Structure via PubChem · Public domain (PubChem)
triptolide
Sign in to saveTriptolide is a diterpenoid epoxide which is produced by the thunder god vine, Tripterygium wilfordii. It has in vitro and in vivo activities against mouse models of polycystic kidney disease and pancreatic cancer, but its physical properties and severe toxicity limit its therapeutic potential. Consequently, a synthetic water-soluble prodrug, minnelide, is being studied clinically instead.
Chemical data
- Formula
- C20H24O6
- Molecular weight
- 360.4 g/mol
- IUPAC name
- (1S,2S,4S,5S,7R,8R,9S,11S,13S)-8-hydroxy-1-methyl-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one
- SMILES
- CC(C)[C@@]12[C@@H](O1)[C@H]3[C@@]4(O3)[C@]5(CCC6=C([C@@H]5C[C@H]7[C@]4([C@@H]2O)O7)COC6=O)C
- InChIKey
- DFBIRQPKNDILPW-CIVMWXNOSA-N
- XLogP
- 0.2
- Polar surface area
- 84.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- infection, HIV infection, Autosomal dominant polycystic kidney disease, non-small cell lung carcinoma
via ChEMBL · EBI
Research
2,094 papers- Triptolide-targeted delivery methods.European journal of medicinal chemistry · 2019
- Triptolide prevents LPS-induced skeletal muscle atrophy via inhibiting NF-κB/TNF-α and regulating protein synthesis/degradation pathway.British journal of pharmacology · 2021
- Triptolide-induced cuproptosis is a novel antitumor strategy for the treatment of cervical cancer.Cellular & molecular biology letters · 2024
- Triptolide, A Potential Autophagy Modulator.Chinese journal of integrative medicine · 2019
- Triptolide: pharmacological spectrum, biosynthesis, chemical synthesis and derivatives.Theranostics · 2021
via PubMed
Wikidata facts
- Mass
- 360.157
Show 6 more facts
- chemical formula
- C₂₀H₂₄O₆
- canonical SMILES
- CC(C)C12C(O1)C3C4(O3)C5(CCC6=C(C5CC7C4(C2O)O7)COC6=O)C
- isomeric SMILES
- CC(C)[C@@]12[C@@H](O1)[C@H]3[C@@]4(O3)[C@]5(CCC6=C([C@@H]5C[C@H]7[C@]4([C@@H]2O)O7)COC6=O)C
- subject has role
- alkylating antineoplastic agent
- Commons category
- Triptolide
- found in taxon
- Tripterygium wilfordii
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- Mechanism of action
- Water-soluble prodrugs
- References
Triptolide is a diterpenoid epoxide which is produced by the thunder god vine, Tripterygium wilfordii. It has in vitro and in vivo activities against mouse models of polycystic kidney disease and pancreatic cancer, but its physical properties and severe toxicity limit its therapeutic potential. Consequently, a synthetic water-soluble prodrug, minnelide, is being studied clinically instead.
Triptolide is a component of ContraPest, a contraceptive pest control liquid used to reduce rat populations in the United States.
Excerpted from Wikipedia’s “triptolide” article, available under the CC BY-SA 4.0 licence.