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Details

Stereochemistry ACHIRAL
Molecular Formula C14H21N3O5
Molecular Weight 311.3342
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEONURINE

SMILES

COc1cc(cc(c1O)OC)C(=O)OCCCCNC(=N)N

InChI

InChIKey=WNGSUWLDMZFYNZ-UHFFFAOYSA-N
InChI=1S/C14H21N3O5/c1-20-10-7-9(8-11(21-2)12(10)18)13(19)22-6-4-3-5-17-14(15)16/h7-8,18H,3-6H2,1-2H3,(H4,15,16,17)

HIDE SMILES / InChI
Leonurine (LN) is a natural alkaloid extracted from Herba leonuri which is used in Chinese traditional medicine and possesses anti-inflammatory properties. Leonurine has potential as a therapeutic agent for rheumatoid arthritis and might be a promising therapeutic compound to treat osteoclast-related diseases, such as osteoporosis. These effects are achieved through the inhibition of NF-κB and mitogen-activated protein kinase pathways. In addition, it was found that leonurine protects BBB integrity by regulating the HDAC4/NOX4/MMP-9 tight junction pathway and could therfeore represent a new class of potential drugs against the acute onset of ischemic stroke. In experiments on mice with adenomyosis leonurine attenuated generalized hyperalgesia, however, the mechanism responsible for alleviating pain was not readily apparent.

CNS Activity

Curator's Comment:: Leonurine (also named SCM-198) could decrease infarct volume and improve neurological deficit by protecting against blood-brain barrier (BBB) breakdown

Approval Year

PubMed

PubMed

TitleDatePubMed
Endothelium-independent vasorelaxation by leonurine, a plant alkaloid purified from Chinese motherwort.
2001 Jan 12
Effect of leonurine on the activity of creatine kinase.
2004 Dec
Protective effects of leonurine in neonatal rat hypoxic cardiomyocytes and rat infarcted heart.
2009 Jul
Magnesium Lithospermate B Protects Cardiomyocytes from Ischemic Injury Via Inhibition of TAB1-p38 Apoptosis Signaling.
2010
Antiapoptotic effect of novel compound from Herba leonuri - leonurine (SCM-198): a mechanism through inhibition of mitochondria dysfunction in H9c2 cells.
2010 Dec
Leonurine (SCM-198) improves cardiac recovery in rat during chronic infarction.
2010 Dec 15
Patents

Patents

Sample Use Guides

mice with adenomyosis: group 1 received a low-dose (30 mg/kg body weight) leonurine treatment; group 2 received a high-dose (60 mg/kg body weight) leonurine
Route of Administration: Oral
Leonurine could obviously attenuate the spontaneous excitatory postsynaptic current amplitude and frequency on pyramidal neurons. In in vitro study, there were control group, OGD group, OGD+ 100µM leonurin group, and OGD+ 10µM donepezil group.
Name Type Language
LEONURINE
MI  
Common Name English
4-GUANIDINO-1-BUTANOL SYRINGATE
Systematic Name English
LEONURINE [MI]
Common Name English
BENZOIC ACID, 4-HYDROXY-3,5-DIMETHOXY-, 4-((AMINOIMINOMETHYL)AMINO)BUTYL ESTER
Common Name English
(4-(4-HYDROXY-3,5-DIMETHOXYBENZOYLOXY)BUTYL)GUANIDINE
Systematic Name English
4-HYDROXY-3,5-DIMETHOXYBENZOIC ACID .DELTA.-GUANIDINOBUTYL ESTER
Systematic Name English
SYRINGIC ACID .DELTA.-GUANIDINOBUTYL ESTER
Systematic Name English
BENZOIC ACID, 4-HYDROXY-3,5-DIMETHOXY-, ESTER WITH (4-HYDROXYBUTYL)GUANIDINE
Common Name English
Code System Code Type Description
CAS
24697-74-3
Created by admin on Sat Jun 26 00:46:16 UTC 2021 , Edited by admin on Sat Jun 26 00:46:16 UTC 2021
PRIMARY
MERCK INDEX
M6765
Created by admin on Sat Jun 26 00:46:16 UTC 2021 , Edited by admin on Sat Jun 26 00:46:16 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
LEONURINE
Created by admin on Sat Jun 26 00:46:16 UTC 2021 , Edited by admin on Sat Jun 26 00:46:16 UTC 2021
PRIMARY
EPA CompTox
24697-74-3
Created by admin on Sat Jun 26 00:46:16 UTC 2021 , Edited by admin on Sat Jun 26 00:46:16 UTC 2021
PRIMARY
FDA UNII
09Q5W34QDA
Created by admin on Sat Jun 26 00:46:16 UTC 2021 , Edited by admin on Sat Jun 26 00:46:16 UTC 2021
PRIMARY
MESH
C013587
Created by admin on Sat Jun 26 00:46:16 UTC 2021 , Edited by admin on Sat Jun 26 00:46:16 UTC 2021
PRIMARY
PUBCHEM
161464
Created by admin on Sat Jun 26 00:46:16 UTC 2021 , Edited by admin on Sat Jun 26 00:46:16 UTC 2021
PRIMARY