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

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24O6
Molecular Weight 360.401
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIPTOLIDE

SMILES

[H][C@@]12C[C@@H]3O[C@@]34[C@H](O)[C@]5(O[C@H]5[C@@H]6O[C@]46[C@@]1(C)CCC7=C2COC7=O)C(C)C

InChI

InChIKey=DFBIRQPKNDILPW-CIVMWXNOSA-N
InChI=1S/C20H24O6/c1-8(2)18-13(25-18)14-20(26-14)17(3)5-4-9-10(7-23-15(9)21)11(17)6-12-19(20,24-12)16(18)22/h8,11-14,16,22H,4-7H2,1-3H3/t11-,12-,13-,14-,16+,17-,18-,19+,20+/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H24O6
Molecular Weight 360.401
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Triptolide, the active component of Tripterygium wilfordii Hook F has been used to treat autoimmune and inflammatory conditions for over two hundred years in traditional Chinese medicine. Triptolide possesses immunosuppressive, anti-inflammatory, and anti-cancer effects. Triptolide is a woody vine which is widely distributed in Eastern and Southern China. In China, triptolide is frequently used to treat autoimmune and/or inflammatory diseases due to its favorable cost–benefit ratio. Commercial preparations of triptolide have been commonly used for the treatment of inflammatory and autoimmune diseases such as rheumatoid arthritis, systemic lupus erythematosus, nephritis and psoriasis.Triptolide has been demonstrated to exert novel chondroprotective and anti-inflammatory effects on rheumatoid arthritis. Triptolide has been used to treat ADPKD patients in clinical trials in China. Triptolide significantly protected glomerular filtration rate (eGFR) of ADPKD patients compared with placebo. Two recent small clinical studies have demonstrated tiptolide’s effectiveness against rheumatoid arthritis. A larger study confirmed the therapeutic effects of triptolide in the aforementioned studies. Triptolide is among the most powerful and broadly active antiinflammatory/immunomodulating natural products ever discovered. Triptolide acts at nanomolar concentrations and inhibits the production of various cellular targets including inflammatory cytokines, cyclooxygenase, inducible nitric oxide synthase and metalloproteinases and transcription factors. The anti-tumor activity of Triptolide in vitro and in various tumor-bearing animal models has been investigated for years, and many findings showed that Triptolide is a promising agent in anti-tumor therapy. Triptolide has been approved for Phase I clinical trials for the treatment of prostate cancer, but the anti-tumor effect and mechanism of TPL need to be further elucidated.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
14.18 µM [IC50]
8.36 µM [IC50]
12.6 nM [IC50]
30.0 pM [IC50]
14.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Minnelide will be administered at the dose of 0.67 mg/m2 as a 30 min infusion intravenously daily on days 1-21 of each cycle followed by a 7 day rest period (days 22-28)
Route of Administration: Intravenous
In Vitro Use Guide
The A549/Taxol cells were treated with different concentrations of Triptolide (0.03, 0.3 or 3 uM/l) for 2, 4, 6 and 12 h. On exposure to 3 uM Triptolide for 2, 4, 6 and 12 h, the extent of cell apoptosis observed markedly increased. The inhibitory effect reached a maximum with 3 uM Triptolide at the 12 h time point (cell apoptotic rate, 65.33%), whereas the apoptotic rate of the control group was 7.23% at 12 h.
Substance Class Chemical
Record UNII
19ALD1S53J
Record Status Validated (UNII)
Record Version