID: 22200590. 10: Bellei PM, Terra MM, Peters VM, Guerra Mde O, Andrade AT. [Effect of ipriflavone on Wistar rats and their litters]. Rev Bras Ginecol Obstet. 2012 Jan;34(1):22-7. Portuguese. PubMed PMID: 22358344. 11: Lee DY, Chung HJ, Choi YH, Lee U, Kim SH, Lee I, Lee MG. Pharmacokinetics of ipriflavone and its two metabolites, M1 and M5, after the intravenous and oral administration of ipriflavone to rat model of diabetes mellitus induced by streptozotocin. Eur J Pharm Sci. 2009 Dec 8;38(5):465-71. doi: 10.1016/j.ejps.2009.09.008. Epub 2009 Sep 15. PubMed PMID: 19761842. 12: Alexandersen P, Toussaint A, Christiansen C, Devogelaer JP, Roux C, Fechtenbaum J, Gennari C, Reginster JY; Ipriflavone Multicenter European Fracture Study. Ipriflavone in the treatment of postmenopausal osteoporosis: a randomized controlled trial. JAMA. 2001 Mar 21;285(11):1482-8. PubMed PMID: 11255425. 13: El-Desoky HS, Beltagi AM, Ghoneim MM. Determination of the anti-osteoporosis drug ipriflavone in pharmaceutical formulation by stripping voltammetric and chromatographic methods. J AOAC Int. 2009 May-Jun;92(3):806-12. PubMed PMID: 19610371. 14: Chung HJ, Kang HE, Bae EJ, Lee I, Kim SG, Lee MG. Effects of E. Coli lipopolysaccharide on the pharmacokinetics of ipriflavone and its metabolites, M1 and M5, after intravenous and oral administration of ipriflavone to rats: decreased metabolism of ipriflavone due to decreased expression of hepatic CYP1A2 and 2C11. J Pharm Sci. 2008 Nov;97(11):5024-36. doi: 10.1002/jps.21343. PubMed PMID: 18314883. 15: Chung HJ, Lee I, Lee MG. Effects of water deprivation for 72 h on the pharmacokinetics of ipriflavone in rats. Res Vet Sci. 2008 Aug;85(1):149-55. Epub 2007 Oct 4. PubMed PMID: 17919668.