LEONURINE

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 Search

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

Molecular Formula	C14H21N3O5
Molecular Weight	311.3336
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28389633 | https://www.ncbi.nlm.nih.gov/pubmed/28431044 | https://www.ncbi.nlm.nih.gov/pubmed/28690765

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
NF-kappa B signaling pathway 87 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25708053/	Inhibitor 8504
HDAC4/NOX4/MMP-9 tight junction pathway 1 Target ID: HDAC4/NOX4/MMP-9 tight junction pathway Sources: https://www.ncbi.nlm.nih.gov/pubmed/28690765	Modulator 846

Conditions

Condition	Modality	Highest Phase	Product
Adenomyosis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28389633	Palliative	Preclinical	Unknown Approved Use Unknown
Osteoporosis 101 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25708053/	Primary	Basic research	Unknown Approved Use Unknown
Rheumatoid arthritis 320 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28431044	Primary	Preclinical	Unknown Approved Use Unknown
Ischemic stroke 35 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28690765	Preventing	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Leonurine (SCM-198) improves cardiac recovery in rat during chronic infarction.	2010-12-15	20854808
Synthesis and biological evaluation of novel leonurine-SPRC conjugate as cardioprotective agents.	2010-12-01	20980147
Antiapoptotic effect of novel compound from Herba leonuri - leonurine (SCM-198): a mechanism through inhibition of mitochondria dysfunction in H9c2 cells.	2010-12	20874679
Development and validation of an UPLC-DAD-MS method for the determination of leonurine in Chinese motherwort (Leonurus japonicus).	2010-11	21044409
Leonurine protects middle cerebral artery occluded rats through antioxidant effect and regulation of mitochondrial function.	2010-11	20947850
Leonurine improves ischemia-induced myocardial injury through antioxidative activity.	2010-08	20185283
Magnesium Lithospermate B Protects Cardiomyocytes from Ischemic Injury Via Inhibition of TAB1-p38 Apoptosis Signaling.	2010	21607062
Neuroprotective effects of leonurine on ischemia/reperfusion-induced mitochondrial dysfunctions in rat cerebral cortex.	2010	21139233
4-Guanidino-n-butyl syringate (Leonurine, SCM 198) protects H9c2 rat ventricular cells from hypoxia-induced apoptosis.	2009-11	19940642
Protective effects of leonurine in neonatal rat hypoxic cardiomyocytes and rat infarcted heart.	2009-07	19594556
Herba leonurine attenuates doxorubicin-induced apoptosis in H9c2 cardiac muscle cells.	2009-06-10	19356731
[Determination of leonurine in leonurus granule and extractum by UPLC].	2009-06	19777834
Effect of leonurine on the activity of creatine kinase.	2004-12	15621588
[Determination of stachydrine and leonurine in Herba Leonuri by ion- pair reversed-phase high-performance liquid chromatography].	2004-11	15567762
Enhancement of phenylephrine-induced contraction in the isolated rat aorta with endothelium by H2O-extract from an Oriental medicinal plant Leonuri herba.	2001-06	11459124
Endothelium-independent vasorelaxation by leonurine, a plant alkaloid purified from Chinese motherwort.	2001-01-12	11213365

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:56:37 GMT 2025` Edited by `admin` on `Mon Mar 31 20:56:37 GMT 2025`
Record UNII	09Q5W34QDA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEONURINE

Common Name

English

BENZOIC ACID, 4-HYDROXY-3,5-DIMETHOXY-, 4-((AMINOIMINOMETHYL)AMINO)BUTYL ESTER

Preferred Name

English

4-GUANIDINO-1-BUTANOL SYRINGATE

Systematic Name

English

LEONURINE [MI]

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