Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H18O3 |
Molecular Weight | 294.3444 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=COC2=C1C(=O)C(=O)C3=C2C=CC4=C3CCCC4(C)C
InChI
InChIKey=HYXITZLLTYIPOF-UHFFFAOYSA-N
InChI=1S/C19H18O3/c1-10-9-22-18-12-6-7-13-11(5-4-8-19(13,2)3)15(12)17(21)16(20)14(10)18/h6-7,9H,4-5,8H2,1-3H3
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/15849732Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27446335
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15849732
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27446335
Tanshinone IIA is a derivative of phenanthrene-quinone isolated from Danshen, a widely used Chinese herbal medicine. It has antioxidant properties and cytotoxic activity against multiple human cancer cell lines, inducing apoptosis and differentiation of some human cancer cell lines. It was found, that tanshinone IIA might have potential anticancer activity on breast cancers through upregulation and downregulation of multiple genes involved in cell cycle regulation, cell proliferation, apoptosis, signal transduction, transcriptional regulation, angiogenesis, invasive potential and metastatic potential of cancer cells. ADPRTL1 might be the main target at which tanshinone IIA acted. Recently was discovered that tanshinone IIA exerts its cardio protective effects against H2O2-induced cell death by upregulating the expression of Bcl-2 via the activation of the PI3K/Akt signaling pathway, however, further studies are required in order to define and clarify the rationale for its clinical use.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12809358
Curator's Comment: Known to be CNS penetrant in mouse. Human data not available.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: map04151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27446335 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Preventing | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Potential anticancer activity of tanshinone IIA against human breast cancer. | 2005 Sep 20 |
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Tanshinone IIA protects cardiac myocytes against oxidative stress-triggered damage and apoptosis. | 2007 Jul 30 |
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Tanshinone IIA protects H9c2 cells from oxidative stress-induced cell death via microRNA-133 upregulation and Akt activation. | 2016 Aug |
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Tanshinone IIA decreases the protein expression of EGFR, and IGFR blocking the PI3K/Akt/mTOR pathway in gastric carcinoma AGS cells both in vitro and in vivo. | 2016 Aug |
|
Tanshinone IIA attenuates epithelial-mesenchymal transition to inhibit the tracheal narrowing. | 2016 Nov |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15849732
in mice: Seven nude mice bearing human breast s.c. injection of tanshinone IIA at a dose of 30 mg/kg 3 times/week for 10 weeks.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15849732
Tanshinone IIA demonstrated a dose- and time-dependent inhibitory effect on cell growth (IC50 = 0.25 microg/ml), and it significantly inhibited colony formation and BrdU incorporation of human breast cancer cells. Oligonucleotide microarray analysis identified 41 upregulated (1.22%) and 24 downregulated (0.71%) genes after tanshinone IIA treatment
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SUBSTANCE RECORD