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Details

Stereochemistry ABSOLUTE
Molecular Formula C13H15NO2
Molecular Weight 217.2637
Optical Activity ( - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SECURININE

SMILES

[H][C@]12CCCCN1[C@H]3C[C@@]24OC(=O)C=C4C=C3

InChI

InChIKey=SWZMSZQQJRKFBP-WZRBSPASSA-N
InChI=1S/C13H15NO2/c15-12-7-9-4-5-10-8-13(9,16-12)11-3-1-2-6-14(10)11/h4-5,7,10-11H,1-3,6,8H2/t10-,11-,13+/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28943934 | https://www.ncbi.nlm.nih.gov/pubmed/27792748 |

Securinine is a plant-derived alkaloid from the Securinega plant that has been used clinically as a therapeutic for primarily neurological related diseases. Securinine is well-known GABAA antagonist and recently it was found that Securinine is able to up-regulate p53 protein and to modulate the related family member p73 protein in a p53-dependent fashion, inducing p73 in the HCT116 p53(-) cells and down-regulating it in the p53(+) cells. Securinine induces G1 phase cell cycle arrest, upregulates expression of p53 and Bax, and downregulates expression of Bcl-2, PI3K, mTOR, and p70s6k in breast cancer cells and promyelocytic leukemia cells. Securinine activates p38 MAPK, enhancing monocyte antibacterial activity in vitro as well. This compound also exhibits antimicrobial activity against Alternaria, Curvularia, and Helminthosporum. Additionally, securinine decreases AChE activity and suppresses amyloid-β (Aβ)-induced glial inflammatory responses in animal models of Alzheimer’s disease, improving cognitive deficits. Securinine’s activity as a GABA antagonist, likely explains its reported clinical success in limited studies for the treatment of neurological conditions such as amyotrophic lateral sclerosis (ALS), poliomyelitis and multiple sclerosis. Securinine has not been utilized in the United States, it has been used clinically in several other countries particularly China and Russia. In China, it is considered one of the 50 fundamental Chinese herbs and is used in Chinese herbal medicine.

Originator

Sources: Metabolism, Clinical and Experimental (1956), 5, 682-96

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
57.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Toxoplasma gondii: inhibitory activity and encystation effect of securinine and pyrrolidine derivatives on Toxoplasma growth.
2011 Feb
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Zhonghua Yixue Zazhi. Chinese Medical Journal. Vol. 54, Pg. 234, 1974.
LD50: mouse/subcutaneous 20.42mg/kg; mouse/oral 270mg/kg; mouse/intravenous 6.23mg/kg; mouse/intraperitoneal 31.8mg/kg; mouse/intramuscular 19.32mg/kg
Route of Administration: Other
The human lung cancer A549 cell line were used for activity evaluation. The exponentially growing human lung cancer cell suspension (5,000 cells/100 μl) was seeded into each well of 96 well plates. The cells were pre incubated for 24 h in the humidified incubator at 37˚C with 5% CO2. Various concentrations of L securinine from 0 to 160 μg/ml (10 μl) were added into each well. The cells were then incubated for 24, 36 and 48 h in the incubator. CCK 8 solution (10 μl; cat no. KGA317; Nanjing KeyGen Biotech Co., Ltd., Nanjing, China) was added to each well and incubated for 3 h. The absorbance of the wells at 450 nm was measured using a microplate reader
Name Type Language
SECURININE
INN   MI   WHO-DD  
INN  
Official Name English
SECURININ
Common Name English
NSC-107413
Code English
(6S,11AR,11BS)-9,10,11,11A-TETRAHYDRO-8H-6,11B-METHANOFURO(2,3-C)PYRIDO(1,2-A)AZEPIN-2(6H)-ONE
Common Name English
L-SECURININE
Common Name English
SECURINAN-11-ONE
Common Name English
securinine [INN]
Common Name English
Securinine [WHO-DD]
Common Name English
6,10-METHANOPYRIDO(1,2-A)AZEPINE-.GAMMA.9(6H),.ALPHA.-ACETIC ACID,1,2,3,4,10,10A-HEXAHYDRO-10-HYDROXY-, .GAMMA.-LACTONE
Systematic Name English
SECURININE [MI]
Common Name English
(-)-SECURININE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C221
Created by admin on Sat Dec 16 16:16:04 GMT 2023 , Edited by admin on Sat Dec 16 16:16:04 GMT 2023
Code System Code Type Description
MERCK INDEX
m9829
Created by admin on Sat Dec 16 16:16:04 GMT 2023 , Edited by admin on Sat Dec 16 16:16:04 GMT 2023
PRIMARY Merck Index
PUBCHEM
442872
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PRIMARY
INN
3888
Created by admin on Sat Dec 16 16:16:04 GMT 2023 , Edited by admin on Sat Dec 16 16:16:04 GMT 2023
PRIMARY
WIKIPEDIA
Securinine
Created by admin on Sat Dec 16 16:16:04 GMT 2023 , Edited by admin on Sat Dec 16 16:16:04 GMT 2023
PRIMARY
FDA UNII
G4VS580P5E
Created by admin on Sat Dec 16 16:16:04 GMT 2023 , Edited by admin on Sat Dec 16 16:16:04 GMT 2023
PRIMARY
CAS
5610-40-2
Created by admin on Sat Dec 16 16:16:04 GMT 2023 , Edited by admin on Sat Dec 16 16:16:04 GMT 2023
PRIMARY
NSC
107413
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PRIMARY
ChEMBL
CHEMBL303062
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PRIMARY
EPA CompTox
DTXSID7045944
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PRIMARY
EVMPD
SUB10470MIG
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PRIMARY
SMS_ID
100000084105
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PRIMARY
MESH
C000785
Created by admin on Sat Dec 16 16:16:04 GMT 2023 , Edited by admin on Sat Dec 16 16:16:04 GMT 2023
PRIMARY
NCI_THESAURUS
C81359
Created by admin on Sat Dec 16 16:16:04 GMT 2023 , Edited by admin on Sat Dec 16 16:16:04 GMT 2023
PRIMARY