Icariin

Drugbox
IUPAC_name = 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7- [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] oxy-3- [(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl] oxychromen-4-one

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width = 280
CAS_number = 489-32-7
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PubChem = 5318997
DrugBank =
C=33|H=40|O=15
molecular_weight = 676.662 g/mol
smiles = C [C@H] 1 [C@@H] ( [C@H] ( [C@H] ( [C@@H] (O1)OC2=C(OC3=C(C2=O)C(=CC(=C3CC=C(C)C)O [C@H] 4 [C@@H] ( [C@H] ( [C@@H] ( [C@H] (O4)CO)O)O)O)O)C5=CC=C(C=C5)OC)O)O)O
bioavailability =
protein_bound =
metabolism =
elimination_half-life =
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legal_US =
legal_status = Legal
routes_of_administration = Oral

Icariin is a flavonoid glycoside compound derived from several species of plants in the "Epimedium" family, which are commonly known as Horny Goat Weed or Yin Yang Huo. [Liu JJ, Li SP, Wang YT. Optimization for quantitative determination of four flavonoids in Epimedium by capillary zone electrophoresis coupled with diode array detection using central composite design. "Journal of Chromatography A". 2006 Jan 27;1103(2):344-9. PMID 16337210] Extracts from these plants are reputed to produce aphrodisiac effects, and are commonly used in Chinese herbal medicine to enhance erectile function, [Makarova MN, Pozharitskaya ON, Shikov AN, Tesakova SV, Makarov VG, Tikhonov VP. Effect of lipid-based suspension of Epimedium koreanum Nakai extract on sexual behavior in rats. "Journal of Ethnopharmacology". 2007 Dec 3;114(3):412-6. PMID 17890032] as well as for several other indications.

It is thought that icariin is likely to be the primary active component of "Epimedium" extracts, as it has been shown to share several mechanisms of action with compounds used in Western medicine to treat impotence and improve sexual function. In particular, icariin has been demonstrated to act as a PDE5 inhibitor [53: Related Articles, LinksJiang Z, Hu B, Wang J, Tang Q, Tan Y, Xiang J, Liu J. Effect of icariin on cyclic GMP levels and on the mRNA expression of cGMP-binding cGMP-specific phosphodiesterase (PDE5) in penile cavernosum. "Journal of the Huazhong University of Science and Technology". 2006;26(4):460-2. PMID 17120748] [Ning H, Xin ZC, Lin G, Banie L, Lue TF, Lin CS. Effects of icariin on phosphodiesterase-5 activity in vitro and cyclic guanosine monophosphate level in cavernous smooth muscle cells. "Urology". 2006 Dec;68(6):1350-4. PMID 17169663] [Dell'agli M, Galli GV, Dal Cero E, Belluti F, Matera R, Zironi E, Pagliuca G, Bosisio E. Potent Inhibition of Human Phosphodiesterase-5 by Icariin Derivatives. "Journal of Natural Products". 2008 Sep 9. PMID 18778098] and to enhance the production of bioactive nitric oxide, [Xu HB, Huang ZQ. Icariin enhances endothelial nitric-oxide synthase expression on human endothelial cells in vitro. "Vascular Pharmacology". 2007 Jul;47(1):18-24. PMID 17499557] as well as mimicing the effects of testosterone. [Zhang ZB, Yang QT. The testosterone mimetic properties of icariin. "Asian Journal of Andrology". 2006 Sep;8(5):601-5. PMID 16751992] It also shows antioxidant, [Xie J, Sun W, Duan K, Zhang Y. Chemical constituents of roots of Epimedium wushanense and evaluation of their biological activities. "Natural Product Research". 2007 Jun;21(7):600-5. PMID 17613817] [Zhao F, Tang YZ, Liu ZQ. Protective effect of icariin on DNA against radical-induced oxidative damage. "Journal of Pharmacy and Pharmacology". 2007 Dec;59(12):1729-32. PMID 18053336] antidepressant [Pan Y, Kong L, Xia X, Zhang W, Xia Z, Jiang F. Antidepressant-like effect of icariin and its possible mechanism in mice. "Pharmacology, Biochemistry and Behaviour". 2005 Dec;82(4):686-94. PMID 16380159] [Pan Y, Zhang WY, Xia X, Kong LD. Effects of icariin on hypothalamic-pituitary-adrenal axis action and cytokine levels in stressed Sprague-Dawley rats. "Biological and Pharmaceutical Bulletin". 2006 Dec;29(12):2399-403. PMID 17142971] [Pan Y, Kong LD, Li YC, Xia X, Kung HF, Jiang FX. Icariin from Epimedium brevicornum attenuates chronic mild stress-induced behavioral and neuroendocrinological alterations in male Wistar rats. "Pharmacology, Biochemistry and Behaviour". 2007 May;87(1):130-40. PMID 17509675] and nootropic [Luo Y, Nie J, Gong QH, Lu YF, Wu Q, Shi JS. Protective effects of icariin against learning and memory deficits induced by aluminium in rats. "Clinical and Experimental Pharmacology and Physiology". 2007 Aug;34(8):792-5. PMID 17600559] [Zheng M, Qu L, Lou Y. Effects of icariin combined with Panax notoginseng saponins on ischemia reperfusion-induced cognitive impairments related with oxidative stress and CA1 of hippocampal neurons in rat. "Phytotherapy Research". 2008 May;22(5):597-604. PMID 18398927] effects in animal studies, as well as stimulating osteoblast activity in bone tissue which has been linked to a possible therapeutic role in the treatment of osteoporosis. [Yin XX, Chen ZQ, Liu ZJ, Ma QJ, Dang GT. Icariine stimulates proliferation and differentiation of human osteoblasts by increasing production of bone morphogenetic protein 2. "Chinese Medical Journal (English)". 2007 Feb 5;120(3):204-10. PMID 17355822] [Zhang G, Qin L, Shi Y. Epimedium-derived phytoestrogen flavonoids exert beneficial effect on preventing bone loss in late postmenopausal women: a 24-month randomized, double-blind and placebo-controlled trial. "Journal of Bone and Mineral Research". 2007 Jul;22(7):1072-9. PMID 17419678] [Chen KM, Ge BF, Liu XY, Ma PH, Lu MB, Bai MH, Wang Y. Icariin inhibits the osteoclast formation induced by RANKL and macrophage-colony stimulating factor in mouse bone marrow culture. "Pharmazie". 2007 May;62(5):388-91. PMID 17557750] [Huang J, Yuan L, Wang X, Zhang TL, Wang K. Icaritin and its glycosides enhance osteoblastic, but suppress osteoclastic, differentiation and activity in vitro. "Life Sciences". 2007 Aug 16;81(10):832-40. PMID 17764702] [Zhang DW, Cheng Y, Wang NL, Zhang JC, Yang MS, Yao XS. Effects of total flavonoids and flavonol glycosides from Epimedium koreanum Nakai on the proliferation and differentiation of primary osteoblasts. "Phytomedicine". 2008 Jan;15(1-2):55-61. PMID 17482445] [Qin L, Han T, Zhang Q, Cao D, Nian H, Rahman K, Zheng H. Antiosteoporotic chemical constituents from Er-Xian Decoction, a traditional Chinese herbal formula. "Journal of Ethnopharmacology". 2008 Jul 23;118(2):271-9. PMID 18501540]

References