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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H20O3
Molecular Weight 248.3175
Optical Activity ( - )
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PARTHENOLIDE

SMILES

[H][C@@]12CCC(C)=CCC[C@@]3(C)O[C@@H]3[C@@]1([H])OC(=O)C2=C

InChI

InChIKey=KTEXNACQROZXEV-ZRPLFPEYSA-N
InChI=1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5-/t11-,12-,13+,15+/m0/s1

HIDE SMILES / InChI

Molecular Formula C15H20O3
Molecular Weight 248.3175
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Parthenolide is a sesquiterpene lactone found in Tanacetum that exhibits anticancer chemotherapeutic, anti-metastatic, anti-angiogenic, anti-inflammatory, and antinociceptive activities. Parthenolide acts as a partial agonist at transient receptor potential ankyrin 1 (TRPA1) channels and desensitizes them, preventing release of calcitonin gene-related peptide (CGRP). Additionally, parthenolide inhibits ATPase activity of NLRP3 and protease activity of caspase 1. In multiple myeloma cells, parthenolide decreases expression of NF-κB, VEGF, and IL-6 and increases expression of IκB kinase, inhibiting cell migration and tubule formation. In non-small cell lung cancer (NSCLC) cells, parthenolide decreases levels of MCL-1 and increases levels of MAIP-1, triggering ER stress and inducing cell cycle arrest and apoptosis. In breast cancer cells, this compound activates NADPH oxidase and increases ROS generation, increasing levels of p-JNK and downregulating NF-κB, VEGF, and matrix metalloproteinases 2 and 9 (MMP2/9); in vivo, parthenolide inhibits tumor growth and metastasis. Parthenolide has being shown to have agonistic activity against adiponectin receptor 2. Parthenolide is in phase I clinical trials by Ashbury Biologicals for the treatment of cancer. However, there is no recent report of this research.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
5.8 µM [IC50]
6.0 µM [EC50]
1.5 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Patients were to receive increasing dosages of oral parthenolide from 1 to 5 mg per day in 1 mg increments.
Route of Administration: Oral
In Vitro Use Guide
Parthenolide at 10 uM and 20 uM markedly reduced the percentage of cells expressing MITF at high level in patient-derived melanoma cells
Substance Class Chemical
Record UNII
2RDB26I5ZB
Record Status Validated (UNII)
Record Version