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
| Molecular Formula | C33H40O15 |
| Molecular Weight | 676.6617 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|
| [Quantitative determination of icariin in "tangzhi shuangjiang cha" by high performance liquid chromatography]. | 2001 Jul |
|
| Chemical and pharmacological investigations of Epimedium species: a survey. | 2003 |
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| Quantitative and qualitative HPLC analysis of thermogenic weight loss products. | 2004 Nov |
|
| Effects of Icariin on expression of OPN mRNA and type I collagen in rat osteoblasts in vitro. | 2005 |
|
| [Species and geographic distribution of large-flowered taxa of Epimedium in China]. | 2005 Apr |
|
| Inducible effects of icariin, icaritin, and desmethylicaritin on directional differentiation of embryonic stem cells into cardiomyocytes in vitro. | 2005 Apr |
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| Antidepressant-like effect of icariin and its possible mechanism in mice. | 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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| Optimization for quantitative determination of four flavonoids in Epimedium by capillary zone electrophoresis coupled with diode array detection using central composite design. | 2006 Jan 27 |
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| Icariin: a special antioxidant to protect linoleic acid against free-radical-induced peroxidation in micelles. | 2006 May 18 |
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| Icariin enhances endothelial nitric-oxide synthase expression on human endothelial cells in vitro. | 2007 Jul |
|
| 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. | 2007 Jul |
|
| HPLC analysis and pharmacokinetics of icariin in rats. | 2007 Jun |
|
| Icariin from Epimedium brevicornum attenuates chronic mild stress-induced behavioral and neuroendocrinological alterations in male Wistar rats. | 2007 May |
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| Taxonomic, genetic, chemical and estrogenic characteristics of Epimedium species. | 2007 May |
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| [Systematic studies on quality of main species of Herba epimedii]. | 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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| Simultaneous extraction of epimedin A, B, C and icariin from Herba Epimedii by ultrasonic technique. | 2008 Apr |
|
| Statistically designed enzymatic hydrolysis for optimized production of icariside II as a novel melanogenesis inhibitor. | 2008 Jan |
|
| Ethanol extract from Epimedium brevicornum attenuates left ventricular dysfunction and cardiac remodeling through down-regulating matrix metalloproteinase-2 and -9 activity and myocardial apoptosis in rats with congestive heart failure. | 2008 Jan |
|
| Effects of total flavonoids and flavonol glycosides from Epimedium koreanum Nakai on the proliferation and differentiation of primary osteoblasts. | 2008 Jan |
|
| Determination of icariin in rat plasma by reverse-phase high-performance liquid chromatography after oral administration of a lipid-based suspension of Epimedium koreanum extract. | 2008 Jun |
|
| Chemical markers for the quality control of herbal medicines: an overview. | 2008 Jun 28 |
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:05:05 GMT 2023
by
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on
Fri Dec 15 18:05:05 GMT 2023
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| Record UNII |
VNM47R2QSQ
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| Record Status |
Validated (UNII)
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1125 (Number of products:24)
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1788871
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ICARIIN
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m4942
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SUB182587
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| Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR |
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