LIGUSTRAZINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H12N2
Molecular Weight	136.1943
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=NC(C)=C(C)N=C1C

InChI

InChIKey=FINHMKGKINIASC-UHFFFAOYSA-N

InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24660601 | https://www.ncbi.nlm.nih.gov/pubmed/27523814 | https://www.ncbi.nlm.nih.gov/pubmed/27668034

Ligustrazine (tetramethylpyrazine) is a bioactive ingredient extracted from the widely-used Chinese herb, Chuanxiong. It inhibits of platelet aggregation, enhances of vessel dilation, increases cerebral blood flow and possesses neuroprotective properties. The injection solution of ligustrazine has been used especially in China to treat ischemic stroke, coronary heart disease, diabetic nephropathy, and knee osteoarthritis. Ligustrazine was also evaluated in clinical as a remedy for pressure sores, as a salvage agent for patients with non-Hodgkin's lymphoma, as a treatment for bronchial asthma and vertebrobasilar insufficiency.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Platelet activation 4 Target ID: map04611 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9526946	Inhibitor 8297
Voltage-gated L-type calcium channel 92 Target ID: CHEMBL2095229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23058991	Inhibitor 8297
nitric oxide production involved in inflammatory response 17 Target ID: GO:0002537 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27668034	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Osteoarthritis of knee 23 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16951526	Primary	Approved 8429	Unknown Approved Use Unknown
Ischemic stroke 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24660601	Primary	Approved 8429	Unknown Approved Use Unknown
Coronary heart disease 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18198639	Primary	Approved 8429	Unknown Approved Use Unknown
Diabetic nephropathy 35 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22298446	Primary	Approved 8429	Unknown Approved Use Unknown
Bronchial asthma 50 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18853120	Primary	Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Effect of ligustrazine peritoneal dialysate on CD40 expression of rat peritoneal mesothellial cells].	2001 Dec	12575594
[Therapeutic mechanism of combination therapy of ligustrazine and nitrendipine in treating patients with chronic obstructive pulmonary disease].	2001 Jan	12577373
Effects of tetramethylpyrazine on prostaglandin E(2)- and prostaglandin E(2) receptor agonist-induced disruption of blood-aqueous barrier in pigmented rabbits.	2001 May-Jun	11369370
The effect of ligustrazine on peritoneal transport in peritoneal dialysis.	2002	12674773
Protective effects of ligustrazine on ischemia-reperfusion injury in rat kidneys.	2002	12497570
[Effects of ligustrazine on blood vessels and blood components].	2002 Feb	14740662
Effects of various principles from Chinese herbal medicine on rhodamine123 accumulation in brain capillary endothelial cells.	2002 Jul	12100750
[The intervention effects of Angelica sinensis, Salvia miltiorrhiza and ligustrazine on peritoneal macrophages during peritoneal dialysis].	2002 Mar	12585104
[Preparation and in vitro release of tetramethylpyrazine phosphate pulsincap capsule controlled by an erodible plug].	2002 Sep	12567902
In vitro permeation of tetramethylpyrazine across porcine buccal mucosa.	2002 Sep	12230946
Tetramethylpyrazine protects mice against thioacetamide-induced acute hepatotoxicity.	2002 Sep-Oct	12218355
The effects of Ligustrazine on the expression of bFGF and bFGFR in bone marrow in radiation injured mice.	2003	15015632
Comparative studies of LFA-1/ICAM-1 interaction by micropipette and flow chamber techniques.	2003	12454403
Iron-induced oxidative damage and apoptosis in cerebellar granule cells: attenuation by tetramethylpyrazine and ferulic acid.	2003 Apr 25	12706453
[Effect of ligustrazine on proliferative glomerulonephritis].	2003 Aug	14649206
[Effects of tetramethylpyrazine on cytosolic free calcium concentration in penis corpus cavernsum smooth muscle cells in rabbits].	2003 Aug	14513636
[Protective effect of ligustrazine on insulin resistance after local cerebral ischemia of rat].	2003 Dec	15617507
Basolateral membrane mechanisms involved in ligustrazine-stimulated anion secretion in rat distal colon.	2003 Dec 25	14695481
[Effect of ligustrazine on the expression of Bcl-2 protein and apoptosis in rabbit articular chondrocytes in monolayer culture].	2003 Jun	14653072
[Comparing effect in the management of erectile dysfunction by using 2 sets of drugs of intracavernosal injection].	2003 Jun	12861835
Mechanisms responsible for the in vitro relaxation of ligustrazine on porcine left anterior descending coronary artery.	2003 May 16	12754058
Tetramethylpyrazine elicits disparate responses in cardiac contraction and intracellular Ca(2+) transients in isolated adult rat ventricular myocytes.	2003 Nov	14746828
Effect of tetramethylpyrazine on exocrine pancreatic and bile secretion.	2003 Nov	14606085
[Effect of tetramethylpyrazine on learning, memory and cholinergic system in D-galactose-lesioned mice].	2003 Oct	14650157
The oxygen radical generator pyrogallol impairs cardiomyocyte contractile function via a superoxide and p38 MAP kinase-dependent pathway: protection by anisodamine and tetramethylpyrazine.	2004	15531780
Effect of ligustrazine on the expression of LFA-1, ICAM-1 following bone marrow transplantation in mice.	2004	15315336
[Experimental study on prevention and treatment of bronchial asthma by compound Chinese herbal monomer recipe].	2004 Aug	15366597
Preparative isolation and purification of chuanxiongzine from the medicinal plant Ligusticum chuanxiong by high-speed counter-current chromatography.	2004 Aug 27	15460256
Liquid chromatography-mass spectrometry method for determination of tetramethylpyrazine and its metabolite in dog plasma.	2004 Dec 25	15556542
[Chemical profiles of methylpyrazines contained in commercially available natto].	2004 Jan	14768353
Preparation of cardiovascular disease-related genes microarray and its application in exploring ligustrazine-induced changes in endothelial gene expression.	2004 Jul-Aug	15520497
[Effects of combination therapy of rehin and tetramethylpyrazine on experimental hepatic fibrosis induced by tetrachloride].	2004 Nov	15623384
[Study on ligustrazine in reversing multidrug resistance of HepG2/ADM cell in vitro].	2004 Oct	15631086

Patents

Sample Use Guides

In Vivo Use Guide

In a clinical trial for the treatment of pressure sores, ligustrazine was applied with a transdermal patch. For treatment of bronchial asthma, ligustrazine was administered by inhalation. For treatment of vertebrobasilar insufficiency, ligustrazine was administered intravenously (80 mg of ligustrazine in 250 ml of 5% glucose or 0.9% normal saline for 15 days).

Route of Administration: Other

In Vitro Use Guide

Tetramethylpyrazine was tested for its antiplatelet activities in human platelet suspensions. In human platelets, tetramethylpyrazine (0.5-1.5 mM) dose-dependently inhibited platelet aggregation, as measured by a turbidimetric method.

Name

Type

Language

LIGUSTRAZINE

Common Name

English

PYRAZINE, 2,3,5,6-TETRAMETHYL-

Systematic Name

English

2,3,5,6-TETRAMETHYLPYRAZINE [FHFI]

Common Name

English

CHUANXINGZINE

Common Name

English

FEMA NO. 3237

Code

English

NSC-46451

Code

English

LIGUSTRAZIN

Common Name

English

TETRAPYRAZINE

Common Name

English

TETRAMETHYLPYRAZINE

Systematic Name

English

2,3,5,6-TETRAMETHYLPYRAZINE [FCC]

Common Name

English

NSC-36080

Code

English

Ligustrazine [WHO-DD]

Common Name

English

2,3,5,6-TETRAMETHYLPYRAZINE

Systematic Name

English

PYRAZINE, TETRAMETHYL-

Systematic Name

English

CHUANXIONGQIN

Brand Name

English

Classification Tree Code System Code

JECFA EVALUATION

2,3,5,6-TETRAMETHYLPYRAZINE