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
Molecular Formula | C20H24O6 |
Molecular Weight | 360.401 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
|||
Primary | Unknown Approved UseUnknown |
|||
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 |
---|---|---|
Triptolide binds covalently to a 90 kDa nuclear protein. Role of epoxides in binding and activity. | 2007 |
|
Differential expression and oxidation of MKP-1 modulates TNF-alpha gene expression. | 2007 Sep |
|
Triptolide cooperates with chemotherapy to induce apoptosis in acute myeloid leukemia cells. | 2008 Dec |
|
Upregulation of ICAM-1 expression in bronchial epithelial cells by airway secretions in bronchiectasis. | 2008 Feb |
|
Phase I dose-escalation study of F60008, a novel apoptosis inducer, in patients with advanced solid tumours. | 2009 Jul |
|
Caspase 3 is involved in the apoptosis induced by triptolide in HK-2 cells. | 2009 Jun |
|
Interleukin-6-independent expression of glucocorticoid receptor is upregulated by triptolide in multiple myeloma. | 2009 May |
|
Triptolide alters histone H3K9 and H3K27 methylation state and induces G0/G1 arrest and caspase-dependent apoptosis in multiple myeloma in vitro. | 2010 Jan 12 |
|
Identification of triptolide, a natural diterpenoid compound, as an inhibitor of lung inflammation. | 2010 Jun |
|
Cytotoxicity of Triptolide and Triptolide loaded polymeric micelles in vitro. | 2011 Dec |
|
Effect of triptolide on progesterone production from cultured rat granulosa cells. | 2012 Jun |
|
Minnelide: a novel therapeutic that promotes apoptosis in non-small cell lung carcinoma in vivo. | 2013 |
|
Interleukin-17 mediates triptolide-induced liver injury in mice. | 2014 Sep |
|
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:01:53 UTC 2023
by
admin
on
Fri Dec 15 19:01:53 UTC 2023
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Record UNII |
19ALD1S53J
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Record Status |
Validated (UNII)
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Record Version |
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-
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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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Related Record | Type | Details | ||
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PRODRUG -> METABOLITE ACTIVE |
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PRODRUG -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |