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Details

Stereochemistry ACHIRAL
Molecular Formula C14H21N3O5
Molecular Weight 311.3336
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEONURINE

SMILES

COC1=CC(=CC(OC)=C1O)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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: HDAC4/NOX4/MMP-9 tight junction pathway
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Endothelium-independent vasorelaxation by leonurine, a plant alkaloid purified from Chinese motherwort.
2001 Jan 12
Enhancement of phenylephrine-induced contraction in the isolated rat aorta with endothelium by H2O-extract from an Oriental medicinal plant Leonuri herba.
2001 Jun
Effect of leonurine on the activity of creatine kinase.
2004 Dec
[Determination of stachydrine and leonurine in Herba Leonuri by ion- pair reversed-phase high-performance liquid chromatography].
2004 Nov
Protective effects of leonurine in neonatal rat hypoxic cardiomyocytes and rat infarcted heart.
2009 Jul
[Determination of leonurine in leonurus granule and extractum by UPLC].
2009 Jun
Herba leonurine attenuates doxorubicin-induced apoptosis in H9c2 cardiac muscle cells.
2009 Jun 10
4-Guanidino-n-butyl syringate (Leonurine, SCM 198) protects H9c2 rat ventricular cells from hypoxia-induced apoptosis.
2009 Nov
Magnesium Lithospermate B Protects Cardiomyocytes from Ischemic Injury Via Inhibition of TAB1-p38 Apoptosis Signaling.
2010
Neuroprotective effects of leonurine on ischemia/reperfusion-induced mitochondrial dysfunctions in rat cerebral cortex.
2010
Leonurine improves ischemia-induced myocardial injury through antioxidative activity.
2010 Aug
Antiapoptotic effect of novel compound from Herba leonuri - leonurine (SCM-198): a mechanism through inhibition of mitochondria dysfunction in H9c2 cells.
2010 Dec
Synthesis and biological evaluation of novel leonurine-SPRC conjugate as cardioprotective agents.
2010 Dec 1
Leonurine (SCM-198) improves cardiac recovery in rat during chronic infarction.
2010 Dec 15
Development and validation of an UPLC-DAD-MS method for the determination of leonurine in Chinese motherwort (Leonurus japonicus).
2010 Nov
Leonurine protects middle cerebral artery occluded rats through antioxidant effect and regulation of mitochondrial function.
2010 Nov
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 Dec 16 01:39:13 UTC 2023 , Edited by admin on Sat Dec 16 01:39:13 UTC 2023
PRIMARY
MERCK INDEX
m6765
Created by admin on Sat Dec 16 01:39:13 UTC 2023 , Edited by admin on Sat Dec 16 01:39:13 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
LEONURINE
Created by admin on Sat Dec 16 01:39:13 UTC 2023 , Edited by admin on Sat Dec 16 01:39:13 UTC 2023
PRIMARY
EPA CompTox
DTXSID70179434
Created by admin on Sat Dec 16 01:39:13 UTC 2023 , Edited by admin on Sat Dec 16 01:39:13 UTC 2023
PRIMARY
FDA UNII
09Q5W34QDA
Created by admin on Sat Dec 16 01:39:13 UTC 2023 , Edited by admin on Sat Dec 16 01:39:13 UTC 2023
PRIMARY
MESH
C013587
Created by admin on Sat Dec 16 01:39:13 UTC 2023 , Edited by admin on Sat Dec 16 01:39:13 UTC 2023
PRIMARY
PUBCHEM
161464
Created by admin on Sat Dec 16 01:39:13 UTC 2023 , Edited by admin on Sat Dec 16 01:39:13 UTC 2023
PRIMARY