Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C33H40O15 |
| Molecular Weight | 676.6617 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(C=C1)C2=C(O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)C(=O)C4=C(O)C=C(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C(CC=C(C)C)=C4O2
InChI
InChIKey=TZJALUIVHRYQQB-XLRXWWTNSA-N
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
Icariin is a naturally occurring compound isolatable from several plant species within the genus Epimedium which is mostly endemic to China. Plant extracts containing icarrin have been used in traditional Chinese medicine as aphrodisiacs and to treat erectile dysfunction. Icariin has been investigated in humans as a treatment method for bipolar disorder and alcohol or cocaine abuse (Phase III). For the treatment of impotence, icariin has been shown to be a weak PDE5 inhibitor capable of enhancing the production of nitric oxide. Also related to PDE5 activity icarrin has been investigated as a potential treatment in mouse models of Alzheimer's disease. Icariin is sold worldwide as an over-the-counter medication for sexual performance, athletic performance, and other health benefits (it improves memory function, protects from osteoporosis, etc).
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: O76074 Gene ID: 8654.0 Gene Symbol: PDE5A Target Organism: Homo sapiens (Human) |
5.9 µM [IC50] | ||
Target ID: P56818 Gene ID: 23821.0 Gene Symbol: Bace1 Target Organism: Mus musculus (Mouse) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Icariin 60 Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Icariin 60 Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Purification of icariin from the extract of Epimedium segittatum using high-speed counter-current chromatography. | 2002 Jul 12 |
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| Effects of icariin on cGMP-specific PDE5 and cAMP-specific PDE4 activities. | 2003 Mar |
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| The antioxidative effect of icariin in human erythrocytes against free-radical-induced haemolysis. | 2004 Dec |
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| Cytotoxic effects of Coptis chinensis and Epimedium sagittatum extracts and their major constituents (berberine, coptisine and icariin) on hepatoma and leukaemia cell growth. | 2004 Jan-Feb |
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| Quantitative and qualitative HPLC analysis of thermogenic weight loss products. | 2004 Nov |
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| Determination of icariin and metabolites in rat serum by capillary zone electrophoresis: rat pharmacokinetic studies after administration of icariin. | 2004 Oct 29 |
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| Icariin, a flavonoid from the herb Epimedium enhances the osteogenic differentiation of rat primary bone marrow stromal cells. | 2005 Dec |
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| Effects of icariin on erectile function and expression of nitric oxide synthase isoforms in castrated rats. | 2005 Dec |
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| [Effects of Epimedium pubescens icariine on proliferation and differentiation of human osteoblasts]. | 2005 Feb |
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| [Study on water extraction process of Herba epimedii with microwave technology]. | 2005 Jan |
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| Preparative isolation and purification of three flavonoids from the Chinese medicinal plant Epimedium koreamum Nakai by high-speed counter-current chromatography. | 2005 Jan 28 |
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| Icariin-mediated modulation of cell cycle and p53 during cardiomyocyte differentiation in embryonic stem cells. | 2005 May 9 |
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| Estrogenic effects of two derivatives of icariin on human breast cancer MCF-7 cells. | 2005 Nov |
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| The osteoprotective effect of Herba epimedii (HEP) extract in vivo and in vitro. | 2005 Sep |
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| Effects of icariin on phosphodiesterase-5 activity in vitro and cyclic guanosine monophosphate level in cavernous smooth muscle cells. | 2006 Dec |
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| [Effect of er xian decoction and its subdivisions on granulosa cells secretory function in rats]. | 2006 Jun |
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| Icariin-mediated expression of cardiac genes and modulation of nitric oxide signaling pathway during differentiation of mouse embryonic stem cells into cardiomyocytes in vitro. | 2006 Mar |
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| Hypouricemic action of selected flavonoids in mice: structure-activity relationships. | 2007 Aug |
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| Icaritin and its glycosides enhance osteoblastic, but suppress osteoclastic, differentiation and activity in vitro. | 2007 Aug 16 |
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| Protective effect of icariin on DNA against radical-induced oxidative damage. | 2007 Dec |
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| Simultaneous determination of nine flavonoids and qualitative evaluation of Herba Epimedii by high performance liquid chromatography with ultraviolet detection. | 2007 Dec |
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| Simultaneous determination of icariin, icariside II and osthole in rat plasma after oral administration of the extract of Gushudan (a Chinese compound formulation) by LC-MS/MS. | 2007 Dec 1 |
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| Effect of lipid-based suspension of Epimedium koreanum Nakai extract on sexual behavior in rats. | 2007 Dec 3 |
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| Icariine stimulates proliferation and differentiation of human osteoblasts by increasing production of bone morphogenetic protein 2. | 2007 Feb 5 |
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| HPLC analysis and pharmacokinetics of icariin in rats. | 2007 Jun |
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| Chemical constituents of roots of Epimedium wushanense and evaluation of their biological activities. | 2007 Jun |
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| [A review on research of raw material and cut crude drug of Herba epimedii in last ten years]. | 2007 Mar |
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| Icariin inhibits the osteoclast formation induced by RANKL and macrophage-colony stimulating factor in mouse bone marrow culture. | 2007 May |
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| [Effects of Erxian Decoction and its separate prescriptions on the levels of luteinizing hormone and follicle-stimulating hormone in anterior pituitary cells from female rats]. | 2007 Nov |
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| LC-MS/MS method for the simultaneous determination of icariin and its major metabolites in rat plasma. | 2007 Nov 30 |
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| Pharmacological activity of cardiovascular agents from herbal medicine. | 2007 Oct |
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| Icariin promotes expression of PGC-1alpha, PPARalpha, and NRF-1 during cardiomyocyte differentiation of murine embryonic stem cells in vitro. | 2007 Oct |
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| Reactive oxygen species involved in prenylflavonoids, icariin and icaritin, initiating cardiac differentiation of mouse embryonic stem cells. | 2008 Apr 1 |
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| Effects of total flavonoids and flavonol glycosides from Epimedium koreanum Nakai on the proliferation and differentiation of primary osteoblasts. | 2008 Jan |
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| A rapid method for simultaneous determination of 15 flavonoids in Epimedium using pressurized liquid extraction and ultra-performance liquid chromatography. | 2008 Jan 22 |
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| Simultaneous quantitation of five flavonoid glycosides in Herba Epimedii by high-performance liquid chromatography-tandem mass spectrometry. | 2008 Jan-Feb |
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| Fast quality control of Herba Epimedii by using Fourier transform infrared spectroscopy. | 2008 Jul |
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| Involvement of NF-kappaB and AP-1 activation in icariin promoted cardiac differentiation of mouse embryonic stem cells. | 2008 May 31 |
Sample Use Guides
In an open-label pilot trial, adults with current bipolar disorder and current cocaine or alcohol use disorders were treated with 100 mg/day icariin. After 3 weeks patients who had less than 30% reduction in the Hamilton Rating Scale for Depression or still abusing substances were titrated up to a dose of 200 mg/day. At week 6 patients who had less than 50% reduction in HAMD score continued to abuse alcohol/cocaine were titrated up to a maximum dose of 300 mg/day.
Route of Administration:
Oral
Isolated segments of rabbit corpus cavernosum were exposed to increasing concentrations of icariin while the accumulation of cGMP and cAMP was monitored by means of a 1251 radioimmunoassay. Icariin increased accumulated cGMP and cAMP in a dose-dependent manner. An EC50 of 4.62 uM was determined for icariin, which was contrasted to an EC50 of 0.42 uM for Sildenafil under similar conditions.
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DSLD |
1125 (Number of products:24)
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100000168995
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1788871
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ICARIIN
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5318997
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m4942
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VNM47R2QSQ
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VNM47R2QSQ
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DB12052
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DTXSID00964133
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489-32-7
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SUB182587
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SUBSTANCE RECORD
