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
SMILES
CC1=CCC[C@@]2(C)O[C@@H]2[C@H]3OC(=O)C(=C)[C@@H]3CC1
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
| Molecular Formula | C15H20O3 |
| Molecular Weight | 248.3175 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/15122077Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17656318 https://www.lktlabs.com/product/parthenolide/
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15122077
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17656318 https://www.lktlabs.com/product/parthenolide/
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12417429
Curator's Comment: Parthenolide might have a potential in the treatment of CNS diseases where NO is part of the pathophysiology (demonstrated in rats)
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL325 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17656318 |
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Target ID: CHEMBL1741165 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26824319 |
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Target ID: CHEMBL612794 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27536701 |
5.8 µM [IC50] | ||
Target ID: M9-ENL1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26540463 |
6.0 µM [EC50] | ||
Target ID: CHEMBL3392947 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23691032 |
1.5 µM [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 |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
8.1% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15114499/ |
PARTHENOLIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
4 mg 1 times / day multiple, oral Highest studied dose Dose: 4 mg, 1 times / day Route: oral Route: multiple Dose: 4 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: |
|
0.1 % single, topical Studied dose |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Disc. AE: Contact dermatitis... AEs leading to discontinuation/dose reduction: Contact dermatitis Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Contact dermatitis | Disc. AE | 0.1 % single, topical Studied dose |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Elucidation and in planta reconstitution of the parthenolide biosynthetic pathway. | 2014-05 |
|
| The lipophilic hapten parthenolide induces interferon-gamma and interleukin-13 production by peripheral blood-derived CD8+ T cells from contact allergic subjects in vitro. | 2008-01 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15122077
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26824319
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
Created
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2RDB26I5ZB
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Validated (UNII)
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DSLD |
3154 (Number of products:2)
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NDF-RT |
N0000185508
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N0000175629
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PRIMARY | Increased Histamine Release [PE] | ||
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N0000184306
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PRIMARY | Cell-mediated Immunity [PE] | ||
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DB13063
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7939
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5420805
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SUB176432
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32941
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20554-84-1
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2RDB26I5ZB
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N0000171131
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PRIMARY | Allergens [Chemical/Ingredient] | ||
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1500400
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C002669
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DTXSID2040579
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100000162612
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m8422
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PARTHENOLIDE
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157035
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PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT |
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TARGET -> AGONIST |
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TARGET -> INHIBITOR |
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ACTIVE MOIETY |
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