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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

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

HIDE SMILES / InChI

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

Description
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

Curator's Comment: Parthenolide might have a potential in the treatment of CNS diseases where NO is part of the pathophysiology (demonstrated in rats)

Approval Year

Targets

Targets

Conditions
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
8.1%
PARTHENOLIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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
Dose: 0.1 %
Route: topical
Route: single
Dose: 0.1 %
Sources:
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

AEs

AESignificanceDosePopulation
Contact dermatitis Disc. AE
0.1 % single, topical
Studied dose
Dose: 0.1 %
Route: topical
Route: single
Dose: 0.1 %
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
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

Patients were to receive increasing dosages of oral parthenolide from 1 to 5 mg per day in 1 mg increments.
Route of Administration: Oral
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
by admin
on Mon Mar 31 18:37:41 GMT 2025
Edited
by admin
on Mon Mar 31 18:37:41 GMT 2025
Record UNII
2RDB26I5ZB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PARTHENOLIDE
MI   USP-RS   WHO-DD  
INCI  
Official Name English
NSC-157035
Preferred Name English
PARTHENOLIDE (CONSTITUENT OF FEVERFEW) [DSC]
Common Name English
4,5.ALPHA.-EPOXY-6.BETA.-HYDROXY-GERMACRA-1(10),11(13)-DIEN-12-OIC ACID .GAMMA.-LACTONE
Common Name English
(1AR,4E,7AS,10AS,10BS)-2,3,6,7,7A,8,10A,10B-OCTAHYDRO-1A,5-DIMETHYL-8-METHYLENEOXIRENO(9,10)CYCLODECA(1,2-B)FURAN-9(1AH)-ONE
Common Name English
PARTHENOLIDE [USP-RS]
Common Name English
PARTHENOLIDE [MI]
Common Name English
Parthenolide [WHO-DD]
Common Name English
Classification Tree Code System Code
DSLD 3154 (Number of products:2)
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
NDF-RT N0000185508
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
Code System Code Type Description
NDF-RT
N0000175629
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
PRIMARY Increased Histamine Release [PE]
NDF-RT
N0000184306
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
PRIMARY Cell-mediated Immunity [PE]
DRUG BANK
DB13063
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
PRIMARY
CHEBI
7939
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
PRIMARY
PUBCHEM
5420805
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
PRIMARY
EVMPD
SUB176432
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
PRIMARY
RXCUI
32941
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
PRIMARY RxNorm
CAS
20554-84-1
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
PRIMARY
FDA UNII
2RDB26I5ZB
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
PRIMARY
NDF-RT
N0000171131
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
PRIMARY Allergens [Chemical/Ingredient]
RS_ITEM_NUM
1500400
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
PRIMARY
MESH
C002669
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
PRIMARY
EPA CompTox
DTXSID2040579
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
PRIMARY
SMS_ID
100000162612
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
PRIMARY
MERCK INDEX
m8422
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
PARTHENOLIDE
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
PRIMARY
NSC
157035
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
PRIMARY
DAILYMED
2RDB26I5ZB
Created by admin on Mon Mar 31 18:37:41 GMT 2025 , Edited by admin on Mon Mar 31 18:37:41 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT
TARGET -> AGONIST
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY