U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C19H18O3
Molecular Weight 294.3451
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TANSHINONE IIA

SMILES

Cc1coc2-c3ccc4c(CCCC4(C)C)c3C(=O)C(=O)c12

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

HIDE SMILES / InChI

Molecular Formula C19H18O3
Molecular Weight 294.3451
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Curator's Comment:: Known to be CNS penetrant in mouse. Human data not available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Potential anticancer activity of tanshinone IIA against human breast cancer.
2005 Sep 20
Tanshinone IIA protects cardiac myocytes against oxidative stress-triggered damage and apoptosis.
2007 Jul 30
Tanshinone IIA protects H9c2 cells from oxidative stress-induced cell death via microRNA-133 upregulation and Akt activation.
2016 Aug
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 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
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
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:27:07 UTC 2021
Edited
by admin
on Sat Jun 26 11:27:07 UTC 2021
Record UNII
4GPC9FQG6L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TANSHINONE IIA
USP-RS  
Common Name English
TANSHINONE IIA (CONSTITUENT OF CHINESE SALVIA) [DSC]
Common Name English
TANSHINON II
Common Name English
TANSHINONE B
Common Name English
1,6,6-TRIMETHYL-6,7,8,9-TETRAHYDROPHENANTHRO(1,2-B)FURAN-10,11-DIONE
Systematic Name English
TANSHINONE IIA [USP-RS]
Common Name English
TASHINONE IIA
Common Name English
NSC-686519
Code English
TANSHINONE IIA [WHO-DD]
Common Name English
TANSHINONE II
Common Name English
SALVIOL IIA
Common Name English
DAN SHEN KETONE
Common Name English
PHENANTHRO(1,2-B)FURAN-10,11-DIONE, 6,7,8,9-TETRAHYDRO-1,6,6-TRIMETHYL-
Systematic Name English
NSC-686518
Code English
6,7,8,9-TETRAHYDRO-1,6,6-TRIMETHYLPHENANTHRO(1,2-B)FURAN-10,11-DIONE
Systematic Name English
Code System Code Type Description
HSDB
8104
Created by admin on Sat Jun 26 11:27:07 UTC 2021 , Edited by admin on Sat Jun 26 11:27:07 UTC 2021
PRIMARY
CAS
568-72-9
Created by admin on Sat Jun 26 11:27:07 UTC 2021 , Edited by admin on Sat Jun 26 11:27:07 UTC 2021
PRIMARY
USP_CATALOG
1643339
Created by admin on Sat Jun 26 11:27:07 UTC 2021 , Edited by admin on Sat Jun 26 11:27:07 UTC 2021
PRIMARY USP-RS
EPA CompTox
568-72-9
Created by admin on Sat Jun 26 11:27:07 UTC 2021 , Edited by admin on Sat Jun 26 11:27:07 UTC 2021
PRIMARY
EVMPD
SUB33493
Created by admin on Sat Jun 26 11:27:07 UTC 2021 , Edited by admin on Sat Jun 26 11:27:07 UTC 2021
PRIMARY
PUBCHEM
164676
Created by admin on Sat Jun 26 11:27:07 UTC 2021 , Edited by admin on Sat Jun 26 11:27:07 UTC 2021
PRIMARY
FDA UNII
4GPC9FQG6L
Created by admin on Sat Jun 26 11:27:07 UTC 2021 , Edited by admin on Sat Jun 26 11:27:07 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT