| 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 |
MOL RATIO
1 MOL RATIO (average) |
| 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).
CNS Activity
Approval Year
PubMed
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.
