LIGUSTRAZINE PHOSPHATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H12N2.H3O4P
Molecular Weight	234.1895
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OP(O)(O)=O.CC1=NC(C)=C(C)N=C1C

InChI

InChIKey=KWWLGXNRLABSMP-UHFFFAOYSA-N

InChI=1S/C8H12N2.H3O4P/c1-5-6(2)10-8(4)7(3)9-5;1-5(2,3)4/h1-4H3;(H3,1,2,3,4)

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
[Effect of combination of ligustrazine and nitrendipine on hemodynamics in patients with chronic obstructive pulmonary disease].	2001 Mar	12577333
The effect of ligustrazine on peritoneal transport in peritoneal dialysis.	2002	12674773
Effects of ligustrazine on hematopoiesis in the early phase of bone marrow transplantation mice.	2002	12658803
The prediction of plasma and brain levels of 2,3,5,6-tetramethylpyrazine following transdermal application.	2002	12646016
[Effects of ligustrazine on blood vessels and blood components].	2002 Feb	14740662
[Advances in the study on transdermal permeation of active elements of natural drugs in vitro].	2002 Jan	14730719
[The intervention effects of Angelica sinensis, Salvia miltiorrhiza and ligustrazine on peritoneal macrophages during peritoneal dialysis].	2002 Mar	12585104
[Effect of ligustrazine on bone marrow hematopoiesis in mice after bone marrow transplantation].	2002 May	12584839
The effects of Ligustrazine on the expression of bFGF and bFGFR in bone marrow in radiation injured mice.	2003	15015632
[Effect of tetramethylpyrazine on endothelin, von Willebrand factor and thromboxane A2 during cardiopulmonary bypass in patients of congenital heart disease with pulmonary hypertension].	2003 Apr	12764908
Tetramethylpyrazine scavenges superoxide anion and decreases nitric oxide production in human polymorphonuclear leukocytes.	2003 Apr 18	12650854
AgC(CN)3-based coordination polymers.	2003 Apr 21	12691573
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
[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
Synthesis of the novel liqustrazine derivatives and Their protective effect on injured vascular endothelial cell damaged by hydrogen peroxide.	2003 Jul 7	12798318
[Effect of ligustrazine on the expression of Bcl-2 protein and apoptosis in rabbit articular chondrocytes in monolayer culture].	2003 Jun	14653072
Tetramethylpyrazine as potassium channel opener to lower calcium influx into cultured aortic smooth muscle cells.	2003 Jun	12865978
[Comparing effect in the management of erectile dysfunction by using 2 sets of drugs of intracavernosal injection].	2003 Jun	12861835
Convolution method to predict drug concentration profiles of 2,3,5,6-tetramethylpyrazine following transdermal application.	2003 Jun 18	12787634
Physicochemical characterization and percutaneous delivery of 2,3,5,6-tetramethylpyrazine.	2003 Mar 6	12593948
[Progress on TCM drug-therapy of antagonizing arteriosclerosis].	2003 May	12800427
[Clinical application and pharmacological actions of ligustrazine].	2003 May	12800423
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 ligustrazine on cell cycle and prostacyclin of injured vascular endothelial cells induced by hypoxia and lack of glucose].	2003 Oct	14768390
[Effect of tetramethylpyrazine on learning, memory and cholinergic system in D-galactose-lesioned mice].	2003 Oct	14650157
[Ligustrazine and Salvia miltiorrhiza injection solution in complementary therapy of pregnancy-induced hypertension: clinical analysis of 60 cases].	2003 Sep	13129738
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
Inhibitory effects of ligustrazine, a modulator of thromboxane-prostacycline-nitric oxide balance, on renal injury in rats with passive Heyman nephritis.	2004	15528953
Inhibition of shear-induced platelet aggregation in rat by tetramethylpyrazine and salvianolic acid B.	2004	15310944
Liquid chromatography-mass spectrometry method for determination of tetramethylpyrazine and its metabolite in dog plasma.	2004 Dec 25	15556542
[Effect of Ligustrazine on the expression of vascular endothelial growth factor in bone marrow stromal cells of radiation injured mice].	2004 Feb	14989777
Nitric oxide-mediated vasorelaxation by Rhizoma Ligustici wallichii in isolated rat thoracic aorta.	2004 Jan	14971721
[Chemical profiles of methylpyrazines contained in commercially available natto].	2004 Jan	14768353
Studies on the aroma of cupuassu liquor by headspace solid-phase microextraction and gas chromatography.	2004 Jan 30	14753678
Effect of tetramethylpyrazine on acute nociception mediated by signaling of P2X receptor activation in rat.	2004 Jan 9	14672814
Preparation of cardiovascular disease-related genes microarray and its application in exploring ligustrazine-induced changes in endothelial gene expression.	2004 Jul-Aug	15520497
[Effect of ligustrazine on expressions of basic fibroblast growth factor and its receptor in bone marrow of mice with acute radiation injury].	2004 May	15199631
[Cardiac hemodynamics after suprarenal ligation of the inferior vena cava and the resection of the right kidney or injection of ligustrazine in rats].	2004 May	15142439
[Effects of combination therapy of rehin and tetramethylpyrazine on experimental hepatic fibrosis induced by tetrachloride].	2004 Nov	15623384
Tetramethylpyrazine reduces ischemic brain injury in rats.	2004 Nov 30	15531085
[Study on ligustrazine in reversing multidrug resistance of HepG2/ADM cell in vitro].	2004 Oct	15631086
[Protective effect of tetramethylpyrazine and L-arginine on rats with acute myocardial infarction].	2004 Oct	15553826
[Effect of tetramethylpyrazine on lipopolysaccharides induced macrophage cyclo-oxidase-2 expression and apoptosis of cardiac myocytes].	2004 Oct	15553825
Effect of ligustrazine on ischemia-reperfusion injury in murine kidney.	2004 Sep	15518708
Protective effect of tetramethylpyrazine on learning and memory function in D-galactose-lesioned mice.	2004 Sep	15506643

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 PHOSPHATE

Common Name

English

TETRAMETHYLPYRAZINE PHOSPHATE (1:1)

Systematic Name

English

Ligustrazine phosphate [WHO-DD]

Common Name

English

TETRAMETHYLPYRAZINE PHOSPHATE

Systematic Name

English

PHOSPHORIC ACID; 2,3,5,6-TETRAMETHYLPYRAZINE

Systematic Name

English

PYRAZINE, 2,3,5,6-TETRAMETHYL-, PHOSPHATE (1:1)

Systematic Name

English

PYRAZINE, TETRAMETHYL-, PHOSPHATE (1:1)

Systematic Name

English

Code System Code Type Description

EVMPD

SUB130943