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Details

Stereochemistry ACHIRAL
Molecular Formula C21H20O6
Molecular Weight 368.3799
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ICARITIN

SMILES

COC1=CC=C(C=C1)C2=C(O)C(=O)C3=C(O)C=C(O)C(CC=C(C)C)=C3O2

InChI

InChIKey=TUUXBSASAQJECY-UHFFFAOYSA-N
InChI=1S/C21H20O6/c1-11(2)4-9-14-15(22)10-16(23)17-18(24)19(25)20(27-21(14)17)12-5-7-13(26-3)8-6-12/h4-8,10,22-23,25H,9H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C21H20O6
Molecular Weight 368.3799
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Icaritin is a monoprenylated favonol with 4′-methoxyl from Epimedium Genus. It has been documented to have osteoblastic and neuroprotective activities. It can reduce the incidence of steroid-associated oesteonecrosis in rabbit with inhibition of both intravascular thrombosis and extravascular lipid deposition for maintaining the integrity of intraosseous vasculature. Icaritin shows anti-infammatory activity and inhibitory activities against cancer cells. The phase III clinical trial is planned for the treatment of Hepatocellular carcinoma.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
7.89 ng/mL
80 mg single, oral
ICARIIN plasma
Homo sapiens
10.08 ng/mL
80 mg single, oral
ICARISIDE II plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
279 ng × h/mL
80 mg single, oral
ICARIIN plasma
Homo sapiens
255 mg × h/mL
80 mg single, oral
ICARISIDE II plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.16 h
80 mg single, oral
ICARIIN plasma
Homo sapiens
2.21 h
80 mg single, oral
ICARISIDE II plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
600 mg/time, 2 times/day
Route of Administration: Oral
In Vitro Use Guide
Icaritin strongly inhibited the growth of breast cancer MDA-MB-453 and MCF7 cells. At concentrations of 2-3 uM, icaritin induced cell cycle arrest at the G(2)/M phase accompanied by a down-regulation of the expression levels of the G(2)/M regulatory proteins such as cyclinB, cdc2 and cdc25C. Icaritin at concentrations of 4-5 uM, however, induced apoptotic cell death characterized by the accumulation of the annexin V- and propidium iodide-positive cells, cleavage of poly ADP-ribose polymerase (PARP) and down-regulation of the Bcl-2 expression.
Substance Class Chemical
Record UNII
UFE666UELY
Record Status Validated (UNII)
Record Version