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
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
DescriptionSources: https://clinicaltrials.gov/ct2/show/NCT03117920 | https://clinicaltrials.gov/ct2/show/NCT01927965 | https://clinicaltrials.gov/ct2/show/NCT03760523
https://www.ncbi.nlm.nih.gov/pubmed/31109340 | https://www.ncbi.nlm.nih.gov/pubmed/28543919https://www.ncbi.nlm.nih.gov/pubmed/30599444 | https://adisinsight.springer.com/drugs/800016015 | https://www.ncbi.nlm.nih.gov/pubmed/19251409/ | https://www.ncbi.nlm.nih.gov/pubmed/21255694https://www.ncbi.nlm.nih.gov/pubmed/27222828 | https://www.ncbi.nlm.nih.gov/pubmed/25400429Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27921038
https://www.drugs.com/npp/thunder-god-vine.html
Sources: https://clinicaltrials.gov/ct2/show/NCT03117920 | https://clinicaltrials.gov/ct2/show/NCT01927965 | https://clinicaltrials.gov/ct2/show/NCT03760523
https://www.ncbi.nlm.nih.gov/pubmed/31109340 | https://www.ncbi.nlm.nih.gov/pubmed/28543919https://www.ncbi.nlm.nih.gov/pubmed/30599444 | https://adisinsight.springer.com/drugs/800016015 | https://www.ncbi.nlm.nih.gov/pubmed/19251409/ | https://www.ncbi.nlm.nih.gov/pubmed/21255694https://www.ncbi.nlm.nih.gov/pubmed/27222828 | https://www.ncbi.nlm.nih.gov/pubmed/25400429
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27921038
https://www.drugs.com/npp/thunder-god-vine.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22220673 | https://www.ncbi.nlm.nih.gov/pubmed/23126204
Curator's Comment: Triptolide crosses the blood-brain barrier easily due to its small molecular size and lipophilic property. Triptolide inhibits amyloid-β production and protects neural cells by inhibiting CXCR2 activity.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26874845 |
14.18 µM [IC50] | ||
Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26874845 |
8.36 µM [IC50] | ||
Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26531258 |
|||
Target ID: HuCCT1, human cholangiocarcinoma Sources: https://www.ncbi.nlm.nih.gov/pubmed/24742042 |
12.6 nM [IC50] | ||
Target ID: GO:0034205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23126204 |
30.0 pM [IC50] | ||
Target ID: CHEMBL5963 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23895492 |
14.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [Inhibition 100 uM] | ||||
no [Inhibition 100 uM] | ||||
no [Inhibition 100 uM] | ||||
no [Inhibition 100 uM] | ||||
no [Inhibition 100 uM] | ||||
no [Inhibition 50 uM] | ||||
no [Inhibition 50 uM] | ||||
no | ||||
yes [IC50 14.18 uM] | ||||
yes [IC50 8.36 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes | yes (co-administration study) Comment: Grapefruit juice increased AUC and Cmax by 153% and 141% Sources: https://pubmed.ncbi.nlm.nih.gov/30112986/ |
PubMed
Title | Date | PubMed |
---|---|---|
PG490-88, a derivative of triptolide, blocks bleomycin-induced lung fibrosis. | 2001 Mar |
|
Caspase 3 is involved in the apoptosis induced by triptolide in HK-2 cells. | 2009 Jun |
|
Heat shock protein 72 protects kidney proximal tubule cells from injury induced by triptolide by means of activation of the MEK/ERK pathway. | 2009 May-Jun |
|
Sex differences in subacute toxicity and hepatic microsomal metabolism of triptolide in rats. | 2010 Apr 30 |
|
Knockout of hepatic P450 reductase aggravates triptolide-induced toxicity. | 2011 Aug 10 |
|
Minnelide: a novel therapeutic that promotes apoptosis in non-small cell lung carcinoma in vivo. | 2013 |
|
Establishment of hypoxia induction in an in vivo animal replacement model for experimental evaluation of pancreatic cancer. | 2014 Jul |
|
Triptolide disrupts fatty acids and peroxisome proliferator-activated receptor (PPAR) levels in male mice testes followed by testicular injury: A GC-MS based metabolomics study. | 2015 Oct 2 |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT03117920
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26531258
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.
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triptolide
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C001899
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100000128444
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DTXSID5041144
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Triptolide
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163062
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107985
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19ALD1S53J
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DB12025
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m11193
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38748-32-2
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SUB35481
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ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)
PRODRUG (METABOLITE ACTIVE)