Details of the Drug

General Information of Drug (ID: DMC0WNB)

Drug Name
Tetramethylpyrazine
Synonyms Ligustizine; Ligustrazine; 2,3,5,6-Tetramethylpyrazine
Indication
Disease Entry ICD 11 Status REF
Neurological disorder 6B60 Discontinued in Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 136.19
Logarithm of the Partition Coefficient (xlogp) 1.3
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C8H12N2
IUPAC Name
2,3,5,6-tetramethylpyrazine
Canonical SMILES
CC1=C(N=C(C(=N1)C)C)C
InChI
InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3
InChIKey
FINHMKGKINIASC-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
14296
ChEBI ID
CHEBI:133246
CAS Number
1124-11-4
TTD ID
D09WFI

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Endothelin-1 (EDN1) TTJR60Z EDN1_HUMAN Modulator [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Acid-sensing ion channel 3 (ASIC3) OTE9SSM4 ASIC3_HUMAN Gene/Protein Processing [3]
Actin, aortic smooth muscle (ACTA2) OTEDLG8E ACTA_HUMAN Gene/Protein Processing [4]
Apolipoprotein C-III (APOC3) OTW3520C APOC3_HUMAN Gene/Protein Processing [3]
Catalase (CAT) OTHEBX9R CATA_HUMAN Gene/Protein Processing [5]
Catenin beta-1 (CTNNB1) OTZ932A3 CTNB1_HUMAN Gene/Protein Processing [4]
Collagen alpha-1(I) chain (COL1A1) OTI31178 CO1A1_HUMAN Gene/Protein Processing [4]
Cystic fibrosis transmembrane conductance regulator (CFTR) OT6B22QH CFTR_HUMAN Gene/Protein Processing [6]
Cytochrome P450 11B1, mitochondrial (CYP11B1) OTKKL894 C11B1_HUMAN Gene/Protein Processing [3]
Fibronectin (FN1) OTB5ZN4Q FINC_HUMAN Gene/Protein Processing [4]
Glutamate--cysteine ligase catalytic subunit (GCLC) OTESDI4D GSH1_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Determination of tetramethylpyrazine in animal serum and cerebrospinal fluid by high performance liquid chromatography. Se Pu. 2000 Jan;18(1):46-8.
2 Tetramethylpyrazine, a Chinese drug, blocks coronary vasoconstriction by endothelin-1 and decreases plasma endothelin-1 levels in experimental animals. J Cardiovasc Pharmacol. 1998;31 Suppl 1:S313-6.
3 Preparation of cardiovascular disease-related genes microarray and its application in exploring ligustrazine-induced changes in endothelial gene expression. Pol J Pharmacol. 2004 Jul-Aug;56(4):427-33.
4 Nrf2 knockdown attenuates the ameliorative effects of ligustrazine on hepatic fibrosis by targeting hepatic stellate cell transdifferentiation. Toxicology. 2016 Jul 15;365:35-47. doi: 10.1016/j.tox.2016.07.018. Epub 2016 Jul 28.
5 Effects of tetramethylpyrazine from Chinese black vinegar on antioxidant and hypolipidemia activities in HepG2 cells. Food Chem Toxicol. 2017 Nov;109(Pt 2):930-940.
6 Activation of apical CFTR and basolateral Ca(2+)-activated K+ channels by tetramethylpyrazine in Caco-2 cell line. Eur J Pharmacol. 2005 Mar 14;510(3):187-95. doi: 10.1016/j.ejphar.2005.01.026.
7 Effect of dihydropyrazines on human hepatoma HepG2 cells: a comparative study using 2,3-dihydro-5,6-dimethylpyrazine and 3-hydro-2,2,5,6-tetramethylpyrazine. J Toxicol Sci. 2014 Aug;39(4):601-8. doi: 10.2131/jts.39.601.