Icariin | CAS#489-32-7 | PDE5 inhibitor | inhibiting AAPH-induced oxidative DNA damage

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

MedKoo CAT#: 540217

CAS#: 489-32-7

Description: Icariin is a PDE5 inhibitor found in Epimedium. It displays many activities, including inhibiting AAPH-induced oxidative DNA damage, decreasing immobility time in the forced swim test, and suppressing osteoclast growth and differentiation.

Chemical Structure

Icariin

CAS# 489-32-7

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 540217
Name: Icariin
CAS#: 489-32-7
Chemical Formula: C33H40O15
Exact Mass: 676.24
Molecular Weight: 676.668
Elemental Analysis: C, 58.58; H, 5.96; O, 35.47

Price and Availability

Size	Price	Availability
1g	USD 300	2 Weeks
5g	USD 850	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: 3-((6-Deoxymannopyranosyl)oxy)-7-(glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one; Icariin;

IUPAC/Chemical Name: 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

InChi Key: TZJALUIVHRYQQB-XLRXWWTNSA-N

InChi Code: InChI=1S/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1

SMILES Code: O=C1C(O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)=C(C3=CC=C(OC)C=C3)OC4=C(C/C=C(C)\C)C(O[C@H]5[C@@H]([C@H]([C@@H]([C@@H](CO)O5)O)O)O)=CC(O)=C14

Appearance: Solid powder

Purity: >97% (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

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	Icariin inhibits PDE5 and PDE4 activities with IC50s of 432 nM and 73.50 μM, respectively. Icariin also is a PPARα activator.
In vitro activity:	Cell viability following IL-1β treatment was markedly decreased compared to the control. However, ICA (icariin) pretreatment increased cell viability. These results demonstrate that pretreatment with ICA can significantly rescue IL-1β-mediated growth inhibition in SW1353 cells. Reference: Eur J Med Res. 2022 Oct 17;27(1):204. https://pubmed.ncbi.nlm.nih.gov/36253872/
In vivo activity:	Also the height of intervertebral disc decreased in the IVDD (intervertebral disc degeneration) group, and this could be reversed by ICA (icariin) administration. These results indicated that ICA could alleviate IVDD progression and CEP (cartilage endplates) degeneration. Reference: Front Pharmacol. 2022 Sep 13;13:937502. https://pubmed.ncbi.nlm.nih.gov/36176424/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	20.0	29.56
	DMSO	65.0	96.06
	DMSO:PBS (pH 7.2) (1:10)	0.1	0.15

Preparing Stock Solutions

The following data is based on the product molecular weight 676.67 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. Chen Y, Pan X, Zhao J, Li C, Lin Y, Wang Y, Liu X, Tian M. Icariin alleviates osteoarthritis through PI3K/Akt/mTOR/ULK1 signaling pathway. Eur J Med Res. 2022 Oct 17;27(1):204. doi: 10.1186/s40001-022-00820-x. PMID: 36253872; PMCID: PMC9575285. 2. Yin Y, Xu W, Song Y, Zhou Z, Sun X, Zhang F. Icariin Regulates the hsa_circ_0003159/eIF4A3/bcl-2 Axis to Promote Gastric Cancer Cell Apoptosis. Evid Based Complement Alternat Med. 2022 Jul 15;2022:1955101. doi: 10.1155/2022/1955101. PMID: 35873631; PMCID: PMC9307325. 3. Shao Y, Sun L, Yang G, Wang W, Liu X, Du T, Chen F, Jing X, Cui X. Icariin protects vertebral endplate chondrocytes against apoptosis and degeneration via activating Nrf-2/HO-1 pathway. Front Pharmacol. 2022 Sep 13;13:937502. doi: 10.3389/fphar.2022.937502. PMID: 36176424; PMCID: PMC9513224. 4. Shaukat A, Shaukat I, Rajput SA, Shukat R, Hanif S, Huang S, Aleem MT, Li K, Li Q, Chen C, Zhang X, Lv H, Yao Z, Yang L. Icariin Alleviates Escherichia coli Lipopolysaccharide-Mediated Endometritis in Mice by Inhibiting Inflammation and Oxidative Stress. Int J Mol Sci. 2022 Sep 6;23(18):10219. doi: 10.3390/ijms231810219. PMID: 36142129; PMCID: PMC9499631.
In vitro protocol:	1. Chen Y, Pan X, Zhao J, Li C, Lin Y, Wang Y, Liu X, Tian M. Icariin alleviates osteoarthritis through PI3K/Akt/mTOR/ULK1 signaling pathway. Eur J Med Res. 2022 Oct 17;27(1):204. doi: 10.1186/s40001-022-00820-x. PMID: 36253872; PMCID: PMC9575285. 2. Yin Y, Xu W, Song Y, Zhou Z, Sun X, Zhang F. Icariin Regulates the hsa_circ_0003159/eIF4A3/bcl-2 Axis to Promote Gastric Cancer Cell Apoptosis. Evid Based Complement Alternat Med. 2022 Jul 15;2022:1955101. doi: 10.1155/2022/1955101. PMID: 35873631; PMCID: PMC9307325.
In vivo protocol:	1. Shao Y, Sun L, Yang G, Wang W, Liu X, Du T, Chen F, Jing X, Cui X. Icariin protects vertebral endplate chondrocytes against apoptosis and degeneration via activating Nrf-2/HO-1 pathway. Front Pharmacol. 2022 Sep 13;13:937502. doi: 10.3389/fphar.2022.937502. PMID: 36176424; PMCID: PMC9513224. 2. Shaukat A, Shaukat I, Rajput SA, Shukat R, Hanif S, Huang S, Aleem MT, Li K, Li Q, Chen C, Zhang X, Lv H, Yao Z, Yang L. Icariin Alleviates Escherichia coli Lipopolysaccharide-Mediated Endometritis in Mice by Inhibiting Inflammation and Oxidative Stress. Int J Mol Sci. 2022 Sep 6;23(18):10219. doi: 10.3390/ijms231810219. PMID: 36142129; PMCID: PMC9499631.

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1: Xiao HB, Liu ZK, Lu XY, Deng CN, Luo ZF. Icariin regulates PRMT/ADMA/DDAH pathway to improve endothelial function. Pharmacol Rep. 2015 Dec;67(6):1147-54. doi: 10.1016/j.pharep.2015.04.017. Epub 2015 May 11. PubMed PMID: 26481534.

2: Xiang J, Zhao J, Wang Y, Hua X, Huang H, Lei Y. [Effect of icariin on hypoxia/reoxygenation injury in neonatal rat cardiomyocytes]. Zhonghua Yi Xue Za Zhi. 2015 Dec 1;95(45):3701-4. Chinese. PubMed PMID: 26849936.

3: Kong L, Liu J, Wang J, Luo Q, Zhang H, Liu B, Xu F, Pang Q, Liu Y, Dong J. Icariin inhibits TNF-α/IFN-γ induced inflammatory response via inhibition of the substance P and p38-MAPK signaling pathway in human keratinocytes. Int Immunopharmacol. 2015 Dec;29(2):401-7. doi: 10.1016/j.intimp.2015.10.023. Epub 2015 Oct 24. PubMed PMID: 26507164.

4: Zhang L, Shen C, Chu J, Liu Y, Li Y, Zhang L, Li L. Icariin reduces α-synuclein over-expression by promoting α-synuclein degradation. Age (Dordr). 2015 Aug;37(4):9811. doi: 10.1007/s11357-015-9811-z. Epub 2015 Jul 14. PubMed PMID: 26169945; PubMed Central PMCID: PMC4501328.

5: Hu Y, Liu K, Yan M, Zhang Y, Wang Y, Ren L. Effects and mechanisms of icariin on atherosclerosis. Int J Clin Exp Med. 2015 Mar 15;8(3):3585-9. eCollection 2015. PubMed PMID: 26064253; PubMed Central PMCID: PMC4443087.

6: Li F, Dong HX, Gong QH, Wu Q, Jin F, Shi JS. Icariin decreases both APP and Aβ levels and increases neurogenesis in the brain of Tg2576 mice. Neuroscience. 2015 Sep 24;304:29-35. doi: 10.1016/j.neuroscience.2015.06.010. Epub 2015 Jun 12. PubMed PMID: 26079110.

7: Wang Z, Zhang H, Dai L, Song T, Li P, Liu Y, Wang L. Arsenic Trioxide and Icariin Show Synergistic Anti-leukemic Activity. Cell Biochem Biophys. 2015 Sep;73(1):213-9. doi: 10.1007/s12013-015-0660-2. PubMed PMID: 25721870.

8: Yang H, Yan L, Qian P, Duan H, Wu J, Li B, Wang S. Icariin inhibits foam cell formation by down-regulating the expression of CD36 and up-regulating the expression of SR-BI. J Cell Biochem. 2015 Apr;116(4):580-8. doi: 10.1002/jcb.25009. PubMed PMID: 25389062.

9: Li F, Gao B, Dong H, Shi J, Fang D. Icariin induces synoviolin expression through NFE2L1 to protect neurons from ER stress-induced apoptosis. PLoS One. 2015 Mar 25;10(3):e0119955. doi: 10.1371/journal.pone.0119955. eCollection 2015. PubMed PMID: 25806530; PubMed Central PMCID: PMC4373914.

10: Zhang X, Liu T, Huang Y, Wismeijer D, Liu Y. Icariin: does it have an osteoinductive potential for bone tissue engineering? Phytother Res. 2014 Apr;28(4):498-509. doi: 10.1002/ptr.5027. Epub 2013 Jul 4. Review. PubMed PMID: 23824956.

11: Xu SF, Jin T, Lu YF, Li LS, Liu J, Shi JS. Effect of icariin on UDP-glucuronosyltransferases in mouse liver. Planta Med. 2014 Mar;80(5):387-92. doi: 10.1055/s-0034-1368265. Epub 2014 Apr 7. PubMed PMID: 24710854.

12: Fu SP, Yang L, Hong H, Ou C, Zhang RH. [Icariin Promoted Osteogenic Differentiation of SD Rat Bone Marrow Mesenchymal Stem Cells: an Experimental Study]. Zhongguo Zhong Xi Yi Jie He Za Zhi. 2015 Jul;35(7):839-46. Chinese. PubMed PMID: 26380448.

13: Wang ZM, Song N, Ren YL. Anti-proliferative and cytoskeleton-disruptive effects of icariin on HepG2 cells. Mol Med Rep. 2015 Nov;12(5):6815-20. doi: 10.3892/mmr.2015.4282. Epub 2015 Sep 2. PubMed PMID: 26329131.

14: Shao H, Shen J, Wang M, Cui J, Wang Y, Zhu S, Zhang W, Yang H, Xu Y, Geng D. Icariin protects against titanium particle-induced osteolysis and inflammatory response in a mouse calvarial model. Biomaterials. 2015 Aug;60:92-9. doi: 10.1016/j.biomaterials.2015.04.048. Epub 2015 May 15. PubMed PMID: 25985156.

15: Yang L, Wang Y, Guo H, Guo M. Synergistic Anti-Cancer Effects of Icariin and Temozolomide in Glioblastoma. Cell Biochem Biophys. 2015 Apr;71(3):1379-85. doi: 10.1007/s12013-014-0360-3. PubMed PMID: 25384619.

16: Zhou H, Yuan Y, Liu Y, Ni J, Deng W, Bian ZY, Dai J, Tang QZ. Icariin protects H9c2 cardiomyocytes from lipopolysaccharide induced injury via inhibition of the reactive oxygen species dependent c Jun N terminal kinases/nuclear factor-κB pathway. Mol Med Rep. 2015 Jun;11(6):4327-32. doi: 10.3892/mmr.2015.3289. Epub 2015 Jan 30. PubMed PMID: 25647547.

17: Liu B, Xu C, Wu X, Liu F, Du Y, Sun J, Tao J, Dong J. Icariin exerts an antidepressant effect in an unpredictable chronic mild stress model of depression in rats and is associated with the regulation of hippocampal neuroinflammation. Neuroscience. 2015 May 21;294:193-205. doi: 10.1016/j.neuroscience.2015.02.053. Epub 2015 Mar 17. PubMed PMID: 25791226.

18: Ma P, Zhang S, Su X, Qiu G, Wu Z. Protective effects of icariin on cisplatin-induced acute renal injury in mice. Am J Transl Res. 2015 Oct 15;7(10):2105-14. eCollection 2015. PubMed PMID: 26692955; PubMed Central PMCID: PMC4656788.

19: Zhai M, He L, Ju X, Shao L, Li G, Zhang Y, Liu Y, Zhao H. Icariin Acts as a Potential Agent for Preventing Cardiac Ischemia/Reperfusion Injury. Cell Biochem Biophys. 2015 Jun;72(2):589-97. doi: 10.1007/s12013-014-0506-3. PubMed PMID: 25663532.

20: Chen M, Hao J, Yang Q, Li G. Effects of icariin on reproductive functions in male rats. Molecules. 2014 Jul 3;19(7):9502-14. doi: 10.3390/molecules19079502. PubMed PMID: 24995929.

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