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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H20O3
Molecular Weight 296.361
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CRYPTOTANSHINONE

SMILES

C[C@@]1([H])COC2=C1C(=O)C(=O)c3c4CCCC(C)(C)c4ccc32

InChI

InChIKey=GVKKJJOMQCNPGB-JTQLQIEISA-N
InChI=1S/C19H20O3/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/h6-7,10H,4-5,8-9H2,1-3H3/t10-/m0/s1

HIDE SMILES / InChI

Molecular Formula C19H20O3
Molecular Weight 296.361
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Cryptotanshinone is one of the major tanshinones isolated from the roots of the plant Salvia miltiorrhiza Bunge (Danshen). Danshen has been widely used in traditional Chinese medicine for treatment of a variety of diseases, including coronary artery disease, acute ischemic stroke, hyperlipidemia, chronic renal failure, chronic hepatitis, and Alzheimer's disease, showing no serious adverse effects. Recent studies have shown that cryptotanshinone not only possesses the potential for treatment and prevention of the above-mentioned diseases, but also is a potent anticancer agent. In vitro studies have demonstrated that cryptotanshinone inhibits cell proliferation in a variety of cancer cell lines, including rhabdomyosarcoma, melanoma, cervical, colon, breast and prostate cancer cells. It has been described that cryptotanshinone induced a G1/G0 cell cycle arrest in rhabdomyosarcoma (Rh30) and prostate cancer (DU145) cells by downregulating expression of cyclin D1 and phosphorylation of retinoblastoma protein (Rb), but induced a G2/ M cell cycle arrest in melanoma (B16) cells via upregulating expression of Cdc25c, cyclin A1 and cyclin B1. Cryptotanshinone inhibiting expression of Aurora A kinase led to significant suppression of prostate cancer cells in vitro and in mice. Cryptotanshinone also induces cell death in cancer cells.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
PXR-mediated transcriptional activation of CYP3A4 by cryptotanshinone and tanshinone IIA.
2009 Jan 15
Interaction study of two diterpenes, cryptotanshinone and dihydrotanshinone, to human acetylcholinesterase and butyrylcholinesterase by molecular docking and kinetic analysis.
2010 Sep 6
Induction of cytochromes P450 1A1 and 1A2 by tanshinones in human HepG2 hepatoma cell line.
2011 Apr 1
Anticancer activity of cryptotanshinone on acute lymphoblastic leukemia cells.
2016 Sep
Patents

Sample Use Guides

Intraperitoneal injection of Cryptotanshinone (0, 10, or 25 mg/kg) for 4 weeks significantly inhibited the growth of HCCC-9810 xenografts in athymic nude mice.
Route of Administration: Intraperitoneal
Cryptotanshinone (7 uM) dramatically blocks STAT3 Tyr705 phosphorylation but not STAT3 Ser727 phosphorylation in DU145 cells, and significantly inhibits JAK2 phosphorylation with IC50 of ~5 uM without affecting the phosphorylation of upstream kinases c-Src and EGFR, suggesting the inhibition of STAT3 Tyr705 phosphorylation might due to a direct mechanism probably by binding to the SH2 domain of STAT3. Cryptotanshinone significantly inhibits the proliferation of DU145 prostate cancer cells harboring constitutively active STAT3 with GI50 of 7 uM by blocking STAT3 activity, which leads to the down-regulation of cyclin D1, Bcl-xL, and survivin, subsequently the accumulation in the G0-G1 phase. Cryptotanshinone exhibits less growth inhibitory effect on PC3, LNCaP and MDA-MB-468 cells.
Substance Class Chemical
Created
by admin
on Sat Jun 26 12:24:16 UTC 2021
Edited
by admin
on Sat Jun 26 12:24:16 UTC 2021
Record UNII
5E9SXT166N
Record Status Validated (UNII)
Record Version
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Name Type Language
CRYPTOTANSHINONE
Common Name English
(15R)-CRYPTOTANSHINONE
Common Name English
CRYPTOTANSHINONE (CONSTITUENT OF CHINESE SALVIA) [DSC]
Common Name English
CRYPTOTANSHINON
Common Name English
PHENANTHRO(1,2-B)FURAN-10,11-DIONE, 1,2,6,7,8,9-HEXAHYDRO-1,6,6-TRIMETHYL-, (1R)-
Systematic Name English
TANSHINONE C
Common Name English
Code System Code Type Description
FDA UNII
5E9SXT166N
Created by admin on Sat Jun 26 12:24:16 UTC 2021 , Edited by admin on Sat Jun 26 12:24:16 UTC 2021
PRIMARY
CAS
35825-57-1
Created by admin on Sat Jun 26 12:24:16 UTC 2021 , Edited by admin on Sat Jun 26 12:24:16 UTC 2021
PRIMARY
PUBCHEM
160254
Created by admin on Sat Jun 26 12:24:16 UTC 2021 , Edited by admin on Sat Jun 26 12:24:16 UTC 2021
PRIMARY
DRUG BANK
DB15579
Created by admin on Sat Jun 26 12:24:16 UTC 2021 , Edited by admin on Sat Jun 26 12:24:16 UTC 2021
PRIMARY
EPA CompTox
35825-57-1
Created by admin on Sat Jun 26 12:24:16 UTC 2021 , Edited by admin on Sat Jun 26 12:24:16 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT