トリプトライド

Also known as Triptolide

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.

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 Å²
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

Sources (3)

via Wikidata · CC0

Article · 日本語

トリプトリド（英:Triptolide）はPG490とも呼ばれるジテルペンであり、分子中に3つのエポキシ基を有している。中国原産のニシキギ科のつる植物である（Tripterygium wilfordii）に含まれる成分であり、漢方薬としては雷公藤（）の主要成分である。トリプトリドは抗腫瘍効果の他、免疫抑制作用や抗炎症効果を持つ。 in vitro とin vivo で多発性嚢胞腎や膵癌のマウスモデルに有効性を示したが、その特性や強い毒性の問題から、治療薬としての使用は困難である。トリプトリドに代わり、その水溶性プロドラッグであるミンネリド（英:Minnelide）（下記参照）の臨床試験が進行中である。

Abstract from DBpedia / Wikipedia · CC BY-SA

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via Wikidata sitelinks · CC0