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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
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
PubMed

PubMed

TitleDatePubMed
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 Jan
Elucidation and in planta reconstitution of the parthenolide biosynthetic pathway.
2014 May
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 Fri Dec 15 16:53:56 UTC 2023
Edited
by admin
on Fri Dec 15 16:53:56 UTC 2023
Record UNII
2RDB26I5ZB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PARTHENOLIDE
MI   USP-RS   WHO-DD  
INCI  
Official 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
NSC-157035
Code 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
PARTHENOLIDE [INCI]
Common Name English
Classification Tree Code System Code
DSLD 3154 (Number of products:2)
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
NDF-RT N0000185508
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
Code System Code Type Description
NDF-RT
N0000175629
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
PRIMARY Increased Histamine Release [PE]
NDF-RT
N0000184306
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
PRIMARY Cell-mediated Immunity [PE]
DRUG BANK
DB13063
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
PRIMARY
CHEBI
7939
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
PRIMARY
PUBCHEM
5420805
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
PRIMARY
EVMPD
SUB176432
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
PRIMARY
RXCUI
32941
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
PRIMARY RxNorm
CAS
20554-84-1
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
PRIMARY
FDA UNII
2RDB26I5ZB
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
PRIMARY
NDF-RT
N0000171131
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
PRIMARY Allergens [Chemical/Ingredient]
RS_ITEM_NUM
1500400
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
PRIMARY
MESH
C002669
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
PRIMARY
EPA CompTox
DTXSID2040579
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
PRIMARY
SMS_ID
100000162612
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
PRIMARY
MERCK INDEX
m8422
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
PARTHENOLIDE
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
PRIMARY
NSC
157035
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
PRIMARY
DAILYMED
2RDB26I5ZB
Created by admin on Fri Dec 15 16:53:56 UTC 2023 , Edited by admin on Fri Dec 15 16:53:56 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT
TARGET -> AGONIST
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY